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Tuning Crystal Structures of Iron-Based Metal–Organic Frameworks for Drug Delivery Applications
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  • Hao Pham
    Hao Pham
    Department of Physical Sciences, Long Beach City College, Long Beach, California 90808, United States
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  • Kimberly Ramos
    Kimberly Ramos
    Chemistry Department, Cerritos College, Norwalk, California 90650, United States
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  • Andy Sua
    Andy Sua
    Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
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  • Jessica Acuna
    Jessica Acuna
    Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
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  • Katarzyna Slowinska
    Katarzyna Slowinska
    Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
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    Orcidhttp://orcid.org/0000-0001-6468-2918
  • Travis Nguyen
    Travis Nguyen
    Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
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  • Angela Bui
    Angela Bui
    Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
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  • Mark D. R. Weber
    Mark D. R. Weber
    Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
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  • Fangyuan Tian*
    Fangyuan Tian
    Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
    *E-mail: [email protected]. Phone: 1-(562)-985-2115. Fax: 1-(562)-985-8557.
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    Orcidhttp://orcid.org/0000-0003-4141-7286
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ACS Omega

Cite this: ACS Omega 2020, 5, 7, 3418–3427
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https://doi.org/10.1021/acsomega.9b03696
Published February 12, 2020

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Abstract

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Iron-based metal–organic frameworks (Fe-MOFs) have emerged as promising candidates for drug delivery applications due to their low toxicity, structural flexibility, and safe biodegradation in a physiological environment. Here, we studied two types of Fe-MOFs: MIL-53 and MIL-88B, for in vitro drug loading and releasing of ibuprofen as a model drug. Both Fe-MOFs are based on the same iron clusters and organic ligands but form different crystal structures as a result of two different nucleation pathways. The MIL-53 structure demonstrates one-dimensional channels, while MIL-88B exhibits a three-dimensional cage structure. Our studies show that MIL-53 adsorbs more ibuprofen (37.0 wt %) compared to MIL-88B (19.5 wt %). A controlled drug release was observed in both materials with a slower elution pattern in the case of the ibuprofen-encapsulated MIL-88B. This indicates that a complex cage structure of MIL-88 is beneficial to control the rate of drug release. A linear correlation was found between cumulative drug release and the degree of material degradation, suggesting the biodegradation of Fe-MILs as the main drug elution mechanism. The cytotoxicity of MIL-88B was evaluated in vitro with NIH-3T3 Swiss mouse fibroblasts, and it shows that MIL-88B has no adverse effects on cell viability up to 0.1 mg/mL. This low toxicity was attributed to the morphology of MIL-88B nanocrystals. The very low toxicity and controlled drug release behavior of Fe-MIL-88B suggest that better materials for drug-delivery applications can be created by controlling not only the composition but also the crystal structure and nanoparticle morphology of the material.

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1. Introduction

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The rapid growth of drug discovery and the increasing demand for drug-eluting medical implants accelerate the search for new drug carrier systems with low toxicity, better control of drug loading capacity, and sustainable drug releasing. So far, polymeric and inorganic complexes have been widely applied for the drug delivery and controllable release of pharmaceutical compounds. In particular, poly(lactic-co-glycolic acid) (PLGA), polymers and their polymeric particles have been used in a variety of therapeutic devices due to their excellent biocompatibility. (1−3) The inorganic solids, such as porous silicon, functionalized silica, and zeolites, are also utilized as drug carriers. (4−6) Some of these organic and inorganic materials have limited drug loading capacity and complex interactions of loaded drugs at the guest–host interface. As an alternative, a type of hybrid materials, metal–organic frameworks (MOFs), combining the advantages of polymers and inorganic mesoporous solids, have emerged as drug delivery matrices. (7−11)
MOFs are solid porous crystals composing of metal ions or clusters as secondary building blocks (SBUs) cross-linked by organic ligands. (12,13) Due to the high porosity, large surface area, and suitable pore sizes, MOFs have exhibited potential in many applications, such as gas separation and storage, catalysis, and loading other guest molecules. (14−18) More recently, increasing interest has been attracted to apply MOFs for biomedical applications, such as imaging, sensing, and loading therapeutic agents as delivery vehicles. (19−21) Compared to other traditional drug carriers (i.e., polymers, nanoparticles, bacteria, etc.), MOFs exhibit an excellent drug loading capacity and controlled release profile of many therapeutic agents, attributed to their porous structures. (19,22) In addition, MOFs can be engineered for specific drug delivery due to the flexibility and versatile chemical composition of the framework. For example, a rigid MOF, MIL-100 (MIL stands for Material Institut Lavoisier), is able to hold up to 21.2 wt % azidothymidine triphosphate (AZT-TP, an antiretroviral drug for HIV/AIDS treatment), while its loading capacity can be increased to 42.0 wt % when amino-functionalized MIL-100 is used. (9) In comparison, traditional drug carriers have a much lower loading capacity (i.e., polymer nanoparticles, ∼6 wt %; liposomal systems, <1 wt %). (23,24) Despite the MOFs advantage of high drug loading and effective delivery, an ongoing issue of its safety and biocompatibility is questioned. In the last five years, many studies have been conducted to test cytotoxicity of MOFs with various cell and animal models. (25,26) One type of MOF, iron-containing MOFs (Fe-MOFs), has truly stood out for their supreme safety and biodegradability. (11,22,27) A majority of Fe-MOFs belong to the MIL and BioMOF families, including MIL-53, MIL-88, MIL-100, MIL-101, BioMOF-1, and BioMOF-5. (10,19,28−31) Selection of a drug delivery system is based on drug formulation, delivery routes, targeting organs/cells, etc. Therefore, it is crucial to select the correct MOF for a particular drug and for a specific target. So far, little research has been done to optimize MOF structures for a certain delivery route. In addition, other factors should also be considered, such as the guest–host interaction, pore size, cavity volume, and stability, especially when a MOF is paired with a therapeutic agent. Most MOFs contain hydrophobic properties due to their organic ligands, making them efficient in adsorbing hydrocolloids and lipophilic drugs. However, most MOFs lack stability in aqueous conditions due to their relatively weak coordination bonding between metal clusters and ligands. The degradation of MOFs in aqueous solutions can be viewed as an advantage when considering a potential biodegradable drug delivery system. Structural decomposition provides an easy method for releasing encapsulated drug molecules; however, the kinetics of decomposition and retention of MOF structure in a biological environment is not well understood. Additionally, when designing MOFs for drug delivery, it is important to take into consideration their wettability and stability.
In this study, we focused on using unstable Fe-MOFs as biodegradable drug delivery systems. This work aims at studying two aspects of Fe-MOFs: (A) the effect of crystal structure on drug loading/adsorption and (B) the interactions between the guest molecules and host matrix (drug and MOFs), including drug elution kinetics and material degradation.
Fe-based MIL-53 and MIL-88B are two flexible Fe-MOFs consisting of iron ligands connected by terephthalate (TA) linkers. It has been found that MIL-53 forms through a homogenous nucleation and MIL-88B through a heterogeneous nucleation. (32) MIL-53 consists of oxygen-centered iron-carboxylate trimers (octahedral shaped FeO6) connected by TA linkers forming rhomb-shaped 1D channels. (33) Composing of the same FeO6 clusters and TA ligands, MIL-88B exhibits a hexagonal 3D structure. (30) Here, we show that differences in crystal structure results in various characteristics in drug (ibuprofen) loading and delivery. Ibuprofen was selected as the model drug in this study due to its structural simplicity and size. Powder X-ray diffraction (PXRD), infrared spectroscopic studies, and nitrogen sorption isotherms have been performed to determine the drug adsorption and interface interactions within the carriers’ systems. Various kinetic models were used to evaluate the drug release profiles of MIL-53 and MIL-88B. The biocompatibility was tested in vitro with NIH-3T3 Swiss mouse fibroblasts. We believe that the joint effort of MIL synthesis coupled with cell model studies will provide a deep and systematic understanding of these two Fe-based MIL materials as drug delivery systems. Additionally, we focused on the role of the crystal structure toward drug delivery by illustrating three drug elution models that can be applied to other MOFs.

2. Results and Discussion

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2.1. Characterization of Materials and Drug Loading Studies

MIL-88B and MIL-53 contain the same ligands, but their formation is guided by different nucleation processes that can be controlled by different synthetic conditions. The crystal structures of MIL-88B and MIL-53 before and after loading with ibuprofen were studied using powder X-ray diffraction (PXRD). As shown in Figure 1a, the PXRD patterns of MIL-88B are in good agreement with previous studies. (39,40) MIL-88B exhibited three characteristic diffraction peaks at 9.14°, 10.60°, and 11.48° representing the 002, 100, and 101 phases, respectively. (10) We noticed that the diffraction feature was shifted from 10.62° for as-synthesis MIL-88B to 11.48° for the same bulk crystal after solvent exchange followed by further thermal activation. A diffraction angle shifting to a larger angle indicates the shrinkage of the crystal cell based on the Bragg’s Law, (41) This increase in the angle confirms the decreased cage volume of MIL-88B once the trapped DMF solvent inside crystals was replaced and removed. Moreover, after loading with ibuprofen, the MIL-88B pore volume was expanded reflected by the decrease in diffraction angle for the same 101 peak. Our results confirmed the structural flexibility of both MIL-53 and MIL-88B as the “breathing effect” enables both materials to trap guest molecules with shrinkable frameworks, which is consistent with previous literature. (28,42−44)Figure 1b shows the PXRD patterns for MIL-53 as synthesized, after solvent exchange, and loaded with ibuprofen. The diffraction angle at 9.1° is a significant feature for MIL-53. (45,46) After loading with ibuprofen, both MIL-53 and MIL-88B exhibited crystal structures from both host and guest materials. Extra PXRD features at 16.6° and 19.4° were observed on both MILs after loading with ibuprofen, indicating that ibuprofen was added to both porous solids. (47) It is critically important to determine the location of guest drug molecules relative to the host material; therefore, we further performed gas sorption studies to study the porosity changes corresponding to drug loading in the next part. The chemical compositions of both MILs are identical as confirmed by our attenuated total reflectance infrared (ATR-IR) studies, shown in Figure 2. Both MILs exhibited a Fe–O stretch at 549 cm–1, a carboxylate —C═O stretch at 1602 cm–1, a and −C–O stretch at 1389 cm–1, which are consistent with those previously reported in the literature. (25,28,48) After the structural studies, we optimized drug loading conditions for each material. Considering the polarity of ibuprofen and stability of MILs in organic solvents, we immersed MILs into ibuprofen/hexane solutions with various concentrations for different amounts of time. We found that the best drug loading condition for MIL-88B was 10 mg/mL with a soaking time of 24 h, while for MIL-53, the condition is 30 mg/mL for 72 h with a nanoparticle-to-drug ratio of 1:3. After loading ibuprofen in hexane, the crystal structures of both MIL-88B and MIL-53 were still present (Figure 1), indicating that both materials did not degrade during drug loading procedures. Additionally, ATR-IR studies confirmed that the ibuprofen has been successfully incorporated into both materials, indicated by an increasing intensity of the —C═O stretch by comparison with pure ibuprofen shown in Figure 1b. By analyzing IR and PXRD studies of MIL-88B, we concluded that ibuprofen was successfully incorporated in MIL-88B. However, at this point, we were unclear about whether ibuprofen was adsorbed on the outer surface or encapsulated inside of MIL-53 crystals. Therefore, we applied N2 gas sorption analysis to monitor the changes in the surface area and available pore sizes of both Fe-MILs after ibuprofen treatments, Figure 3. The specific surface area (SSA) was calculated based on the Brunauer–Emmett–Teller (BET) theory (49) with N2 sorption isotherms at 77 K (details are available in the Supporting Information). We noticed that the SSA of MIL-53 decreased from 30.1 to 22.1 m2/g after loading with ibuprofen, indicating that ibuprofen was encapsulated inside of MIL-53 and occupied available channels. A similar trend was also observed for MIL-88B by comparing SSA before and after ibuprofen loading. Table S1 summarizes the surface area changes of both MILs corresponding to drug loading. We also examined the external surface area of both MILs before and after loading with ibuprofen. The t-plot studies (50) using Micromeritics software show that the external surface area of ibu-MIL-88B decreased to 21.7 cm2/g compared to that of pristine MIL-88 of 27.9 cm2/g. The micropore surface area of MIL-88B decreases from 14.4 to 3.9 cm2/g after loading with ibuprofen, confirming that majority internal cages were filled with ibuprofen. A similar trend was also noticed on the MIL-53 system with a decrease in the external surface area. To eliminate solvent molecules that may interfere with our results, all testing samples were thermally activated in a vacuum oven at 65 °C for over 72 h. Based on their unique crystal structures, the maximum accessible surface areas (theoretical SSA) for MIL-53 and MIL-88B are 2203 m2/g (H2 as a probe) and 3042 m2/g (N2 as a probe), respectively. (28,51,52) Although the surface areas obtained experimentally are typically smaller than those predicted based on single-crystal structures, this is due to some solvent molecules still remain and a small fraction of framework bonds break, thus block channels during degassing. Furthermore, a strong surface tension can be formed between the adsorbent and adsorbate during the removal of the solvent in vacuum, which may further promote the collapse of channels. The structural loss of porosity affects more for porous crystals with 1D channels, such as MIL-53. Another explanation is attributed to the structural flexibility of iron-based MILs. Unlike their Cr or Al analogues, the channels remain closed for Fe-MIL-53 after the solvent or guest molecule is removed, thus unable nitrogen molecules to enter. (53−55)Scheme S1 illustrates the flexibility of MIL-53 frameworks. Relatively small SSA was also reported for MIL-53 in other studies. (10,28,56) Combining results from PXRD, ATR-IR, and N2 sorption analyses, we concluded that ibuprofen was successfully encapsulated in MIL-88B and MIL-53.

Figure 1

Figure 1. PXRD patterns of (a) MIL-88B and (b) MIL-53 at the condition of (i) as-synthesized, (ii) after solvent exchange, and (iii) after loading with ibuprofen, in comparison to the PXRD patterns of (iv) pure ibuprofen.

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Figure 2

Figure 2. ATR-IR spectra of (a) pure ibuprofen, (b) pristine Fe-MIL-88B, (c) ibuprofen loaded Fe-MIL-88B, (d) pristine Fe-MIL-53, and (e) ibuprofen loaded Fe-MIL-53.

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Figure 3

Figure 3. N2 sorption isotherms of Fe-MIL-88B (black) and Fe-MIL-53 (red) at 77 K before and after loading with ibuprofen. Solid symbols correspond to adsorption plots, and open symbols correspond to desorption plots.

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The driving force for ibuprofen loading is the strong hydrogen-bonding and weak van der Waals interactions between ibuprofen and the hydroxyl groups from the matrix. (10) We also tried a one-pot synthesis method (57) to mix therapeutic agents together with MOF starting materials in a solvothermal setting; however, no desired MIL crystals were formed. We suspect that the carboxylate groups in ibuprofen may compete with terephthalic acid for coordinating with FeO3 clusters, thus disturbed the formation of MIL-88B and MIL-53. Therefore, we continued with the immersion method for drug loading in this study. To quantify the drug loading capacity of MIL materials, we applied a UV–vis spectrometer to monitor the concentration of ibuprofen at 264 nm (λmax), before and after incorporation into MIL materials. The detailed UV spectra were provided in the Supporting Information. Based on eq 1, the calculated ibuprofen loading amounts approximates 372.2 mg/g of MIL-53 and 194.6 mg/g of MIL-88B, respectively. The drug loading capacities are consistent with previously reported values. (9,10) Although these values are not as large as the values reported for other MOFs, for example, MIL-101 and MIL-100 (containing much larger volumes because of their rigid structures), both MIL-53 and MIL-88B are significantly better than other porous materials for drug delivery (usually less than 50 mg of drug per gram of the host material, of 5 wt %). (24,58) In our studies, MIL-53 was able to be incorporated about 17% more ibuprofen compared to MIL-88B. We suspected that the higher drug loading capacity observed for MIL-53 is mainly due to the monoclinic symmetry of its structure, facilitating the diffusion of guest molecules. The crystal structures and drug loading capacity for each MIL have been summarized in Table 1. Although Fe-MIL-88B contains a larger pore volume than MIL-53, the drug loading capacity is lower than for MIL-53. We presume that the 1D channel of MIL-53 may account for a faster mass transfer of guest molecules compared to the cage-like structure of MIL-88B crystals.
Table 1. Structures of Fe-Based MIL-88B and MIL-53 and Comparison of Ibuprofen Loading Capacity
a

Structures are viewed along the c-axis.

b

Space group of dehydrated form. (55,59)

c

Maximum available pore volume with solvent. (10,28)

d

From this study.

Additionally, we studied the changes in morphology of MIL-88B crystals corresponding to drug loading in hexane. Figure 4 presents the scanning electron microscopy (SEM) images of MIL-88B before and after loading of ibuprofen. MIL-88B exhibited a rice-grain shape with a length of around 500 nm along the c-axis. Larger crystals with a dimension of 2 μm were observed in the same synthesis solution that may attribute to an over-grown crystallization process. After being treated with ibuprofen in hexane, MIL-88B showed no obvious change in morphology, although the population of large crystals has increased. This may indicate a continuous crystal growth of MIL-88B during the drug loading process, which may cause ibuprofen molecules encapsulated not only within the pores but also trapped inside the particles.

Figure 4

Figure 4. SEM images of MIL-88B crystals (a) before and (b) after ibuprofen loading.

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2.2. Drug Elution Studies

After confirming ibuprofen was successfully loaded into both Fe-MILs, we studied the drug elution process of each material. We stirred ibuprofen-loaded MIL-53 and MIL-88B in phosphate buffer saline (PBS), respectively, to mimic drug releasing in a physiologic environment. Solutions were collected in periodic intervals up to 10 days for monitoring ibuprofen elution and degradation of MILs and analyzed using a reversed-phase high-performance liquid chromatography (HPLC). Figure 5 displays the cumulative ibuprofen released from treated MIL-53 and MIL-88B as a function of an immersing time. We noticed that the concentration of ibuprofen increased with increasing soaking times for both Fe-MILs, indicating that ibuprofen was released from both materials over time. However, a drug releasing burst was observed for both MILs within the first 24 h, indicating a faster drug elution process, likely due to surface adsorbed species. The drug release profile can be illustrated by two stages: the first stage refers to a fast drug release; the second stage can be treated as a stable phase as the drug concentration increased slightly with respect to the increasing contact time with PBS. A similar two-stage drug release profile was observed previously on Cr-based MIL-53. (10) During our testing period, the accumulative drug releasing amounts were 27.4 and 18.0% for MIL-53 and MIL-88B, respectively. The low drug elution amounts after 10 days indicates that there was still a large amount of ibuprofen that had not been released from the host materials. We think that the low drug releasing amount was due to the slow degradation of Fe-MILs in aqueous. A similar drug elution result was reported by Horcajada et al., showing that Fe-MIL-88B can last up to 21 days in a simulated body fluid. (10) In our study, we noticed that MIL powder was still visible in the testing solution even after 1 month. A slow releasing rate of ibuprofen by MILs after the first two days was similar to the releasing profile of MIL-88B when caffeine was used as the model drug. (60) The slow drug releasing rate is beneficial for drug delivery applications that require drug elution in a controlled manner. Additionally, it is critically important to understand the drug release mechanisms to better adopt MIL materials for drug delivery applications. Therefore, we applied several mathematical models to interpret the drug elution behaviors with consideration of the biodegradable nature of both MILs. Scheme 1 summarizes the drug delivery systems and their fitting models in this work.

Figure 5

Figure 5. Profiles of cumulative ibuprofen release percentage as a function of soaking time in PBS for MIL-53 (squares) and MIL-88B (circles). The data were fitted with the Hill equation as indicated by the red plots.

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Scheme 1

Scheme 1. Illustrative Scheme of Drug Delivery Systems and Models Considered for MIL-88B and MIL-53
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The zero-order (eq 2) kinetics is based on Fick’s law of diffusion and has been widely used to describe release kinetics for diffusion-controlled reservoir systems, such as nanoparticles and membrane-encapsulated vesicles. (61) Studies show that ibuprofen released by Cr- and Fe-based MIL-53 has followed this model for at least one stage. (10) Considering the biodegradation of both MILs, a first-order kinetic model (eq 3) was used to analyze the drug delivery behaviors. The first-order kinetic equation is based on hydrolysis decomposition behaviors. (35) Moreover, the degradation/erosion of a drug delivery system can be distinguished into two models: surface erosion and bulk erosion. Surface erosion refers to the degradation process, which is mainly restricted to the outermost surface of these porous crystals without harm to the interior. The surface erosion model can be described using the Peppas equation (eq 4). (36,62) The bulk erosion model describes a drug delivery system decomposing into smaller fragments due to material cleavage in physiological environment and can be described by the Hixson–Crowell model (eq 5). (23,37) The Hill model (eq 6) takes into consideration of the limited diffusion and erosion of the matrices. (38) Drug release kinetics is the combined results of drug molecular movement (mass transfer) and host material’s behaviors, such as swelling, degradation, and interactions with guest molecules. (61) Based on the crystal structure and stability of MILs, the higher correlation coefficients were observed in the Hill model for both drug delivery systems, shown in Figure 5, indicating that the ibuprofen release kinetics fits better for a combined model of diffusion, surface, and bulk erosion. The monoclinic structure of MIL-53 is expected to promote the mass transfer of ibuprofen to be released. In comparison, MIL-88B has complex 3D pores, which may reduce the drug releasing rate. Such a controlled drug release profile of MIL-88B is favorable for a desired slow drug delivery process.
Another factor that should be considered is the stability of MILs in aqueous conditions. Most Fe-based MILs are not stable in aqueous environment due to interruption in coordination bonds induced by water molecules. To evaluate the stabilities of MIL-53 and MIL-88B, we monitored the concentration change of the building ligand (terephthalate) for both MILs using HPLC, shown in Figure 6a. We noticed an increase in the concentration of terephthalate ligands with a longer immersion time in PBS with a similar kinetic profile as the ibuprofen elution process. With the breakdown of frameworks of each MIL, preloaded guest molecules are able to freely diffuse into the surrounding solution. This degradation of MILs can explain the increasing concentrations of ibuprofen even after 10 days. The degradation process also leads to the increase in concentrations of Fe3+, which was monitored using ICP-AES. This increasing amount of iron is another evidence of MIL decomposition in PBS as a function of time. By performing a linear regression analysis to evaluate the relationship between drug release and material degradation, a linear relationship was observed for both systems (Figure 6b), indicating that material degradation has caused the drug elution. We believe that the drug releasing process is a combination of ibuprofen desorption/diffusion and, more importantly, MIL material degradation. Based on the releasing profiles, we believe that the degradation of carrier matrices is the dominant factor on drug releasing.

Figure 6

Figure 6. (a) Plots of TA concentration as a function of soaking time in PBS for MIL-53 (open squares) and MIL-88B (open circles). (b) Linear regression correlation between TA concentration change and cumulative drug release percents of both MIL-53 (blue solid squares) and MIL-88B (black solid circles).

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2.3. Cytotoxicity Studies

The chemical composition of MIL-88B (iron and terephthalate) was one of the factors why MIL-88B was selected as a carrier for drug delivery applications. The toxicity of Fe-based MOFs is low when compared to Zr-based MOFs that exhibit better stability in aqueous conditions. In addition, Fe-based MOF nanoparticles are also classified as safe for the delivery of contrast agents. (25) We have tested the cytotoxicity of MIL-88B nanoparticles because its monotonic release profile of ibuprofen (Figure 5) seems more suitable for drug delivery applications than MIL-53.
We evaluated the cytotoxicity of the MIL-88B with the NIH-3T3 Swiss mouse fibroblast cells by adding the particles to the media (after sterilization). After 48 h incubation, the CellTiter96 viability assay (Figure 7) shows that the particles have no adverse effect on cell viability up to 0.1 mg/mL. After the addition of 0.25 mg/mL, the viability decreases to about 60% and then drops to about 40% after increasing the concentration to 2 mg/mL. The cell viability did not drop below 40% for the maximum tested concentration of 2.5 mg/mL.

Figure 7

Figure 7. Effect of MIL-88B on viability of NIH-3T3 Swiss mouse fibroblasts. The error bar represents a standard deviation from 18 independent measurements.

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The cellular uptake of nanoparticles strongly depends on their size and surface groups and, in this case, also the MOF composition. Both metal ion and organic ligand can contribute to toxicity. In Figure 4, the size and shape of the studied MIL-88B show that the majority of the material is formed as approximately 500 nm (along the c-axis) rice-grain shaped particles. Thus, the nanoparticles are significantly larger than previously tested MIL-88B by Tamames-Tabar et al. (25) where the average size of nanoparticle was 100 ± 20 nm. The reported toxicity at 50% was 1.26 mg/mL recorded in HeLa cells and 0.37 mg/mL recorded in J774 cells. The differences were attributed to the different phagocytic pathways in tested cell lines since J774 is a macrophage cell line prone to increased phagocytosis. In the case of our studies, the toxicity of the MIL-88B measured with 3T3 cells is lower than in both previously studied cell lines. Both HeLa and 3T3 cells are not macrophages, so the difference in toxicity is most likely related to the larger particle size in our studies. At this point, we cannot conclude with certainty what is the main mechanism of lower toxicity of MIL-88 in our study compered to Tamames-Tabar et al., (25) but we can identify two sources of this behavior. Either the large size of the nanoparticles decreases the cellular uptake or the larger size of nanoparticles slows down the decomposition of individual nanoparticles within the cell and, thus, lowers the toxicity of the tested material.

