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Highly Sensitive Electrochemical Sensor for Anticancer Drug by a Zirconia Nanoparticle-Decorated Reduced Graphene Oxide Nanocomposite
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Cite this: ACS Omega 2018, 3, 11, 14597–14605
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https://doi.org/10.1021/acsomega.8b02129
Published November 1, 2018

Copyright © 2018 American Chemical Society. This publication is licensed under CC-BY.

Abstract

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Because of their large surface area and conductivity, some inorganic materials have emerged as good candidates for the trace-level detection of pharmaceutical drugs. In the present work, we demonstrate the detection of an anticancer drug (regorafenib, REG) by using an electrochemical sensor based on a nanocomposite material. We synthesized a zirconia-nanoparticle-decorated reduced graphene oxide composite (ZrO2/rGO) using a one-pot hydrothermal method. Reduction of the graphene oxide supports of the Zr2+ ions with hydrazine hydrate helped in preventing the agglomeration of the zirconia nanoparticles and in obtaining an excellent electrocatalytic response of the nanostructure ZrO2/rGO-based electrochemical sensor. Structural and morphological characterization of the nanostructure ZrO2/rGO was performed using various analytical methods. A novel regorafenib (REG) electrochemical sensor was fabricated by immobilizing the as-prepared nanostructure ZrO2/rGO on to a glassy carbon electrode (GCE). The resulting ZrO2/rGO/GCE could be used for the rapid and selective determination of REG in the presence of ascorbic acid and uric acid. The ZrO2/rGO/GCE showed a linear response for the REG analysis in the dynamic range 11–343 nM, with a remarkable lower detection limit and limit of quantifications of 17 and 59 nM, respectively. The newly developed sensor was used for the accurate determination of REG in both serum samples and pharmaceutical formulations, with satisfactory results.

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Introduction

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Regorafenib [4-(4-(3-(4-chloro-3-(trifluromethyl) phenyl)-3-flurophenoxy)-N-ethylpicolinamide] (BAY 73-4506) is an orally bioavailable multikinase inhibitor (MKI), which also obstructs multiple tumor pathways, inhibiting targets in the receptors of the vascular endothelial growth factor 1–3 (VEGF 1–3), fibroblast growth factor, and platelet-derived growth factor, including the mutant oncogenic kinesis c-KIT, RET, and B-RAF. (1,2) This MKI generates dynamic metabolites, which could become agglomerated, particularly in elderly, malnourished patients or in patients treated for hepatocellular carcinoma, as in the case of other MKIs. (3) Oral drugs present high protein binding and poor bioavailability and are effectively metabolized by CYP3A4 and UGT1A9 in the liver. (4,5) Regorafenib (REG), being orally administrated, may lead to drug interactions and major toxicities that may lead to early termination of the treatment and thus diminish its chances of success. It is important to maintain the benefits of these treatments, particularly in the elderly or in patients treated for metastatic colon cancer and gastrointestinal tumors, which is approved by FDA. (6−11) The most serious adverse reaction was drug-induced hepatotoxicity, and a black box warning has been indicated by the US-FDA. (12) Thus, the detection of this anticancer active drug is extensively important and a universal challenge. Some of the sophisticated analytical methods such as high-performance liquid chromatography (HPLC), (13) liquid chromatography-mass spectrometry (LC-MS), (14−19) and spectrophotometry (20) are used for the detection of REG in urine, plasma, and other biological samples. However, the aforementioned methods are highly expensive, time-consuming, difficult procedures and require skilled personnel for the specimen, which restricts their particle application. To mitigate these issues, as revealed earlier, much effort has been made to develop novel substituted methods. In this concern, the electrochemical technique is one of the best methods due to its easy operation, spontaneous detection, excellent sensitivity, inexpensiveness, simple pretreatment procedure, and short analysis time for monitoring of bioelectroactive molecules and pharmaceutical drugs. However, for the detection of bioelectroactive molecules, these electrochemical methods have some analytical complications like high overpotential requirement, the reversible process at the bare and carbon paste electrode, GCE, and by-products that may be deposited on the electrode surface, which decrease its activity. Nevertheless, a familiar approach to triumph over these issues is electrodes’ surface modification with various materials, like polymers, (21−23) carbon materials, and metal-oxide nanoparticles. (24−27)
For the last few decades, graphene oxide (GO) and reduced graphene oxide (rGO) have received significant interest owing to their excellent properties in electrochemical applications, such as good electric conductivity, large surface area, high chemical activity, and wide electrochemical window. (28,29) Moreover, chemically, rGO is established as a promising supporting material for the uniform distribution of metal-oxide NPs. (30−34)
In recent years, various metal-oxide-doped graphene oxide composites have been widely used in electrochemical devices and electrocatalysis. Metal oxides, particularly, transition-metal oxides have various physicochemical properties, such as morphological structure, oxygen stoichiometry, good electrochemical conductivity, and interfacial microenvironment of the reaction. Among the transition-metal oxides, zirconium oxide nanoparticles (ZrO2 NPs) show excellent electrochemical properties, including nontoxicity, thermal stability, wide band gap, and good electrical and surface properties and are one of the most abundant metals. (35,36) A critical issue in utilizing bare ZrO2 nanoparticles is that they tend to aggregate and form large clusters during their synthesis. (37,38) In this connection, rGO is an excellent material to mitigate the agglomeration of ZrO2 NPs and subsequently enhance the electrochemical properties. Therefore, researchers have been giving dedicated extensive efforts to synthesize and explore ZrO2 decorated on rGO sheets, for example, Pt/ZrO2-RGO/GCE for significant enhancement of the catechol and hydroquinone oxidation, (39) ZrO2/rGO-based biosensor for detection of the oral cancer drug, (40) and Meth/ZrO2/rGO-based immunosensor. (41)
To the best of our knowledge, this is the first example of electrochemical REG sensing in human blood serum and pharmaceutical formulations using ZrO2/rGO/GCE. In this work, we tried to validate such a voltammetric sensor for the detection of REG. The prepared ZrO2/rGO/GCE can resolve overlapping signals from REG, uric acid (UA), and ascorbic acid (AA). In addition, the present work showed that this sensor possesses an excellent linear dynamic range (LDR) and limit of detection (LOD) for the novel REG determination (Scheme 1).

Scheme 1

Scheme 1. Synthesis of the ZrO2/rGO Nanocomposite for the Electrochemical Sensing of REG
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Results and Discussion

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Characterization of the ZrO2/rGO Nanocomposite

Transmission electron microscopy (TEM), high-resolution TEM (HRTEM), and selected area electron diffraction (SAED) analyses were conducted to examine the morphology and structure of the synthesized nanocomposite. The TEM images of the pristine ZrO2, GO, and ZrO2/rGO nanocomposite are shown in Figure 1. Pristine ZrO2 nanoparticles (Figure 1a) are nearly spherical with a uniform size of size of 6–9 nm, which is in good agreement with the calculated values based on the powder X-ray diffraction (PXRD) result. Moreover, the displaced-lattice spacing of 0.291 nm, determined from the HRTEM images (blue circles in Figure 1b) is consistent with the (111) plane of ZrO2. The pristine GO nanosheets are highly wrinkled, and the ZrO2 nanoparticles (blue circles) are well decorated and uniformly distributed on the surface of the wrinkled rGO (Figure 1d–f). The SAED patterns for ZrO2 (Figure 1c) and the ZrO2/rGO nanocomposite shown in Figure 1f (inset) illustrate the crystalline dots instead of amorphous rings, which indicate the polycrystalline nature of the ZrO2 nanoparticles and nanocomposite. To further confirm the formation of the nanocomposition, energy dispersive X-ray spectroscopy (EDX) analysis was employed. The presence of carbon, zirconium, and oxygen elements confirms the presence of ZrO2 on to the GO surface (Figure S3).

Figure 1

Figure 1. TEM, HRTEM, and SAED images of (a–c) pristine ZrO2 and (d–f) ZrO2/rGO nanocomposite.

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The phase purities of the as-synthesized GO and the ZrO2/rGO nanocomposite were examined using PXRD. Figure S4a shows a diffraction peak at 2θ = 10.7°, corresponding to the (001) planes of GO. The peaks of the ZrO2/rGO nanocomposite, in Figure S4b, show the existence of both tetragonal and monoclinic mixed phases, which coincide with the standard cards (JCPDS card nos. 49-1642 and 37-1484, respectively) and also show that the peak at 2θ = 10.7°, in Figure S4a, has shifted to 22.4° (002), indicating that GO has been reduced after treating it with the ZrO2 nanoparticles. In addition, the particle size of the ZrO2 nanoparticles was calculated using the Debye–Scherrer equation (D = 0.89λ/β cos θ), where D, λ, β, and θ are the average particle size, wavelength of the Cu Kα irradiation, intensity at the full width at half-maximum of the diffraction peak, and diffraction angle of the (111). The average particle size of pristine ZrO2 is about 7 nm, in good agreement with the TEM result. These results clearly confirm the formation of the ZrO2/rGO nanocomposite.
The Fourier transform infrared (FT-IR) spectra of the GO and ZrO2/rGO samples were recorded at wave numbers 500–4000 cm–1. Pristine GO has a large number of surface functional groups, as shown in Figure S5a, such as O–H, C═O, C═C, and C–O, which are confirmed by the IR bands at 3320, 1700, 1604, and 1009 cm–1, respectively. In the ZrO2/rGO sample shown in Figure S5b, the hydroxyl, carbonyl and epoxide functional groups had disappeared and also overall peak intensities decreased significantly, which confirm reduction of pristine GO leads to the formation of ZrO2/rGO nanocomposite.
The chemical composition was further confirmed by X-ray photoelectron spectrometry (XPS). The wide-survey scan spectrum of the ZrO2-doped rGO nanocomposite (ZrO2/rGO) is shown in Figure S6. The major peaks at 182.5, 284.9, and 530.2 eV are attributed to Zr 4p, C 1s, and O 1s, respectively. In addition, the peaks at 27, 333, and 433 eV attributed to Zr 4p, Zr 3p, and Zr 3s, respectively. The deconvolution spectrum of the Zr 3d peak, Figure S6 (inset), shows binding energies at 182.4 and 184.9 eV attributed to Zr 3d5/2 and Zr 3d3/2, respectively, which can be assigned to the Zr(IV) oxidation state. On the basis of these results, we confirmed that ZrO2 is well embedded into the wrinkled rGO.