3. Conclusions

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In all, two types of Fe-MOFs, MIL-88B and MIL-53, were evaluated for drug loading and elution with ibuprofen as a model drug. We concluded that the monoclinic crystal structure of MIL-53 promotes a high drug loading capacity due to a favorable mass transfer within the 1D channels, but the same structure also exhibits a faster and higher drug release profile. MIL-88B with a 3D cage structure offers more flexibility and better control over drug elution behavior. These structural differences between Fe-MOFs that are formed with identical SBUs and ligands strongly suggest that directing crystal structure can tune drug elution behavior. In addition, we show that the MIL-88B in the form of large nanoparticles is biodegradable and noncytotoxic. We believe that the ability to direct structures of Fe-MOFs together with its high biocompatibility will allow in the future to create the “designer” structures for the delivery of particular drug with desired release profile.

4. Experimental Section

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4.1. Materials

All chemicals were reagent grade or better and used as received, included: iron(III) chloride (hexahydrate, 99 + %, Acros), terephthalic acid (TA, 99 + %, Acros), N,N-dimethylformamide (Fisher Chemical, ACS Certified), sodium hydroxide (2.0 N Standardized Solution, Alfa Aesar), hexanes (Fisher Chemical, ACS Certified), ibuprofen (99%, Acros), phosphate-buffered saline (PBS, pH = 7.2, 1×, Gibco), trifluoroacetic acid (HPLC Grade, Acros), Milli-Q water (18 MΩ· cm, Millipore), and acetonitrile (HPLC Grade, Fisher Chemical).

4.2. Synthesis of MIL-53

Fe-MIL-53 was synthesized according to the literature. (10) TA (0.7 mmol) and FeCl3·6H2O (0.7 mmol) were dissolved in 15 mL of DMF in a glass reactor. To obtain a sufficient material, six reactors were prepared together. The mixed solution was placed in a preheated oven at 150 °C for 15 h to form Fe-MIL-53 crystals. After cooling to room temperature, the crystals were separated by vacuum filtration and rinsed with DMF, acetone, and deionized water. After that, the crystals were vacuum dried at room temperature and followed by drying in a gravity oven at 110 °C to remove extra moisture. These crystals were named as-synthesized MIL-53 and were performed PXRD analysis. Solvent exchange for trapped DMF for water by stirring as-synthesized MIL-53 in deionized water for 24 h. The MIL-53 colloid was then centrifuged at 5000 rpm (Eppendorf, Centrifuge 5430). For the removal of water and free up porous space for drug loading, MIL-53 crystals were further dried in a vacuum oven (Fisher Scientific, Isotemp vacuum oven model 281A) at 65 °C for 24 h.

4.3. Synthesis of MIL-88B

Fe-MIL-88B crystals were synthesized via a revised solvothermal method according to a previous reported procedure. (9) FeCl3·6H2O (1 mmol) and TA (1 mmol) were dispersed in 5 mL of DMF with 0.4 mL of sodium hydroxide (2.0 N) in a glass reactor. The mixed solution was sonicated for 3 min before being placed in a preheated oven at 100 °C for 12 h. After the solvothermal synthesis, the orange solid, Fe-MIL-88B, was recovered by filtration and washed with DMF, deionized water, and acetone. The product was then placed in a gravity oven at 110 °C for 24 h to completely dry as-synthesized Fe-MIL-88B.
To make sure the MIL-88B structure was clear from DMF and unreacted ligands, additional solvent exchange procedures were performed: MIL-88B was stirred in deionized water for 24 h, solids were then collected by vacuum filtration, and washed with deionized water three times. Finally, the crystals were dried in a vacuum oven at 65 °C for 24 h.

4.4. Drug Loading Studies

Dry Fe-MIL crystals were stirred in ibuprofen/hexane solutions with varying concentrations for different set amount of times. The material-to-ibuprofen mass ratio was kept at 1:3. We found that the best ibuprofen loading condition for MIL-53 was stirring 50 mg of MIL-53 with 5 mL of ibuprofen/hexane solution (30 mg/mL) for 72 h. The optimal ibuprofen loading condition for MIL-88B was 20 mg of MIL-88 mixed with 6 mL of ibuprofen/hexane (10 mg/mL) for 24 h. After desired soaking period, the drug encapsulated crystals were collected by centrifugation at 5000 rpm for 20 min. The supernatant was saved for UV analysis for drug loading quantification. The precipitate (Fe-MILs loaded with ibuprofen) was dried in a vacuum oven at 65 °C for 24 h. The drug loading capacity (LC, mg of ibuprofen per gram of material) of each Fe-MIL was evaluated based on the following equation
(1)
where C0 is the initial ibuprofen concentration, Ct is the ibuprofen concentration at time t, V is the total volume of ibuprofen solution, and m is the mass of Fe-MIL applied in the mixture solution.

4.5. Drug Elution Studies

An amount of 10 mg of dry ibuprofen encapsulated MILs was soaked and stirred in 40 mL of PBS at room temperature for drug release studies. A 2 mL aliquot of mixed solution was collected at each hour for the first 6 h, one sample was then collected each day for the next ten days. The collected solution was filtered through a syringe filter (PVDF, 0.45 μm, 13 mm diameter) to remove large Fe-MIL solids before analysis. Ibuprofen release amounts and Fe-MIL degradation rates were examined by monitoring the changes in concentrations of ibuprofen and TA over time using a reversed-phase HPLC. Horcajada et al. reported a two-stage drug release profile for MIL-53 materials. (10) In this study, we observed a similar trend on both Fe-based MIL-53 and MIL-88B systems. The release kinetics of each system on both stages was evaluated using different drug delivery models, including zero-order, first-order, Peppas, Hixson–Crowell, and Hill models. If a higher correlation coefficient is observed, it confirms that the drug delivery system follows the corresponding kinetic model.
A zero-order drug delivery model is commonly used to describe the diffusion behaviors of a system and can be expressed in the following equation (34)
(2)
where, Mt and M∞ represent the absolute cumulative amount of released drug at the time t and at infinite time, and k is the release rate constant. The ratio of Mt and M∞ represents the cumulative drug release percent.
The first-order kinetic equation takes consideration of material degradation in water and can be expressed as followed (35)
(3)
The Peppas model was first proposed in 1985 (36) and is now widely used for modeling polymer-based drug delivery systems with surface erosion. It can be expressed as the following equation where n is the release exponent
(4)
We also applied the Hixson–Crowell model to consider a bulk-erosion system since Fe-MILs may degrade into smaller crystals in physiological environment. The Hixson–Crowell model can be expressed as follows (37)
(5)
The Hill model was also applied to fit the cumulative drug release percent as a function of time. This model takes consideration of diffusion and degradation processes of the matrices and can be expresses as follows (38)
(6)
where M0 and MEq represent the drug release amounts at time zero and at an equilibrium condition, and t1/2 represents the time when the slope of the cumulative drug release curve has the highest value.

4.6. Cytotoxicity Studies

A CellTiter 96 nonradioactive cell proliferation assay (MTT) from Promega was used to evaluate the cytotoxicity of MIL-88B with the NIH-3T3 Swiss mouse fibroblasts (ATCC) cell line. Cells were cultured in complete (10% fetal bovine serum, 1% penicillin streptomycin-glutamine) Dulbecco’s modified Eagle medium (DMEM) and incubated at 37 °C in a humidified 5% CO2 atmosphere until 90% confluent. Sterile MIL-88B (3.5 mg) was dissolved in DMEM through sonication to serve as stock solution. PBS and trypsin were used to induce detachment of 3T3 cells. In a 96-well plate, cells were seeded at a density of 1.0 × 104 cells/well. Concentrations (0.05–2.5 mg/mL) of the stock solution were then added to the plate and incubated for 48 h. Subsequently, the CellTiter 96 assay was performed. The plate reader (Thermo Scientific Varioskan Flash Reader) was used to record absorption at 570 nm. Each point was calculated from 18 repeats: 6 wells, 3 plates.

4.7. Characterization

Powder X-ray diffraction (PXRD) measurements were carried out on a SmartLab X-Ray diffractometer (Rigaku). Bragg–Brentano Focusing measurements were conducted using a Cu Kα1 (λ = 1.5406 Å) radiation source. The diffraction angles of measurement were between 7 and 20 degrees with steps of 0.008 degrees.
Infrared spectroscopic studies were performed on a Bruker Alpha I attenuated total reflectance infrared (ATR-IR) spectrometer. All spectra were collected in the range of 4000–400 cm–1 at a resolution of 4 cm–1 with 64 scans per spectrum.
N2 sorption studies of Fe-MILs before and after ibuprofen loading were performed on a Micromeritics 2020PLUS surface characterization analyzer at 77 K using liquid nitrogen. Prior to measurements, approximately 50 mg of sample was degassed under vacuum at 60 °C for over 12 h. The sample tube was immersed in a liquid nitrogen dewar during measurements. The gas adsorption isotherms were collected as a function of pressure up to 800 torr.
Scanning electron microscopy (SEM, FEI Quanta 650) was applied to study the morphology changes of MIL-88B crystals before and after drug loading. The images were taken with an acceleration voltage of 20 kV and a working distance of 9.4 mm in a high vacuum condition. Gold-coated silicon substrates were coated with desired MIL crystal samples by a dip-coater (Chemat Technology). For increased resolution, all samples were sputter-coated with gold prior to SEM imaging.
A UV–vis spectrophotometer (Shimadzu, UV-1700) was applied to measure ibuprofen loading amounts by monitoring the wavelength at 264 nm (λmax for ibuprofen in hexane). A standard curve of ibuprofen in hexane was created based on a concentration range of 0.001–0.025 mg/mL. The absorbance of ibuprofen before and after drug loading was measured in triplicate with hexane as the blank. For solutions with concentrations out of range of the standard curve, samples were diluted with hexane before measurements.
High-performance liquid chromatography (HPLC, Thermo Scientific, Ultimate 3000) was employed to study drug release kinetics. A reverse-phase C18 analytical column (Agilent, Zorbax 300SB-C18, 4.6 x 250 mm 5-μm) was used along with the mobile phase of water and acetonitrile (50:50 v/v) with 0.08% trifluoroacetic acid in each solvent with a pump rate of 1.5 mL/min. The UV detector was set at wavelengths of 215 and 242 nm at room temperature. A sample volume of 20 μL was injected, and all analyses were performed in triplicate. Standard calibration curves of ibuprofen and TA in PBS were created separately by plotting retention time peak area (mV × s) versus concentration. The peak of ibuprofen was observed at a retention time of 5.2 min in a UV channel of 215 nm. The peak of TA showed up at 1.9 min in the channel of 242 nm.

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.9b03696.

  • UV–vis spectra, BET plots and parameters, and drug release models (PDF)

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Author Information

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  • Corresponding Author
  • Authors
    • Hao Pham - Department of Physical Sciences, Long Beach City College, Long Beach, California 90808, United States;  Present Address: Current Address: Department of Chemistry and Biochemistry, University of California, San Diego, San Diego, California 92110, United States (H.P.)
    • Kimberly Ramos - Chemistry Department, Cerritos College, Norwalk, California 90650, United States;  Present Address: Current Address: School of Veterinary Medicine, University of California, Davis, Davis, California 95616, United States (K.R.)
    • Andy Sua - Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
    • Jessica Acuna - Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
    • Katarzyna Slowinska - Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States;  Orcidhttp://orcid.org/0000-0001-6468-2918
    • Travis Nguyen - Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
    • Angela Bui - Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States
    • Mark D. R. Weber - Department of Chemistry and Biochemistry, California State University Long Beach, Long Beach, California 90840, United States;  Present Address: Current Address: School of Materials Science and Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States (M.D.R.W.)
  • Author Contributions

    All authors have given approval to the final version of the manuscript.

  • Notes
    The authors declare no competing financial interest.

Acknowledgments

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Research reported in this publication was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award numbers 8UL1GM118979-02 and 5UL1GM118979-03. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health. H.P. and K.R. would like to acknowledge the NIH BRIDGE program at CSULB. K.S. acknowledges the NIH under Award number of GM099594. T.N. acknowledges the NIH-BUILD program at CSULB under Award Numbers 5UL1GM118979; 5TL4GM118980; and 5RL5GM118978. A.B. would like to acknowledge the NIH-MARC U*STAR program at CSULB under Award number of T34GM008074. The project is partially supported by grant from National Science Foundation (MRI-1828334).

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    A new metal org. framework (MOF) built up from non-toxic iron and the therapeutically active linker nicotinic acid, with pellagra-curative, vasodilating, and antilipemic properties, has been isolated and characterized via single crystal methods. The release of the therapeutic agent, which is a constituent of the framework, is achieved through the degrdn. of the hybrid phase, under simulated physiol. conditions, allowing for the delivery of the bioactive mol.
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  12. 12
    Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O’Keeffe, M.; Yaghi, O. M. Modular Chemistry: Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal–organic Carboxylate Frameworks. Acc. Chem. Res. 2001, 34, 319– 330,  DOI: 10.1021/AR000034B
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    Modular Chemistry: Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal-Organic Carboxylate Frameworks
    Eddaoudi, Mohamed; Moler, David B.; Li, Hailian; Chen, Banglin; Reineke, Theresa M.; O'Keeffe, Michael; Yaghi, Omar M.
    Accounts of Chemical Research (2001), 34 (4), 319-330CODEN: ACHRE4; ISSN:0001-4842. (American Chemical Society)
    A review, with 38 refs. Secondary building units (SBUs) are mol. complexes and cluster entities in which ligand coordination modes and metal coordination environments can be used in the transformation of these fragments into extended porous networks using polytopic linkers (1,4-benzenedicarboxylate, 1,3,5,7-adamantanetetracarboxylate, etc.). Consideration of the geometric and chem. attributes of the SBUs and linkers leads to prediction of the framework topol., and in turn to the design and synthesis of a new class of porous materials with robust structures and high porosity.
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    Ruiz, M. A.; Sua, A.; Tian, F. Covalent Attachment of Metal-organic Framework Thin Films on Surfaces. In Encyclopedia of Interfacial Chemistry: Surface Science and Electrochemistry; Elsevier: 2018; Vol. 4, pp 646– 671.
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    Li, J.-R.; Kuppler, R. J.; Zhou, H.-C. Selective Gas Adsorption and Separation in Metal-organic Frameworks. Chem. Soc. Rev. 2009, 38, 1477– 1504,  DOI: 10.1039/b802426j
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    Selective gas adsorption and separation in metal-organic frameworks
    Li, Jian-Rong; Kuppler, Ryan J.; Zhou, Hong-Cai
    Chemical Society Reviews (2009), 38 (5), 1477-1504CODEN: CSRVBR; ISSN:0306-0012. (Royal Society of Chemistry)
    A review. Adsorptive sepn. is very important in industry. Generally, the process uses porous solid materials such as zeolites, activated carbons, or silica gels as adsorbents. With an ever increasing need for a more efficient, energy-saving, and environmentally benign procedure for gas sepn., adsorbents with tailored structures and tunable surface properties must be found. Metal-org. frameworks (MOFs), constructed by metal-contg. nodes connected by org. bridges, are such a new type of porous materials. They are promising candidates as adsorbents for gas sepns. due to their large surface areas, adjustable pore sizes and controllable properties, as well as acceptable thermal stability. This crit. review starts with a brief introduction to gas sepn. and purifn. based on selective adsorption, followed by a review of gas selective adsorption in rigid and flexible MOFs. Based on possible mechanisms, selective adsorptions obsd. in MOFs are classified, and primary relationships between adsorption properties and framework features are analyzed. As a specific example of tailor-made MOFs, mesh-adjustable mol. sieves are emphasized and the underlying working mechanism elucidated. In addn. to the exptl. aspect, theor. investigations from adsorption equil. to diffusion dynamics via mol. simulations are also briefly reviewed. Furthermore, gas sepns. in MOFs, including the mol. sieving effect, kinetic sepn., the quantum sieving effect for H2/D2 sepn., and MOF-based membranes are also summarized (227 refs.).
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    Farrusseng, D.; Aguado, S.; Pinel, C. Metal-organic Frameworks: Opportunities for Catalysis. Angew. Chem., Int. Ed. 2009, 48, 7502– 7513,  DOI: 10.1002/anie.200806063
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    Metal-Organic Frameworks: Opportunities for Catalysis
    Farrusseng, David; Aguado, Sonia; Pinel, Catherine
    Angewandte Chemie, International Edition (2009), 48 (41), 7502-7513CODEN: ACIEF5; ISSN:1433-7851. (Wiley-VCH Verlag GmbH & Co. KGaA)
    A review; the role of metal-org. frameworks (MOFs) in the field of catalysis is discussed, and special focus is placed on their assets and limits in light of current challenges in catalysis and green chem. Their structural and dynamic features are presented in terms of catalytic functions along with how MOFs can be designed to bridge the gap between zeolites and enzymes. The contributions of MOFs to the field of catalysis are comprehensively reviewed and a list of catalytic candidates is given. The subject is presented from a multidisciplinary point of view covering solid-state chem., materials science, and catalysis.
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    Kuo, C.-H.; Tang, Y.; Chou, L.-Y.; Sneed, B. T.; Brodsky, C. N.; Zhao, Z.; Tsung, C.-K. Yolk-Shell Nanocrystal@ZIF-8 Nanostructures for Gas-Phase Heterogeneous Catalysis with Selectivity Control. J. Am. Chem. Soc. 2012, 134, 14345– 14348,  DOI: 10.1021/ja306869j
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    Yolk-Shell Nanocrystal@ZIF-8 Nanostructures for Gas-Phase Heterogeneous Catalysis with Selectivity Control
    Kuo, Chun-Hong; Tang, Yang; Chou, Lien-Yang; Sneed, Brian T.; Brodsky, Casey N.; Zhao, Zipeng; Tsung, Chia-Kuang
    Journal of the American Chemical Society (2012), 134 (35), 14345-14348CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
    A general synthetic strategy for yolk-shell nanocrystal@ZIF-8 nanostructures has been developed. The yolk-shell nanostructures possess the functions of nanoparticle cores, microporous shells, and a cavity in between, which offer great potential in heterogeneous catalysis. The synthetic strategy involved first coating the nanocrystal cores with a layer of Cu2O as the sacrificial template and then a layer of polycryst. ZIF-8. The clean Cu2O surface assists in the formation of the ZIF-8 coating layer and is etched off spontaneously and simultaneously during this process. The yolk-shell nanostructures were characterized by transmission electron microscopy, SEM, X-ray diffraction, and nitrogen adsorption. To study the catalytic behavior, hydrogenations of ethylene, cyclohexene, and cyclooctene as model reactions were carried out over the Pd@ZIF-8 catalysts. The microporous ZIF-8 shell provides excellent mol.-size selectivity. The results show high activity for the ethylene and cyclohexene hydrogenations but not in the cyclooctene hydrogenation. Different activation energies for cyclohexene hydrogenation were obtained for nanostructures with and without the cavity in between the core and the shell. This demonstrates the importance of controlling the cavity because of its influence on the catalysis.
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    Yang, J.; Zhang, F.; Lu, H.; Hong, X.; Jiang, H.; Wu, Y.; Li, Y. Hollow Zn/Co ZIF Particles Derived from Core-Shell ZIF-67@ZIF-8 as Selective Catalyst for the Semi-Hydrogenation of Acetylene. Angew. Chem., Int. Ed. 2015, 127, 11039– 11043,  DOI: 10.1002/ange.201504242
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    Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. Commercial Metal-organic Frameworks as Heterogeneous Catalysts. Chem. Commun. 2012, 48, 11275– 11288,  DOI: 10.1039/c2cc34329k
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    Commercial metal-organic frameworks as heterogeneous catalysts
    Dhakshinamoorthy, Amarajothi; Alvaro, Mercedes; Garcia, Hermenegildo
    Chemical Communications (Cambridge, United Kingdom) (2012), 48 (92), 11275-11288CODEN: CHCOFS; ISSN:1359-7345. (Royal Society of Chemistry)
    A review. Metal-org. frameworks (MOFs) are porous cryst. materials that have promising applications as heterogeneous catalysts. After describing the compn., textural properties and crystal structure of four com. available MOFs, the authors summarize org. transformations for which these com. MOFs exhibit higher catalytic activity than the corresponding sol. metal salts or metal ion-exchanged zeolites. The authors have focused on reactions requiring Lewis-acid sites or redox centers to illustrate the potential applications and limitations of com. MOFs. In a final section, the authors provide the views on future developments whose ultimate target will be the use of a com. MOF as a heterogeneous catalyst for a real industrial process in fine chem., thus, realizing the advantages of these materials with respect to zeolites or other solid catalysts in liq.-phase reactions.
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    Giménez-Marqués, M.; Hidalgo, T.; Serre, C.; Horcajada, P. Nanostructured Metal–organic Frameworks and Their Bio-Related Applications. Coord. Chem. Rev. 2016, 307, 342– 360,  DOI: 10.1016/j.ccr.2015.08.008
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    Nanostructured metal-organic frameworks and their bio-related applications
    Gimenez-Marques, M.; Hidalgo, T.; Serre, C.; Horcajada, P.
    Coordination Chemistry Reviews (2016), 307 (Part_2), 342-360CODEN: CCHRAM; ISSN:0010-8545. (Elsevier B.V.)
    Miniaturization of metal-org. frameworks (MOFs) results of great interest in order to integrate these materials in strategic applications such as sensing or drug delivery. This emerging class of nanoscaled MOFs (nanoMOFs), combining the intrinsic properties of the porous materials and the benefits of nanostructures, are expected to improve in some cases the performances of classical bulk cryst. MOFs. In the field of biomedicine, the benefits of MOF miniaturization have already been proved to be effective, not only because establishes a strong influence over the choice of the administration route but also governs their in vivo fate and therefore, their toxicity and/or activity.The scope of this review focuses on the prepn. of nanostructured MOFs and their related biomedical applications. We will cover all aspects concerning the various synthetic methods reported so far, as well as the shaping and surface engineering routes required for their use in biomedicine.
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    Gaudin, C.; Cunha, D.; Ivanoff, E.; Horcajada, P.; Chevé, G.; Yasri, A.; Loget, O.; Serre, C.; Maurin, G. A Quantitative Structure Activity Relationship Approach to Probe the Influence of the Functionalization on the Drug Encapsulation of Porous Metal-organic Frameworks. Microporous Mesoporous Mater. 2012, 157, 124– 130,  DOI: 10.1016/j.micromeso.2011.06.011
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    A quantitative structure activity relationship approach to probe the influence of the functionalization on the drug encapsulation of porous metal-organic frameworks
    Gaudin, C.; Cunha, D.; Ivanoff, E.; Horcajada, P.; Cheve, G.; Yasri, A.; Loget, O.; Serre, C.; Maurin, G.
    Microporous and Mesoporous Materials (2012), 157 (), 124-130CODEN: MIMMFJ; ISSN:1387-1811. (Elsevier Inc.)
    A series of 10 MIL-88B(Fe) iron(III) dicarboxylate MOFs wherein the org. linker is functionalized by a large variety of polar and apolar functional groups (-H, -Br, -F, -CF3, -CH3, -NH2, -NO2, -OH) was investigated as a potential carrier for encapsulating drugs, using the cosmetic amphiphilic caffeine as a model mol. Encapsulation using impregnation followed by thermogravimetric anal. (TGA) and high performance liq. chromatog. (HPLC) measurements to quant. est. the caffeine uptake, have been first performed on the functionalized MIL-88B(Fe) samples. This set of exptl. data was further used as an ideal platform to conduct a quant. structure activity relationship approach based on multiple linear regression (MLR) method with the aim to find out the most relevant chem. and structural features of the MIL-88B(Fe) that significantly affect the therapeutic mol. uptake. Individual QSAR models showed that tuning the polarity and the H-donor capacity of the org. linker can enhance the caffeine encapsulation, suggesting that the functional groups serve as anchoring points for the drug mol., consistent with previous conclusions drawn from mol. simulations performed on similar functionalized MOFs. Consensus modeling approach based on the selection of the most diverse individual models was also employed to build more representative QSAR models over the chem. space that could be further used to predict the drug encapsulation performance of the MOFs grafted by other functional groups.
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    Wu, M.-X.; Yang, Y.-W. Metal-organic Framework (MOF)-Based Drug/Cargo Delivery and Cancer Therapy. Adv. Mater. 2017, 29, 1606134,  DOI: 10.1002/adma.201606134
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    Keskin, S.; Kızılel, S. Biomedical Applications of Metal organic Frameworks. Ind. Eng. Chem. Res. 2011, 50, 1799– 1812,  DOI: 10.1021/ie101312k
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    Biomedical Applications of Metal Organic Frameworks
    Keskin, Seda; Kizilel, Seda
    Industrial & Engineering Chemistry Research (2011), 50 (4), 1799-1812CODEN: IECRED; ISSN:0888-5885. (American Chemical Society)
    A review. We have witnessed a rapid growth in the field of a new nanoporous material group, metal org. frameworks (MOFs), over the past decade. MOFs possess a wide array of potential applications in chem. engineering, chem., and materials science, including gas storage, gas sepn., and catalysis. One of the areas MOFs started to appear recently is biomedical applications. The unique phys. and chem. characteristics of MOFs make them promising candidates for drug storage and drug delivery, nitric oxide storage and delivery, imaging, and sensing. In this review, we outline the recent progress of using MOFs as a promising platform in biomedical applications due to their high drug loading capacity, biodegradability, and versatile functionality. We also demonstrate the potential of MOFs for continuous development and implementation in biomedical applications by discussing issues including stability, toxicol., and biocompatibility. Although significant progress has been made in utilizing MOFs for biomedical applications, further improvements must still occur before MOFs can become viable therapeutics options.
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    Huang, W.; Tsui, C. P.; Tang, C. Y.; Gu, L. Effects of Compositional Tailoring on Drug Delivery Behaviours of Silica Xerogel/Polymer Core-Shell Composite Nanoparticles. Sci. Rep. 2018, 8, 13002,  DOI: 10.1038/s41598-018-31070-9
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    Effects of Compositional Tailoring on Drug Delivery Behaviours of Silica Xerogel/Polymer Core-shell Composite Nanoparticles
    Huang Wenfei; Tsui Chi Pong; Tang Chak Yin; Gu Linxia
    Scientific reports (2018), 8 (1), 13002 ISSN:.
    Conventional core-shell polymer nanoparticles usually exhibit a rapid release rate with their release kinetics mainly adjusted through changing composition of the polymer shells, limiting their applications for prolonged drug delivery. As a solution to these problems, silica xerogel/polymer core-shell-structured composite nanoparticles have been proposed. Different with our previous work centring on studying process variables, we here focused on investigating the effects of key compositional variables on essential properties of the composite nanoparticles. The drug release profiles (in vitro) were well interpreted by the Baker and Lonsdale model on a predicted two-stage basis. The first stage (<1 day) was well controlled from 18.6% to 45.9%; the second stage (1-14 days) was tailored in a range from 28.7 to 58.2% by changing the composition of the silica xerogel cores and polymeric shells. A substantial achievement was reducing the release rate by more than 40 times compared with that of conventional polymer nanoparticles by virtue of the silica xerogel cores. A semi-empirical model was also established in the first attempt to describe the effects of polymer concentration and drug loading capacity on the size of the composite nanoparticles. All these results indicated that the composite nanoparticles are promising candidates for prolonged drug delivery applications.
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    Cullis, P. R.; Mayer, L. D.; Bally, M. B.; Madden, T. D.; Hope, M. J. Generating and Loading of Liposomal Systems for Drug-Delivery Applications. Adv. Drug Delivery Rev. 1989, 3, 267– 282,  DOI: 10.1016/0169-409X
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    Generating and loading of liposomal systems for drug-delivery applications
    Cullis, P. R.; Mayer, L. D.; Bally, M. B.; Madden, T. D.; Hope, M. J.
    Advanced Drug Delivery Reviews (1989), 3 (3), 267-82CODEN: ADDREP; ISSN:0169-409X.
    A review with 53 refs. Factors affecting the design of liposomal systems, methods of generating liposomes, and methods of loading liposomes with drugs are discussed.
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    Tamames-Tabar, C.; Cunha, D.; Imbuluzqueta, E.; Ragon, F.; Serre, C.; Blanco-Prieto, M. J.; Horcajada, P. Cytotoxicity of Nanoscaled Metal–organic Frameworks. J. Mater. Chem. B 2014, 2, 262– 271,  DOI: 10.1039/C3TB20832J
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    Cytotoxicity of nanoscaled metal-organic frameworks
    Tamames-Tabar, Cristina; Cunha, Denise; Imbuluzqueta, Edurne; Ragon, Florence; Serre, Christian; Blanco-Prieto, Maria J.; Horcajada, Patricia
    Journal of Materials Chemistry B: Materials for Biology and Medicine (2014), 2 (3), 262-271CODEN: JMCBDV; ISSN:2050-7518. (Royal Society of Chemistry)
    A series of fourteen porous Metal-Org. Frameworks (MOFs) with different compns. (Fe, Zn, and Zr; carboxylates or imidazolates) and structures have been successfully synthesized at the nanoscale and fully characterised by XRPD, FTIR, TGA, N2 porosimetry, TEM, DLS and ζ-potential. Their toxicol. assessment was performed using two different cell lines: human epithelial cells from fetal cervical carcinoma (HeLa) and murine macrophage cell line (J774). It appears that MOF nanoparticles (NPs) exhibit low cytotoxicity, comparable to those of other commercialised nanoparticulate systems, the less toxic being the Fe carboxylate and the more toxic being the zinc imidazolate NPs. The cytotoxicity values, higher in J774 cells than in HeLa cells, are mainly function of their compn. and cell internalisation capacity. Finally, cell uptake of one of the most relevant Fe-MOF-NPs for drug vectorization has been investigated by confocal microscopy studies, and indicates a faster kinetics of cell penetration within J774 compared to HeLa cells.
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    Filippousi, M.; Turner, S.; Leus, K.; Siafaka, P. I.; Tseligka, E. D.; Vandichel, M.; Nanaki, S. G.; Vizirianakis, I. S.; Bikiaris, D. N.; Van Der Voort, P. Biocompatible Zr-Based Nanoscale MOFs Coated with Modified Poly(ε-Caprolactone) as Anticancer Drug Carriers. Int. J. Pharm. 2016, 509, 208– 218,  DOI: 10.1016/J.IJPHARM.2016.05.048
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    Biocompatible Zr-based nanoscale MOFs coated with modified poly(ε-caprolactone) as anticancer drug carriers
    Filippousi, Maria; Turner, Stuart; Leus, Karen; Siafaka, Panoraia I.; Tseligka, Eirini D.; Vandichel, Matthias; Nanaki, Stavroula G.; Vizirianakis, Ioannis S.; Bikiaris, Dimitrios N.; Van Der Voort, Pascal; Van Tendeloo, Gustaaf
    International Journal of Pharmaceutics (Amsterdam, Netherlands) (2016), 509 (1-2), 208-218CODEN: IJPHDE; ISSN:0378-5173. (Elsevier B.V.)
    Nanoscale Zr-based metal org. frameworks (MOFs) UiO-66 and UiO-67 were studied as potential anticancer drug delivery vehicles. Two model drugs were used, hydrophobic paclitaxel and hydrophilic cisplatin, and were adsorbed onto/into the nano MOFs (NMOFs). The drug loaded MOFs were further encapsulated inside a modified poly(ε-caprolactone) with D-α-tocopheryl polyethylene glycol succinate polymeric matrix, in the form of microparticles, in order to prep. sustained release formulations and to reduce the drug toxicity. The drugs phys. state and release rate was studied at 37 °C using Simulated Body Fluid. It was found that the drug release depends on the interaction between the MOFs and the drugs while the controlled release rates can be attributed to the microencapsulated formulations. The in vitro antitumor activity was assessed using HSC-3 (human oral squamous carcinoma; head and neck) and U-87 MG (human glioblastoma grade IV; astrocytoma) cancer cells. Cytotoxicity studies for both cell lines showed that the polymer coated, drug loaded MOFs exhibited better anticancer activity compared to free paclitaxel and cisplatin solns. at different concns.
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    Al Haydar, M.; Abid, H.; Sunderland, B.; Wang, S. Metal organic Frameworks as a Drug Delivery System for Flurbiprofen. Drug Des., Dev. Ther. 2017, Volume 11, 2685– 2695,  DOI: 10.2147/DDDT.S145716
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    Horcajada, P.; Salles, F.; Wuttke, S.; Devic, T.; Heurtaux, D.; Maurin, G.; Vimont, A.; Daturi, M.; David, O.; Magnier, E. How Linker’s Modification Controls Swelling Properties of Highly Flexible Iron(III) Dicarboxylates MIL-88. J. Am. Chem. Soc. 2011, 133, 17839– 17847,  DOI: 10.1021/ja206936e
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    How Linker's Modification Controls Swelling Properties of Highly Flexible Iron(III) Dicarboxylates MIL-88
    Horcajada, Patricia; Salles, Fabrice; Wuttke, Stefan; Devic, Thomas; Heurtaux, Daniela; Maurin, Guillaume; Vimont, Alexandre; Daturi, Marco; David, Olivier; Magnier, Emmanuel; Stock, Norbert; Filinchuk, Yaroslav; Popov, Dmitry; Riekel, Christian; Ferey, Gerard; Serre, Christian
    Journal of the American Chemical Society (2011), 133 (44), 17839-17847CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
    Organically modified Fe(III) terephthalate MIL-88B and Fe(III) 4,4'-biphenyl dicarboxylate MIL-88D flexible solids were synthesized and characterized through a combination of x-ray diffraction, IR spectroscopy, and thermal anal. (MIL stands for Material from Institut Lavoisier). The swelling amplitude of the highly flexible MOFs tuned by introducing functional groups onto the Ph rings shows a clear dependence on the steric hindrance and on the no. of groups per arom. ring. For instance, while the introduction of four Me groups per spacer in dried MIL-88B results in a large permanent porosity, introducing two or four Me groups in MIL-88D allows an easier pore opening in the presence of liqs. without drastically decreasing the swelling magnitude. The influence of the degree of satn. of the metal center and the nature of the solvent on the swelling is also discussed. Finally, a computationally assisted structure detn. led to a proposal of plausible structures for the closed (dried) and open forms of modified MIL-88B and MIL-88D and to evaluation of their framework energies subject to the nature of the functional groups.
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    Serre, C.; Surblé, S.; Mellot-Draznieks, C.; Filinchuk, Y.; Férey, G. Evidence of Flexibility in the Nanoporous Iron(Iii) Carboxylate MIL-89. Dalton Trans. 2008, 0, 5462,  DOI: 10.1039/b805408h
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    Evidence of flexibility in the nanoporous iron(iii) carboxylate MIL-89
    Serre, C.; Surble, S.; Mellot-Draznieks, C.; Filinchuk, Y.; Ferey, G.
    Dalton Transactions (2008), (40), 5462-5464CODEN: DTARAF; ISSN:1477-9226. (Royal Society of Chemistry)
    The very large expansion upon adsorption of liqs., up to 160% in cell vol., has been obsd. in the iron(iii) trans,trans muconate MIL-89 [MIL = Material Institut Lavoisier]. The structure of lutidine-contg. MIL-89 (lutidine = 2,6-dimethylpyridine) has been detd. using X-ray powder diffraction and computer simulations. Finally, the consequences of adsorption of various polar and apolar liqs. have been evaluated using ex situ synchrotron X-ray powder diffraction data and reveals that the swelling behavior of MIL-89 is selective but slightly different from the MIL-88 analogs.
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    Surblé, S.; Serre, C.; Mellot-Draznieks, C.; Millange, F.; Férey, G. A New Isoreticular Class of Metal-organic-Frameworks with the MIL-88 Topology. Chem. Commun. 2006, 3, 284– 286,  DOI: 10.1039/b512169h
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    McKinlay, A. C.; Morris, R. E.; Horcajada, P.; Férey, G.; Gref, R.; Couvreur, P.; Serre, C. BioMOFs: Metal-organic Frameworks for Biological and Medical Applications. Angew. Chem. Int. Ed. 2010, 49, 6260– 6266,  DOI: 10.1002/anie.201000048
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    BioMOFs: Metal-Organic Frameworks for Biological and Medical Applications
    McKinlay, Alistair C.; Morris, Russell E.; Horcajada, Patricia; Ferey, Gerard; Gref, Ruxandra; Couvreur, Patrick; Serre, Christian
    Angewandte Chemie, International Edition (2010), 49 (36), 6260-6266CODEN: ACIEF5; ISSN:1433-7851. (Wiley-VCH Verlag GmbH & Co. KGaA)
    A review. The class of highly porous materials called metal-org. frameworks offer many opportunities for applications across biol. and medicine. Their wide range of chem. compn. makes toxicol. acceptable formulation possible, and their high level of functionality enables possible applications as imaging agents and as delivery vehicles for therapeutic agents. The challenges in the area encompass not only the development of new solids but also improvements in the formulation and processing of the materials, including tailoring the morphol. and surface chem. of the frameworks to fit the proposed applications.
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    Scherb, C.; Schödel, A.; Bein, T. Directing the Structure of Metal-organic Frameworks by Oriented Surface Growth on an organic Monolayer. Angew. Chem. Int. 2008, 47, 5777– 5779,  DOI: 10.1002/anie.200704034
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    Directing the structure of metal-organic frameworks by oriented surface growth on an organic monolayer
    Scherb, Camilla; Schoedel, Alexander; Bein, Thomas
    Angewandte Chemie, International Edition (2008), 47 (31), 5777-5779CODEN: ACIEF5; ISSN:1433-7851. (Wiley-VCH Verlag GmbH & Co. KGaA)
    Crystal growth and structures of metal-org. frameworks (MOFs) based on iron and 1,4-benzenedicarboxylic (terephthalic) acid are investigated. A dramatic change in the MOFs crystn. takes place on moving from homogeneous nucleation in soln. to heterogeneous nucleation on a mercaptohexadecanoic acid (MHDA) self-assembled monolayer (SAM). Thus, the product of homogeneous nucleation is the MOF Fe-MIL-53, whereas in the same crystn. soln., oriented Fe-MIL-88B grows on a MHDA-functionalized gold surface.
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    Whitfield, T. R.; Wang, X.; Liu, L.; Jacobson, A. J. Metal-organic Frameworks Based on Iron Oxide Octahedral Chains Connected by Benzenedicarboxylate Dianions. Solid State Sci. 2005, 7, 1096– 1103,  DOI: 10.1016/J.SOLIDSTATESCIENCES.2005.03.007
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    Metal-organic frameworks based on iron oxide octahedral chains connected by benzenedicarboxylate dianions
    Whitfield, Tabatha R.; Wang, Xiqu; Liu, Lumei; Jacobson, Allan J.
    Solid State Sciences (2005), 7 (9), 1096-1103CODEN: SSSCFJ; ISSN:1293-2558. (Elsevier B.V.)
    Three new Fe benzenedicarboxylates were synthesized by solvothermal techniques, and their structures detd. from single crystal x-ray data: Fe(OH)(BDC)(py)0.85 (1), Fe(BDC)(DMF) (2), and Fe(BDC)(py)0.42(DMF)0.25 (3) (BDC = 1,4-benzenedicarboxylate, py = pyridine). 1 And 2 are the Fe(III)- and Fe(II)-structural analogs of the known Cr benzenedicarboxylate compd. (MIL-53). Both contain trans corner-sharing FeO6 octahedral chains connected by benzenedicarboxylate dianions. Compd. 3 contains chains of Fe O octahedra that share both corners and edges. Each chain is linked by BDC to six other chains to form a three-dimensional framework. Crystal data: 1, space group I2/a, a 6.889(2), b 11.073(3), c 18.280(6) Å, β 92.6(1)°; 2, space group Pn21a, a 19.422(2), b 7.3022(5), c 8.8468(7) Å; 3, space group P21/n, a 9.234(2), b 17.243(3), c 9.978(2) Å, β 93.9(1)°.
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    Huang, X.; Brazel, C. S. On the Importance and Mechanisms of Burst Release in Matrix-Controlled Drug Delivery Systems. J. Controlled Release 2001, 73, 121– 136,  DOI: 10.1016/S0168-3659(01)00248-6
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    On the importance and mechanisms of burst release in matrix-controlled drug delivery systems
    Huang, X.; Brazel, C. S.
    Journal of Controlled Release (2001), 73 (2-3), 121-136CODEN: JCREEC; ISSN:0168-3659. (Elsevier Science Ireland Ltd.)
    A review with refs. Although the significance of burst release in controlled delivery systems has not been entirely ignored, no successful theories have been put forth to fully describe the phenomenon. Despite the fact that the fast release of drug in a burst stage is utilized in certain drug administration strategies, the neg. effects brought about by burst can be pharmacol. dangerous and economically inefficient. Therefore a thorough understanding of the burst effect in controlled release systems is undoubtedly necessary. In this article, we review exptl. observations of burst release in monolithic polymer controlled drug delivery systems, theories of the phys. mechanisms causing burst, some of the unique ideas used to prevent burst, and the treatment of burst release in controlled release models.
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    Körber, M. PLGA Erosion: Solubility- or Diffusion-Controlled?. Pharm. Res. 2010, 27, 2414– 2420,  DOI: 10.1007/s11095-010-0232-5
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    PLGA erosion: solubility- or diffusion-controlled?
    Korber Martin
    Pharmaceutical research (2010), 27 (11), 2414-20 ISSN:.
    PURPOSE: To calculate the degradation time-dependent formation of water-soluble PLGA oligomers and to evaluate the relation between calculated oligomer formation and actual erosion of a PLGA-based delivery system. A proper model of the erosion process would be expected to facilitate forecasting of drug release profiles from PLGA matrices due to the close relationship of erosional mass loss and drug release described in the literature. METHODS: The molecular weight distribution (MWD), degradation and erosion behaviour of PLGA were characterized by gel permeation chromatography. RESULTS: PLGA was characterized by a lognormal distribution of mass fractions of individual molecular weights. Implementation of the pseudo-first-order reaction kinetics into the MWD function facilitated calculating the formation of water-soluble oligomers during degradation. The calculated soluble oligomer formation agreed excellently with measured erosional mass loss of a PLGA matrix in aqueous buffer, which suggested that the bulk erosion process was solely controlled by the kinetic of the formation of soluble oligomers and thus solubility-controlled and not diffusion-limited as conventionally assumed. CONCLUSION: The accurately calculated formation of soluble PLGA oligomers was in excellent agreement with the actual erosional mass loss of a PLGA matrix, suggesting that bulk erosion of PLGA represents a degradation-controlled dissolution process.
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    Peppas, N. A. Analysis of Fickian and Non-Fickian Drug Release from Polymers. Pharm. Acta Helv. 1985, 60, 110– 111
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    Analysis of Fickian and non-Fickian drug release from polymers
    Peppas, Nikolaos A.
    Pharmaceutica Acta Helvetiae (1985), 60 (4), 110-11CODEN: PAHEAA; ISSN:0031-6865.
    A simple, semiempirical equation is presented which can be used to analyze data of controlled release of water-sol. drugs from polymers. This equation predicts that the fractional release of drug is exponentially related to release time. The exponent n is characteristic of the mechanism of diffusional release. When n = 0.5, Fickian diffusion is obsd. and the release rate is dependent on t-0.5. When n = 1.0, case-II transport of the drug occurs and the release rate is independent of time (zero-order release kinetics).
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    Costa, P.; Sousa Lobo, J. M. Modeling and Comparison of Dissolution Profiles. Eur. J. Pharm. Sci. 2001, 13, 123– 133,  DOI: 10.1016/S0928-0987(01)00095-1
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    Modeling and comparison of dissolution profiles
    Costa, P.; Sousa Lobo, J. M.
    European Journal of Pharmaceutical Sciences (2001), 13 (2), 123-133CODEN: EPSCED; ISSN:0928-0987. (Elsevier Science Ireland Ltd.)
    A review with refs. Over recent years, drug release/dissoln. from solid pharmaceutical dosage forms has been the subject of intense and profitable scientific developments. Whenever a new solid dosage form is developed or produced, it is necessary to ensure that drug dissoln. occurs in an appropriate manner. The pharmaceutical industry and the registration authorities do focus, nowadays, on drug dissoln. studies. The quant. anal. of the values obtained in dissoln./release tests is easier when math. formulas that express the dissoln. results as a function of some of the dosage forms characteristics are used. In some cases, these mathematic models are derived from the theor. anal. of the occurring process. In most of the cases the theor. concept does not exist and some empirical equations have proved to be more appropriate. Drug dissoln. from solid dosage forms has been described by kinetic models in which the dissolved amt. of drug (Q) is a function of the test time, t or Q=f(t). Some anal. definitions of the Q(t) function are commonly used, such as zero order, first order, Hixson-Crowell, Weibull, Higuchi, Baker-Lonsdale, Korsmeyer-Peppas and Hopfenberg models. Other release parameters, such as dissoln. time (tx%), assay time (tx min), dissoln. efficacy (ED), difference factor (f1), similarity factor (f2) and Rescigno index (ξ1 and ξ2) can be used to characterize drug dissoln./release profiles.
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    Goutelle, S.; Maurin, M.; Rougier, F.; Barbaut, X.; Bourguignon, L.; Ducher, M.; Maire, P. The Hill Equation: A Review of Its Capabilities in Pharmacological Modelling. Fundam. Clin. Pharmacol. 2008, 22, 633– 648,  DOI: 10.1111/j.1472-8206.2008.00633.x
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    The Hill equation: a review of its capabilities in pharmacological modeling
    Goutelle, Sylvain; Maurin, Michel; Rougier, Florent; Barbaut, Xavier; Bourguignon, Laurent; Ducher, Michel; Maire, Pascal
    Fundamental & Clinical Pharmacology (2008), 22 (6), 633-648CODEN: FCPHEZ; ISSN:0767-3981. (Wiley-Blackwell)
    A review. The Hill equation was first introduced by A.V. Hill to describe the equil. relationship between oxygen tension and the satn. of Hb. In pharmacol., the Hill equation has been extensively used to analyze quant. drug-receptor relationships. Many pharmacokinetic-pharmacodynamic models have used the Hill equation to describe nonlinear drug dose-response relationships. Although the Hill equation is widely used, its many properties are not all well known. This article aims at reviewing the various properties of the Hill equation. The descriptive aspects of the Hill equation, in particular math. and graphical properties, are examd., and related to Hill's original work. The mechanistic aspect of the Hill equation, involving a strong connection with the Guldberg and Waage law of mass action, is also described. Finally, a probabilistic view of the Hill equation is examd. Here, we provide some new calcn. results, such as Fisher information and Shannon entropy, and we introduce multivariate probabilistic Hill equations. The main features and potential applications of this probabilistic approach are also discussed. Thus, within the same formalism, the Hill equation has many different properties which can be of great interest for those interested in math. modeling in pharmacol. and biosciences.
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    Xu, B.; Yang, H.; Cai, Y.; Yang, H.; Li, C. Preparation and Photocatalytic Property of Spindle-like MIL-88B(Fe) Nanoparticles. Inorg. Chem. Commun. 2016, 67, 29– 31,  DOI: 10.1016/J.INOCHE.2016.03.003
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    Preparation and photocatalytic property of spindle-like MIL-88B(Fe) nanoparticles
    Xu, Bo; Yang, He; Cai, Yong; Yang, Hongxun; Li, Cuncheng
    Inorganic Chemistry Communications (2016), 67 (), 29-31CODEN: ICCOFP; ISSN:1387-7003. (Elsevier B.V.)
    Fe(III) based nanoparticles MIL-88B(Fe) with spindle-like morphol. were synthesized by a facile method. TEM and SEM revealed that the MIL-88B(Fe) nanoparticles had an uniform size of ∼385 nm in length and 195 nm in width. The obtained nanoparticles were further characterized by powder XRD and UV-visible spectroscopy (UV-visible). Also, as MIL-88B(Fe) shows obvious adsorption in the visible region, it has good degrdn. activity for methylene blue (MB) and rhodamine B (RB) dye under visible light.