Electrochemical Behavior of REG

Figure 2 shows the cyclic voltammograms for the electrocatalytic oxidation of REG on the bare and modified GCE electrodes, recorded in the supporting electrolyte solution (phosphate buffered saline (PBS) 0.1 M, pH 7.0) in the presence of 0.01 mM REG at 50 mV s–1. The voltammograms recorded on the bare GCE in the absence of REG did not show any redox peaks (Figure 2a), indicating that no faradic reactions occurred on the surface of the unmodified GCE electrode. Figure 2b shows that the addition of 0.01 mM REG to the supporting electrolyte solution results in the GCE exhibiting a lowest sensitivity reversible couple peak of high separation; ΔEp = 208 mV, which suggests a slow electron transfer. Figure 2c,d shows the recognizable electrochemical response of the ZrO2/GCE and ZrO2/rGO/GCE, respectively, during the oxidation of 0.01 mM REG, which is interpreted as a result of the enhanced sensitivity, electrode surface area, and improvement of the electrochemical activity of the GO support with ZrO2 NPs. Figure 2d shows the ZrO2/rGO/GCE and reveals well-defined reversible couple peaks at about Epa = 275 mV and Epc = 306 mV, attributed to the high catalytic effect during the oxidation of 0.1 mM REG. The ZrO2/rGO/GCE remarkably improved the reversible couple peaks and it should be emphasized that the peak-to-peak separation, that is ΔEp, decreased to 31 mV. Finally, the results confirmed that the prepared ZrO2/rGO/GCE significantly improves the electrocatalytic ability to oxidize REG.

Figure 2

Figure 2. Cyclic voltammograms recorded in 0.1 M PBS, pH 7.0, at the scan rate of 100 mV s–1 (a) blank and bare GCE electrode without REG, (b) bare GCE in the presence of 0.01 mM REG, (c) ZrO2-modified GC electrode in the presence of 0.01 mM REG, and (d) ZrO2/rGO/GCE in the presence of 0.01 mM REG.

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Effect of pH

The significant effects of the electrolyte pH on the determination of REG by electrocatalysis of ZrO2/rGO/GCE were studied for both current and potential. Figure 3 shows the effect of different pH values, in the range 5.5–8.0, investigated by differential pulse voltammetry (DPV) in a 0.01 mM REG solution and the relationship between Ipa and Epa (anionic peak current and potential, respectively) with the buffer pH. Figure 3b shows that the anodic peak current of the REG electro-oxidation increases until the pH value becomes 7.0 and then decreases until the end of the experiment (pH 8.0). For this reason, the electrolytic solution with pH 7.0 was chosen for the complete electrocatalytic study. Figure 3b also shows that the formal REG potential shifts toward lower values with the increase in the supporting electrolytic solution. A better correlation coefficient was obtained for the pH vs Epa, which was confirmed by a slope of 0.053 09 V/pH (R2 = 0.9621), in the range 5.5–8.0. According to the linear regression analysis, the slope of the dEp/dpH being close to the theoretical value of 0.059 V/pH indicates that the irreversible couple peaks involved the transfer of the same number of electrons and protons, (42) in agreement with literature data. (43) The ZrO2/rGO/GCE responds to the oxidation of REG according to the mechanism presented in Scheme 2. Thus, REG-keto oxidizes to REG-enol (the amide derivative) after an exchange of one electron and one proton via ZrO2/rGO nanocomposite. (36)

Figure 3

Figure 3. (a) DPV voltammograms obtained with the ZrO2/rGO/GCE in an electrolyte solution at different pH values, with 0.01 mM REG. (b) Calibration plot of the anodic peak current (curve-I) and the anodic peak potential (curve-II) vs the pH of the 0.1 M PBS solution, during the electro-oxidation of 0.01 mM REG, at a scan rate of 100 mV s–1.

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Scheme 2

Scheme 2. Electrochemical Redox Process of REG by ZrO2/rGO/GCE
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Influence of the Scan Rate

Figure 4a shows the influence of the scan rate, from 10 to 100 mV s–1, on the cyclic voltammetry (CV) peak potential and current of 0.01 mM REG in the presence of 0.1 M PBS, pH 7.0, at the ZrO2/rGO/GCE. The REG reversible couple peak current increases gradually with an increase in the scan rate. In addition, the REG oxidation and reduction peak currents (Ipa and Ipc) showed good linear correlation coefficients (R2) as a function of the square root of the scan rates of the anodic and cathodic peaks with 10–100 mV s–1 changing scan rates (Figure 4b), obeying the following linear regression equations
These results indicate that the electrochemical reactions of REG on the ZrO2/rGO/GCE are diffusion-controlled processes. The estimation of the REG electrochemical parameters, at different scan rates, was made with Laviron’s eqs 1–3. (44)
(1)
(2)
(3)
where α is the electron transfer coefficient (0.76), n is the number of electrons, F is the Faraday constant (96 485 C mol–1), R and T are the universal gas constant and temperature (K), respectively, and ks is the standard heterogeneous rate constant (1.18) determining the slowest step of the REG electrochemical oxidation.

Figure 4

Figure 4. (a) Cyclic voltammograms recorded at the ZrO2/rGO/GCE in the electrolyte solution at different scan rates from 10 to 100 mV s–1. (b) Calibration plot of the anodic and cathode peak currents versus the square root of the scan rate, during the electro-oxidation of 0.01 mM REG in the presence of 0.1 M PBS, pH 7.0.

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Analytical Performance of ZrO2/rGO/GCE for REG Detection

The ZrO2/rGO/GCE was tested by differential pulse voltammetry (DPV), to investigate the sensitivity of its response to various REG concentrations in the linear dynamic range of 11–343 nM REG in 0.1 M PBS, pH 7.0, at pulse height 60, pulse width 10, and scan rate 100 mV s–1, as shown in Figure 5a. The intensity of the anodic peak current increased with the REG concentration. Figure 5b shows the linear dynamic-range plotting of the anodic peak current (Ipa) versus the REG concentrations and its linear regression equation Ipa = 9.4911(REG) + 3.434, (R2 = 0.9963). The limits of detection and quantification can be calculated according to eqs 4 and 5 (45,46)
(4)
(5)
where SD is the standard deviation and B is the slope of the calibration plot. From the calibration plot, a detection limit of 11 nM and quantification limit of 59 nM were calculated, on the basis of S/N = 3 (signal to noise). These results confirmed that the ZrO2/rGO/GCE is a promising platform for the electrochemical determination of ultratrace of REG concentration.

Figure 5

Figure 5. (a) Differential pulse voltammograms recorded at the ZrO2/rGO/GCE over an REG concentration of 11–343 nM in 0.1 M PBS at pH 7.0. (b) Linear calibration plot of the anodic peak current versus REG concentration.

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Simultaneous Detection of REG, AA, and UA by ZrO2/rGO/GCE

The main objective of this study was sensing of REG, AA, and UA in a mixture. REG, AA, and UA mixture solution with different concentrations in 0.1 M PBS with pH 7 was prepared. DPV result for the simultaneous detection of REG, AA, and UA is presented in Figure 6. The oxidation peak current increased synchronously on increasing the concentration of REG, AA, and UA. The DPV signal shows the linear relationship between the oxidation peak current and REG concentrations (Figure 6 inset) with LDR 0.32–0.66 μM and the linear regression equation as follows: Ipa (μA) = 15.46CREG + 0.5232 (μM) (R2 = 0.9943). The oxidation current increased parallel AA and UA concentrations with LDRs 0.58–1.26 and 0.08–0.52 μM, respectively, and the linear regression equations as follows: Ipa (μA) = 3.92CAA + 2.417 (μM) (R2 = 0.9749) and Ipa (μA) = 15.85CUA + 4.97 (μM) (R2 = 0.9795). This result indicated that the proposed electrochemical sensor enables the synergetic and sensitive detection of REG in the presence of AA and UA without significant interference from each other.

Figure 6

Figure 6. DPVs recorded on the ZrO2/rGO/GCE during simultaneous determination of 0.32–0.66 μM REG, 0.58–1.26 μM AA, and 0.08–0.52 μM UA in 0.1 M PBS, pH 7.0. Insets: plots of the anodic peak currents against concentrations of REG, AA, and UA.

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Effect of Interference Compounds

The effect of interferences for the determination of REG, AA, and UA mixture solution was investigated in 0.1 M PBS (pH 7.0) electrolyte solution in the presence of a possible interfering factor such as metal ions (Ca2+, Mg2+, and Zn2+), glutathione, folic acid, or l-cysteine. The observed results are summarized in Table S1. No significant signal intensity change (less than 5% difference from their original signal intensity) was observed in the presence of interfering ions and molecules. The results indicate that the designed ZrO2/rGO/GCE displays good ability for simultaneous sensing of AA, UA, and REG in a matrix mixture, without any interference of the above-mentioned species.

Real-Sample Analysis

The real-sample monitoring of the performance of the ZrO2/rGO/GCE was validated by the DPV determination of REG in human blood serum samples. To determine the accuracy of the results, 1.0 mL human blood serum samples were diluted 50 times with PBS to prevent the matrix effects of analytical determinations. The human blood serum samples were centrifuged before the measurements; the results are summarized in Table 1. The recovery rates for the different volumes of the samples ranged between 96.5 and 101.9% and the relative standard deviations were in the range 0.3–2.4%, showing the accuracy and efficiency of the constructed electrochemical sensor. Therefore, the ZrO2/rGO/GCE can be applied to real bioclinical samples.
Table 1. Real-Sample Analysis of REG Using the Proposed Method by Triplicate (n = 3) Readings
samplesspiked sample (mM)found (mM)recovery (%)RSD (%) ±SE
pharmaceutical formulation0.0100.0098982.54 ± 0.05
0.0500.0509101.81.98 ± 0.08
0.1000.0990991.32 ± 0.06
blood serum0.0100.0098982.42 ± 0.11
0.0500.048697.21.65 ± 0.07
0.1000.1026102.61.09 ± 0.05

Comparison with Other Established Methods

The sensitivity of the developed electroanalytical method was compared to that of some of the chromatography and spectrophotometry methods. Recently, Fujita et al., reported one method using high-performance liquid chromatography (HPLC) for simultaneous quantitative determination of REG in the human plasma and achieved LOQ of 10 ng mL–1. In addition, Erp et al., reported liquid chromatography tandem mass spectrometry (LC-MS/MS) can achieve LOQ of 100 ng mL–1 for REG. The other spectroscopic method can analyze REG with an LOQ of 290 ng mL–1. Compared with the reported methods, the presented method shows a better limit of detection and limit of quantification limit (Table 2). Due to its low cost, simplicity, high sensitivity, and rapid analysis time, the presented method has advantages over the other analytical methods.
Table 2. Comparison of the Electroanalytical Method with Reported Analytical Techniques
methodLDR (ng mL–1)LOD (ng mL–1)LOQ (ng mL–1)refs
HPLC10–10 000 10.0 (13)
LC-MS/MS25–25 000 25.0 (14)
LC-MS/MS100–4000 100 (15)
spectrophotometric method500–25 000110290 (20)
electroanalytical method1.5–107 (11–343 nM)5.00 (17 nM)18.5 (59 nM)present work

Conclusions

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Inorganic metal-oxide nanoparticles have been enormously employed as electrode material for a developed efficient electrochemical sensor. A simple one-pot hydrothermal synthesis of ZrO2/rGO nanocomposite was successfully synthesized. The pristine ZrO2 nanoparticles are about 7 nm and uniformly dispersed on the reduced graphene oxide sheet. Due to reduced graphene oxide support, the ZrO2 metal-oxide nanoparticles illustrate excellent electrocatalytic performance toward REG anticancer drug. The developed ZrO2/rGO nanocomposite was characterized by TEM, EDX, PXRD, FT-IR, and XPS measurements. TEM images clearly show the zirconia nanoparticles have uniform size and uniform distribution on the surface of rGO. The inorganic nanocomposite-based electrochemical sensor was successfully applied first time for the detection of REG anticancer drug. The fabricated ZrO2/rGO nanocomposite exhibited an excellent electrocatalytic activity toward REG, with a linear dynamic range of 11–343 nM and the detection limit as low as 17 nM toward the detection of REG drug. The ZrO2/rGO/GCE was applicable for the joint determination of REG and a commonly reported interference AA and UA at pH 7.0. The calculated LOD/LOQ values by the present electrochemical method are better than those from chromatography and spectrophotometry methods. This electrochemical sensor shows promise for future exploration of rapid detection of other anticancer drugs in human blood serum and pharmaceutical formulation.