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    Shi, L.; Wang, T.; Zhang, H.; Chang, K.; Meng, X.; Liu, H.; Ye, J. An Amine-Functionalized Iron(III) Metal-organic Framework as Efficient Visible-Light Photocatalyst for Cr(VI) Reduction. Adv. Sci. 2015, 2, 1500006,  DOI: 10.1002/advs.201500006
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    An Amine-Functionalized Iron(III) Metal-Organic Framework as Efficient Visible-Light Photocatalyst for Cr(VI) Reduction
    Shi Li; Meng Xianguang; Wang Tao; Zhang Huabin; Chang Kun; Liu Huimin; Ye Jinhua
    Advanced science (Weinheim, Baden-Wurttemberg, Germany) (2015), 2 (3), 1500006 ISSN:2198-3844.
    The photocatalytic reduction of Cr(VI) is investigated over iron(III)-based metal-organic frameworks (MOFs) structured as MIL-88B. It is found that MIL-88B (Fe) MOFs, containing Fe3-μ3-oxo clusters, can be used as photocatalyst for the reduction of Cr(VI) under visible light irradiation, which is due to the direct excitation of Fe3-μ3-oxo clusters. The amine-functionalized MIL-88B (Fe) MOFs (denoted as NH2-MIL-88B (Fe)) shows much higher efficiency for the photocatalytic Cr(VI) reduction under visible-light irradiation compared with MIL-88B (Fe). It is revealed that in addition to the direct excitation of Fe3-μ3-oxo clusters, the amine functionality in NH2-MIL-88B (Fe) can also be excited and then transferred an electron to Fe3-μ3-oxo clusters, which is responsible for the enhanced photocatalytic activity for Cr(VI) reduction. The enhanced photocatalytic activity for Cr(VI) reduction is also achieved for other two amine-functionalized iron(III)-based MOFs (NH2-MIL-53 (Fe) and NH2-MIL-101 (Fe)).
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    Bragg, W. L. The Diffraction of Short Electromagnetic Waves by a Crystal. Proc. Camb. Philol. Soc. 1913, 17, 43– 57
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    Diffraction of Short Electromagnetic Waves by a Crystal
    Bragg, W. L.
    Proceedings of the Cambridge Philosophical Society (1913), 17 (), 43-57CODEN: PCPSA4; ISSN:0068-6735.
    A small bundle of X-rays is isolated by means of Pb screens with small holes. A small crystal is put in its path and beyond this a photographic plate perpendicular to the path. Besides the spot due to the ray itself, a complicated geometrical system of spots is shown on the plate. The crystal acts as a diffraction grating and the interference phenomena as shown by these spots are interpreted to throw light on crystal structure. In cubic ZnS the arrangement of the mols. point to the 3-point system of closest packing, suggested by Pope and Barlow, in which each element of the crystal pattern has a mol. at each corner of the cube face and its center.
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    Loiseau, T.; Serre, C.; Huguenard, C.; Fink, G.; Taulelle, F.; Henry, M.; Bataille, T.; Férey, G. A Rationale for the Large Breathing of the Porous Aluminum Terephthalate (MIL-53) upon Hydration. Chemistry 2004, 10, 1373– 1382,  DOI: 10.1002/chem.200305413
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    A rationale for the large breathing of the porous aluminum terephthalate (MIL-53) upon hydration
    Loiseau, Thierry; Serre, Christian; Huguenard, Clarisse; Fink, Gerhard; Taulelle, Francis; Henry, Marc; Bataille, Thierry; Ferey, Gerard
    Chemistry - A European Journal (2004), 10 (6), 1373-1382CODEN: CEUJED; ISSN:0947-6539. (Wiley-VCH Verlag GmbH & Co. KGaA)
    Al 1,4-benzenedicarboxylate Al(OH)[O2CC6H4CO2][HO2C-C6H4-CO2H]0.70 or MIL-53as (Al) was hydrothermally synthesized by heating a mixt. of Al nitrate, 1,4-benzenedicarboxylic acid, and H2O, for three days at 220°. Its 3 D framework is built up of infinite trans chains of corner-sharing AlO4(OH)2 octahedra. The chains are interconnected by the 1,4-benzenedicarboxylate groups, creating 1 D rhombic-shaped tunnels. Disordered 1,4-benzenedicarboxylic acid mols. are trapped inside these tunnels. Their evacuation upon heating, between 275 and 420°, leads to a nanoporous open-framework (MIL-53ht (Al) or Al(OH)[O2CC6H4CO2]) with empty pores of diam. 8.5 Å. This solid exhibits a Langmuir surface area. of 1590(1) m2g-1 together with a remarkable thermal stability, since it starts to decomp. only at 500°. At room temp., the solid reversibly absorbs H2O in its tunnels, causing a very large breathing effect and shrinkage of the pores. Anal. of the hydration process by solid-state NMR (1H, 13C, 27Al) has clearly indicated that the trapped H2O mols. interact with the carboxylate groups through H bonds, but do not affect the hydroxyl species bridging the Al atoms. The H bonds between H2O and the O atoms of the framework are responsible for the contraction of the rhombic channels. The structures of the three forms were detd. by powder x-ray diffraction anal. Crystal data for MIL-53as (Al) are as follows: orthorhombic system, Pnma (no. 62), a 17.129(2), b 6.628(1), c 12.182(1) Å; for MIL-53ht (Al), orthorhombic system, Imma (no. 74), a 6.608(1), b 16.675(3), c 12.813(2) Å; for MIL-53lt (Al), monoclinic system, Cc (no. 9), a 19.513(2), b 7.612(1), c 6.576(1) Å, β 104.24(1)°.
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    Ma, M.; Noei, H.; Mienert, B.; Niesel, J.; Bill, E.; Muhler, M.; Fischer, R. A.; Wang, Y.; Schatzschneider, U.; Metzler-Nolte, N. Iron Metal-organic Frameworks MIL-88B and NH 2 -MIL-88B for the Loading and Delivery of the Gasotransmitter Carbon Monoxide. Chem. - A Eur. J. 2013, 19, 6785– 6790,  DOI: 10.1002/chem.201201743
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    Iron Metal-Organic Frameworks MIL-88B and NH2-MIL-88B for the Loading and Delivery of the Gasotransmitter Carbon Monoxide
    Ma, Mingyan; Noei, Heshmat; Mienert, Bernd; Niesel, Johanna; Bill, Eckhard; Muhler, Martin; Fischer, Roland A.; Wang, Yuemin; Schatzschneider, Ulrich; Metzler-Nolte, Nils
    Chemistry - A European Journal (2013), 19 (21), 6785-6790CODEN: CEUJED; ISSN:0947-6539. (Wiley-VCH Verlag GmbH & Co. KGaA)
    Crystals of MIL-88B-Fe and NH2-MIL-88B-Fe were prepd. by a new rapid microwave-assisted solvothermal method. High-purity, spindle-shaped crystals of MIL-88B-Fe with a length of about 2 μm and a diam. of 1 μm and needle-shaped crystals of NH2-MIL-88B-Fe with a length of about 1.5 μm and a diam. of 300 nm were produced with uniform size and excellent crystallinity. The possibility to reduce the as-prepd. frameworks and the chem. capture of carbon monoxide in these materials was studied by in situ ultrahigh vacuum Fourier-transform IR (UHV-FTIR) spectroscopy and Moessbauer spectroscopy. CO binding occurs to unsatd. coordination sites (CUS). The release of CO from the as-prepd. materials was studied by a myoglobin assay in physiol. buffer. The release of CO from crystals of MIL-88B-Fe with t1/2=38 min and from crystals of NH2-MIL-88B-Fe with t1/2=76 min were found to be controlled by the degrdn. of the MIL materials under physiol. conditions. These MIL-88B-Fe and NH2-MIL-88B-Fe materials show good biocompatibility and have the potential to be used in pharmacol. and therapeutic applications as carriers and delivery vehicles for the gasotransmitter carbon monoxide.
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    Walton, R. I.; Munn, A. S.; Guillou, N.; Millange, F. Uptake of Liquid Alcohols by the Flexible FeIII Metal-organic Framework MIL-53 Observed by Time-Resolved In Situ X-Ray Diffraction. Chem. - A Eur. J. 2011, 17, 7069– 7079,  DOI: 10.1002/chem.201003634
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    Uptake of Liquid Alcohols by the Flexible FeIII Metal-Organic Framework MIL-53 Observed by Time-Resolved In Situ X-ray Diffraction
    Walton, Richard I.; Munn, Alexis S.; Guillou, Nathalie; Millange, Franck
    Chemistry - A European Journal (2011), 17 (25), 7069-7079, S7069/1-S7069/15CODEN: CEUJED; ISSN:0947-6539. (Wiley-VCH Verlag GmbH & Co. KGaA)
    A comprehensive, time-resolved, energy-dispersive x-ray diffraction study of the uptake of liq. alcs. (methanol, ethanol, propan-1-ol and propan-2-ol) by the flexible metal-org. framework solid MIL-53(Fe)[H2O] is reported. In the case of the primary alcs., a fluorinated version of the MIL-53(Fe) host (C2/c symmetry V ∼ 1000 Å3), in which a fraction of framework hydroxides are replaced by fluoride, shows uptake of alcs. to give initially a partially expanded phase (C2/c symmetry, V ∼ 1200 Å3) followed by an expanded form of the material (either Imcm or Pnam symmetry, V ∼ 1600 Å3). In the case of methanol-water mixts., the EDXRD data show that the partially open intermediate phase undergoes vol. expansion during its existence, before switching to a fully open structure if concd. methanol is used; analogous behavior is seen if the initial guest is propan-2-ol, which then is replaced by pyridine, where a continuous shift of Bragg peaks within C2/c symmetry is obsd. In contrast to the partially fluorinated materials, the purely hydroxylated host materials show little tendency to stabilize partially open forms of MIL-53(Fe) with primary alcs. and the kinetics of guest introduction are markedly slower without the framework fluorination: this is exemplified by the exchange of water by propan-2-ol, where a partially open C2/c phase is formed in a step-wise manner. The study defines the various possible pathways of liq.-phase uptake of mol. guests by flexible solid MIL-53(Fe).
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    Nikseresht, A.; Daniyali, A.; Ali-Mohammadi, M.; Afzalinia, A.; Mirzaie, A. Ultrasound-Assisted Biodiesel Production by a Novel Composite of Fe(III)-Based MOF and Phosphotangestic Acid as Efficient and Reusable Catalyst. Ultrason. Sonochem. 2017, 37, 203– 207,  DOI: 10.1016/J.ULTSONCH.2017.01.011
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    Ultrasound-assisted biodiesel production by a novel composite of Fe(III)-based MOF and phosphotangestic acid as efficient and reusable catalyst
    Nikseresht, Ahmad; Daniyali, Asra; Ali-Mohammadi, Mahdi; Afzalinia, Ahmad; Mirzaie, Abbas
    Ultrasonics Sonochemistry (2017), 37 (), 203-207CODEN: ULSOER; ISSN:1350-4177. (Elsevier B.V.)
    In this work, esterification of oleic acid by various alcs. is achieved with high yields under ultrasonic irradn. This reaction performed with a novel heterogeneous catalyst that fabricated by heteropoly acid and Fe(III)-based MOF, namely MIL-53 (Fe). Syntheses of MIL-53 and encapsulation process carry out by ultrasound irradn. at ambient temp. and atm. pressure. The prepd. composite was characterized by various techniques such as XRD, FT-IR, SEM, BET and ICP that demonstrate excellent catalytic activities, while being highly convenient to synthesize. The obtained results revealed that ultrasound irradn. could be used for the appropriate and rapid biodiesel prodn.
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    Feng, X.; Chen, H.; Jiang, F. In-Situ Ethylenediamine-Assisted Synthesis of a Magnetic Iron-Based Metal-organic Framework MIL-53(Fe) for Visible Light Photocatalysis. J. Colloid Interface Sci. 2017, 494, 32– 37,  DOI: 10.1016/J.JCIS.2017.01.060
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    In-situ ethylenediamine-assisted synthesis of a magnetic iron-based metal-organic framework MIL-53(Fe) for visible light photocatalysis
    Feng, Xiangwen; Chen, Huan; Jiang, Fang
    Journal of Colloid and Interface Science (2017), 494 (), 32-37CODEN: JCISA5; ISSN:0021-9797. (Elsevier B.V.)
    A novel magnetic MIL-53(Fe) photocatalyst (MAG-MIL) has been synthesized by an in-situ ethylenediamine (EDA)-assisted solvothermal method. The well dispersed γ-Fe2O3 nanoparticles embedded in the MAG-MIL framework contribute to a red shift of the light absorption edge as well as the superparamagnetism characteristic.
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    Alsop, R. J.; Armstrong, C. L.; Maqbool, A.; Toppozini, L.; Dies, H.; Rheinstädter, M. C. Cholesterol Expels Ibuprofen from the Hydrophobic Membrane Core and Stabilizes Lamellar Phases in Lipid Membranes Containing Ibuprofen. Soft Matter 2015, 11, 4756– 4767,  DOI: 10.1039/c5sm00597c
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    Cholesterol expels ibuprofen from the hydrophobic membrane core and stabilizes lamellar phases in lipid membranes containing ibuprofen
    Alsop, Richard J.; Armstrong, Clare L.; Maqbool, Amna; Toppozini, Laura; Dies, Hannah; Rheinstadter, Maikel C.
    Soft Matter (2015), 11 (24), 4756-4767CODEN: SMOABF; ISSN:1744-683X. (Royal Society of Chemistry)
    There is increasing evidence that common drugs, such as aspirin and ibuprofen, interact with lipid membranes. Ibuprofen is one of the most common over the counter drugs in the world, and is used for relief of pain and fever. It interacts with the cyclooxygenase pathway leading to inhibition of prostaglandin synthesis. From X-ray diffraction of highly oriented model membranes contg. between 0 and 20 mol% ibuprofen, 20 mol% cholesterol, and dimyristoylphosphatidylcholine (DMPC), we present evidence for a non-specific interaction between ibuprofen and cholesterol in lipid bilayers. At a low ibuprofen concns. of 2 mol%, three different populations of ibuprofen mols. were found: two in the lipid head group region and one in the hydrophobic membrane core. At higher ibuprofen concns. of 10 and 20 mol%, the lamellar bilayer structure is disrupted and a lamellar to cubic phase transition was obsd. In the presence of 20 mol% cholesterol, ibuprofen (at 5 mol%) was found to be expelled from the membrane core and reside solely in the head group region of the bilayers. 20 mol% cholesterol was found to stabilize lamellar membrane structure and the formation of a cubic phase at 10 and 20 mol% ibuprofen was suppressed. The results demonstrate that ibuprofen interacts with lipid membranes and that the interaction is strongly dependent on the presence of cholesterol.
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    Wang, Y.; Muramatsu, A.; Sugimoto, T. FTIR Analysis of Well-Defined α-Fe2O3 Particles. Colloids Surf., A 1998, 134, 281– 297,  DOI: 10.1016/S0927-7757(97)00102-7
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    FTIR analysis of well-defined α-Fe2O3 particles
    Wang, Yinsheng; Muramatsu, Atsushi; Sugimoto, Tadao
    Colloids and Surfaces, A: Physicochemical and Engineering Aspects (1998), 134 (3), 281-297CODEN: CPEAEH; ISSN:0927-7757. (Elsevier Science B.V.)
    The FTIR spectra of well-defined hematite (α-Fe2O3) particles varying in size, shape and internal structure have systematically been analyzed. The absorption peak frequencies of the pseudocubic particles are located between the corresponding theor. peak frequencies of spheres and cubes and shift to lower frequencies as particle size increases, corresponding approx. with the Mie theory. However, the basic spectrum pattern was detd. by the morphol. of the particles. The observation of ellipsoids with various aspect ratios revealed some essential discrepancies in the peak frequency between expt. and the theory on the surface phonon modes in small particles, even if the particles were completely dispersed in the medium. The internal structure mainly affects the peak width, which increases with the decreasing subcrystal size. Finally, the effects of aggregation on the IR spectrum are discussed.
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    Brunauer, S.; Emmett, P. H.; Teller, E. Adsorption of Gases in Multimolecular Layers. J. Am. Chem. Soc. 1938, 60, 309– 319,  DOI: 10.1021/ja01269a023
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    Adsorption of gases in multimolecular layers
    Brunauer, Stephen; Emmett, P. H.; Teller, Edward
    Journal of the American Chemical Society (1938), 60 (), 309-19CODEN: JACSAT; ISSN:0002-7863.
    The polarization theory of multimolecular adsorption is discussed critically. The adsorption energy due to attraction of dipoles induced into a nonpolar gas such as A is insufficient to constitute a major portion of the binding energy between adsorbed layers. Adsorption-isotherm equations for multimolecular adsorption are derived on the assumption that the same forces that produce condensation are responsible also for multimolecular adsorption. Numerous applications of the equations are given to exptl. adsorption isotherms. Cf. C. A. 32, 1159.3.
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    Harkins, W. D.; Jura, G. An Adsorption Method for the Determination of the Area of a Solid without the Assumption of a Molecular Area, and the Area Occupied by Nitrogen Molecules on the Surfaces of Solids. J. Chem. Phys. 1943, 11, 431– 432,  DOI: 10.1063/1.1723871
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    50
    An adsorption method for the determination of the area of a solid without the assumption of a molecular area, and the area occupied by nitrogen molecules on the surfaces of solids
    Harkins, Wm. D.; Jura, Geo.
    Journal of Chemical Physics (1943), 11 (), 431-2CODEN: JCPSA6; ISSN:0021-9606.
    cf. preceding abstr. It is shown that Σ = 4.06s0.5 (Σ = area in sq. m./g.; s = slope of the isotherm obtained from the equation in the preceding abstr.). The surface areas of 58 of 60 solids investigated, detd. by this method, agreed within ±9% with detns. made by the Brunauer, Emmett and Teller isotherm (C. A. 32, 4037.9). The area of the N2 mols. on these solids was calcd. to be in the range 13.6-16.9 sq. A. Langmuir's isotherm was found to be valueless, since it applies only to unimol. adsorption.
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    Düren, T.; Millange, F.; Férey, G.; Walton, K. S.; Snurr, R. Q. Calculating Geometric Surface Areas as a Characterization Tool for Metal - organic Frameworks. J. Phys. Chem. C 2007, 111, 15350– 15356,  DOI: 10.1021/jp074723h
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    Calculating Geometric Surface Areas as a Characterization Tool for Metal-Organic Frameworks
    Dueren, Tina; Millange, Franck; Ferey, Gerard; Walton, Krista S.; Snurr, Randall Q.
    Journal of Physical Chemistry C (2007), 111 (42), 15350-15356CODEN: JPCCCK; ISSN:1932-7447. (American Chemical Society)
    Metal-org. frameworks (MOFs) synthesized in a building-block approach from org. linkers and metal corner units offer the opportunity to design materials with high surface areas for adsorption applications by assembling the appropriate building blocks. In this paper, we show that the surface area calcd. in a geometric fashion from the crystal structure is a useful tool for characterizing MOFs. We argue that the accessible surface area rather than the widely used Connolly surface area is the appropriate surface area to characterize cryst. solids for adsorption applications. The accessible surface area calcd. with a probe diam. corresponding to the adsorbate of interest provides a simple way to screen and compare adsorbents. We investigate the effects of the probe mol. diam. on the accessible surface area and discuss the implications for increasing the surface area of metal-org. frameworks by the use of catenated structures. We also demonstrate that the accessible surface area provides a useful tool for judging the quality of a synthesized sample. Exptl. surface areas can be adversely affected by incomplete solvent removal during activation, crystal collapse, or interpenetration. The easily calcd. accessible surface area provides a benchmark for the theor. upper limit for a perfect crystal.
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    First, E. L.; Floudas, C. A. MOFomics: Computational Pore Characterization of Metal-organic Frameworks. Microporous Mesoporous Mater. 2013, 165, 32– 39,  DOI: 10.1016/j.micromeso.2012.07.049
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    MOFomics: Computational pore characterization of metal-organic frameworks
    First, Eric L.; Floudas, Christodoulos A.
    Microporous and Mesoporous Materials (2013), 165 (), 32-39CODEN: MIMMFJ; ISSN:1387-1811. (Elsevier Inc.)
    Microporous materials, such as zeolites and metal-org. frameworks (MOFs), are commonly considered for shape-selective sepns. and catalysis. With the large no. of known and hypothetical structures available, computational techniques are needed to identify the most promising structures for applications of interest. The authors have developed an automated computational framework based on optimization, geometry, and graph algorithms to fully characterize the three-dimensional pore structures of MOFs. The authors' methods automatically identify the portals, channels, and cages of a MOF and describe their geometry and connectivity. Also, the authors calc. quantities of interest including pore size distribution, accessible vol., accessible surface area, pore limiting diam., and largest cavity diam. The authors' computational framework was applied to over 800 exptl. MOFs, including zeolitic imidazolate frameworks (ZIFs), and over 1600 hypothetical MOFs. MOFomics, an online database of pore characterizations and the 1st web tool for MOFs that allows user submissions, is made freely available to the scientific communit (http://helios.princeton.edu/mofomics/).
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  53. 53
    Vu, T. A.; Le, G. H.; Dao, C. D.; Dang, L. Q.; Nguyen, K. T.; Nguyen, Q. K.; Dang, P. T.; Tran, H. T. K.; Duong, Q. T.; Nguyen, T. V. Arsenic Removal from Aqueous Solutions by Adsorption Using Novel MIL-53(Fe) as a Highly Efficient Adsorbent. RSC Adv. 2015, 5, 5261– 5268,  DOI: 10.1039/c4ra12326c
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    53
    Arsenic removal from aqueous solutions by adsorption using novel MIL-53(Fe) as a highly efficient adsorbent
    Vu, Tuan. A.; Le, Giang. H.; Dao, Canh. D.; Dang, Lan. Q.; Nguyen, Kien. T.; Nguyen, Quang. K.; Dang, Phuong. T.; Tran, Hoa. T. K.; Duong, Quang. T.; Nguyen, Tuyen. V.; Lee, Gun. D.
    RSC Advances (2015), 5 (7), 5261-5268CODEN: RSCACL; ISSN:2046-2069. (Royal Society of Chemistry)
    A MIL-53(Fe) analog was successfully synthesized by a HF free-solvothermal method. The sample was characterized by XRD, N2 adsorption (BET), TEM, FTIR, XPS and AAS. From the N2 adsorption-desorption isotherms, it can be seen that the structure of MIL-53(Fe) in the anhyd. form exhibits closed pores with almost no accessible porosity to nitrogen gas. The XPS results reveal that Fe is really incorporated into the MIL-53(Fe) framework. In the hydrated form, the pores of MIL-53(Fe) are filled with water mols. Thus, MIL-53(Fe) exhibited a very high adsorption capacity of As(V) in aq. soln. (Qmax of 21.27 mg g-1). Adsorption kinetics data revealed that As(V) adsorption isotherms fit the Langmuir model and obey the pseudo-second-order kinetic equation.
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    Millange, F.; Guillou, N.; Walton, R. I.; Grenèche, J.-M.; Margiolaki, I.; Férey, G. Effect of the Nature of the Metal on the Breathing Steps in MOFs with Dynamic Frameworks. Chem. Commun. 2008, 39, 4732– 4734,  DOI: 10.1039/b809419e
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    Devic, T.; Horcajada, P.; Serre, C.; Salles, F.; Maurin, G.; Moulin, B.; Heurtaux, D.; Clet, G.; Vimont, A.; Grenéche, J.-M. Functionalization in Flexible Porous Solids: Effects on the Pore Opening and the Host-Guest Interactions. J. Am. Chem. Soc. 2010, 132, 1127– 1136,  DOI: 10.1021/ja9092715
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    Functionalization in Flexible Porous Solids: Effects on the Pore Opening and the Host-Guest Interactions
    Devic, Thomas; Horcajada, Patricia; Serre, Christian; Salles, Fabrice; Maurin, Guillaume; Moulin, Beatrice; Heurtaux, Daniela; Clet, Guillaume; Vimont, Alexandre; Greneche, Jean-Marc; Le Ouay, Benjamin; Moreau, Florian; Magnier, Emmanuel; Filinchuk, Yaroslav; Marrot, Jerome; Lavalley, Jean-Claude; Daturi, Marco; Ferey, Gerard
    Journal of the American Chemical Society (2010), 132 (3), 1127-1136CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
    The synthesis on the gram scale and characterization of flexible functionalized iron terephthalate MIL-53(Fe) type solids are reported. Chem. groups of various polarities, hydrophilicities, and acidities (-Cl, -Br, -CF3, -Me, -NH2, -OH, -CO2H) were introduced through the arom. linker, to systematically modify the pore surface. X-ray powder diffraction (XRPD), mol. simulations, thermogravimetric analyses, and in situ IR and 57Fe Moessbauer spectrometries indicate some similarities with the pristine MIL-53(Fe) solid, with the adoption of the narrow pore form for all solids in both the hydrated and dry forms. Combined XRPD and computational structure detns. allow concluding that the geometry of the pore opening is predominantly correlated with the intraframework interactions rather than the steric hindrance of the substituent. Only (MIL-53(Fe)(CF3)2) exhibits a nitrogen accessible porosity (SBET ≈ 100 m2 g-1). The adsorption of some liqs. leads to pore openings showing some very specific behaviors depending on the guest-MIL-53(Fe) framework interactions, which can be related to the energy difference between the narrow and large pore forms evaluated by mol. simulation.
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    Matsuyama, K.; Hayashi, N.; Yokomizo, M.; Kato, T.; Ohara, K.; Okuyama, T. Supercritical Carbon Dioxide-Assisted Drug Loading and Release from Biocompatible Porous Metal-organic Frameworks. J. Mater. Chem. B 2014, 2, 7551– 7558,  DOI: 10.1039/c4tb00725e
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    56
    Supercritical carbon dioxide-assisted drug loading and release from biocompatible porous metal-organic frameworks
    Matsuyama, Kiyoshi; Hayashi, Nobukatsu; Yokomizo, Misaki; Kato, Takafumi; Ohara, Kiyomi; Okuyama, Tetsuya
    Journal of Materials Chemistry B: Materials for Biology and Medicine (2014), 2 (43), 7551-7558CODEN: JMCBDV; ISSN:2050-7518. (Royal Society of Chemistry)
    Herein the authors describe the supercrit. carbon dioxide (scCO2)-assisted drug loading and release from nontoxic and biocompatible porous iron(III) polycarboxylate metal-org. frameworks (MOFs), which exhibited very high cargo loadings and gradual release. MIL-53(Fe) and MIL-100(Fe) were investigated as potential carriers for drug mols., using ibuprofen as a model drug candidate. The loading and release behavior of ibuprofen were monitored by thermogravimetric analyses (TGA) and high performance liq. chromatog. (HPLC) measurements to quant. det. the ibuprofen uptake, and were performed for the first time using scCO2-based technol. After the prepn. of the MOFs within a particular solvent, the internal surface area of MIL-53(Fe) and MIL-100(Fe) increased as a result of the scCO2 drying method. Furthermore, ibuprofen could be impregnated into the pores of the MOFs by utilizing a scCO2-hexane soln. ScCO2-assisted impregnation could also be used to deliver ibuprofen to the pores of the MOFs. As a result, a large amt. of ibuprofen was able to be loaded into MIL-53(Fe) and MIL-100(Fe).
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    Zheng, H.; Zhang, Y.; Liu, L.; Wan, W.; Guo, P.; Nyström, A. M.; Zou, X. One-Pot Synthesis of Metal-organic Frameworks with Encapsulated Target Molecules and Their Applications for Controlled Drug Delivery. J. Am. Chem. Soc. 2016, 138, 962– 968,  DOI: 10.1021/jacs.5b11720
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    One-pot Synthesis of Metal-Organic Frameworks with Encapsulated Target Molecules and Their Applications for Controlled Drug Delivery
    Zheng, Haoquan; Zhang, Yuning; Liu, Leifeng; Wan, Wei; Guo, Peng; Nystroem, Andreas M.; Zou, Xiaodong
    Journal of the American Chemical Society (2016), 138 (3), 962-968CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
    Many medical and chem. applications require target mols. to be delivered in a controlled manner at precise locations. Metal-org. frameworks (MOFs) have high porosity, large surface area, and tunable functionality and are promising carriers for such purposes. Current approaches for incorporating target mols. are based on multistep postfunctionalization. Here, we report a novel approach that combines MOF synthesis and mol. encapsulation in a one-pot process. We demonstrate that large drug and dye mols. can be encapsulated in zeolitic imidazolate framework (ZIF) crystals. The mols. are homogeneously distributed within the crystals, and their loadings can be tuned. We show that ZIF-8 crystals loaded with the anticancer drug doxorubicin (DOX) are efficient drug delivery vehicles in cancer therapy using pH-responsive release. Their efficacy on breast cancer cell lines is higher than that of free DOX. Our one-pot process opens new possibilities to construct multifunctional delivery systems for a wide range of applications.
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    Spokoyny, A. M.; Kim, D.; Sumrein, A.; Mirkin, C. A. Infinite Coordination Polymer Nano- and Microparticle Structures. Chem. Soc. Rev. 2009, 38, 1218,  DOI: 10.1039/b807085g
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    Infinite coordination polymer nano- and microparticle structures
    Spokoyny, Alexander M.; Kim, Dongwoo; Sumrein, Abdelqader; Mirkin, Chad A.
    Chemical Society Reviews (2009), 38 (5), 1218-1227CODEN: CSRVBR; ISSN:0306-0012. (Royal Society of Chemistry)
    This tutorial review introduces the reader to the field of infinite coordination polymer particles (ICPs), providing a guide to the work done so far, with an emphasis on synthesis, applications and future prospects. ICPs represent an area of growing interest in chem. and materials science due to their unique and highly tailorable properties. These structures can be conveniently synthesized in high yields from the appropriate metal salts and bifunctional ligand precursors. Unlike conventional metal-org. framework materials (MOFs), these ICPs exhibit a higher level of structural tailorability, including size- and morphol.-dependent properties, and therefore, the promise of a wider scope of utility. A variety of methods now exist for making numerous compns., with modest control over particle size and shape. These structures can exhibit microporosity, tunable fluorescence, magnetic susceptibility, and unusual catalytic activity and selectivity. Perhaps most importantly, many of these ICP structures can be depolymd. (sometimes reversibly) much faster and under milder conditions than MOFs, which makes them attractive for a variety of biomedical applications. Thus far, several types of ICPs have been explored as contrast agents for magnetic resonance imaging and drug delivery systems. The groundwork for this emerging field of ICPs has been laid only in the past few years, yet significant advances have already been made.
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    Serre, C.; Mellot-Draznieks, C.; Surblé, S.; Audebrand, N.; Filinchuk, Y.; Férey, G. Role of Solvent-Host Interactions That Lead to Very Large Swelling of Hybrid Frameworks. Science 2007, 315, 1828– 1831,  DOI: 10.1126/science.1137975
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    Role of Solvent-Host Interactions That Lead to Very Large Swelling of Hybrid Frameworks
    Serre, C.; Mellot-Draznieks, C.; Surble, S.; Audebrand, N.; Filinchuk, Y.; Ferey, G.
    Science (Washington, DC, United States) (2007), 315 (5820), 1828-1831CODEN: SCIEAS; ISSN:0036-8075. (American Association for the Advancement of Science)
    An unusually large expansion upon solvent adsorption occurs without apparent bond breaking in the network of a series of isoreticular chromium(III) or iron(III) dicarboxylates labeled MIL-88A to D [dicarbox = fumarate (88A); terephthalate (1,4-BDC) (88B); 2,6-naphthalenedicarboxylate (2,6-NDC) (88C); and 4-4'-biphenyldicarboxylate (4-4'-BPDC) (88D)]. This reversible "breathing" motion was analyzed in terms of cell dimensions (extent of breathing), movements within the framework (mechanism of transformation), and the interactions between the guests and the skeleton. In situ techniques show that these flexible solids are highly selective absorbents and that this selectivity is strongly dependent on the nature of the org. linker.
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    Liédana, N.; Galve, A.; Rubio, C.; Téllez, C.; Coronas, J. CAF@ZIF-8: One-Step Encapsulation of Caffeine in MOF. ACS Appl. Mater. Interfaces 2012, 4, 5016– 5021,  DOI: 10.1021/am301365h
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    60
    CAF@ZIF-8: One-Step Encapsulation of Caffeine in MOF
    Liedana, Nuria; Galve, Alejandro; Rubio, Cesar; Tellez, Carlos; Coronas, Joaquin
    ACS Applied Materials & Interfaces (2012), 4 (9), 5016-5021CODEN: AAMICK; ISSN:1944-8244. (American Chemical Society)
    Two strategies for encapsulating caffeine in ZIF-8 were carried out in this work: (1) one-step, in situ encapsulation where caffeine is added to a ZIF-8 synthesis soln. and the MOF structure is formed around the entrapped mol.; and (2) ex situ encapsulation whereby caffeine is put into contact with previously synthesized or purchased ZIF-8. The products obtained were analyzed with XRD, TGA, Vis-UV, GC-MS, FTIR, 13C NMR, and N 1s XPS to compare both encapsulation methods. Chem. and structural evidence indicated that the preferential adsorption site of caffeine mols. inside the ZIF-8 structure is near the Me and CH groups of 2-methylimidazole ligand. These two groups interact with caffeine by van der Waals forces with Me groups and via CH-O hydrogen bonds with C=O groups, resp. In addn., the one-step encapsulation of caffeine in ZIF-8 produced high guest loading (∼28 wt.% in only 2 h at 25°) and controlled release (during 27 days).
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    Siepmann, J.; Siepmann, F. Mathematical Modeling of Drug Delivery. Int. J. Pharm. 2008, 364, 328– 343,  DOI: 10.1016/J.IJPHARM.2008.09.004
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    Mathematical modeling of drug delivery
    Siepmann, J.; Siepmann, F.
    International Journal of Pharmaceutics (2008), 364 (2), 328-343CODEN: IJPHDE; ISSN:0378-5173. (Elsevier B.V.)
    A review. Due to the significant advances in information technol. math. modeling of drug delivery is a field of steadily increasing academic and industrial importance with an enormous future potential. The in silico optimization of novel drug delivery systems can be expected to significantly increase in accuracy and easiness of application. Analogous to other scientific disciplines, computer simulations are likely to become an integral part of future research and development in pharmaceutical technol. Math. programs can be expected to be routinely used to help optimizing the design of novel dosage forms. Good ests. for the required compn., geometry, dimensions and prepn. procedure of various types of delivery systems will be available, taking into account the desired administration route, drug dose and release profile. Thus, the no. of required exptl. studies during product development can be significantly reduced, saving time and reducing costs. In addn., the quant. anal. of the phys., chem. and potentially biol. phenomena, which are involved in the control of drug release, offers another fundamental advantage: The underlying drug release mechanisms can be elucidated, which is not only of academic interest, but a pre-requisite for an efficient improvement of the safety of the pharmaco-treatments and for effective trouble-shooting during prodn. This article gives an overview on the current state of the art of math. modeling of drug delivery, including empirical/semi-empirical and mechanistic realistic models. Anal. as well as numerical solns. are described and various practical examples are given. One of the major challenges to be addressed in the future is the combination of mechanistic theories describing drug release out of the delivery systems with math. models quantifying the subsequent drug transport within the human body in a realistic way. Ideally, the effects of the design parameters of the dosage form on the resulting drug concn. time profiles at the site of action and the pharmacodynamic effects will become predictable.
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    Rothstein, S. N.; Federspiel, W. J.; Little, S. R. A Unified Mathematical Model for the Prediction of Controlled Release from Surface and Bulk Eroding Polymer Matrices. Biomaterials 2009, 30, 1657– 1664,  DOI: 10.1016/J.BIOMATERIALS.2008.12.002
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    A unified mathematical model for the prediction of controlled release from surface and bulk eroding polymer matrices
    Rothstein, Sam N.; Federspiel, William J.; Little, Steven R.
    Biomaterials (2009), 30 (8), 1657-1664CODEN: BIMADU; ISSN:0142-9612. (Elsevier Ltd.)
    A unified model has been developed to predict release not only from bulk eroding and surface eroding systems but also from matrixes that transition from surface eroding to bulk eroding behavior during the course of degrdn. This broad applicability is afforded by fundamental diffusion/reaction equations that can describe a wide variety of scenarios including hydration of and mass loss from a hydrolyzable polymer matrix. Together, these equations naturally account for spatial distributions of polymer degrdn. rate. In this model paradigm, the theor. minimal size required for a matrix to exhibit degrdn. under surface eroding conditions was calcd. for various polymer types and then verified by empirical data from the literature. An addnl. set of equations accounts for dissoln.- and/or degrdn.-based release, which are dependent upon hydration of the matrix and erosion of the polymer. To test the model's accuracy, predictions for agent egress were compared to exptl. data from polyanhydride and polyorthoester implants that were postulated to undergo either dissoln.-limited or degrdn.-controlled release. Because these predictions are calcd. solely from readily attainable design parameters, it seems likely that this model could be used to guide the design controlled release formulations that produce a broad array of custom release profiles.
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  • Abstract