Experimental Section

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Modification of the Glassy Carbon Electrode

Preparation of the ZrO2/rGO/GCE: prior to use, the bare GCE was polished with alumina powder (1, 0.3, and 0.05 μm) and washed with an ethanol solution, followed by Millipore water under ultrasonication. For the preparation of the electrochemical sensor, 3 mg of the prepared ZrO2/rGO was dispersed in 3 mL of Millipore water with 0.3 mL of Nafion solution and then ultrasonicated for 30 min until a uniformly dispersed ink was obtained. The ZrO2/rGO ink (7 μL) was drop cast onto the clean GCE surface and allowed to dry for 15 min at room temperature. The ZrO2/GCE was fabricated in a similar manner.

Reproducibility and Stability of the Modified Electrode

Reproducibility and stability are key elements for electrode performance. To evaluate the reproducibility of the ZrO2/rGO/GCE, we made five sensing electrodes and used them to investigate their CV current response on 1 μM REG in phosphate buffered saline (PBS), pH 7.0, as shown in Figure S1a. The calibrated histograms in Figure S1b show a relatively standard deviation (RSD) of 0.54%. The repeatability of the modified electrochemical sensor values was obtained for the detection of 1 μM REG in presence of the supporting electrolyte, PBS (pH 7.0). The ZrO2/rGO/GCE average voltammetric response for seven successive determinations was 3.34% (Figure S2a). Moreover, the stability of the ZrO2/rGO/GCE was verified by the daily detection for 7 weeks of 1 μM REG solution in presence of the supporting PBS electrolyte (pH 7.0). After each test of stability, the electrode was washed with deionized water, dried under an argon stream, and kept in empty glass tubes at room temperature. The electrochemical oxidation of the 1 μM REG solution, in presence of the supporting PBS electrolyte (pH 7.0), using the ZrO2/rGO/GCE diminished by about 9.6% of their initial response during the 7 weeks, as shown in Figure S2b. Hence, the proposed method and the modified electrochemical sensor determined REG with higher reproducibility and stability than the ZrO2/GCE sensor.

Preparation of Real Samples for Analysis

A powdered Stivarga tablet (Nexus Lifecare Pvt. Ltd., Mumbai, India) containing 40 mg of REG was dissolved by ultrasonication in 25 mL of 0.1 M PBS buffer solution at pH 7.0. This solution was filtered and quantitatively diluted with buffer solution to get 0.1 mM REG solution that was used for the analyses. Fresh human blood serum samples were collected from healthy volunteers (S. V. University Health Center, S. V. University, Tirupati, India). Approximately, 2.0 mL of human blood serum was diluted with 100 mL of 0.1 M PBS, at pH 7.0, and the solution thus prepared was used for analysis, without any further treatment.

Supporting Information

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsomega.8b02129.

  • Cyclic voltammogram, EDS data, FT-IR, materials and methods, XPS analysis, XRD, and interferences of some foreign species (PDF)

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Author Information

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  • Corresponding Authors
    • Vinod Kumar Gupta - Department of Applied Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park 2006, South Africa;  Department of Biological Sciences, King Abdulaziz University, Jeddah 21589, Saudi Arabia;  Email: [email protected]
    • Minyoung Yoon - Department of Nanochemistry and , Gachon University, Sungnam 13120, Republic of Korea;  Orcidhttp://orcid.org/0000-0001-7436-6273;  Email: [email protected]
    • Gajulapalli Madhavi - Electrochemical Research Laboratory, Department of Chemistry, Sri Venkateswara University, Tirupati 517502, India;  Email: [email protected]
  • Authors
    • Manthrapudi Venu - Electrochemical Research Laboratory, Department of Chemistry, Sri Venkateswara University, Tirupati 517502, India
    • Sada Venkateswarlu - Department of Nanochemistry and , Gachon University, Sungnam 13120, Republic of Korea
    • Yenugu Veera Manohara Reddy - Electrochemical Research Laboratory, Department of Chemistry, Sri Venkateswara University, Tirupati 517502, India;  Orcidhttp://orcid.org/0000-0001-8699-922X
    • Ankireddy Seshadri Reddy - Department of Chemical and Biological Engineering and , Gachon University, Sungnam 13120, Republic of Korea;  Orcidhttp://orcid.org/0000-0002-0395-3515
  • Author Contributions

    The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

    M.V. and S.V. contributed equally in this work.

    Author Contributions

    The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

    M.V. and S.V. contributed equally in this work.

  • Notes
    The authors declare no competing financial interest.

Acknowledgments

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Mr. Manthrapudi Venu is grateful to the UGC Letter No. F. 25-1/2013-14 (BSR)/7-187/2007 (BSR) dated: 19-11-2014 from Government of India, New Delhi, for providing financial assistance in the form of an award of Research Fellowships in Science for meritorious students (RFSMS). This work was also supported by a National Research Foundation of Korea (NRF) grant funded by the Ministry of Science and ICT (NRF-2017R1C1B5076834, S.V. and NRF-2018M2A2A6A01057259, M.Y.)

Abbreviations

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AA

ascorbic acid

CV

cyclic voltammetry

DPV

differential pulse voltammetry

EDX

energy dispersive X-ray spectroscopy

FT-IR

Fourier transform infrared

GCE

glassy carbon electrode

HRTEM

high-resolution transmission electron microscopy

LOD

lower detection limit

LOQ

limit of quantifications

REG

regorafenib

rGO

reduced graphene oxide

SAED

selected area electron diffraction pattern

TEM

transmission electron microscopy

UA

uric acid

XPS

X-ray photoelectron spectrometry

XRD

X-ray diffraction

ZrO2 NPs

zirconium oxide nanoparticles

References

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    Chen, Dongshi; Wei, Liang; Yu, Jian; Zhang, Lin
    Clinical Cancer Research (2014), 20 (13), 3472-3484CODEN: CCREF4; ISSN:1078-0432. (American Association for Cancer Research)
    Purpose: Regorafenib, a multikinase inhibitor targeting the Ras/Raf/MEK/ERK pathway, has recently been approved for the treatment of metastatic colorectal cancer. However, the mechanisms of action of regorafenib in colorectal cancer cells have been unclear. We investigated how regorafenib suppresses colorectal cancer cell growth and potentiates effects of other chemotherapeutic drugs. Exptl. Design: We detd. whether and how regorafenib induces the expression of PUMA, a p53 target and a crit. mediator of apoptosis in colorectal cancer cells. We also investigated whether PUMA is necessary for the killing and chemosensitization effects of regorafenib in colorectal cancer cells. Furthermore, xenograft tumors were used to test if PUMA mediates the in vivo antitumor, antiangiogenic, and chemosensitization effects of regorafenib. Results: We found that regorafenib treatment induces PUMA in colorectal cancer cells irresp. of p53 status through the NF-κB pathway following ERK inhibition and glycogen synthase kinase 3β activation. Upregulation of PUMA is correlated with apoptosis induction in different colorectal cancer cell lines. PUMA is necessary for regorafenib-induced apoptosis in colorectal cancer cells. Chemosensitization by regorafenib is mediated by enhanced PUMA induction through different pathways. Furthermore, deficiency in PUMA abrogates the in vivo antitumor, antiangiogenic, and chemosensitization effects of regorafenib. Conclusions: Our results demonstrate a key role of PUMA in mediating the anticancer effects of regorafenib in colorectal cancer cells. They suggest that PUMA induction can be used as an indicator of regorafenib sensitivity, and also provide a rationale for manipulating the apoptotic machinery to improve the therapeutic efficacy of regorafenib and other targeted drugs. Clin Cancer Res; 20(13); 3472-84. ©2014 AACR.
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  2. 2
    Wilhelm, S. M.; Dumas, J.; Adnane, L.; Lynch, M.; Carter, C. A.; Schutz, G.; Thierauch, K. H.; Zopf, D. Regorafenib (bay 73-4506): A New Oral Multikinase Inhibitor of Angiogenic, Stromal and Oncogenic Receptor Tyrosine Kinases with Potent Preclinical Antitumor Activity. Int. J. Cancer 2011, 129, 245– 255,  DOI: 10.1002/ijc.25864
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    2
    Regorafenib (BAY 73-4506): A new oral multikinase inhibitor of angiogenic, stromal and oncogenic receptor tyrosine kinases with potent preclinical antitumor activity
    Wilhelm, Scott M.; Dumas, Jacques; Adnane, Lila; Lynch, Mark; Carter, Christopher A.; Schuetz, Gunnar; Thierauch, Karl-Heinz; Zopf, Dieter
    International Journal of Cancer (2011), 129 (1), 245-255CODEN: IJCNAW; ISSN:0020-7136. (Wiley-Liss, Inc.)
    Angiogenesis, a crit. driver of tumor development, is controlled by interconnected signaling pathways. Vascular endothelial growth factor receptor (VEGFR) 2 and tyrosine kinase with Ig and epidermal growth factor homol. domain 2 play crucial roles in the biol. of normal and tumor vasculature. Regorafenib (BAY 73-4506), a novel oral multikinase inhibitor, potently inhibits these endothelial cell kinases in biochem. and cellular kinase phosphorylation assays. Furthermore, regorafenib inhibits addnl. angiogenic kinases (VEGFR1/3, platelet-derived growth factor receptor-β and fibroblast growth factor receptor 1) and the mutant oncogenic kinases KIT, RET and B-RAF. The antiangiogenic effect of regorafenib was demonstrated in vivo by dynamic contrast-enhanced magnetic resonance imaging. Regorafenib administered once orally at 10 mg/kg significantly decreased the extravasation of Gadomer in the vasculature of rat GS9L glioblastoma tumor xenografts. In a daily (qd)×4 dosing study, the pharmacodynamic effects persisted for 48 h after the last dosing and correlated with tumor growth inhibition (TGI). A significant redn. in tumor microvessel area was obsd. in a human colorectal xenograft after qd×5 dosing at 10 and 30 mg/kg. Regorafenib exhibited potent dose-dependent TGI in various preclin. human xenograft models in mice, with tumor shrinkages obsd. in breast MDA-MB-231 and renal 786-O carcinoma models. Pharmacodynamic analyses of the breast model revealed strong redn. in staining of proliferation marker Ki-67 and phosphorylated extracellular regulated kinases 1/2. These data demonstrate that regorafenib is a well-tolerated, orally active multikinase inhibitor with a distinct target profile that may have therapeutic benefit in human malignancies.
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  3. 3
    Di Gion, P.; Kanefendt, F.; Lindauer, A.; Scheffler, M.; Doroshyenko, O.; Fuhr, U.; Wolf, J.; Jaehde, U. Clinical Pharmacokinetics of Tyrosine Kinase Inhibitors: Focus on Pyrimidines, Pyridines, and Pyrroles. Clin. Pharmacokinet. 2011, 50, 551– 603,  DOI: 10.2165/11593320-000000000-00000
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    Clinical pharmacokinetics of tyrosine kinase inhibitors: focus on pyrimidines, pyridines and pyrroles
    Di Gion, Paola; Kanefendt, Friederike; Lindauer, Andreas; Scheffler, Matthias; Doroshyenko, Oxana; Fuhr, Uwe; Wolf, Juergen; Jaehde, Ulrich
    Clinical Pharmacokinetics (2011), 50 (9), 551-603CODEN: CPKNDH; ISSN:0312-5963. (Wolters Kluwer Health)
    A review. Pyrimidine (imatinib, dasatinib, nilotinib and pazopanib), pyridine (sorafenib) and pyrrole (sunitinib) tyrosine kinase inhibitors (TKIs) are multi-targeted TKIs with high activity towards several families of receptor and non-receptor tyrosine kinases involved in angiogenesis, tumor growth and metastatic progression of cancer. These orally administered TKIs have quite diverse characteristics with regard to absorption from the gastrointestinal tract. Abs. bioavailability in humans has been investigated only for imatinib (almost 100%) and pazopanib (14-39%; n = 3). On the basis of human radioactivity data, dasatinib is considered to be well absorbed after oral administration (19% and 0.1% of the total radioactivity were excreted as unchanged dasatinib in the faeces and urine, resp.). Quite low abs. bioavailability under fasted conditions is assumed for nilotinib (31%), sorafenib (50%) and sunitinib (50%). Imatinib, dasatinib and sunitinib exhibit dose-proportional increases in their area under the plasma concn.-time curve values over their therapeutic dose ranges. Less than dose-proportional increases were obsd. for nilotinib at doses ≥400 mg/day and for sorafenib and pazopanib at doses ≥800 mg/day. At steady state, the accumulation ratios are 1.5-2.5 (unchanged imatinib), 2.0 (nilotinib once-daily dosing), 3.4 (nilotinib twice-daily dosing), 1.2-4.5 (pazopanib), 5.7-6.4 (sorafenib) and 3.0-4.5 (sunitinib). Concomitant intake of a high-fat meal does not alter exposure to imatinib, dasatinib and sunitinib but leads to considerably increased bioavailability of nilotinib and pazopanib and decreased bioavailability of sorafenib. With the exception of pazopanib, the TKIs described here have large apparent vols. of distribution, exceeding the vol. of body water by at least 4-fold. Very low penetration into the central nervous system in humans has been reported for imatinib and dasatinib, but there are currently no published human data for nilotinib, pazopanib, sorafenib or sunitinib. All TKIs that have been described are more than 90% bound to the plasma proteins: α1-acid glycoprotein and/or albumin. They are metabolized primarily via cytochrome P 450 (CYP) 3A4, the only exception being sorafenib, for which uridine diphosphate glucuronosyltransferase 1A9 is the other main enzyme involved. Active metabolites of imatinib and sunitinib contribute to their antitumor activity. Although some patient demographics have been identified as significant co-factors that partly explain interindividual variability in exposure to TKIs, these findings have not been regarded as sufficient to recommend age-, sex-, bodyweight- or ethnicity-specific dose adjustment. Systemic exposure to imatinib, sorafenib and pazopanib increases in patients with hepatic impairment, and redn. of the initial therapeutic dose is recommended in this subpopulation. The starting dose of imatinib should also be reduced in renally impaired subjects. Because the soly. of dasatinib is pH dependent, co-administration of histamine H2-receptor antagonists and proton pump inhibitors with dasatinib should be avoided. With the exception of sorafenib, systemic exposure to TKIs is significantly decreased/increased by co-administration of potent CYP3A4 inducers/inhibitors, and so it is strongly recommended that the TKI dose is adjusted or that such co-administration is avoided. Caution is also recommended for co-administration of CYP3A4 substrates with TKIs, esp. for those with a narrow therapeutic index. However, current recommendations with regard to dose adjustment of TKIs need to be validated in clin. studies. Further investigations are needed to explain the large interindividual variability in the pharmacokinetics of these drugs and to assess the clin. relevance of their interaction potential and inhibitory effects on metabolizing enzymes and transporters.
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  4. 4
    Josephs, D. H.; Fisher, D. S.; Spicer, J.; Flanagan, R. Clinical Pharmacokinetics of Tyrosine Kinase Inhibitors: Implications for Therapeutic Drug Monitoring. Ther. Drug Monit. 2013, 35, 562– 587,  DOI: 10.1097/FTD.0b013e318292b931
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    4
    Clinical Pharmacokinetics of Tyrosine Kinase Inhibitors: Implications for Therapeutic Drug Monitoring
    Josephs, Debra H.; Fisher, Danielle S.; Spicer, James; Flanagan, Robert J.
    Therapeutic Drug Monitoring (2013), 35 (5), 562-587CODEN: TDMODV; ISSN:0163-4356. (Lippincott Williams & Wilkins)