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    Figure 1

    Figure 1. PXRD patterns of (a) MIL-88B and (b) MIL-53 at the condition of (i) as-synthesized, (ii) after solvent exchange, and (iii) after loading with ibuprofen, in comparison to the PXRD patterns of (iv) pure ibuprofen.

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    Figure 2

    Figure 2. ATR-IR spectra of (a) pure ibuprofen, (b) pristine Fe-MIL-88B, (c) ibuprofen loaded Fe-MIL-88B, (d) pristine Fe-MIL-53, and (e) ibuprofen loaded Fe-MIL-53.

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    Figure 3

    Figure 3. N2 sorption isotherms of Fe-MIL-88B (black) and Fe-MIL-53 (red) at 77 K before and after loading with ibuprofen. Solid symbols correspond to adsorption plots, and open symbols correspond to desorption plots.

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    Figure 4

    Figure 4. SEM images of MIL-88B crystals (a) before and (b) after ibuprofen loading.

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    Figure 5

    Figure 5. Profiles of cumulative ibuprofen release percentage as a function of soaking time in PBS for MIL-53 (squares) and MIL-88B (circles). The data were fitted with the Hill equation as indicated by the red plots.

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    Scheme 1

    Scheme 1. Illustrative Scheme of Drug Delivery Systems and Models Considered for MIL-88B and MIL-53
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    Figure 6

    Figure 6. (a) Plots of TA concentration as a function of soaking time in PBS for MIL-53 (open squares) and MIL-88B (open circles). (b) Linear regression correlation between TA concentration change and cumulative drug release percents of both MIL-53 (blue solid squares) and MIL-88B (black solid circles).

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    Figure 7

    Figure 7. Effect of MIL-88B on viability of NIH-3T3 Swiss mouse fibroblasts. The error bar represents a standard deviation from 18 independent measurements.