    A review. The treatment of many malignancies has been improved in recent years by the introduction of mol. targeted therapies. These drugs interact preferentially with specific targets that are mutated and/or overexpressed in malignant cells. A group of such targets are the tyrosine kinases, against which a no. of inhibitors (tyrosine kinase inhibitors, TKIs) have been developed. Imatinib, a TKI with targets that include the breakpoint cluster region-Abelson (bcr-abl) fusion protein kinase and mast/stem cell growth factor receptor kinase (c-Kit), was the first clin. successful drug of this type and revolutionized the treatment and prognosis of chronic myeloid leukemia and gastrointestinal stromal tumors. This success paved the way for the development of other TKIs for the treatment of a range of hematol. malignancies and solid tumors. To date, 14 TKIs have been approved for clin. use and many more are under investigation. All these agents are given orally and are substrates of a range of drug transporters and metabolizing enzymes. In addn., some TKIs are capable of inhibiting their own transporters and metabolizing enzymes, making their disposition and metab. at steady-state unpredictable. A given dose can therefore give rise to markedly different plasma concns. in different patients, favoring the selection of resistant clones in the case of subtherapeutic exposure, and increasing the risk of toxicity if dosage is excessive. The aim of this review was to summarize current knowledge of the clin. pharmacokinetics and known adverse effects of the TKIs that are available for clin. use and to provide practical guidance on the implications of these data in patient management, in particular with respect to therapeutic drug monitoring.
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  5. 5
    Ly, J. Q.; Messick, K.; Qin, A.; Takahashi, R. H.; Choo, E. F. Utility of CYP3A4 and PXR-CAR-CYP3A4/3A7 Transgenic Mouse Models to Assess the Magnitude of CYP3A4 Mediated Drug–Drug Interactions. Mol. Pharmaceutics 2017, 14, 1754– 1759,  DOI: 10.1021/acs.molpharmaceut.7b00006
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    5
    Utility of CYP3A4 and PXR-CAR-CYP3A4/3A7 Transgenic Mouse Models To Assess the Magnitude of CYP3A4 Mediated Drug-Drug Interactions
    Ly, Justin Q.; Messick, Kirsten; Qin, Ann; Takahashi, Ryan H.; Choo, Edna F.
    Molecular Pharmaceutics (2017), 14 (5), 1754-1759CODEN: MPOHBP; ISSN:1543-8384. (American Chemical Society)
    Species differences in the expression, activity, regulation, and substrate specificity of metabolizing enzymes preclude the use of animal models to predict clin. drug-drug interactions (DDIs). The objective of this work is to det. if the transgenic (Tg) Cyp3a-/-Tg-3A4Hep/Int and Nr1i2/Nr1i3-/--Cyp3a-/-Tg-PXR-CAR-3A4/3A7Hep/Int (PXR-CAR-CYP3A4/3A7) mouse models could be used to predict in vivo DDI of 10 drugs; alprazolam, bosutinib, crizotinib, dasatinib, gefitinib, ibrutinib, regorafenib, sorafenib, triazolam, and vandetinib (as victims); with varying magnitudes of reported CYP3A4 clin. DDI. As an assessment of the effect of CYP3A4 inhibition, these drugs were coadministered to Cyp3a-/-Tg-3A4Hep/Int mice with the CYP3A inhibitor, itraconazole. For crizotinib, regorafenib, sorafenib, and vandetanib, there was no significant increase of AUC obsd.; with alprazolam, bosutinib, ibrutinib, dasatinib, and triazolam, pretreatment with itraconazole resulted in a 2-, 4-, 17-, 7-, and 15-fold increase in AUC, resp. With the exception of gefinitib for which the DDI effect was overpredicted (12-fold in Tg-mice vs 2-fold in the clinic), the magnitude of AUC increase obsd. in this study was consistent (within 2-fold) with the clin. DDI obsd. following administration with itraconazole/ketoconazole. As an assessment of CYP3A4 induction, following rifampin pretreatment to PXR-CAR-3A4/3A7Hep/Int mice, an 8% decrease in vandetanib mean AUC was obsd.; 39-52% redn. in AUC were obsd. for dasatinib, ibrutinib, regorafenib, and sorafenib compared to vehicle treated mice. The greatest effect of rifampin induction was obsd. with alprazolam, bosutinib, crizotinib, gefitinib, and triazolam where 72-91% decrease in AUC were obsd. With the exception of vandetanib for which rifampin induction was under-predicted, the magnitude of induction obsd. in this study was consistent (within 2-fold) with clin. observations. These data sets suggest that, with two exceptions, these transgenic mice models were able to exclude or capture the magnitude of CYP3A4 clin. inhibition and induction. Data generated in transgenic mice may be used to gain confidence and complement in vitro and in silico methods for assessing DDI potential/liability.
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  6. 6
    Cheng, A. L.; Kang, Y. K.; Lin, D. Y.; Park, J. W.; Kudo, M.; Qin, S.; Chung, H. C.; Song, X.; Xu, J.; Poggi, G.; Omata, M.; Pitman Lowenthal, S.; Lanzalone, S.; Yang, L.; Lechuga, M. J.; Raymond, E. Sunitinib Versus Sorafenib in Advanced Hepatocellular Cancer: Results of a Randomized Phase III Trial. J. Clin. Oncol. 2013, 31, 4067– 4075,  DOI: 10.1200/JCO.2012.45.8372
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    6
    Sunitinib versus sorafenib in advanced hepatocellular cancer: results of a randomized phase III trial
    Cheng, Ann-Lii; Kang, Yoon-Koo; Lin, Deng-Yn; Park, Joong-Won; Kudo, Masatoshi; Qin, Shukui; Chung, Hyun-Cheol; Song, Xiangqun; Xu, Jianming; Poggi, Guido; Omata, Masao; Lowenthal, Susan Pitman; Lanzalone, Silvana; Yang, Liqiang; Lechuga, Maria Jose; Raymond, Eric
    Journal of Clinical Oncology (2013), 31 (32), 4067-4075CODEN: JCONDN; ISSN:0732-183X. (American Society of Clinical Oncology)
    Purpose Open-label, phase III trial evaluating whether sunitinib was superior or equiv. to sorafenib in hepatocellular cancer. Patients and Methods Patients were stratified and randomly assigned to receive sunitinib 37.5 mg once per day or sorafenib 400 mg twice per day. Primary end point was overall survival (OS). Results Early trial termination occurred for futility and safety reasons. A total of 1,074 patients were randomly assigned to the study (sunitinib arm, n = 530; sorafenib arm, n = 544). For sunitinib and sorafenib, resp., median OS was 7.9 vs. 10.2 mo (hazard ratio [HR], 1.30; one-sided P = .9990; two-sided P = .0014); median progression-free survival (PFS; 3.6 v 3.0 mo; HR, 1.13; one-sided P = .8785; two-sided P = .2286) and time to progression (TTP; 4.1 v 3.8 mo; HR, 1.13; one-sided P = .8312; two-sided P = .3082) were comparable. Median OS was similar among Asian (7.7 v 8.8 mo; HR, 1.21; one-sided P = .9829) and hepatitis B-infected patients (7.6 v 8.0 mo; HR, 1.10; one-sided P = .8286), but was shorter with sunitinib in hepatitis C-infected patients (9.2 v 17.6 mo; HR, 1.52; one-sided P = .9835). Sunitinib was assocd. with more frequent and severe adverse events (AEs) than sorafenib. Common grade 3/4 AEs were thrombocytopenia (29.7%) and neutropenia (25.7%) for sunitinib; hand-foot syndrome (21.2%) for sorafenib. Discontinuations owing to AEs were similar (sunitinib, 13.3%; sorafenib, 12.7%). Conclusion OS with sunitinib was not superior or equiv. but was significantly inferior to sorafenib. OS was comparable in Asian and hepatitis B-infected patients. OS was superior in hepatitis C-infected patients who received sorafenib. Sunitinib-treated patients reported more frequent and severe toxicity.
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  7. 7
    Cheng, A. L.; Kang, Y. K.; Chen, A. L.; Tsao, Z.; Qin, C. J.; Kim, S.; Luo, J. S.; Feng, R.; Ye, J.; Yang, S.; Xu, T. S.; Sun, J.; Liang, Y.; Liu, H.; Wang, J.; Tak, J.; Pan, W. Y.; Burock, H.; Zou, K.; Voliotis, J.; Guan, D. Z. Efficacy, and Safety of Sorafenib in Patients in the Asia-Pacific Region with Advanced Hepatocellular Carcinoma: A Phase III Randomized, Double-Blind, Placebo-Controlled Trial. Lancet Oncol. 2009, 10, 25– 34,  DOI: 10.1016/S1470-2045(08)70285-7
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    7
    Efficacy and safety of sorafenib in patients in the Asia-Pacific region with advanced hepatocellular carcinoma: a phase III randomized, double-blind, placebo-controlled trial
    Cheng, Ann-Lii; Kang, Yoon-Koo; Chen, Zhendong; Tsao, Chao-Jung; Qin, Shukui; Kim, Jun Suk; Luo, Rongcheng; Feng, Jifeng; Ye, Shenglong; Yang, Tsai-Sheng; Xu, Jianming; Sun, Yan; Liang, Houjie; Liu, Jiwei; Wang, Jiejun; Tak, Won Young; Pan, Hongming; Burock, Karin; Zou, Jessie; Voliotis, Dimitris; Guan, Zhongzhen
    Lancet Oncology (2009), 10 (1), 25-34CODEN: LOANBN; ISSN:1470-2045. (Elsevier Ltd.)
    Most cases of hepatocellular carcinoma occur in the Asia-Pacific region, where chronic hepatitis B infection is an important etiol. factor. Assessing the efficacy and safety of new therapeutic options in an Asia-Pacific population is thus important. We did a multinational phase III, randomized, double-blind, placebo-controlled trial to assess the efficacy and safety of sorafenib in patients from the Asia-Pacific region with advanced (unresectable or metastatic) hepatocellular carcinoma. Between Sept 20, 2005, and Jan 31, 2007, patients with hepatocellular carcinoma who had not received previous systemic therapy and had Child-Pugh liver function class A, were randomly assigned to receive either oral sorafenib (400 mg) or placebo twice daily in 6-wk cycles, with efficacy measured at the end of each 6-wk period. Eligible patients were stratified by the presence or absence of macroscopic vascular invasion or extrahepatic spread (or both), Eastern Cooperative Oncol. Group performance status, and geog. region. Randomization was done centrally and in a 2:1 ratio by means of an interactive voice-response system. There was no predefined primary endpoint; overall survival, time to progression (TTP), time to symptomatic progression (TTSP), disease control rate (DCR), and safety were assessed. Efficacy analyses were done by intention to treat. This trial is registered with, no. Two hundred and seventy-one 271 patients from 23 centers in China, South Korea, and Taiwan were enrolled in the study. Of these, 226 patients were randomly assigned to the exptl. group (n=150) or to the placebo group (n=76). Median overall survival was 6.5 mo (95% CI 5.56-7.56) in patients treated with sorafenib, compared with 4.2 mo (3.75-5.46) in those who received placebo (hazard ratio [HR] 0.68 [95% CI 0.50-0.93]; p=0.014). Median TTP was 2.8 mo (2.63-3.58) in the sorafenib group compared with 1.4 mo (1.35-1.55) in the placebo group (HR 0.57 [0.42-0.79]; p=0.0005). The most frequently reported grade 3/4 drug-related adverse events in the 149 assessable patients treated with sorafenib were hand-foot skin reaction (HFSR; 16 patients [10.7%]), diarrhea (nine patients [6.0%]), and fatigue (five patients [3.4%]). The most common adverse events resulting in dose redns. were HFSR (17 patients [11.4%]) and diarrhea (11 patients [7.4%]); these adverse events rarely led to discontinuation. Sorafenib is effective for the treatment of advanced hepatocellular carcinoma in patients from the Asia-Pacific region, and is well tolerated. Taken together with data from the Sorafenib Hepatocellular Carcinoma Assessment Randomized Protocol (SHARP) trial, sorafenib seems to be an appropriate option for the treatment of advanced hepatocellular carcinoma. Funding: Bayer HealthCare Pharmaceuticals and Onyx Pharmaceuticals, Inc.
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  8. 8
    Hutson, T. E.; Escudier, B.; Esteban, E.; Bjarnason, G. A.; Lim, H. Y.; Pittman, K. B.; Senico, P.; Niethammer, A.; Lu, D. R.; Hariharan, S.; Motzer, R. J. Randomized Phase III Trial of Temsirolimus versus Sorafenib as Second-Line Therapy after Sunitinib in Patients with Metastatic Renal Cell Carcinoma. J. Clin. Oncol. 2014, 32, 760– 767,  DOI: 10.1200/JCO.2013.50.3961
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    8
    Randomized phase III trial of temsirolimus versus sorafenib as second-line therapy after sunitinib in patients with metastatic renal cell carcinoma
    Hutson, Thomas E.; Escudier, Bernard; Esteban, Emilio; Bjarnason, Georg A.; Lim, Ho Yeong; Pittman, Kenneth B.; Senico, Peggy; Niethammer, Andreas; Lu, Dongrui Ray; Hariharan, Subramanian; Motzer, Robert J.
    Journal of Clinical Oncology (2014), 32 (8), 760-767CODEN: JCONDN; ISSN:0732-183X. (American Society of Clinical Oncology)
    Purpose This international phase III trial (Investigating Torisel As Second-Line Therapy [INTORSECT]) compared the efficacy of temsirolimus (mammalian target of rapamycin inhibitor) and sorafenib (vascular endothelial growth factor receptor [VEGFR] tyrosine kinase inhibitor) as second-line therapy in patients with metastatic renal cell carcinoma (mRCC) after disease progression on sunitinib. Patients and Methods In total, 512 patients were randomly assigned 1:1 to receive i.v. temsirolimus 25 mg once weekly (n = 259) or oral sorafenib 400 mg twice per day (n = 253), with stratification according to duration of prior sunitinib therapy (≤ or > 180 days), prognostic risk, histol. (clear cell or non-clear cell), and nephrectomy status. The primary end point was progression-free survival (PFS) by independent review committee assessment. Safety, objective response rate (ORR), and overall survival (OS) were secondary end points. Results Primary anal. revealed no significant difference between treatment arms for PFS (stratified hazard ratio [HR], 0.87; 95% CI, 0.71 to 1.07; two-sided P = .19) or ORR. Median PFS in the temsirolimus and sorafenib arms were 4.3 and 3.9 mo, resp. There was a significant OS difference in favor of sorafenib (stratified HR, 1.31; 95% CI, 1.05 to 1.63; two-sided P = .01). Median OS in the temsirolimus and sorafenib arms was 12.3 and 16.6 mo, resp. Safety profiles of both agents were consistent with previous studies. Conclusion In patients with mRCC and progression on sunitinib, second-line temsirolimus did not demonstrate a PFS advantage compared with sorafenib. The longer OS obsd. with sorafenib suggests sequenced VEGFR inhibition may benefit patients with mRCC.
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  9. 9
    Grothey, A.; Van Cutsem, E.; Sobrero, A.; Siena, S.; Falcone, A.; Ychou, M.; Humblet, Y.; Bouché, O.; Mineur, L.; Barone, C.; Adenis, A.; Tabernero, J.; Yoshino, T.; Lenz, H. J.; Goldberg, R. M.; Sargent, D. J.; Cihon, F.; Cupit, L.; Wagner, A.; Laurent, D. Correct Study Group, Regorafenib Monotherapy for Previously Treated Metastatic Colorectal Cancer (Correct): An International, Multicentre, Randomised, Placebo-Controlled, Phase III Trial. Lancet 2013, 381, 303– 312,  DOI: 10.1016/S0140-6736(12)61900-X
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  10. 10
    Escudier, B.; Eisen, T.; Stadle, W. M.; Szczylik, C.; Oudard, S.; Siebels, M.; Negrier, S.; Chevreau, C.; Solska, E.; Desai, A. A. Sorafenib in Advanced Clear-Cell Renal-Cell Carcinoma. N. Engl. J. Med. 2007, 356, 125– 134,  DOI: 10.1056/NEJMoa060655
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    10
    Sorafenib in advanced clear-cell renal-cell carcinoma
    Escudier, Bernard; Eisen, Tim; Stadler, Walter M.; Szczylik, Cezary; Oudard, Stephane; Siebels, Michael; Negrier, Sylvie; Chevreau, Christine; Solska, Ewa; Desai, Apurva A.; Rolland, Frederic; Demkow, Tomasz; Hutson, Thomas E.; Gore, Martin; Freeman, Scott; Schwartz, Brian; Shan, Minghua; Simantov, Ronit; Bukowski, Ronald M.; Blajman, C.; Fein, L.; Martin, C.; Taber, R.; Boyer, M.; Davis, I.; Gurney, H.; Hovey, E.; Leong, D.; Steer, C.; DeGreve, J.; Gil, T.; Barrios, C.; David, W.; Skare, N. G.; Notari, A.; Schwartsmann, G.; Gunnar, N.; Ernst, S.; Hotte, S.; Miller, W.; Moore, M.; North, S.; Fodor, M.; Caty, A.; Chevreau, C.; Duclos, B.; Gravis, G.; Negrier, S.; Oudard, S.; Ravaud, A.; Rolland, F.; Sevin, E.; Grimm, M. O.; Gschwennd, J.; Heinzer, H.; Jager, E.; Krause, S.; Michel, M.-S.; Rohde, D.; Siebels, M.; Siegsmund, M.; Staehler, M.; Wirth, M.; Baki, M.; Bodrogi, I.; Cseh, J.; Ruzsa, A.; Toth, C.; Ben-Yosef, R.; Gez, E.; Bajetta, E.; Boni, C.; Bracarda, S.; Cognetti, F.; Conte, P.; Porta, C.; Spronsen, D. J.; Blasinka-Morawiec, M.; Dernkow, T.; Lorenz, J.; Mazurkiewicz, M.; Roslki, J.; Sikorski, A.; Solska, E.; Tomczak, P.; Bolotina, L.; Karlov, P.; Karyakin, O.; Khasanov, R.; Lichinitser, M.; Lubennikov, V.; Moiseenko, V.; Sherman, N.; Abratt, R.; Coetzee, L.; Cohen, G.; Heyns, C.; Jordaan, J.; Ruff, P.; Wentzel, S.; Bellmunt, J.; Climent, M. A.; Gonzalez, J. L.; Lopez, G.; Bashtan, V.; Dumamsky, Y.; Klimenko, I.; Pilipenko, N.; Shparik, Y.; Hawkins, R.; McMenemin, R.; Nathan, P.; Porfiri, E.; Savage, P.; White, J.; Anderson, C.; Bains, Y.; Bleickardt, E.; Bradof, J.; Brooks, D.; Cardi, G.; Cervera, A.; Davis, N.; Desai, A.; Drabkin, H.; Dudek, A.; Dutcher, J.; Formanek, G.; Gabrail, N.; Gorss, H.; Haung, Y.; Henderson, C.; Hutson, T.; Jonasch, E.; Lara, P.; McCracken, J.; McDermott, D.; Mena, R.; Middleton, R.; Petrylak, D.; Picus, D.; Quinn, D.; Rausch, P.; Rinaldi, D.; Ryan, C.; Tchekmedyian, N.; Vuky, J.
    New England Journal of Medicine (2007), 356 (2), 125-134CODEN: NEJMAG; ISSN:0028-4793. (Massachusetts Medical Society)
    We conducted a phase 3, randomized, double-blind, placebo-controlled trial of sorafenib, a multikinase inhibitor of tumor-cell proliferation and angiogenesis, in patients with advanced clear-cell renal-cell carcinoma. From Nov. 2003 to Mar. 2005, we randomly assigned 903 patients with renal-cell carcinoma that was resistant to std. therapy to receive either continuous treatment with oral sorafenib (at a dose of 400 mg twice daily) or placebo; 451 patients received sorafenib and 452 received placebo. The primary end point was overall survival. A single planned anal. of progression-free survival in Jan. 2005 showed a statistically significant benefit of sorafenib over placebo. Consequently, crossover was permitted from placebo to sorafenib, beginning in May 2005. At the Jan. 2005 cutoff, the median progression-free survival was 5.5 mo in the sorafenib group and 2.8 mo in the placebo group (hazard ratio for disease progression in the sorafenib group, 0.44; 95% confidence interval [CI], 0.35 to 0.55). The 1st interim anal. of overall survival in May 2005 showed that sorafenib reduced the risk of death, as compared with placebo (hazard ratio, 0.72; 95% CI, 0.54 to 0.94), although this benefit was not statistically significant according to the O'Brien-Fleming threshold. Partial responses were reported as the best response in 10% of patients receiving sorafenib and in 2% of those receiving placebo. Diarrhea, rash, fatigue, and hand-foot skin reactions were the most common adverse events assocd. with sorafenib. Hypertension and cardiac ischemia were rare serious adverse events that were more common in patients receiving sorafenib than in those receiving placebo. As compared with placebo, treatment with sorafenib prolongs progression-free survival in patients with advanced clear-cell renal-cell carcinoma in whom previous therapy has failed; however, treatment is assocd. with increased toxic effects. (ClinicalTrials.gov no., NCT00073307).
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  11. 11
    Mross, K.; Frost, A.; Steinbild, S.; Hedbom, S.; Buchert, M.; Fasol, U.; Unger, C.; Kratzschmar, J.; Heinig, R.; Boix, O.; Christensen, O. A Phase I Dose-Escalation Study of Regorafenib (BAY 73–4506), an Inhibitor of Oncogenic, Angiogenic, and Stromal Kinases, in Patients with Advanced Solid Tumors. Clin. Cancer Res. 2012, 18, 2658– 2667,  DOI: 10.1158/1078-0432.CCR-11-1900
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    11
    A Phase I Dose-Escalation Study of Regorafenib (BAY 73-4506), an Inhibitor of Oncogenic, Angiogenic, and Stromal Kinases, in Patients with Advanced Solid Tumors
    Mross, Klaus; Frost, Annette; Steinbild, Simone; Hedbom, Susanne; Buechert, Martin; Fasol, Ulrike; Unger, Clemens; Kraetzschmar, Joern; Heinig, Roland; Boix, Oliver; Christensen, Olaf
    Clinical Cancer Research (2012), 18 (9), 2658-2667CODEN: CCREF4; ISSN:1078-0432. (American Association for Cancer Research)
    PURPOSE: Regorafenib is a novel oral multikinase inhibitor of angiogenic (VEGFR1-3, TIE2), stromal (PDGFR-β, FGFR), and oncogenic kinases (KIT, RET, and RAF). This first-in-man, phase I dose-escalation study assessed the safety, pharmacokinetic, pharmacodynamic, and efficacy profiles of regorafenib in patients with advanced solid tumors. PATIENTS AND METHODS: Patients aged 18 years or older with advanced solid tumors refractory to std. treatment were recruited. Regorafenib was administered orally for 21 days on/seven days off in repeating cycles, until discontinuation due to toxicity or tumor progression. Adverse events (AE) were assessed using National Cancer Institute Common Terminol. Criteria for Adverse Events v3.0. Pharmacokinetic profiles were measured after a single dose and on day 21. Pharmacodynamic and efficacy evaluations included tumor perfusion assessment using dynamic contrast-enhanced MRI, plasma cytokines, and tumor response using RECIST (v1.0). RESULTS: Fifty-three patients were enrolled into eight cohorts at dose levels from 10 to 220 mg daily. The recommended dose for future studies was detd. to be 160 mg daily, with a treatment schedule of 21 days on/seven days off in repeating 28-day cycles. The most common drug-related grade 3 or 4 AEs were dermatol. AEs (hand-foot skin reaction, rash), hypertension, and diarrhea. Pharmacokinetic anal. revealed a similar exposure at steady state for the parent compd. and two pharmacol. active metabolites. Tumor perfusion and plasma cytokine anal. showed biol. activity of regorafenib. Three of 47 evaluable patients achieved a partial response (renal cell carcinoma, colorectal carcinoma, and osteosarcoma). CONCLUSION: Regorafenib showed an acceptable safety profile and preliminary evidence of antitumor activity in patients with solid tumors. Clin Cancer Res; 18(9); 2658-67.
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  12. 12
    Crona, D. J.; Keisler, M. D.; Walko, C. M. Regorafenib: A Novel Multitargeted Tyrosinekinase Inhibitor for Colorectal Cancer and Gastrointestinal Stromal Tumors. Ann. Pharmacother. 2013, 47, 1685– 1696,  DOI: 10.1177/1060028013509792
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  13. 13
    Fujita, K.; Miura, M.; Shibata, H. Quantitative Determination of Regorafenib and its Two Major Metabolites in Human Plasma with High-Performance Liquid Chromatography and Ultraviolet Detection. Biomed. Chromatogr. 2016, 30, 1611– 1617,  DOI: 10.1002/bmc.3730
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    13
    Quantitative determination of regorafenib and its two major metabolites in human plasma with high-performance liquid chromatography and ultraviolet detection
    Fujita, Kazuma; Miura, Masatomo; Shibata, Hiroyuki
    Biomedical Chromatography (2016), 30 (10), 1611-1617CODEN: BICHE2; ISSN:0269-3879. (John Wiley & Sons Ltd.)