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  • References

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      Biol. drugs generated via recombinant techniques are uniquely positioned due to their high potency and high selectivity of action. The major drawback of this class of therapeutics, however, is their poor stability upon oral administration and during subsequent circulation. As a result, biol. drugs have very low bioavailability and short therapeutic half-lives. Fortunately, tools of chem. and biotechnol. have been developed into an elaborate arsenal, which can be applied to improve the pharmacokinetics of biol. drugs. Depot-type release systems are available to achieve sustained release of drugs over time. Conjugation to synthetic or biol. polymers affords long circulating formulations. Administration of biol. drugs through non-parenteral routes shows excellent performance and the first products have reached the market. This Review presents the main accomplishments in this field and illustrates the materials and methods behind existing and upcoming successful formulations and delivery strategies for biol. drugs.
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      Nano Letters (2011), 11 (2), 808-813CODEN: NALEFD; ISSN:1530-6984. (American Chemical Society)
      The fabrication of engineered poly(lactic acid-co-glycolic acid) nanoparticles via the PRINT (particle replication in nonwetting templates) process with high and efficient loadings of docetaxel, up to 40% (wt./wt.) with encapsulation efficiencies >90% is reported. The PRINT process enables independent control of particle properties leading to a higher degree of tailorability than traditional methods. Particles with 40% loading display better in vitro efficacy than particles with lower loadings and the clin. formulation of docetaxel, Taxotere.
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      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC3MXht1entrs%253D&md5=4bdd4095c158ed74c8346408002b7508
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      Zhu, L.; Li, M.; Liu, X.; Jin, Y. Drug-Loaded PLGA Electrospraying Porous Microspheres for the Local Therapy of Primary Lung Cancer via Pulmonary Delivery. ACS Omega 2017, 2, 2273– 2279,  DOI: 10.1021/acsomega.7b00456
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      Drug-Loaded PLGA Electrospraying Porous Microspheres for the Local Therapy of Primary Lung Cancer via Pulmonary Delivery
      Zhu, Lifei; Li, Miao; Liu, Xiaoyan; Jin, Yiguang
      ACS Omega (2017), 2 (5), 2273-2279CODEN: ACSODF; ISSN:2470-1343. (American Chemical Society)
      Nonsmall-cell lung cancer is a severe disease with high morbidity and mortality. However, the systemic administration of anticancer drugs generally leads to serious toxicity and low anti-lung cancer efficiency because of very limited drug distribution in the lung. In our previous research, we have confirmed the high anti-lung cancer effect of inhalable oridonin microparticles in spite of their long and complicated prepn. process. Here, we develop a novel, simple, and quick method for prepg. inhalable oridonin-loaded poly(D,L-lactic-co-glycolic)acid (PLGA) porous microspheres using the electrospraying technique. The formulation and prepn. processes were screened. The electrospraying porous microspheres (EPMs) were rough, porous, and suitable for pulmonary delivery. Most of the oridonin was released from the EPMs within 20 h based on drug diffusion and via PLGA erosion. The EPMs exhibited efficient lung deposition in vitro and in vivo because of their ideal aerodynamic diams. Chem. carcinogens were used to prep. primary lung cancer rat models by direct pulmonary delivery. The EPMs showed high anti-lung cancer effect after pulmonary delivery according to CT images and pathol. Inhibition of angiogenesis and enhancement of lung cancer cell apoptosis could be the major anticancer mechanism. Electrospraying is an efficient method for the prepn. of inhalable drug-loaded porous microspheres. The oridonin-loaded EPMs are promising dry powder inhalers for the local therapy of primary lung cancer.
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      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC2sXot1elsr8%253D&md5=fea4e5e9521878772bccf084de3adac8
    4. 4
      Wang, J.; Kumeria, T.; Bezem, M. T.; Wang, J.; Sailor, M. J. Self-Reporting Photoluminescent Porous Silicon Microparticles for Drug Delivery. ACS Appl. Mater. Interfaces 2018, 10, 3200– 3209,  DOI: 10.1021/acsami.7b09071
      4
      Self-Reporting Photoluminescent Porous Silicon Microparticles for Drug Delivery
      Wang, Joanna; Kumeria, Tushar; Bezem, Maria Teresa; Wang, Jian; Sailor, Michael J.
      ACS Applied Materials & Interfaces (2018), 10 (4), 3200-3209CODEN: AAMICK; ISSN:1944-8244. (American Chemical Society)
      A porous Si (pSi) microparticle-based delivery system is investigated, and the intrinsic luminescence from the particles is employed as a probe to monitor the release of a model protein payload, bovine serum albumin (BSA). The microparticles consist of a core Si skeleton surrounded by a SiO2 shell. Two types of pSi are tested, one with smaller (10 nm) pores and the other with larger (20 nm) pores. The larger pore material yields a higher mass loading of BSA (3 vs 20%). Two different methods are used to load BSA into these nanostructures: the first involves loading by electrostatic physisorption, and the second involves trapping of BSA in the pSi matrix by local pptn. of magnesium silicate. Protein release from the former system is characterized by a burst release, whereas in the latter system, release is controlled by dissoln. of the pSi/magnesium silicate matrix. The protein release characteristics are studied under accelerated (0.1 M aq. KOH, 21 °C) and physiol. relevant (phosphate-buffered saline, pH 7.4, 37 °C) conditions, and the near-IR photoluminescence signal from the pSi skeleton is monitored as a function of time and correlated with protein release and silicon dissoln. The thickness of the Si core and the SiO2 shell are systematically varied, and it is found that the luminescence signature can be tuned to provide a signal that either scales with protein elution or that changes rapidly near the end of useful life of the delivery system. Although payload release and particle dissoln. are not driven by the same mechanism, the correlations between luminescence and payload elution for the various formulations can be used to define design rules for this self-reporting delivery system.
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      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC2sXitVelt7rL&md5=b2654910383b8f1b78886e06a2e465f8
    5. 5
      Singh, N.; Karambelkar, A.; Gu, L.; Lin, K.; Miller, J. S.; Chen, C. S.; Sailor, M. J.; Bhatia, S. N. Bioresponsive Mesoporous Silica Nanoparticles for Triggered Drug Release. J. Am. Chem. Soc. 2011, 133, 19582– 19585,  DOI: 10.1021/ja206998x
      5
      Bioresponsive Mesoporous Silica Nanoparticles for Triggered Drug Release
      Singh, Neetu; Karambelkar, Amrita; Gu, Luo; Lin, Kevin; Miller, Jordan S.; Chen, Christopher S.; Sailor, Michael J.; Bhatia, Sangeeta N.
      Journal of the American Chemical Society (2011), 133 (49), 19582-19585CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
      Mesoporous silica nanoparticles (MSNPs) have garnered a great deal of attention as potential carriers for therapeutic payloads. However, achieving triggered drug release from MSNPs in vivo has been challenging. Here, we describe the synthesis of stimulus-responsive polymer-coated MSNPs and the loading of therapeutics into both the core and shell domains. We characterize MSNP drug-eluting properties in vitro and demonstrate that the polymer-coated MSNPs release doxorubicin in response to proteases present at a tumor site in vivo, resulting in cellular apoptosis. These results demonstrate the utility of polymer-coated nanoparticles in specifically delivering an antitumor payload.
      >> More from SciFinder ®
      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC3MXht1OrtrvL&md5=e660e1f2d1ea200be0f3fa1e0c87927c
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      Tavolaro, A.; Riccio, I. I.; Tavolaro, P. Hydrothermal Synthesis of Zeolite Composite Membranes and Crystals as Potential Vectors for Drug-Delivering Biomaterials. Microporous Mesoporous Mater. 2013, 167, 62– 70,  DOI: 10.1016/j.micromeso.2012.04.024
      6
      Hydrothermal synthesis of zeolite composite membranes and crystals as potential vectors for drug-delivering biomaterials
      Tavolaro, Adalgisa; Riccio, Ilaria Iolanda; Tavolaro, Palmira
      Microporous and Mesoporous Materials (2013), 167 (), 62-70CODEN: MIMMFJ; ISSN:1387-1811. (Elsevier Inc.)
      We synthesized various zeolite nanocrystals and composite membranes with mordenite (MOR), ZSM-5, and B-silicalite (MFI) structures under hydrothermal conditions and we demonstrated their ability to immobilize famotidine. Ion-exchange expts. using metal salt solns. were carried out to obtain Cu(II)- and Zn(II)-contg. nanosized crystals. All zeolite particles were synthesized obtaining high purity, as evidenced by powder X-ray diffraction (XRD) anal. performed on the zeolite crystals and scraped films. The crystal and membrane morphologies and sizes were detd. by SEM (FESEM). The equil. and kinetic characteristics of the drug on these materials were studied by varying the incubation time, the famotidine concn. and the pH values. The adsorption percentage of the drug at pH 7.4 in both Cu-MOR and B-MFI crystals was obsd. to be higher than that obtained with Cu-ZSM-5, Zn-ZSM-5, and Zn-MOR. The desorption behavior of B-silicalite after 1 h is remarkable and has important implications for biomedical applications.
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      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC38XhvVyhsLrL&md5=26fe40e7a13f5d38a72cb3fe697c6bdf
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      Huxford, R. C.; Della Rocca, J.; Lin, W. Metal–organic Frameworks as Potential Drug Carriers. Curr. Opin. Chem. Biol. 2010, 14, 262– 268,  DOI: 10.1016/J.CBPA.2009.12.012
      7
      Metal-organic frameworks as potential drug carriers
      Huxford, Rachel C.; Della Rocca, Joseph; Lin, Wen-Bin
      Current Opinion in Chemical Biology (2010), 14 (2), 262-268CODEN: COCBF4; ISSN:1367-5931. (Elsevier B.V.)
      A review. Nanoparticle-based therapeutics have received increasing attention, as these systems can alleviate many drawbacks of conventional therapy. Metal-org. frameworks (MOFs), a new class of hybrid materials composed of metal ions and org. bridging ligands, have emerged as a promising platform for drug delivery, owing to their high drug loadings, biodegradability, and versatile functionality. The bulk MOF materials can absorb and release large amts. of therapeutics including ibuprofen, procainamide, and nitric oxide. Scale-down of MOFs to the nanoregime yields nanoscale metal-org. frameworks (NMOFs) that are more applicable as delivery vehicles, such as selective delivery of cisplatin prodrugs. Although progress has been made in utilizing NMOFs for drug delivery, many improvements must occur before they can become viable nanotherapeutics.
      >> More from SciFinder ®
      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC3cXjvFKntL0%253D&md5=365c75653f51604ece60a09cb5926d02
    8. 8
      Rojas, S.; Colinet, I.; Cunha, D.; Hidalgo, T.; Salles, F.; Serre, C.; Guillou, N.; Horcajada, P. Toward Understanding Drug Incorporation and Delivery from Biocompatible Metal–organic Frameworks in View of Cutaneous Administration. ACS Omega 2018, 3, 2994– 3003,  DOI: 10.1021/acsomega.8b00185
      8
      Toward Understanding Drug Incorporation and Delivery from Biocompatible Metal-Organic Frameworks in View of Cutaneous Administration
      Rojas, Sara; Colinet, Isabel; Cunha, Denise; Hidalgo, Tania; Salles, Fabrice; Serre, Christian; Guillou, Nathalie; Horcajada, Patricia
      ACS Omega (2018), 3 (3), 2994-3003CODEN: ACSODF; ISSN:2470-1343. (American Chemical Society)
      Although metal-org. frameworks (MOFs) have widely demonstrated their convenient performances as drug-delivery systems, there is still work to do to fully understand the drug incorporation/delivery processes from these materials. In this work, a combined exptl. and computational investigation of the main structural and physicochem. parameters driving drug adsorption/desorption kinetics was carried out. Two model drugs (aspirin and ibuprofen) and three water-stable, biocompatible MOFs (MIL-100(Fe), UiO-66(Zr), and MIL-127(Fe)) have been selected to obtain a variety of drug-matrix couples with different structural and physicochem. characteristics. This study evidenced that the drug-loading and drug-delivery processes are mainly governed by structural parameters (accessibility of the framework and drug vol.) as well as the MOF/drug hydrophobic/hydrophilic balance. As a result, the delivery of the drug under simulated cutaneous conditions (aq. media at 37 °C) demonstrated that these systems fulfill the requirements to be used as topical drug-delivery systems, such as released payload between 1 and 7 days. These results highlight the importance of the rational selection of MOFs, evidencing the effect of geometrical and chem. parameters of both the MOF and the drug on the drug adsorption and release.
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      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC1cXkt1KqsrY%253D&md5=5ff01dcb26a663a563eb185610dd7582
    9. 9
      Horcajada, P.; Chalati, T.; Serre, C.; Gillet, B.; Sebrie, C.; Baati, T.; Eubank, J. F.; Heurtaux, D.; Clayette, P.; Kreuz, C. Porous Metal-organic-Framework Nanoscale Carriers as a Potential Platform for Drug Delivery and Imaging. Nat. Mater. 2010, 9, 172– 178,  DOI: 10.1038/nmat2608
      9
      Porous metal-organic-framework nanoscale carriers as a potential platform for drug delivery and imaging
      Horcajada, Patricia; Chalati, Tamim; Serre, Christian; Gillet, Brigitte; Sebrie, Catherine; Baati, Tarek; Eubank, Jarrod F.; Heurtaux, Daniela; Clayette, Pascal; Kreuz, Christine; Chang, Jong-San; Hwang, Young Kyu; Marsaud, Veronique; Bories, Phuong-Nhi; Cynober, Luc; Gil, Sophie; Ferey, Gerard; Couvreur, Patrick; Gref, Ruxandra
      Nature Materials (2010), 9 (2), 172-178CODEN: NMAACR; ISSN:1476-1122. (Nature Publishing Group)
      In the domain of health, one important challenge is the efficient delivery of drugs in the body using non-toxic nanocarriers. Most of the existing carrier materials show poor drug loading (usually less than 5 wt% of the transported drug vs. the carrier material) and/or rapid release of the proportion of the drug that is simply adsorbed (or anchored) at the external surface of the nanocarrier. In this context, porous hybrid solids, with the ability to tune their structures and porosities for better drug interactions and high loadings, are well suited to serve as nanocarriers for delivery and imaging applications. Here we show that specific non-toxic porous iron(III)-based metal-org. frameworks with engineered cores and surfaces, as well as imaging properties, function as superior nanocarriers for efficient controlled delivery of challenging antitumoral and retroviral drugs (i.e., busulfan, azidothymidine triphosphate, doxorubicin or cidofovir) against cancer and AIDS. In addn. to their high loadings, they also potentially assoc. therapeutics and diagnostics, thus opening the way for theranostics, or personalized patient treatments.
      >> More from SciFinder ®
      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC3cXhtVOnt70%253D&md5=74f3e60d481f39e0000fd93db0e40a64
    10. 10
      Horcajada, P.; Serre, C.; Maurin, G.; Ramsahye, N. A.; Balas, F.; Vallet-Regí, M.; Sebban, M.; Taulelle, F.; Férey, G. Flexible Porous Metal-organic Frameworks for a Controlled Drug Delivery. J. Am. Chem. Soc. 2008, 130, 6774– 6780,  DOI: 10.1021/ja710973k
      10
      Flexible Porous Metal-Organic Frameworks for a Controlled Drug Delivery
      Horcajada, Patricia; Serre, Christian; Maurin, Guillaume; Ramsahye, Naseem A.; Balas, Francisco; Vallet-Regi, Marila; Sebban, Muriel; Taulelle, Francis; Ferey, Geard
      Journal of the American Chemical Society (2008), 130 (21), 6774-6780CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
      Flexible nanoporous chromium or iron terephthalates (BDC) MIL-53(Cr, Fe) or M(OH)[BDC] have been used as matrixes for the adsorption and in vitro drug delivery of Ibuprofen (or α-p-isobutylphenylpropionic acid). Both MIL-53(Cr) and MIL-53(Fe) solids adsorb around 20 wt % of Ibuprofen (Ibuprofen/dehydrated MIL-53 molar ratio = 0.22(1)), indicating that the amt. of inserted drug does not depend on the metal (Cr, Fe) constitutive of the hybrid framework. Structural and spectroscopic characterizations are provided for the solid filled with Ibuprofen. In each case, the very slow and complete delivery of Ibuprofen was achieved under physiol. conditions after 3 wk with a predictable zero-order kinetics, which highlights the unique properties of flexible hybrid solids for adapting their pore opening to optimize the drug-matrix interactions.
      >> More from SciFinder ®
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    11. 11
      Miller, S. R.; Heurtaux, D.; Baati, T.; Horcajada, P.; Grenèche, J.-M.; Serre, C. Biodegradable Therapeutic MOFs for the Delivery of Bioactive Molecules. Chem. Commun. 2010, 46, 4526– 4528,  DOI: 10.1039/c001181a
      11
      Biodegradable therapeutic MOFs for the delivery of bioactive molecules
      Miller, Stuart R.; Heurtaux, Daniela; Baati, Tarek; Horcajada, Patricia; Greneche, Jean-Marc; Serre, Christian
      Chemical Communications (Cambridge, United Kingdom) (2010), 46 (25), 4526-4528CODEN: CHCOFS; ISSN:1359-7345. (Royal Society of Chemistry)
      A new metal org. framework (MOF) built up from non-toxic iron and the therapeutically active linker nicotinic acid, with pellagra-curative, vasodilating, and antilipemic properties, has been isolated and characterized via single crystal methods. The release of the therapeutic agent, which is a constituent of the framework, is achieved through the degrdn. of the hybrid phase, under simulated physiol. conditions, allowing for the delivery of the bioactive mol.
      >> More from SciFinder ®
      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC3cXnsF2itL8%253D&md5=7454e595280ccb91d13aa1ab3363f723
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      Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O’Keeffe, M.; Yaghi, O. M. Modular Chemistry: Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal–organic Carboxylate Frameworks. Acc. Chem. Res. 2001, 34, 319– 330,  DOI: 10.1021/AR000034B
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      Modular Chemistry: Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal-Organic Carboxylate Frameworks
      Eddaoudi, Mohamed; Moler, David B.; Li, Hailian; Chen, Banglin; Reineke, Theresa M.; O'Keeffe, Michael; Yaghi, Omar M.
      Accounts of Chemical Research (2001), 34 (4), 319-330CODEN: ACHRE4; ISSN:0001-4842. (American Chemical Society)
      A review, with 38 refs. Secondary building units (SBUs) are mol. complexes and cluster entities in which ligand coordination modes and metal coordination environments can be used in the transformation of these fragments into extended porous networks using polytopic linkers (1,4-benzenedicarboxylate, 1,3,5,7-adamantanetetracarboxylate, etc.). Consideration of the geometric and chem. attributes of the SBUs and linkers leads to prediction of the framework topol., and in turn to the design and synthesis of a new class of porous materials with robust structures and high porosity.
      >> More from SciFinder ®
      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BD3MXhtFymsL0%253D&md5=e3df2f7492090aee280676f044e3b7af
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      Ruiz, M. A.; Sua, A.; Tian, F. Covalent Attachment of Metal-organic Framework Thin Films on Surfaces. In Encyclopedia of Interfacial Chemistry: Surface Science and Electrochemistry; Elsevier: 2018; Vol. 4, pp 646– 671.
      There is no corresponding record for this reference.
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      Li, J.-R.; Kuppler, R. J.; Zhou, H.-C. Selective Gas Adsorption and Separation in Metal-organic Frameworks. Chem. Soc. Rev. 2009, 38, 1477– 1504,  DOI: 10.1039/b802426j
      14
      Selective gas adsorption and separation in metal-organic frameworks
      Li, Jian-Rong; Kuppler, Ryan J.; Zhou, Hong-Cai
      Chemical Society Reviews (2009), 38 (5), 1477-1504CODEN: CSRVBR; ISSN:0306-0012. (Royal Society of Chemistry)
      A review. Adsorptive sepn. is very important in industry. Generally, the process uses porous solid materials such as zeolites, activated carbons, or silica gels as adsorbents. With an ever increasing need for a more efficient, energy-saving, and environmentally benign procedure for gas sepn., adsorbents with tailored structures and tunable surface properties must be found. Metal-org. frameworks (MOFs), constructed by metal-contg. nodes connected by org. bridges, are such a new type of porous materials. They are promising candidates as adsorbents for gas sepns. due to their large surface areas, adjustable pore sizes and controllable properties, as well as acceptable thermal stability. This crit. review starts with a brief introduction to gas sepn. and purifn. based on selective adsorption, followed by a review of gas selective adsorption in rigid and flexible MOFs. Based on possible mechanisms, selective adsorptions obsd. in MOFs are classified, and primary relationships between adsorption properties and framework features are analyzed. As a specific example of tailor-made MOFs, mesh-adjustable mol. sieves are emphasized and the underlying working mechanism elucidated. In addn. to the exptl. aspect, theor. investigations from adsorption equil. to diffusion dynamics via mol. simulations are also briefly reviewed. Furthermore, gas sepns. in MOFs, including the mol. sieving effect, kinetic sepn., the quantum sieving effect for H2/D2 sepn., and MOF-based membranes are also summarized (227 refs.).
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      Farrusseng, D.; Aguado, S.; Pinel, C. Metal-organic Frameworks: Opportunities for Catalysis. Angew. Chem., Int. Ed. 2009, 48, 7502– 7513,  DOI: 10.1002/anie.200806063
      15
      Metal-Organic Frameworks: Opportunities for Catalysis
      Farrusseng, David; Aguado, Sonia; Pinel, Catherine
      Angewandte Chemie, International Edition (2009), 48 (41), 7502-7513CODEN: ACIEF5; ISSN:1433-7851. (Wiley-VCH Verlag GmbH & Co. KGaA)
      A review; the role of metal-org. frameworks (MOFs) in the field of catalysis is discussed, and special focus is placed on their assets and limits in light of current challenges in catalysis and green chem. Their structural and dynamic features are presented in terms of catalytic functions along with how MOFs can be designed to bridge the gap between zeolites and enzymes. The contributions of MOFs to the field of catalysis are comprehensively reviewed and a list of catalytic candidates is given. The subject is presented from a multidisciplinary point of view covering solid-state chem., materials science, and catalysis.
      >> More from SciFinder ®
      https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BD1MXht1Sru73L&md5=70017c2bece6b49b77ca02a915c7a5d2
    16. 16
      Kuo, C.-H.; Tang, Y.; Chou, L.-Y.; Sneed, B. T.; Brodsky, C. N.; Zhao, Z.; Tsung, C.-K. Yolk-Shell Nanocrystal@ZIF-8 Nanostructures for Gas-Phase Heterogeneous Catalysis with Selectivity Control. J. Am. Chem. Soc. 2012, 134, 14345– 14348,  DOI: 10.1021/ja306869j
      16
      Yolk-Shell Nanocrystal@ZIF-8 Nanostructures for Gas-Phase Heterogeneous Catalysis with Selectivity Control
      Kuo, Chun-Hong; Tang, Yang; Chou, Lien-Yang; Sneed, Brian T.; Brodsky, Casey N.; Zhao, Zipeng; Tsung, Chia-Kuang
      Journal of the American Chemical Society (2012), 134 (35), 14345-14348CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
      A general synthetic strategy for yolk-shell nanocrystal@ZIF-8 nanostructures has been developed. The yolk-shell nanostructures possess the functions of nanoparticle cores, microporous shells, and a cavity in between, which offer great potential in heterogeneous catalysis. The synthetic strategy involved first coating the nanocrystal cores with a layer of Cu2O as the sacrificial template and then a layer of polycryst. ZIF-8. The clean Cu2O surface assists in the formation of the ZIF-8 coating layer and is etched off spontaneously and simultaneously during this process. The yolk-shell nanostructures were characterized by transmission electron microscopy, SEM, X-ray diffraction, and nitrogen adsorption. To study the catalytic behavior, hydrogenations of ethylene, cyclohexene, and cyclooctene as model reactions were carried out over the Pd@ZIF-8 catalysts. The microporous ZIF-8 shell provides excellent mol.-size selectivity. The results show high activity for the ethylene and cyclohexene hydrogenations but not in the cyclooctene hydrogenation. Different activation energies for cyclohexene hydrogenation were obtained for nanostructures with and without the cavity in between the core and the shell. This demonstrates the importance of controlling the cavity because of its influence on the catalysis.
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    17. 17
      Yang, J.; Zhang, F.; Lu, H.; Hong, X.; Jiang, H.; Wu, Y.; Li, Y. Hollow Zn/Co ZIF Particles Derived from Core-Shell ZIF-67@ZIF-8 as Selective Catalyst for the Semi-Hydrogenation of Acetylene. Angew. Chem., Int. Ed. 2015, 127, 11039– 11043,  DOI: 10.1002/ange.201504242
      There is no corresponding record for this reference.
    18. 18
      Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. Commercial Metal-organic Frameworks as Heterogeneous Catalysts. Chem. Commun. 2012, 48, 11275– 11288,  DOI: 10.1039/c2cc34329k
      18
      Commercial metal-organic frameworks as heterogeneous catalysts
      Dhakshinamoorthy, Amarajothi; Alvaro, Mercedes; Garcia, Hermenegildo
      Chemical Communications (Cambridge, United Kingdom) (2012), 48 (92), 11275-11288CODEN: CHCOFS; ISSN:1359-7345. (Royal Society of Chemistry)
      A review. Metal-org. frameworks (MOFs) are porous cryst. materials that have promising applications as heterogeneous catalysts. After describing the compn., textural properties and crystal structure of four com. available MOFs, the authors summarize org. transformations for which these com. MOFs exhibit higher catalytic activity than the corresponding sol. metal salts or metal ion-exchanged zeolites. The authors have focused on reactions requiring Lewis-acid sites or redox centers to illustrate the potential applications and limitations of com. MOFs. In a final section, the authors provide the views on future developments whose ultimate target will be the use of a com. MOF as a heterogeneous catalyst for a real industrial process in fine chem., thus, realizing the advantages of these materials with respect to zeolites or other solid catalysts in liq.-phase reactions.
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    19. 19
      Giménez-Marqués, M.; Hidalgo, T.; Serre, C.; Horcajada, P. Nanostructured Metal–organic Frameworks and Their Bio-Related Applications. Coord. Chem. Rev. 2016, 307, 342– 360,  DOI: 10.1016/j.ccr.2015.08.008
      19
      Nanostructured metal-organic frameworks and their bio-related applications
      Gimenez-Marques, M.; Hidalgo, T.; Serre, C.; Horcajada, P.
      Coordination Chemistry Reviews (2016), 307 (Part_2), 342-360CODEN: CCHRAM; ISSN:0010-8545. (Elsevier B.V.)
      Miniaturization of metal-org. frameworks (MOFs) results of great interest in order to integrate these materials in strategic applications such as sensing or drug delivery. This emerging class of nanoscaled MOFs (nanoMOFs), combining the intrinsic properties of the porous materials and the benefits of nanostructures, are expected to improve in some cases the performances of classical bulk cryst. MOFs. In the field of biomedicine, the benefits of MOF miniaturization have already been proved to be effective, not only because establishes a strong influence over the choice of the administration route but also governs their in vivo fate and therefore, their toxicity and/or activity.The scope of this review focuses on the prepn. of nanostructured MOFs and their related biomedical applications. We will cover all aspects concerning the various synthetic methods reported so far, as well as the shaping and surface engineering routes required for their use in biomedicine.
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    20. 20
      Gaudin, C.; Cunha, D.; Ivanoff, E.; Horcajada, P.; Chevé, G.; Yasri, A.; Loget, O.; Serre, C.; Maurin, G. A Quantitative Structure Activity Relationship Approach to Probe the Influence of the Functionalization on the Drug Encapsulation of Porous Metal-organic Frameworks. Microporous Mesoporous Mater. 2012, 157, 124– 130,  DOI: 10.1016/j.micromeso.2011.06.011
      20
      A quantitative structure activity relationship approach to probe the influence of the functionalization on the drug encapsulation of porous metal-organic frameworks
      Gaudin, C.; Cunha, D.; Ivanoff, E.; Horcajada, P.; Cheve, G.; Yasri, A.; Loget, O.; Serre, C.; Maurin, G.
      Microporous and Mesoporous Materials (2012), 157 (), 124-130CODEN: MIMMFJ; ISSN:1387-1811. (Elsevier Inc.)
      A series of 10 MIL-88B(Fe) iron(III) dicarboxylate MOFs wherein the org. linker is functionalized by a large variety of polar and apolar functional groups (-H, -Br, -F, -CF3, -CH3, -NH2, -NO2, -OH) was investigated as a potential carrier for encapsulating drugs, using the cosmetic amphiphilic caffeine as a model mol. Encapsulation using impregnation followed by thermogravimetric anal. (TGA) and high performance liq. chromatog. (HPLC) measurements to quant. est. the caffeine uptake, have been first performed on the functionalized MIL-88B(Fe) samples. This set of exptl. data was further used as an ideal platform to conduct a quant. structure activity relationship approach based on multiple linear regression (MLR) method with the aim to find out the most relevant chem. and structural features of the MIL-88B(Fe) that significantly affect the therapeutic mol. uptake. Individual QSAR models showed that tuning the polarity and the H-donor capacity of the org. linker can enhance the caffeine encapsulation, suggesting that the functional groups serve as anchoring points for the drug mol., consistent with previous conclusions drawn from mol. simulations performed on similar functionalized MOFs. Consensus modeling approach based on the selection of the most diverse individual models was also employed to build more representative QSAR models over the chem. space that could be further used to predict the drug encapsulation performance of the MOFs grafted by other functional groups.
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    21. 21