    A simple, highly sensitive and specific high-performance liq. chromatog. (HPLC) method was developed for the simultaneous quantitation of regorafenib, N-oxidemetabolite (M-2) and the desmethyl N-oxide metabolite (M-5) in human plasma. Regorafenib, M-2, M-5 and the internal std. sorafenib were sepd. using a mobile phase of 0.5% KH2PO4 (pH 3.5)-acetonitrile (30:70, vol./vol.), on a Capcell PAK MG II column at a flow rate of 0.5 mL/min and measurement at UV 260 nm. The lower limits of quantification for regorafenib, M-2 and M-5 were 10 ng/mL for each analyte. A procedure using solid-phase extn. required only a small amt. of plasma (100 μL) for one anal. while providing high extn. recovery (>81% for all compds.) and good selectivity. Coeffs. of variation for intra- and inter-day assays were <12.2% for regorafenib, <12.3% for M-2 and <15.1% for M-5. Accuracies for intra- and inter-day assays were <9.4% for regorafenib, <8.0% for M-2 and <12.8% for M-5 over a linear range from 10 to 10,000 ng/mL. This HPLC assay is suitable for clin. pharmacokinetic studies of regorafenib. The present HPLC method is currently in use for our observational studies of patients under treatment.
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  14. 14
    Luethi, D.; Durmus, S.; Schinkel, A. H.; Schellens, J. H. M.; Beijnen, J. H.; Sparidans, R. W. Liquid Chromatography–Tandem Mass Spectrometric Assay for the Multikinase Inhibitor Regorafenib in Plasma. Biomed. Chromatogr. 2014, 28, 1366– 1370,  DOI: 10.1002/bmc.3176
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    14
    Liquid chromatography-tandem mass spectrometric assay for the multikinase inhibitor regorafenib in plasma
    Luethi, Dino; Durmus, Selvi; Schinkel, Alfred H.; Schellens, Jan H. M.; Beijnen, Jos H.; Sparidans, Rolf W.
    Biomedical Chromatography (2014), 28 (10), 1366-1370CODEN: BICHE2; ISSN:0269-3879. (John Wiley & Sons Ltd.)
    Regorafenib has recently been approved for the treatment of colorectal cancer. A bioanal. liq. chromatog.-tandem mass spectrometric assay for this multikinase inhibitor was developed and validated in plasma. The concn. range of the assay was 25-25,000 ng/mL. Protein pptn. with acetonitrile was used as sample pre-treatment with sorafenib as internal std. The ext. was dild. with methanol (25%, vol./vol.) and then injected onto the sub-2 μm particle, bridged ethylsilicia hybrid trifunctional bonded C18 column. Isocratic elution using 0.02% (vol./vol.) formic acid in a methanol-water mixt. was used. Compds. were monitored by a triple quadrupole mass spectrometer in the selected reaction monitoring mode after pos. electrospray ionization. Double logarithmic calibration was used; within-day precisions, between-day precisions, and accuracies were 3.2-9.2, 4.1-12.3 and 94.8-103.0%, resp. High drug stability was obsd. under all relevant storage conditions. The assay was used to measure drug concns. in a pharmacokinetic study in wild-type FVB mice. Copyright © 2014 John Wiley & Sons, Ltd.
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  15. 15
    van Erp, N. P.; Wit, D. D.; Guchelaar, H. J.; Gelderblom, H.; Hessing, T. J.; Hartigh, J. D. A Validated Assay for the Simultaneous Quantification of Six Tyrosine Kinase Inhibitors and Two Active Metabolites in Human Serum Using Liquid Chromatography Coupled with Tandem Mass Spectrometry. J. Chromatogr. B 2013, 937, 33– 43,  DOI: 10.1016/j.jchromb.2013.08.013
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    15
    A validated assay for the simultaneous quantification of six tyrosine kinase inhibitors and two active metabolites in human serum using liquid chromatography coupled with tandem mass spectrometry
    van Erp, Nielka P.; de Wit, Djoeke; Guchelaar, Henk-Jan; Gelderblom, Hans; Hessing, Trees J.; den Hartigh, Jan
    Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences (2013), 937 (), 33-43CODEN: JCBAAI; ISSN:1570-0232. (Elsevier B.V.)
    A sensitive, sophisticated and practical bioanal. assay for the simultaneous detn. of six tyrosine kinase inhibitors (imatinib, sunitinib, nilotinib, dasatinib, pazopanib, regorafenib) and two active metabolites (N-desmethyl imatinib and N-desethyl sunitinib) was developed and validated. For the quant. assay, a mixt. of three stable isotopes as internal stds. was added to human serum, stds. and controls. Thereafter, samples were pre-treated using protein pptn. with methanol. The supernatant was dild. with water and injected into an ultra pressure liq. chromatog. system with an Acquity TQ tandem mass spectrometry detector. The compds. were sepd. on an Acquity BEH C18 anal. column (100 mm × 2.1 mm ID, 1.7 μm particle size) and eluted with a linear gradient system. The ions were detected in the multiple reaction monitoring mode. The lower limit of quantification and the linearity of all compds. generously met with the concns. that are to be expected in clin. practice. The developed bioanal. assay can be used for guiding TKI therapy in daily clin. practice as well as for investigator-initiated research.
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  16. 16
    Hafner, F.-T.; Werner, D.; Kaiser, M. Determination of Regorafenib (Bay 73- 4506) and its Major Human Metabolites Bay 75-7495 (M-2) and Bay 81-8752 (M-5) in Human Plasma by Stable-Isotope Dilution Liquid Chromatography–Tandem Ms. Bioanalysis 2014, 6, 1923– 1937,  DOI: 10.4155/bio.14.52
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    There is no corresponding record for this reference.
  17. 17
    Merienne, C.; Rousset, M.; Ducint, D.; Castaing, N.; Titier, K.; Molimard, M.; Bouchet, S. High Throughput Routine Determination of 17 Tyrosine Kinase Inhibitors by LC-MS/MS. J. Pharm. Biomed. Anal. 2018, 150, 112– 120,  DOI: 10.1016/j.jpba.2017.11.060
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    17
    High throughput routine determination of 17 tyrosine kinase inhibitors by LC-MS/MS
    Merienne, Camille; Rousset, Marine; Ducint, Dominique; Castaing, Nadege; Titier, Karine; Molimard, Mathieu; Bouchet, Stephane
    Journal of Pharmaceutical and Biomedical Analysis (2018), 150 (), 112-120CODEN: JPBADA; ISSN:0731-7085. (Elsevier B.V.)
    Several studies have shown that therapeutic drug monitoring of tyrosine kinase inhibitors (TKI) can improve their benefit in cancer. An anal. tool has been developed in order to quantify 17 tyrosine kinase inhibitors and 2 metabolites in human plasma (afatinib, axitinib, bosutinib, crizotinib, dabrafenib, dasatinib, erlotinib, gefitinib, imatinib, lapatinib, nilotinib, ponatinib, regorafenib, regorafenib M2, regorafenib M5, ruxolitinib, sorafenib, sunitinib, vandetanib). Drugs were arranged in four groups, according to their plasma concn. range: 0.1-200 ng/mL, 1-200 ng/mL, 4-800 ng/mL and 25-5000 ng/mL. Solid phase extn. was used and sepn. was performed with HPLC using a gradient system on a solid core particle C18 column (5 × 2.1 mm, 1.6 μm). Ions were detected with a triple quadrupole mass spectrometry system. This assay allows rapid detn. of 19 TKI in less than 5 min per run. This high throughput routine method will be useful to adjust doses of oral anticancer drugs in order to improve treatments efficacy.
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  18. 18
    Pang, Y. Y.; Tan, Y. L.; Ho, H. K. Investigation of the Effect of Plasma Albumin Levels on Regorafenib-Induced Hepatotoxicity Using A Validated Liquid Chromatography-Tandem Mass Spectrometry Method. J. Chromatogr. B 2017, 1061–1062, 220– 224,  DOI: 10.1016/j.jchromb.2017.07.023
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    18
    Investigation of the effect of plasma albumin levels on regorafenib-induced hepatotoxicity using a validated liquid chromatography-tandem mass spectrometry method
    Pang, Yi Yun; Tan, Yeong Lan; Ho, Han Kiat
    Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences (2017), 1061-1062 (), 220-224CODEN: JCBAAI; ISSN:1570-0232. (Elsevier B.V.)
    Regorafenib is an oral multikinase inhibitor indicated for metastatic colorectal cancer and gastrointestinal stromal tumor. Due to its extensive plasma protein binding and low calcd. hepatic extn. ratio, the hepatotoxicity obsd. with usage of the drug may be related to its plasma exposure. To investigate the highly dynamic free:bound drug concn. for regorafenib in the plasma, a bioanal. liq. chromatog.-tandem mass spectrometric assay was developed and validated in human plasma. The concn. range of the assay was 2-1000 ng/mL. Sample prepn. was via protein pptn. using acetonitrile with sorafenib as the internal std. The supernatant was injected into an ultra-performance liq. chromatog. system coupled to a triple quadrupole mass spectrometer. The analytes were sepd. on an AQUITY UPLC BEH C18 column (120 Å, 1.7 μm, 2.1 mm × 50 mm) and eluted with a gradient elution system. The ions were detected in multiple reaction monitoring mode. The linearity, lower limit of quantification, intraday and interday precision and accuracy conformed to FDA guidelines. The validated method was successfully applied to det. the effect of albumin levels in plasma on the extent of protein binding of regorafenib. The results indicated that physiol.-relevant levels of albumin were found to have no significant effect on the extent of protein binding of regorafenib, hence imposing minimal effect on drug disposition.
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  19. 19
    Allard, M.; Khoudour, N.; Rousseau, B.; Joly, C.; Costentin, C.; Blanchet, B.; Tournigand, C.; Hulin, A. Simultaneous Analysis of Regorafenib and Sorafenib and Three of their Metabolites in Human Plasma Using LC–MS/MS. J. Pharm. Biomed. Anal. 2017, 142, 42– 48,  DOI: 10.1016/j.jpba.2017.04.053
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    19
    Simultaneous analysis of regorafenib and sorafenib and three of their metabolites in human plasma using LC-MS/MS
    Allard, Marie; Khoudour, Nihel; Rousseau, Benoit; Joly, Charlotte; Costentin, Charlotte; Blanchet, Benoit; Tournigand, Christophe; Hulin, Anne
    Journal of Pharmaceutical and Biomedical Analysis (2017), 142 (), 42-48CODEN: JPBADA; ISSN:0731-7085. (Elsevier B.V.)
    A new liq. chromatog.-tandem mass spectrometry (LC-MS/MS) method, performed by electrospray ionization in pos. mode using a triple quadrupole mass spectrometry, has been developed and validated for the simultaneous detn. of regorafenib (REGO), its two metabolites regorafenib-M2 and regorafenib-M5, sorafenib (SORA), and its N-oxide metabolite in human plasma. Sepn. is achieved on an Hypersil Gold column using a gradient elution of 10 mM ammonium formate contg. 0.1% formic acid (A) and acetonitrile contg. 0.1% formic acid (B) at a flow rate of 0.3 mL/min. After addn. of two internal stds. and a protein pptn., the supernatant is dild. two-fold in a 0.1% (vol./vol.) formic acid soln. Two selected reaction monitoring transitions are used, for each analyte, one for quantitation and the second one for confirmation. The std. curves are ranged from 50 to 5 000 ng/mL for REGO and its metabolites and 80 to 5 000 ng/mL for SORA and its metabolite and were fitted to a 1/x weighted linear regression model. The method also showed satisfactory results in terms of sensitivity, specificity, precision (intra- and inter-day CV from 2.4 to 10.2%), accuracy (from 91.0 to 111.7%), recovery as well as stability of the analytes under various conditions. The method is usually used in clin. practice to improve the SORA treatment for renal carcinoma, REGO treatment for colorectal cancer and both for hepatocellular carcinoma.
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  20. 20