      Wu, M.-X.; Yang, Y.-W. Metal-organic Framework (MOF)-Based Drug/Cargo Delivery and Cancer Therapy. Adv. Mater. 2017, 29, 1606134,  DOI: 10.1002/adma.201606134
      There is no corresponding record for this reference.
    22. 22
      Keskin, S.; Kızılel, S. Biomedical Applications of Metal organic Frameworks. Ind. Eng. Chem. Res. 2011, 50, 1799– 1812,  DOI: 10.1021/ie101312k
      22
      Biomedical Applications of Metal Organic Frameworks
      Keskin, Seda; Kizilel, Seda
      Industrial & Engineering Chemistry Research (2011), 50 (4), 1799-1812CODEN: IECRED; ISSN:0888-5885. (American Chemical Society)
      A review. We have witnessed a rapid growth in the field of a new nanoporous material group, metal org. frameworks (MOFs), over the past decade. MOFs possess a wide array of potential applications in chem. engineering, chem., and materials science, including gas storage, gas sepn., and catalysis. One of the areas MOFs started to appear recently is biomedical applications. The unique phys. and chem. characteristics of MOFs make them promising candidates for drug storage and drug delivery, nitric oxide storage and delivery, imaging, and sensing. In this review, we outline the recent progress of using MOFs as a promising platform in biomedical applications due to their high drug loading capacity, biodegradability, and versatile functionality. We also demonstrate the potential of MOFs for continuous development and implementation in biomedical applications by discussing issues including stability, toxicol., and biocompatibility. Although significant progress has been made in utilizing MOFs for biomedical applications, further improvements must still occur before MOFs can become viable therapeutics options.
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    23. 23
      Huang, W.; Tsui, C. P.; Tang, C. Y.; Gu, L. Effects of Compositional Tailoring on Drug Delivery Behaviours of Silica Xerogel/Polymer Core-Shell Composite Nanoparticles. Sci. Rep. 2018, 8, 13002,  DOI: 10.1038/s41598-018-31070-9
      23
      Effects of Compositional Tailoring on Drug Delivery Behaviours of Silica Xerogel/Polymer Core-shell Composite Nanoparticles
      Huang Wenfei; Tsui Chi Pong; Tang Chak Yin; Gu Linxia
      Scientific reports (2018), 8 (1), 13002 ISSN:.
      Conventional core-shell polymer nanoparticles usually exhibit a rapid release rate with their release kinetics mainly adjusted through changing composition of the polymer shells, limiting their applications for prolonged drug delivery. As a solution to these problems, silica xerogel/polymer core-shell-structured composite nanoparticles have been proposed. Different with our previous work centring on studying process variables, we here focused on investigating the effects of key compositional variables on essential properties of the composite nanoparticles. The drug release profiles (in vitro) were well interpreted by the Baker and Lonsdale model on a predicted two-stage basis. The first stage (<1 day) was well controlled from 18.6% to 45.9%; the second stage (1-14 days) was tailored in a range from 28.7 to 58.2% by changing the composition of the silica xerogel cores and polymeric shells. A substantial achievement was reducing the release rate by more than 40 times compared with that of conventional polymer nanoparticles by virtue of the silica xerogel cores. A semi-empirical model was also established in the first attempt to describe the effects of polymer concentration and drug loading capacity on the size of the composite nanoparticles. All these results indicated that the composite nanoparticles are promising candidates for prolonged drug delivery applications.
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    24. 24
      Cullis, P. R.; Mayer, L. D.; Bally, M. B.; Madden, T. D.; Hope, M. J. Generating and Loading of Liposomal Systems for Drug-Delivery Applications. Adv. Drug Delivery Rev. 1989, 3, 267– 282,  DOI: 10.1016/0169-409X
      24
      Generating and loading of liposomal systems for drug-delivery applications
      Cullis, P. R.; Mayer, L. D.; Bally, M. B.; Madden, T. D.; Hope, M. J.
      Advanced Drug Delivery Reviews (1989), 3 (3), 267-82CODEN: ADDREP; ISSN:0169-409X.
      A review with 53 refs. Factors affecting the design of liposomal systems, methods of generating liposomes, and methods of loading liposomes with drugs are discussed.
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    25. 25
      Tamames-Tabar, C.; Cunha, D.; Imbuluzqueta, E.; Ragon, F.; Serre, C.; Blanco-Prieto, M. J.; Horcajada, P. Cytotoxicity of Nanoscaled Metal–organic Frameworks. J. Mater. Chem. B 2014, 2, 262– 271,  DOI: 10.1039/C3TB20832J
      25
      Cytotoxicity of nanoscaled metal-organic frameworks
      Tamames-Tabar, Cristina; Cunha, Denise; Imbuluzqueta, Edurne; Ragon, Florence; Serre, Christian; Blanco-Prieto, Maria J.; Horcajada, Patricia
      Journal of Materials Chemistry B: Materials for Biology and Medicine (2014), 2 (3), 262-271CODEN: JMCBDV; ISSN:2050-7518. (Royal Society of Chemistry)
      A series of fourteen porous Metal-Org. Frameworks (MOFs) with different compns. (Fe, Zn, and Zr; carboxylates or imidazolates) and structures have been successfully synthesized at the nanoscale and fully characterised by XRPD, FTIR, TGA, N2 porosimetry, TEM, DLS and ζ-potential. Their toxicol. assessment was performed using two different cell lines: human epithelial cells from fetal cervical carcinoma (HeLa) and murine macrophage cell line (J774). It appears that MOF nanoparticles (NPs) exhibit low cytotoxicity, comparable to those of other commercialised nanoparticulate systems, the less toxic being the Fe carboxylate and the more toxic being the zinc imidazolate NPs. The cytotoxicity values, higher in J774 cells than in HeLa cells, are mainly function of their compn. and cell internalisation capacity. Finally, cell uptake of one of the most relevant Fe-MOF-NPs for drug vectorization has been investigated by confocal microscopy studies, and indicates a faster kinetics of cell penetration within J774 compared to HeLa cells.
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    26. 26
      Filippousi, M.; Turner, S.; Leus, K.; Siafaka, P. I.; Tseligka, E. D.; Vandichel, M.; Nanaki, S. G.; Vizirianakis, I. S.; Bikiaris, D. N.; Van Der Voort, P. Biocompatible Zr-Based Nanoscale MOFs Coated with Modified Poly(ε-Caprolactone) as Anticancer Drug Carriers. Int. J. Pharm. 2016, 509, 208– 218,  DOI: 10.1016/J.IJPHARM.2016.05.048
      26
      Biocompatible Zr-based nanoscale MOFs coated with modified poly(ε-caprolactone) as anticancer drug carriers
      Filippousi, Maria; Turner, Stuart; Leus, Karen; Siafaka, Panoraia I.; Tseligka, Eirini D.; Vandichel, Matthias; Nanaki, Stavroula G.; Vizirianakis, Ioannis S.; Bikiaris, Dimitrios N.; Van Der Voort, Pascal; Van Tendeloo, Gustaaf
      International Journal of Pharmaceutics (Amsterdam, Netherlands) (2016), 509 (1-2), 208-218CODEN: IJPHDE; ISSN:0378-5173. (Elsevier B.V.)
      Nanoscale Zr-based metal org. frameworks (MOFs) UiO-66 and UiO-67 were studied as potential anticancer drug delivery vehicles. Two model drugs were used, hydrophobic paclitaxel and hydrophilic cisplatin, and were adsorbed onto/into the nano MOFs (NMOFs). The drug loaded MOFs were further encapsulated inside a modified poly(ε-caprolactone) with D-α-tocopheryl polyethylene glycol succinate polymeric matrix, in the form of microparticles, in order to prep. sustained release formulations and to reduce the drug toxicity. The drugs phys. state and release rate was studied at 37 °C using Simulated Body Fluid. It was found that the drug release depends on the interaction between the MOFs and the drugs while the controlled release rates can be attributed to the microencapsulated formulations. The in vitro antitumor activity was assessed using HSC-3 (human oral squamous carcinoma; head and neck) and U-87 MG (human glioblastoma grade IV; astrocytoma) cancer cells. Cytotoxicity studies for both cell lines showed that the polymer coated, drug loaded MOFs exhibited better anticancer activity compared to free paclitaxel and cisplatin solns. at different concns.
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    27. 27
      Al Haydar, M.; Abid, H.; Sunderland, B.; Wang, S. Metal organic Frameworks as a Drug Delivery System for Flurbiprofen. Drug Des., Dev. Ther. 2017, Volume 11, 2685– 2695,  DOI: 10.2147/DDDT.S145716
      There is no corresponding record for this reference.
    28. 28
      Horcajada, P.; Salles, F.; Wuttke, S.; Devic, T.; Heurtaux, D.; Maurin, G.; Vimont, A.; Daturi, M.; David, O.; Magnier, E. How Linker’s Modification Controls Swelling Properties of Highly Flexible Iron(III) Dicarboxylates MIL-88. J. Am. Chem. Soc. 2011, 133, 17839– 17847,  DOI: 10.1021/ja206936e
      28
      How Linker's Modification Controls Swelling Properties of Highly Flexible Iron(III) Dicarboxylates MIL-88
      Horcajada, Patricia; Salles, Fabrice; Wuttke, Stefan; Devic, Thomas; Heurtaux, Daniela; Maurin, Guillaume; Vimont, Alexandre; Daturi, Marco; David, Olivier; Magnier, Emmanuel; Stock, Norbert; Filinchuk, Yaroslav; Popov, Dmitry; Riekel, Christian; Ferey, Gerard; Serre, Christian
      Journal of the American Chemical Society (2011), 133 (44), 17839-17847CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
      Organically modified Fe(III) terephthalate MIL-88B and Fe(III) 4,4'-biphenyl dicarboxylate MIL-88D flexible solids were synthesized and characterized through a combination of x-ray diffraction, IR spectroscopy, and thermal anal. (MIL stands for Material from Institut Lavoisier). The swelling amplitude of the highly flexible MOFs tuned by introducing functional groups onto the Ph rings shows a clear dependence on the steric hindrance and on the no. of groups per arom. ring. For instance, while the introduction of four Me groups per spacer in dried MIL-88B results in a large permanent porosity, introducing two or four Me groups in MIL-88D allows an easier pore opening in the presence of liqs. without drastically decreasing the swelling magnitude. The influence of the degree of satn. of the metal center and the nature of the solvent on the swelling is also discussed. Finally, a computationally assisted structure detn. led to a proposal of plausible structures for the closed (dried) and open forms of modified MIL-88B and MIL-88D and to evaluation of their framework energies subject to the nature of the functional groups.
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    29. 29
      Serre, C.; Surblé, S.; Mellot-Draznieks, C.; Filinchuk, Y.; Férey, G. Evidence of Flexibility in the Nanoporous Iron(Iii) Carboxylate MIL-89. Dalton Trans. 2008, 0, 5462,  DOI: 10.1039/b805408h
      29
      Evidence of flexibility in the nanoporous iron(iii) carboxylate MIL-89
      Serre, C.; Surble, S.; Mellot-Draznieks, C.; Filinchuk, Y.; Ferey, G.
      Dalton Transactions (2008), (40), 5462-5464CODEN: DTARAF; ISSN:1477-9226. (Royal Society of Chemistry)
      The very large expansion upon adsorption of liqs., up to 160% in cell vol., has been obsd. in the iron(iii) trans,trans muconate MIL-89 [MIL = Material Institut Lavoisier]. The structure of lutidine-contg. MIL-89 (lutidine = 2,6-dimethylpyridine) has been detd. using X-ray powder diffraction and computer simulations. Finally, the consequences of adsorption of various polar and apolar liqs. have been evaluated using ex situ synchrotron X-ray powder diffraction data and reveals that the swelling behavior of MIL-89 is selective but slightly different from the MIL-88 analogs.
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    30. 30
      Surblé, S.; Serre, C.; Mellot-Draznieks, C.; Millange, F.; Férey, G. A New Isoreticular Class of Metal-organic-Frameworks with the MIL-88 Topology. Chem. Commun. 2006, 3, 284– 286,  DOI: 10.1039/b512169h
      There is no corresponding record for this reference.
    31. 31
      McKinlay, A. C.; Morris, R. E.; Horcajada, P.; Férey, G.; Gref, R.; Couvreur, P.; Serre, C. BioMOFs: Metal-organic Frameworks for Biological and Medical Applications. Angew. Chem. Int. Ed. 2010, 49, 6260– 6266,  DOI: 10.1002/anie.201000048
      31
      BioMOFs: Metal-Organic Frameworks for Biological and Medical Applications
      McKinlay, Alistair C.; Morris, Russell E.; Horcajada, Patricia; Ferey, Gerard; Gref, Ruxandra; Couvreur, Patrick; Serre, Christian
      Angewandte Chemie, International Edition (2010), 49 (36), 6260-6266CODEN: ACIEF5; ISSN:1433-7851. (Wiley-VCH Verlag GmbH & Co. KGaA)
      A review. The class of highly porous materials called metal-org. frameworks offer many opportunities for applications across biol. and medicine. Their wide range of chem. compn. makes toxicol. acceptable formulation possible, and their high level of functionality enables possible applications as imaging agents and as delivery vehicles for therapeutic agents. The challenges in the area encompass not only the development of new solids but also improvements in the formulation and processing of the materials, including tailoring the morphol. and surface chem. of the frameworks to fit the proposed applications.
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    32. 32
      Scherb, C.; Schödel, A.; Bein, T. Directing the Structure of Metal-organic Frameworks by Oriented Surface Growth on an organic Monolayer. Angew. Chem. Int. 2008, 47, 5777– 5779,  DOI: 10.1002/anie.200704034
      32
      Directing the structure of metal-organic frameworks by oriented surface growth on an organic monolayer
      Scherb, Camilla; Schoedel, Alexander; Bein, Thomas
      Angewandte Chemie, International Edition (2008), 47 (31), 5777-5779CODEN: ACIEF5; ISSN:1433-7851. (Wiley-VCH Verlag GmbH & Co. KGaA)
      Crystal growth and structures of metal-org. frameworks (MOFs) based on iron and 1,4-benzenedicarboxylic (terephthalic) acid are investigated. A dramatic change in the MOFs crystn. takes place on moving from homogeneous nucleation in soln. to heterogeneous nucleation on a mercaptohexadecanoic acid (MHDA) self-assembled monolayer (SAM). Thus, the product of homogeneous nucleation is the MOF Fe-MIL-53, whereas in the same crystn. soln., oriented Fe-MIL-88B grows on a MHDA-functionalized gold surface.
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    33. 33
      Whitfield, T. R.; Wang, X.; Liu, L.; Jacobson, A. J. Metal-organic Frameworks Based on Iron Oxide Octahedral Chains Connected by Benzenedicarboxylate Dianions. Solid State Sci. 2005, 7, 1096– 1103,  DOI: 10.1016/J.SOLIDSTATESCIENCES.2005.03.007
      33
      Metal-organic frameworks based on iron oxide octahedral chains connected by benzenedicarboxylate dianions
      Whitfield, Tabatha R.; Wang, Xiqu; Liu, Lumei; Jacobson, Allan J.
      Solid State Sciences (2005), 7 (9), 1096-1103CODEN: SSSCFJ; ISSN:1293-2558. (Elsevier B.V.)
      Three new Fe benzenedicarboxylates were synthesized by solvothermal techniques, and their structures detd. from single crystal x-ray data: Fe(OH)(BDC)(py)0.85 (1), Fe(BDC)(DMF) (2), and Fe(BDC)(py)0.42(DMF)0.25 (3) (BDC = 1,4-benzenedicarboxylate, py = pyridine). 1 And 2 are the Fe(III)- and Fe(II)-structural analogs of the known Cr benzenedicarboxylate compd. (MIL-53). Both contain trans corner-sharing FeO6 octahedral chains connected by benzenedicarboxylate dianions. Compd. 3 contains chains of Fe O octahedra that share both corners and edges. Each chain is linked by BDC to six other chains to form a three-dimensional framework. Crystal data: 1, space group I2/a, a 6.889(2), b 11.073(3), c 18.280(6) Å, β 92.6(1)°; 2, space group Pn21a, a 19.422(2), b 7.3022(5), c 8.8468(7) Å; 3, space group P21/n, a 9.234(2), b 17.243(3), c 9.978(2) Å, β 93.9(1)°.
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    34. 34
      Huang, X.; Brazel, C. S. On the Importance and Mechanisms of Burst Release in Matrix-Controlled Drug Delivery Systems. J. Controlled Release 2001, 73, 121– 136,  DOI: 10.1016/S0168-3659(01)00248-6
      34
      On the importance and mechanisms of burst release in matrix-controlled drug delivery systems
      Huang, X.; Brazel, C. S.
      Journal of Controlled Release (2001), 73 (2-3), 121-136CODEN: JCREEC; ISSN:0168-3659. (Elsevier Science Ireland Ltd.)
      A review with refs. Although the significance of burst release in controlled delivery systems has not been entirely ignored, no successful theories have been put forth to fully describe the phenomenon. Despite the fact that the fast release of drug in a burst stage is utilized in certain drug administration strategies, the neg. effects brought about by burst can be pharmacol. dangerous and economically inefficient. Therefore a thorough understanding of the burst effect in controlled release systems is undoubtedly necessary. In this article, we review exptl. observations of burst release in monolithic polymer controlled drug delivery systems, theories of the phys. mechanisms causing burst, some of the unique ideas used to prevent burst, and the treatment of burst release in controlled release models.
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    35. 35
      Körber, M. PLGA Erosion: Solubility- or Diffusion-Controlled?. Pharm. Res. 2010, 27, 2414– 2420,  DOI: 10.1007/s11095-010-0232-5
      35
      PLGA erosion: solubility- or diffusion-controlled?
      Korber Martin
      Pharmaceutical research (2010), 27 (11), 2414-20 ISSN:.
      PURPOSE: To calculate the degradation time-dependent formation of water-soluble PLGA oligomers and to evaluate the relation between calculated oligomer formation and actual erosion of a PLGA-based delivery system. A proper model of the erosion process would be expected to facilitate forecasting of drug release profiles from PLGA matrices due to the close relationship of erosional mass loss and drug release described in the literature. METHODS: The molecular weight distribution (MWD), degradation and erosion behaviour of PLGA were characterized by gel permeation chromatography. RESULTS: PLGA was characterized by a lognormal distribution of mass fractions of individual molecular weights. Implementation of the pseudo-first-order reaction kinetics into the MWD function facilitated calculating the formation of water-soluble oligomers during degradation. The calculated soluble oligomer formation agreed excellently with measured erosional mass loss of a PLGA matrix in aqueous buffer, which suggested that the bulk erosion process was solely controlled by the kinetic of the formation of soluble oligomers and thus solubility-controlled and not diffusion-limited as conventionally assumed. CONCLUSION: The accurately calculated formation of soluble PLGA oligomers was in excellent agreement with the actual erosional mass loss of a PLGA matrix, suggesting that bulk erosion of PLGA represents a degradation-controlled dissolution process.
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    36. 36
      Peppas, N. A. Analysis of Fickian and Non-Fickian Drug Release from Polymers. Pharm. Acta Helv. 1985, 60, 110– 111
      36
      Analysis of Fickian and non-Fickian drug release from polymers
      Peppas, Nikolaos A.
      Pharmaceutica Acta Helvetiae (1985), 60 (4), 110-11CODEN: PAHEAA; ISSN:0031-6865.
      A simple, semiempirical equation is presented which can be used to analyze data of controlled release of water-sol. drugs from polymers. This equation predicts that the fractional release of drug is exponentially related to release time. The exponent n is characteristic of the mechanism of diffusional release. When n = 0.5, Fickian diffusion is obsd. and the release rate is dependent on t-0.5. When n = 1.0, case-II transport of the drug occurs and the release rate is independent of time (zero-order release kinetics).
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    37. 37
      Costa, P.; Sousa Lobo, J. M. Modeling and Comparison of Dissolution Profiles. Eur. J. Pharm. Sci. 2001, 13, 123– 133,  DOI: 10.1016/S0928-0987(01)00095-1
      37
      Modeling and comparison of dissolution profiles
      Costa, P.; Sousa Lobo, J. M.
      European Journal of Pharmaceutical Sciences (2001), 13 (2), 123-133CODEN: EPSCED; ISSN:0928-0987. (Elsevier Science Ireland Ltd.)
      A review with refs. Over recent years, drug release/dissoln. from solid pharmaceutical dosage forms has been the subject of intense and profitable scientific developments. Whenever a new solid dosage form is developed or produced, it is necessary to ensure that drug dissoln. occurs in an appropriate manner. The pharmaceutical industry and the registration authorities do focus, nowadays, on drug dissoln. studies. The quant. anal. of the values obtained in dissoln./release tests is easier when math. formulas that express the dissoln. results as a function of some of the dosage forms characteristics are used. In some cases, these mathematic models are derived from the theor. anal. of the occurring process. In most of the cases the theor. concept does not exist and some empirical equations have proved to be more appropriate. Drug dissoln. from solid dosage forms has been described by kinetic models in which the dissolved amt. of drug (Q) is a function of the test time, t or Q=f(t). Some anal. definitions of the Q(t) function are commonly used, such as zero order, first order, Hixson-Crowell, Weibull, Higuchi, Baker-Lonsdale, Korsmeyer-Peppas and Hopfenberg models. Other release parameters, such as dissoln. time (tx%), assay time (tx min), dissoln. efficacy (ED), difference factor (f1), similarity factor (f2) and Rescigno index (ξ1 and ξ2) can be used to characterize drug dissoln./release profiles.
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    38. 38
      Goutelle, S.; Maurin, M.; Rougier, F.; Barbaut, X.; Bourguignon, L.; Ducher, M.; Maire, P. The Hill Equation: A Review of Its Capabilities in Pharmacological Modelling. Fundam. Clin. Pharmacol. 2008, 22, 633– 648,  DOI: 10.1111/j.1472-8206.2008.00633.x
      38
      The Hill equation: a review of its capabilities in pharmacological modeling
      Goutelle, Sylvain; Maurin, Michel; Rougier, Florent; Barbaut, Xavier; Bourguignon, Laurent; Ducher, Michel; Maire, Pascal
      Fundamental & Clinical Pharmacology (2008), 22 (6), 633-648CODEN: FCPHEZ; ISSN:0767-3981. (Wiley-Blackwell)
      A review. The Hill equation was first introduced by A.V. Hill to describe the equil. relationship between oxygen tension and the satn. of Hb. In pharmacol., the Hill equation has been extensively used to analyze quant. drug-receptor relationships. Many pharmacokinetic-pharmacodynamic models have used the Hill equation to describe nonlinear drug dose-response relationships. Although the Hill equation is widely used, its many properties are not all well known. This article aims at reviewing the various properties of the Hill equation. The descriptive aspects of the Hill equation, in particular math. and graphical properties, are examd., and related to Hill's original work. The mechanistic aspect of the Hill equation, involving a strong connection with the Guldberg and Waage law of mass action, is also described. Finally, a probabilistic view of the Hill equation is examd. Here, we provide some new calcn. results, such as Fisher information and Shannon entropy, and we introduce multivariate probabilistic Hill equations. The main features and potential applications of this probabilistic approach are also discussed. Thus, within the same formalism, the Hill equation has many different properties which can be of great interest for those interested in math. modeling in pharmacol. and biosciences.
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    39. 39
      Xu, B.; Yang, H.; Cai, Y.; Yang, H.; Li, C. Preparation and Photocatalytic Property of Spindle-like MIL-88B(Fe) Nanoparticles. Inorg. Chem. Commun. 2016, 67, 29– 31,  DOI: 10.1016/J.INOCHE.2016.03.003
      39
      Preparation and photocatalytic property of spindle-like MIL-88B(Fe) nanoparticles
      Xu, Bo; Yang, He; Cai, Yong; Yang, Hongxun; Li, Cuncheng
      Inorganic Chemistry Communications (2016), 67 (), 29-31CODEN: ICCOFP; ISSN:1387-7003. (Elsevier B.V.)
      Fe(III) based nanoparticles MIL-88B(Fe) with spindle-like morphol. were synthesized by a facile method. TEM and SEM revealed that the MIL-88B(Fe) nanoparticles had an uniform size of ∼385 nm in length and 195 nm in width. The obtained nanoparticles were further characterized by powder XRD and UV-visible spectroscopy (UV-visible). Also, as MIL-88B(Fe) shows obvious adsorption in the visible region, it has good degrdn. activity for methylene blue (MB) and rhodamine B (RB) dye under visible light.
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    40. 40
      Shi, L.; Wang, T.; Zhang, H.; Chang, K.; Meng, X.; Liu, H.; Ye, J. An Amine-Functionalized Iron(III) Metal-organic Framework as Efficient Visible-Light Photocatalyst for Cr(VI) Reduction. Adv. Sci. 2015, 2, 1500006,  DOI: 10.1002/advs.201500006
      40
      An Amine-Functionalized Iron(III) Metal-Organic Framework as Efficient Visible-Light Photocatalyst for Cr(VI) Reduction
      Shi Li; Meng Xianguang; Wang Tao; Zhang Huabin; Chang Kun; Liu Huimin; Ye Jinhua
      Advanced science (Weinheim, Baden-Wurttemberg, Germany) (2015), 2 (3), 1500006 ISSN:2198-3844.
      The photocatalytic reduction of Cr(VI) is investigated over iron(III)-based metal-organic frameworks (MOFs) structured as MIL-88B. It is found that MIL-88B (Fe) MOFs, containing Fe3-μ3-oxo clusters, can be used as photocatalyst for the reduction of Cr(VI) under visible light irradiation, which is due to the direct excitation of Fe3-μ3-oxo clusters. The amine-functionalized MIL-88B (Fe) MOFs (denoted as NH2-MIL-88B (Fe)) shows much higher efficiency for the photocatalytic Cr(VI) reduction under visible-light irradiation compared with MIL-88B (Fe). It is revealed that in addition to the direct excitation of Fe3-μ3-oxo clusters, the amine functionality in NH2-MIL-88B (Fe) can also be excited and then transferred an electron to Fe3-μ3-oxo clusters, which is responsible for the enhanced photocatalytic activity for Cr(VI) reduction. The enhanced photocatalytic activity for Cr(VI) reduction is also achieved for other two amine-functionalized iron(III)-based MOFs (NH2-MIL-53 (Fe) and NH2-MIL-101 (Fe)).
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    41. 41
      Bragg, W. L. The Diffraction of Short Electromagnetic Waves by a Crystal. Proc. Camb. Philol. Soc. 1913, 17, 43– 57
      41
      Diffraction of Short Electromagnetic Waves by a Crystal
      Bragg, W. L.
      Proceedings of the Cambridge Philosophical Society (1913), 17 (), 43-57CODEN: PCPSA4; ISSN:0068-6735.
      A small bundle of X-rays is isolated by means of Pb screens with small holes. A small crystal is put in its path and beyond this a photographic plate perpendicular to the path. Besides the spot due to the ray itself, a complicated geometrical system of spots is shown on the plate. The crystal acts as a diffraction grating and the interference phenomena as shown by these spots are interpreted to throw light on crystal structure. In cubic ZnS the arrangement of the mols. point to the 3-point system of closest packing, suggested by Pope and Barlow, in which each element of the crystal pattern has a mol. at each corner of the cube face and its center.
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    42. 42
      Loiseau, T.; Serre, C.; Huguenard, C.; Fink, G.; Taulelle, F.; Henry, M.; Bataille, T.; Férey, G. A Rationale for the Large Breathing of the Porous Aluminum Terephthalate (MIL-53) upon Hydration. Chemistry 2004, 10, 1373– 1382,  DOI: 10.1002/chem.200305413
      42
      A rationale for the large breathing of the porous aluminum terephthalate (MIL-53) upon hydration
      Loiseau, Thierry; Serre, Christian; Huguenard, Clarisse; Fink, Gerhard; Taulelle, Francis; Henry, Marc; Bataille, Thierry; Ferey, Gerard
      Chemistry - A European Journal (2004), 10 (6), 1373-1382CODEN: CEUJED; ISSN:0947-6539. (Wiley-VCH Verlag GmbH & Co. KGaA)
      Al 1,4-benzenedicarboxylate Al(OH)[O2CC6H4CO2][HO2C-C6H4-CO2H]0.70 or MIL-53as (Al) was hydrothermally synthesized by heating a mixt. of Al nitrate, 1,4-benzenedicarboxylic acid, and H2O, for three days at 220°. Its 3 D framework is built up of infinite trans chains of corner-sharing AlO4(OH)2 octahedra. The chains are interconnected by the 1,4-benzenedicarboxylate groups, creating 1 D rhombic-shaped tunnels. Disordered 1,4-benzenedicarboxylic acid mols. are trapped inside these tunnels. Their evacuation upon heating, between 275 and 420°, leads to a nanoporous open-framework (MIL-53ht (Al) or Al(OH)[O2CC6H4CO2]) with empty pores of diam. 8.5 Å. This solid exhibits a Langmuir surface area. of 1590(1) m2g-1 together with a remarkable thermal stability, since it starts to decomp. only at 500°. At room temp., the solid reversibly absorbs H2O in its tunnels, causing a very large breathing effect and shrinkage of the pores. Anal. of the hydration process by solid-state NMR (1H, 13C, 27Al) has clearly indicated that the trapped H2O mols. interact with the carboxylate groups through H bonds, but do not affect the hydroxyl species bridging the Al atoms. The H bonds between H2O and the O atoms of the framework are responsible for the contraction of the rhombic channels. The structures of the three forms were detd. by powder x-ray diffraction anal. Crystal data for MIL-53as (Al) are as follows: orthorhombic system, Pnma (no. 62), a 17.129(2), b 6.628(1), c 12.182(1) Å; for MIL-53ht (Al), orthorhombic system, Imma (no. 74), a 6.608(1), b 16.675(3), c 12.813(2) Å; for MIL-53lt (Al), monoclinic system, Cc (no. 9), a 19.513(2), b 7.612(1), c 6.576(1) Å, β 104.24(1)°.
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    43. 43
      Ma, M.; Noei, H.; Mienert, B.; Niesel, J.; Bill, E.; Muhler, M.; Fischer, R. A.; Wang, Y.; Schatzschneider, U.; Metzler-Nolte, N. Iron Metal-organic Frameworks MIL-88B and NH 2 -MIL-88B for the Loading and Delivery of the Gasotransmitter Carbon Monoxide. Chem. - A Eur. J. 2013, 19, 6785– 6790,  DOI: 10.1002/chem.201201743
      43
      Iron Metal-Organic Frameworks MIL-88B and NH2-MIL-88B for the Loading and Delivery of the Gasotransmitter Carbon Monoxide
      Ma, Mingyan; Noei, Heshmat; Mienert, Bernd; Niesel, Johanna; Bill, Eckhard; Muhler, Martin; Fischer, Roland A.; Wang, Yuemin; Schatzschneider, Ulrich; Metzler-Nolte, Nils
      Chemistry - A European Journal (2013), 19 (21), 6785-6790CODEN: CEUJED; ISSN:0947-6539. (Wiley-VCH Verlag GmbH & Co. KGaA)
      Crystals of MIL-88B-Fe and NH2-MIL-88B-Fe were prepd. by a new rapid microwave-assisted solvothermal method. High-purity, spindle-shaped crystals of MIL-88B-Fe with a length of about 2 μm and a diam. of 1 μm and needle-shaped crystals of NH2-MIL-88B-Fe with a length of about 1.5 μm and a diam. of 300 nm were produced with uniform size and excellent crystallinity. The possibility to reduce the as-prepd. frameworks and the chem. capture of carbon monoxide in these materials was studied by in situ ultrahigh vacuum Fourier-transform IR (UHV-FTIR) spectroscopy and Moessbauer spectroscopy. CO binding occurs to unsatd. coordination sites (CUS). The release of CO from the as-prepd. materials was studied by a myoglobin assay in physiol. buffer. The release of CO from crystals of MIL-88B-Fe with t1/2=38 min and from crystals of NH2-MIL-88B-Fe with t1/2=76 min were found to be controlled by the degrdn. of the MIL materials under physiol. conditions. These MIL-88B-Fe and NH2-MIL-88B-Fe materials show good biocompatibility and have the potential to be used in pharmacol. and therapeutic applications as carriers and delivery vehicles for the gasotransmitter carbon monoxide.
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    44. 44
      Walton, R. I.; Munn, A. S.; Guillou, N.; Millange, F. Uptake of Liquid Alcohols by the Flexible FeIII Metal-organic Framework MIL-53 Observed by Time-Resolved In Situ X-Ray Diffraction. Chem. - A Eur. J. 2011, 17, 7069– 7079,  DOI: 10.1002/chem.201003634
      44
      Uptake of Liquid Alcohols by the Flexible FeIII Metal-Organic Framework MIL-53 Observed by Time-Resolved In Situ X-ray Diffraction
      Walton, Richard I.; Munn, Alexis S.; Guillou, Nathalie; Millange, Franck
      Chemistry - A European Journal (2011), 17 (25), 7069-7079, S7069/1-S7069/15CODEN: CEUJED; ISSN:0947-6539. (Wiley-VCH Verlag GmbH & Co. KGaA)
      A comprehensive, time-resolved, energy-dispersive x-ray diffraction study of the uptake of liq. alcs. (methanol, ethanol, propan-1-ol and propan-2-ol) by the flexible metal-org. framework solid MIL-53(Fe)[H2O] is reported. In the case of the primary alcs., a fluorinated version of the MIL-53(Fe) host (C2/c symmetry V ∼ 1000 Å3), in which a fraction of framework hydroxides are replaced by fluoride, shows uptake of alcs. to give initially a partially expanded phase (C2/c symmetry, V ∼ 1200 Å3) followed by an expanded form of the material (either Imcm or Pnam symmetry, V ∼ 1600 Å3). In the case of methanol-water mixts., the EDXRD data show that the partially open intermediate phase undergoes vol. expansion during its existence, before switching to a fully open structure if concd. methanol is used; analogous behavior is seen if the initial guest is propan-2-ol, which then is replaced by pyridine, where a continuous shift of Bragg peaks within C2/c symmetry is obsd. In contrast to the partially fluorinated materials, the purely hydroxylated host materials show little tendency to stabilize partially open forms of MIL-53(Fe) with primary alcs. and the kinetics of guest introduction are markedly slower without the framework fluorination: this is exemplified by the exchange of water by propan-2-ol, where a partially open C2/c phase is formed in a step-wise manner. The study defines the various possible pathways of liq.-phase uptake of mol. guests by flexible solid MIL-53(Fe).
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    45. 45
      Nikseresht, A.; Daniyali, A.; Ali-Mohammadi, M.; Afzalinia, A.; Mirzaie, A. Ultrasound-Assisted Biodiesel Production by a Novel Composite of Fe(III)-Based MOF and Phosphotangestic Acid as Efficient and Reusable Catalyst. Ultrason. Sonochem. 2017, 37, 203– 207,  DOI: 10.1016/J.ULTSONCH.2017.01.011
      45
      Ultrasound-assisted biodiesel production by a novel composite of Fe(III)-based MOF and phosphotangestic acid as efficient and reusable catalyst
      Nikseresht, Ahmad; Daniyali, Asra; Ali-Mohammadi, Mahdi; Afzalinia, Ahmad; Mirzaie, Abbas
      Ultrasonics Sonochemistry (2017), 37 (), 203-207CODEN: ULSOER; ISSN:1350-4177. (Elsevier B.V.)
      In this work, esterification of oleic acid by various alcs. is achieved with high yields under ultrasonic irradn. This reaction performed with a novel heterogeneous catalyst that fabricated by heteropoly acid and Fe(III)-based MOF, namely MIL-53 (Fe). Syntheses of MIL-53 and encapsulation process carry out by ultrasound irradn. at ambient temp. and atm. pressure. The prepd. composite was characterized by various techniques such as XRD, FT-IR, SEM, BET and ICP that demonstrate excellent catalytic activities, while being highly convenient to synthesize. The obtained results revealed that ultrasound irradn. could be used for the appropriate and rapid biodiesel prodn.
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    46. 46
      Feng, X.; Chen, H.; Jiang, F. In-Situ Ethylenediamine-Assisted Synthesis of a Magnetic Iron-Based Metal-organic Framework MIL-53(Fe) for Visible Light Photocatalysis. J. Colloid Interface Sci. 2017, 494, 32– 37,  DOI: 10.1016/J.JCIS.2017.01.060
      46
      In-situ ethylenediamine-assisted synthesis of a magnetic iron-based metal-organic framework MIL-53(Fe) for visible light photocatalysis
      Feng, Xiangwen; Chen, Huan; Jiang, Fang
      Journal of Colloid and Interface Science (2017), 494 (), 32-37CODEN: JCISA5; ISSN:0021-9797. (Elsevier B.V.)
      A novel magnetic MIL-53(Fe) photocatalyst (MAG-MIL) has been synthesized by an in-situ ethylenediamine (EDA)-assisted solvothermal method. The well dispersed γ-Fe2O3 nanoparticles embedded in the MAG-MIL framework contribute to a red shift of the light absorption edge as well as the superparamagnetism characteristic.
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    47. 47
      Alsop, R. J.; Armstrong, C. L.; Maqbool, A.; Toppozini, L.; Dies, H.; Rheinstädter, M. C. Cholesterol Expels Ibuprofen from the Hydrophobic Membrane Core and Stabilizes Lamellar Phases in Lipid Membranes Containing Ibuprofen. Soft Matter 2015, 11, 4756– 4767,  DOI: 10.1039/c5sm00597c
      47
      Cholesterol expels ibuprofen from the hydrophobic membrane core and stabilizes lamellar phases in lipid membranes containing ibuprofen
      Alsop, Richard J.; Armstrong, Clare L.; Maqbool, Amna; Toppozini, Laura; Dies, Hannah; Rheinstadter, Maikel C.
      Soft Matter (2015), 11 (24), 4756-4767CODEN: SMOABF; ISSN:1744-683X. (Royal Society of Chemistry)
      There is increasing evidence that common drugs, such as aspirin and ibuprofen, interact with lipid membranes. Ibuprofen is one of the most common over the counter drugs in the world, and is used for relief of pain and fever. It interacts with the cyclooxygenase pathway leading to inhibition of prostaglandin synthesis. From X-ray diffraction of highly oriented model membranes contg. between 0 and 20 mol% ibuprofen, 20 mol% cholesterol, and dimyristoylphosphatidylcholine (DMPC), we present evidence for a non-specific interaction between ibuprofen and cholesterol in lipid bilayers. At a low ibuprofen concns. of 2 mol%, three different populations of ibuprofen mols. were found: two in the lipid head group region and one in the hydrophobic membrane core. At higher ibuprofen concns. of 10 and 20 mol%, the lamellar bilayer structure is disrupted and a lamellar to cubic phase transition was obsd. In the presence of 20 mol% cholesterol, ibuprofen (at 5 mol%) was found to be expelled from the membrane core and reside solely in the head group region of the bilayers. 20 mol% cholesterol was found to stabilize lamellar membrane structure and the formation of a cubic phase at 10 and 20 mol% ibuprofen was suppressed. The results demonstrate that ibuprofen interacts with lipid membranes and that the interaction is strongly dependent on the presence of cholesterol.
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    48. 48
      Wang, Y.; Muramatsu, A.; Sugimoto, T. FTIR Analysis of Well-Defined α-Fe2O3 Particles. Colloids Surf., A 1998, 134, 281– 297,  DOI: 10.1016/S0927-7757(97)00102-7
      48
      FTIR analysis of well-defined α-Fe2O3 particles
      Wang, Yinsheng; Muramatsu, Atsushi; Sugimoto, Tadao
      Colloids and Surfaces, A: Physicochemical and Engineering Aspects (1998), 134 (3), 281-297CODEN: CPEAEH; ISSN:0927-7757. (Elsevier Science B.V.)
      The FTIR spectra of well-defined hematite (α-Fe2O3) particles varying in size, shape and internal structure have systematically been analyzed. The absorption peak frequencies of the pseudocubic particles are located between the corresponding theor. peak frequencies of spheres and cubes and shift to lower frequencies as particle size increases, corresponding approx. with the Mie theory. However, the basic spectrum pattern was detd. by the morphol. of the particles. The observation of ellipsoids with various aspect ratios revealed some essential discrepancies in the peak frequency between expt. and the theory on the surface phonon modes in small particles, even if the particles were completely dispersed in the medium. The internal structure mainly affects the peak width, which increases with the decreasing subcrystal size. Finally, the effects of aggregation on the IR spectrum are discussed.
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    49. 49
      Brunauer, S.; Emmett, P. H.; Teller, E. Adsorption of Gases in Multimolecular Layers. J. Am. Chem. Soc. 1938, 60, 309– 319,  DOI: 10.1021/ja01269a023
      49
      Adsorption of gases in multimolecular layers
      Brunauer, Stephen; Emmett, P. H.; Teller, Edward
      Journal of the American Chemical Society (1938), 60 (), 309-19CODEN: JACSAT; ISSN:0002-7863.
      The polarization theory of multimolecular adsorption is discussed critically. The adsorption energy due to attraction of dipoles induced into a nonpolar gas such as A is insufficient to constitute a major portion of the binding energy between adsorbed layers. Adsorption-isotherm equations for multimolecular adsorption are derived on the assumption that the same forces that produce condensation are responsible also for multimolecular adsorption. Numerous applications of the equations are given to exptl. adsorption isotherms. Cf. C. A. 32, 1159.3.
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    50. 50
      Harkins, W. D.; Jura, G. An Adsorption Method for the Determination of the Area of a Solid without the Assumption of a Molecular Area, and the Area Occupied by Nitrogen Molecules on the Surfaces of Solids. J. Chem. Phys. 1943, 11, 431– 432,  DOI: 10.1063/1.1723871
      50
      An adsorption method for the determination of the area of a solid without the assumption of a molecular area, and the area occupied by nitrogen molecules on the surfaces of solids
      Harkins, Wm. D.; Jura, Geo.
      Journal of Chemical Physics (1943), 11 (), 431-2CODEN: JCPSA6; ISSN:0021-9606.
      cf. preceding abstr. It is shown that Σ = 4.06s0.5 (Σ = area in sq. m./g.; s = slope of the isotherm obtained from the equation in the preceding abstr.). The surface areas of 58 of 60 solids investigated, detd. by this method, agreed within ±9% with detns. made by the Brunauer, Emmett and Teller isotherm (C. A. 32, 4037.9). The area of the N2 mols. on these solids was calcd. to be in the range 13.6-16.9 sq. A. Langmuir's isotherm was found to be valueless, since it applies only to unimol. adsorption.
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    51. 51
      Düren, T.; Millange, F.; Férey, G.; Walton, K. S.; Snurr, R. Q. Calculating Geometric Surface Areas as a Characterization Tool for Metal - organic Frameworks. J. Phys. Chem. C 2007, 111, 15350– 15356,  DOI: 10.1021/jp074723h
      51
      Calculating Geometric Surface Areas as a Characterization Tool for Metal-Organic Frameworks
      Dueren, Tina; Millange, Franck; Ferey, Gerard; Walton, Krista S.; Snurr, Randall Q.
      Journal of Physical Chemistry C (2007), 111 (42), 15350-15356CODEN: JPCCCK; ISSN:1932-7447. (American Chemical Society)
      Metal-org. frameworks (MOFs) synthesized in a building-block approach from org. linkers and metal corner units offer the opportunity to design materials with high surface areas for adsorption applications by assembling the appropriate building blocks. In this paper, we show that the surface area calcd. in a geometric fashion from the crystal structure is a useful tool for characterizing MOFs. We argue that the accessible surface area rather than the widely used Connolly surface area is the appropriate surface area to characterize cryst. solids for adsorption applications. The accessible surface area calcd. with a probe diam. corresponding to the adsorbate of interest provides a simple way to screen and compare adsorbents. We investigate the effects of the probe mol. diam. on the accessible surface area and discuss the implications for increasing the surface area of metal-org. frameworks by the use of catenated structures. We also demonstrate that the accessible surface area provides a useful tool for judging the quality of a synthesized sample. Exptl. surface areas can be adversely affected by incomplete solvent removal during activation, crystal collapse, or interpenetration. The easily calcd. accessible surface area provides a benchmark for the theor. upper limit for a perfect crystal.
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    52. 52
      First, E. L.; Floudas, C. A. MOFomics: Computational Pore Characterization of Metal-organic Frameworks. Microporous Mesoporous Mater. 2013, 165, 32– 39,  DOI: 10.1016/j.micromeso.2012.07.049
      52
      MOFomics: Computational pore characterization of metal-organic frameworks
      First, Eric L.; Floudas, Christodoulos A.
      Microporous and Mesoporous Materials (2013), 165 (), 32-39CODEN: MIMMFJ; ISSN:1387-1811. (Elsevier Inc.)
      Microporous materials, such as zeolites and metal-org. frameworks (MOFs), are commonly considered for shape-selective sepns. and catalysis. With the large no. of known and hypothetical structures available, computational techniques are needed to identify the most promising structures for applications of interest. The authors have developed an automated computational framework based on optimization, geometry, and graph algorithms to fully characterize the three-dimensional pore structures of MOFs. The authors' methods automatically identify the portals, channels, and cages of a MOF and describe their geometry and connectivity. Also, the authors calc. quantities of interest including pore size distribution, accessible vol., accessible surface area, pore limiting diam., and largest cavity diam. The authors' computational framework was applied to over 800 exptl. MOFs, including zeolitic imidazolate frameworks (ZIFs), and over 1600 hypothetical MOFs. MOFomics, an online database of pore characterizations and the 1st web tool for MOFs that allows user submissions, is made freely available to the scientific communit (http://helios.princeton.edu/mofomics/).
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    53. 53
      Vu, T. A.; Le, G. H.; Dao, C. D.; Dang, L. Q.; Nguyen, K. T.; Nguyen, Q. K.; Dang, P. T.; Tran, H. T. K.; Duong, Q. T.; Nguyen, T. V. Arsenic Removal from Aqueous Solutions by Adsorption Using Novel MIL-53(Fe) as a Highly Efficient Adsorbent. RSC Adv. 2015, 5, 5261– 5268,  DOI: 10.1039/c4ra12326c
      53
      Arsenic removal from aqueous solutions by adsorption using novel MIL-53(Fe) as a highly efficient adsorbent
      Vu, Tuan. A.; Le, Giang. H.; Dao, Canh. D.; Dang, Lan. Q.; Nguyen, Kien. T.; Nguyen, Quang. K.; Dang, Phuong. T.; Tran, Hoa. T. K.; Duong, Quang. T.; Nguyen, Tuyen. V.; Lee, Gun. D.
      RSC Advances (2015), 5 (7), 5261-5268CODEN: RSCACL; ISSN:2046-2069. (Royal Society of Chemistry)
      A MIL-53(Fe) analog was successfully synthesized by a HF free-solvothermal method. The sample was characterized by XRD, N2 adsorption (BET), TEM, FTIR, XPS and AAS. From the N2 adsorption-desorption isotherms, it can be seen that the structure of MIL-53(Fe) in the anhyd. form exhibits closed pores with almost no accessible porosity to nitrogen gas. The XPS results reveal that Fe is really incorporated into the MIL-53(Fe) framework. In the hydrated form, the pores of MIL-53(Fe) are filled with water mols. Thus, MIL-53(Fe) exhibited a very high adsorption capacity of As(V) in aq. soln. (Qmax of 21.27 mg g-1). Adsorption kinetics data revealed that As(V) adsorption isotherms fit the Langmuir model and obey the pseudo-second-order kinetic equation.
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    54. 54
      Millange, F.; Guillou, N.; Walton, R. I.; Grenèche, J.-M.; Margiolaki, I.; Férey, G. Effect of the Nature of the Metal on the Breathing Steps in MOFs with Dynamic Frameworks. Chem. Commun. 2008, 39, 4732– 4734,  DOI: 10.1039/b809419e
      There is no corresponding record for this reference.
    55. 55
      Devic, T.; Horcajada, P.; Serre, C.; Salles, F.; Maurin, G.; Moulin, B.; Heurtaux, D.; Clet, G.; Vimont, A.; Grenéche, J.-M. Functionalization in Flexible Porous Solids: Effects on the Pore Opening and the Host-Guest Interactions. J. Am. Chem. Soc. 2010, 132, 1127– 1136,  DOI: 10.1021/ja9092715
      55
      Functionalization in Flexible Porous Solids: Effects on the Pore Opening and the Host-Guest Interactions
      Devic, Thomas; Horcajada, Patricia; Serre, Christian; Salles, Fabrice; Maurin, Guillaume; Moulin, Beatrice; Heurtaux, Daniela; Clet, Guillaume; Vimont, Alexandre; Greneche, Jean-Marc; Le Ouay, Benjamin; Moreau, Florian; Magnier, Emmanuel; Filinchuk, Yaroslav; Marrot, Jerome; Lavalley, Jean-Claude; Daturi, Marco; Ferey, Gerard
      Journal of the American Chemical Society (2010), 132 (3), 1127-1136CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
      The synthesis on the gram scale and characterization of flexible functionalized iron terephthalate MIL-53(Fe) type solids are reported. Chem. groups of various polarities, hydrophilicities, and acidities (-Cl, -Br, -CF3, -Me, -NH2, -OH, -CO2H) were introduced through the arom. linker, to systematically modify the pore surface. X-ray powder diffraction (XRPD), mol. simulations, thermogravimetric analyses, and in situ IR and 57Fe Moessbauer spectrometries indicate some similarities with the pristine MIL-53(Fe) solid, with the adoption of the narrow pore form for all solids in both the hydrated and dry forms. Combined XRPD and computational structure detns. allow concluding that the geometry of the pore opening is predominantly correlated with the intraframework interactions rather than the steric hindrance of the substituent. Only (MIL-53(Fe)(CF3)2) exhibits a nitrogen accessible porosity (SBET ≈ 100 m2 g-1). The adsorption of some liqs. leads to pore openings showing some very specific behaviors depending on the guest-MIL-53(Fe) framework interactions, which can be related to the energy difference between the narrow and large pore forms evaluated by mol. simulation.
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    56. 56
      Matsuyama, K.; Hayashi, N.; Yokomizo, M.; Kato, T.; Ohara, K.; Okuyama, T. Supercritical Carbon Dioxide-Assisted Drug Loading and Release from Biocompatible Porous Metal-organic Frameworks. J. Mater. Chem. B 2014, 2, 7551– 7558,  DOI: 10.1039/c4tb00725e
      56
      Supercritical carbon dioxide-assisted drug loading and release from biocompatible porous metal-organic frameworks
      Matsuyama, Kiyoshi; Hayashi, Nobukatsu; Yokomizo, Misaki; Kato, Takafumi; Ohara, Kiyomi; Okuyama, Tetsuya
      Journal of Materials Chemistry B: Materials for Biology and Medicine (2014), 2 (43), 7551-7558CODEN: JMCBDV; ISSN:2050-7518. (Royal Society of Chemistry)
      Herein the authors describe the supercrit. carbon dioxide (scCO2)-assisted drug loading and release from nontoxic and biocompatible porous iron(III) polycarboxylate metal-org. frameworks (MOFs), which exhibited very high cargo loadings and gradual release. MIL-53(Fe) and MIL-100(Fe) were investigated as potential carriers for drug mols., using ibuprofen as a model drug candidate. The loading and release behavior of ibuprofen were monitored by thermogravimetric analyses (TGA) and high performance liq. chromatog. (HPLC) measurements to quant. det. the ibuprofen uptake, and were performed for the first time using scCO2-based technol. After the prepn. of the MOFs within a particular solvent, the internal surface area of MIL-53(Fe) and MIL-100(Fe) increased as a result of the scCO2 drying method. Furthermore, ibuprofen could be impregnated into the pores of the MOFs by utilizing a scCO2-hexane soln. ScCO2-assisted impregnation could also be used to deliver ibuprofen to the pores of the MOFs. As a result, a large amt. of ibuprofen was able to be loaded into MIL-53(Fe) and MIL-100(Fe).
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    57. 57
      Zheng, H.; Zhang, Y.; Liu, L.; Wan, W.; Guo, P.; Nyström, A. M.; Zou, X. One-Pot Synthesis of Metal-organic Frameworks with Encapsulated Target Molecules and Their Applications for Controlled Drug Delivery. J. Am. Chem. Soc. 2016, 138, 962– 968,  DOI: 10.1021/jacs.5b11720
      57
      One-pot Synthesis of Metal-Organic Frameworks with Encapsulated Target Molecules and Their Applications for Controlled Drug Delivery
      Zheng, Haoquan; Zhang, Yuning; Liu, Leifeng; Wan, Wei; Guo, Peng; Nystroem, Andreas M.; Zou, Xiaodong
      Journal of the American Chemical Society (2016), 138 (3), 962-968CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
      Many medical and chem. applications require target mols. to be delivered in a controlled manner at precise locations. Metal-org. frameworks (MOFs) have high porosity, large surface area, and tunable functionality and are promising carriers for such purposes. Current approaches for incorporating target mols. are based on multistep postfunctionalization. Here, we report a novel approach that combines MOF synthesis and mol. encapsulation in a one-pot process. We demonstrate that large drug and dye mols. can be encapsulated in zeolitic imidazolate framework (ZIF) crystals. The mols. are homogeneously distributed within the crystals, and their loadings can be tuned. We show that ZIF-8 crystals loaded with the anticancer drug doxorubicin (DOX) are efficient drug delivery vehicles in cancer therapy using pH-responsive release. Their efficacy on breast cancer cell lines is higher than that of free DOX. Our one-pot process opens new possibilities to construct multifunctional delivery systems for a wide range of applications.
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    58. 58
      Spokoyny, A. M.; Kim, D.; Sumrein, A.; Mirkin, C. A. Infinite Coordination Polymer Nano- and Microparticle Structures. Chem. Soc. Rev. 2009, 38, 1218,  DOI: 10.1039/b807085g
      58
      Infinite coordination polymer nano- and microparticle structures
      Spokoyny, Alexander M.; Kim, Dongwoo; Sumrein, Abdelqader; Mirkin, Chad A.
      Chemical Society Reviews (2009), 38 (5), 1218-1227CODEN: CSRVBR; ISSN:0306-0012. (Royal Society of Chemistry)
      This tutorial review introduces the reader to the field of infinite coordination polymer particles (ICPs), providing a guide to the work done so far, with an emphasis on synthesis, applications and future prospects. ICPs represent an area of growing interest in chem. and materials science due to their unique and highly tailorable properties. These structures can be conveniently synthesized in high yields from the appropriate metal salts and bifunctional ligand precursors. Unlike conventional metal-org. framework materials (MOFs), these ICPs exhibit a higher level of structural tailorability, including size- and morphol.-dependent properties, and therefore, the promise of a wider scope of utility. A variety of methods now exist for making numerous compns., with modest control over particle size and shape. These structures can exhibit microporosity, tunable fluorescence, magnetic susceptibility, and unusual catalytic activity and selectivity. Perhaps most importantly, many of these ICP structures can be depolymd. (sometimes reversibly) much faster and under milder conditions than MOFs, which makes them attractive for a variety of biomedical applications. Thus far, several types of ICPs have been explored as contrast agents for magnetic resonance imaging and drug delivery systems. The groundwork for this emerging field of ICPs has been laid only in the past few years, yet significant advances have already been made.
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    59. 59
      Serre, C.; Mellot-Draznieks, C.; Surblé, S.; Audebrand, N.; Filinchuk, Y.; Férey, G. Role of Solvent-Host Interactions That Lead to Very Large Swelling of Hybrid Frameworks. Science 2007, 315, 1828– 1831,  DOI: 10.1126/science.1137975
      59
      Role of Solvent-Host Interactions That Lead to Very Large Swelling of Hybrid Frameworks
      Serre, C.; Mellot-Draznieks, C.; Surble, S.; Audebrand, N.; Filinchuk, Y.; Ferey, G.
      Science (Washington, DC, United States) (2007), 315 (5820), 1828-1831CODEN: SCIEAS; ISSN:0036-8075. (American Association for the Advancement of Science)
      An unusually large expansion upon solvent adsorption occurs without apparent bond breaking in the network of a series of isoreticular chromium(III) or iron(III) dicarboxylates labeled MIL-88A to D [dicarbox = fumarate (88A); terephthalate (1,4-BDC) (88B); 2,6-naphthalenedicarboxylate (2,6-NDC) (88C); and 4-4'-biphenyldicarboxylate (4-4'-BPDC) (88D)]. This reversible "breathing" motion was analyzed in terms of cell dimensions (extent of breathing), movements within the framework (mechanism of transformation), and the interactions between the guests and the skeleton. In situ techniques show that these flexible solids are highly selective absorbents and that this selectivity is strongly dependent on the nature of the org. linker.
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    60. 60
      Liédana, N.; Galve, A.; Rubio, C.; Téllez, C.; Coronas, J. CAF@ZIF-8: One-Step Encapsulation of Caffeine in MOF. ACS Appl. Mater. Interfaces 2012, 4, 5016– 5021,  DOI: 10.1021/am301365h
      60
      CAF@ZIF-8: One-Step Encapsulation of Caffeine in MOF
      Liedana, Nuria; Galve, Alejandro; Rubio, Cesar; Tellez, Carlos; Coronas, Joaquin
      ACS Applied Materials & Interfaces (2012), 4 (9), 5016-5021CODEN: AAMICK; ISSN:1944-8244. (American Chemical Society)
      Two strategies for encapsulating caffeine in ZIF-8 were carried out in this work: (1) one-step, in situ encapsulation where caffeine is added to a ZIF-8 synthesis soln. and the MOF structure is formed around the entrapped mol.; and (2) ex situ encapsulation whereby caffeine is put into contact with previously synthesized or purchased ZIF-8. The products obtained were analyzed with XRD, TGA, Vis-UV, GC-MS, FTIR, 13C NMR, and N 1s XPS to compare both encapsulation methods. Chem. and structural evidence indicated that the preferential adsorption site of caffeine mols. inside the ZIF-8 structure is near the Me and CH groups of 2-methylimidazole ligand. These two groups interact with caffeine by van der Waals forces with Me groups and via CH-O hydrogen bonds with C=O groups, resp. In addn., the one-step encapsulation of caffeine in ZIF-8 produced high guest loading (∼28 wt.% in only 2 h at 25°) and controlled release (during 27 days).
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    61. 61
      Siepmann, J.; Siepmann, F. Mathematical Modeling of Drug Delivery. Int. J. Pharm. 2008, 364, 328– 343,  DOI: 10.1016/J.IJPHARM.2008.09.004
      61
      Mathematical modeling of drug delivery
      Siepmann, J.; Siepmann, F.
      International Journal of Pharmaceutics (2008), 364 (2), 328-343CODEN: IJPHDE; ISSN:0378-5173. (Elsevier B.V.)
      A review. Due to the significant advances in information technol. math. modeling of drug delivery is a field of steadily increasing academic and industrial importance with an enormous future potential. The in silico optimization of novel drug delivery systems can be expected to significantly increase in accuracy and easiness of application. Analogous to other scientific disciplines, computer simulations are likely to become an integral part of future research and development in pharmaceutical technol. Math. programs can be expected to be routinely used to help optimizing the design of novel dosage forms. Good ests. for the required compn., geometry, dimensions and prepn. procedure of various types of delivery systems will be available, taking into account the desired administration route, drug dose and release profile. Thus, the no. of required exptl. studies during product development can be significantly reduced, saving time and reducing costs. In addn., the quant. anal. of the phys., chem. and potentially biol. phenomena, which are involved in the control of drug release, offers another fundamental advantage: The underlying drug release mechanisms can be elucidated, which is not only of academic interest, but a pre-requisite for an efficient improvement of the safety of the pharmaco-treatments and for effective trouble-shooting during prodn. This article gives an overview on the current state of the art of math. modeling of drug delivery, including empirical/semi-empirical and mechanistic realistic models. Anal. as well as numerical solns. are described and various practical examples are given. One of the major challenges to be addressed in the future is the combination of mechanistic theories describing drug release out of the delivery systems with math. models quantifying the subsequent drug transport within the human body in a realistic way. Ideally, the effects of the design parameters of the dosage form on the resulting drug concn. time profiles at the site of action and the pharmacodynamic effects will become predictable.
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    62. 62
      Rothstein, S. N.; Federspiel, W. J.; Little, S. R. A Unified Mathematical Model for the Prediction of Controlled Release from Surface and Bulk Eroding Polymer Matrices. Biomaterials 2009, 30, 1657– 1664,  DOI: 10.1016/J.BIOMATERIALS.2008.12.002
      62
      A unified mathematical model for the prediction of controlled release from surface and bulk eroding polymer matrices
      Rothstein, Sam N.; Federspiel, William J.; Little, Steven R.
      Biomaterials (2009), 30 (8), 1657-1664CODEN: BIMADU; ISSN:0142-9612. (Elsevier Ltd.)
      A unified model has been developed to predict release not only from bulk eroding and surface eroding systems but also from matrixes that transition from surface eroding to bulk eroding behavior during the course of degrdn. This broad applicability is afforded by fundamental diffusion/reaction equations that can describe a wide variety of scenarios including hydration of and mass loss from a hydrolyzable polymer matrix. Together, these equations naturally account for spatial distributions of polymer degrdn. rate. In this model paradigm, the theor. minimal size required for a matrix to exhibit degrdn. under surface eroding conditions was calcd. for various polymer types and then verified by empirical data from the literature. An addnl. set of equations accounts for dissoln.- and/or degrdn.-based release, which are dependent upon hydration of the matrix and erosion of the polymer. To test the model's accuracy, predictions for agent egress were compared to exptl. data from polyanhydride and polyorthoester implants that were postulated to undergo either dissoln.-limited or degrdn.-controlled release. Because these predictions are calcd. solely from readily attainable design parameters, it seems likely that this model could be used to guide the design controlled release formulations that produce a broad array of custom release profiles.
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  • Supporting Information

    Supporting Information

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.9b03696.

    • UV–vis spectra, BET plots and parameters, and drug release models (PDF)


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