    Albayrak, M. Development and Validation of a New Spectrophotometric Method for the Determination of Regorafenib in Pure and Tablet Dosage Form. Lat. Am. J. Pharm. 2018, 37, 1349– 1353
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  21. 21
    Ma, Z.; Chen, P.; Cheng, W.; Yan, K.; Pan, L.; Shi, Y.; Guihua, Y. Highly Sensitive, Printable Nanostructured Conductive Polymer Wireless Sensor for Food Spoilage Detection. Nano Lett. 2018, 18, 4570– 4575,  DOI: 10.1021/acs.nanolett.8b01825
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    21
    Highly Sensitive, Printable Nanostructured Conductive Polymer Wireless Sensor for Food Spoilage Detection
    Ma, Zhong; Chen, Ping; Cheng, Wen; Yan, Kun; Pan, Lijia; Shi, Yi; Yu, Guihua
    Nano Letters (2018), 18 (7), 4570-4575CODEN: NALEFD; ISSN:1530-6984. (American Chemical Society)
    Near-field communication (NFC) labeling technol. has been recently used to endow smartphones with nonline-of-sight sensing functions to improve the environment, human health, and quality of life. For applications in detecting food spoilage, the development of a sensor with high enough sensitivity to act as a switch for an NFC tag remains a challenge. In this Letter, we developed a nanostructured conductive polymer-based gas sensor with high sensitivity of ΔR/R0 = 225% toward 5 ppm ammonia NH3 and unprecedented sensitivities of 46% and 17% toward 5 ppm putrescine and cadaverine, resp. The gas sensor plays a crit. role as a sensitive switch in the circuit of the NFC tag and enables a smartphone to readout meat spoilage when the concn. of biogenic amines is over a preset threshold. We envision the broad potential use of such intelligent sensing for food status monitoring applications in daily life, storage and supply chains.
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  22. 22
    Ngo, Y. H.; Brothers, M.; Martin, J. A.; Grigsby, C. C.; Fullerton, K.; Naik, R. R.; Kim, S. S. Chemically Enhanced Polymer-Coated Carbon Nanotube Electronic Gas Sensor for Isopropyl Alcohol Detection. ACS Omega 2018, 3, 6230– 6236,  DOI: 10.1021/acsomega.8b01039
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    22
    Chemically Enhanced Polymer-Coated Carbon Nanotube Electronic Gas Sensor for Isopropyl Alcohol Detection
    Ngo, Yen H.; Brothers, Michael; Martin, Jennifer A.; Grigsby, Claude C.; Fullerton, Kathy; Naik, Rajesh R.; Kim, Steve S.
    ACS Omega (2018), 3 (6), 6230-6236CODEN: ACSODF; ISSN:2470-1343. (American Chemical Society)
    Breathing-air quality within com. airline cabins has come under increased scrutiny because of the identification of volatile org. compds. (VOCs) from the engine bleed air used to provide O to cabins. Ideally, a sensor would be placed within the bleed air pipe itself, enabling detection before it permeated through and contaminated the entire cabin. Current gas-phase sensors suffer from issues with selectivity, do not have the appropriate form factor, or are too complex for com. deployment. Here, we chose iso-Pr alc. (IPA), a main component of de-icer spray used in the aerospace community, as a target analyte: IPA exposure has been hypothesized to be a key component of aerotoxic syndrome in pre, during, and postflight. IPAs proposed mechanism of action is that of an anesthetic and central nervous system depressant. Here, we describe IPA sensor development by showing: (1) the integration of a polymer as an IPA capture matrix, (2) the adoption of a redox chem. additives as an IPA oxidizer, and (3) the application of C nanotubes as an electronic sensing conduit. We demonstrate the ability to not only detect IPA at 100-10,000 ppm in unfiltered, lab. air but also discriminate among IPA, isoprene, and acetone, esp. in comparison to a typical photoionization detector. Overall, we show an electronic device that operates at room temp. and responds preferentially to IPA, where the increase in the resistance corresponds directly to the concn. of IPA. Ultimately, this study opens up the pathway to selective electronic sensors that can enable real-time monitoring in a variety of environments for the force health prevention and protection, and the potential through future work to enable low ppm and possibly high ppb selective detection of gas-phase VOCs of interest.
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  23. 23
    Hou, H.; Tingting, X.; Yang, W.; Shengjun, L.; Chu, R.; Zhang, J.; Liu, B. Conductive and Chiral Polymer-Modified Metal–Organic Framework for Enantioselective Adsorption and Sensing. ACS Appl. Mater. Interfaces 2018, 10, 26365– 26371,  DOI: 10.1021/acsami.8b06540
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    23
    Conductive and Chiral Polymer-Modified Metal-Organic Framework for Enantioselective Adsorption and Sensing
    Hou, Xudong; Xu, Tingting; Wang, Yang; Liu, Shengjun; Chu, Runrun; Zhang, Junxiang; Liu, Bo
    ACS Applied Materials & Interfaces (2018), 10 (31), 26365-26371CODEN: AAMICK; ISSN:1944-8244. (American Chemical Society)
    The authors reported integration of cond., chirality, and porosity into MIL-101@chiral-PANI composite for synchronous chiral recognition, adsorption, and sensing toward enantiomers. The core-shell structure of MIL-101@chiral-PANI was characterized in detail by FTIR and CD spectroscopy as well as SEM and TEM. Adsorption behaviors of carvone enantiomers over chiral PANI and MIL-101@chiral-PANI are satisfied with pseudo-first-order fitting. In comparison with chiral PANI, MIL-101@c-PANI exhibits a better enantioselectivity and much higher (>5-fold) adsorption amt. over L-carvone than D-carvone. And MIL-101@c-PANI is able to recognize the chirality of carvone via electrochem. sensing, taking advantage of the elec. cond. of chiral PANI. Result demonstrated the feasibility of applying achiral MOF for enantioselective sensing and adsorption via installing chiral and conductive gates. And this chiral polymer modification strategy represents a universal way to entitle achiral MOFs with chiral functions.
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  24. 24
    Reddy, Y. V. M.; Sravani, B.; Fernandes, D. M.; Madhuri, Ch.; Subramanyam Sarma, L.; Madhavi, G. Facile One-Pot Synthesis of Bimetallic Pd-Ag/Reduced Graphene Oxide Nanocomposite as an Electrochemical Sensor for Sensitive Detection of Antihypotensive Drug. Colloids Surf., A 2018, 546, 293– 300,  DOI: 10.1016/j.colsurfa.2018.03.032
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    Reddy, Y. V. M.; Bathinapatla, S.; Łuczak, T.; Osinska, M.; Maseed, H.; Ragavendhra, P.; Sarma, L. S.; Srikanth, V. V. S. S.; Madhavi, G. An Ultra-Sensitive Electrochemical Sensor for the Detection of Acetaminophen in the Presence of Etilefrine using Bimetallic Pd–Ag/Reduced Graphene Oxide Nanocomposites. New J. Chem. 2018, 42, 3137– 3146,  DOI: 10.1039/C7NJ04775D
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    Reddy, Y. V. M.; Sravani, B.; Agarwal, S.; Guptha, V. K.; Madhavi, G. Electrochemical Sensor for Detection of Uric acid in the Presence of Ascorbic acid and Dopamine Using the Poly (Dpa)/Sio2@Fe3o4 Modified Carbon Paste Electrode. J. Electroanal. Chem. 2018, 820, 168– 75,  DOI: 10.1016/j.jelechem.2018.04.059
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    Sağlam, Ş.; Aysem, U. Z.; Erol, E.; Resat, A. Electrochemical Determination of TNT, DNT, RDX, and HMX with Gold Nanoparticles/Poly (Carbazole-Aniline) Film-Modified Glassy Carbon Sensor Electrodes Imprinted for Molecular Recognition of Nitroaromatics and Nitramines. Anal. Chem. 2018, 90, 7364– 7370,  DOI: 10.1021/acs.analchem.8b00715
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    Li, L.; Chen, M.; Huang, G.; Yang, N.; Zhang, L.; Wang, H.; Liu, Y.; Wang, W.; Gao, J. A Green Method to Prepare Pd–Ag Nanoparticles Supported on Reduced Graphene Oxide and Their Electrochemical Catalysis of Methanol and Ethanol Oxidation. J. Power Sources 2014, 263, 13– 21,  DOI: 10.1016/j.jpowsour.2014.04.021
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    A green method to prepare Pd-Ag nanoparticles supported on reduced graphene oxide and their electrochemical catalysis of methanol and ethanol oxidation
    Li, Lingzhi; Chen, Mingxi; Huang, Guanbo; Yang, Nian; Zhang, Li; Wang, Huan; Liu, Yu; Wang, Wei; Gao, Jianping
    Journal of Power Sources (2014), 263 (), 13-21CODEN: JPSODZ; ISSN:0378-7753. (Elsevier B.V.)
    Bimetallic palladium-silver nanoparticles (NPs) supported on reduced oxide graphene (RGO) with different Pd/Ag ratios (Pd-Ag/RGO) were prepd. by an easy green method which did not use any addnl. reducing agents or a dispersing agent. During the process, simultaneous redox reactions between AgNO3, K2PdCl4, and graphene oxide (GO) led to bimetallic Pd-Ag NPs. The morphol. and compn. of the Pd-Ag/RGO were characterized by transmission electron microscopy, X-ray diffraction, XPS, thermogravimetric anal., and Raman spectroscopy. Cyclic voltammetry and chronoamperometry were used to investigate the electrochem. activities and stabilities of these Pd-Ag/RGO catalysts for the electro-oxidn. of methanol and ethanol in alk. media. Among the different Pd/Ag ratios, the Pd-Ag (1:1)/RGO had the best catalytic activities and stability. So it is a promising catalyst for direct alc. fuel cell applications.
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  29. 29
    Mazloum-Ardakani, M.; Hosseinzadeh, L.; Taleat, Z. Synthesis and Electrocatalytic Effect of Ag@Pt Core–Shell Nanoparticles Supported on Reduced Graphene Oxide for Sensitive and Simple Label-Free Electrochemical Aptasensor. Biosens. Bioelectron. 2015, 74, 30– 36,  DOI: 10.1016/j.bios.2015.05.072
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    Sawangphruk, M.; Srimuk, P.; Chio-chan, P.; Krittayavathananon, A.; Luanwuthi, S.; Limtrakul, J. Limtrakul. the High-Performance Supercapacitor of Manganese Oxide/Reduced Graphene Oxide Nanocomposite Coated on Flexible Carbon Fiber Paper. Carbon 2013, 60, 109– 116,  DOI: 10.1016/j.carbon.2013.03.062
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    30
    High-performance supercapacitor of manganese oxide/reduced graphene oxide nanocomposite coated on flexible carbon fiber paper
    Sawangphruk, Montree; Srimuk, Pattarachai; Chiochan, Poramane; Krittayavathananon, Atiweena; Luanwuthi, Santamon; Limtrakul, Jumras
    Carbon (2013), 60 (), 109-116CODEN: CRBNAH; ISSN:0008-6223. (Elsevier Ltd.)
    Although supercapacitors have higher power d. than batteries, they are still limited by low energy d. and low capacity retention. Here the authors report a high-performance supercapacitor electrode of Mn oxide/reduced graphene oxide nanocomposite coated on flexible C fiber paper (MnO2-rGO/CFP). MnO2-rGO nanocomposite was produced using a colloidal mixing of rGO nanosheets and 1.8 ± 0.2 nm MnO2 nanoparticles. MnO2-rGO nanocomposite was coated on CFP using a spray-coating technique. MnO2-rGO/CFP exhibited ultrahigh specific capacitance and stability. The specific capacitance of MnO2-rGO/CFP detd. by a galvanostatic charge-discharge method at 0.1 A g-1 is ∼393 F g-1, which is 1.6-, 2.2-, 2.5-, and 7.4-fold higher than those of MnO2-GO/CFP, MnO2/CFP, rGO/CFP, and GO/CFP, resp. The capacity retention of MnO2-rGO/CFP is over 98.5% of the original capacitance after 2000 cycles. This electrode has comparatively 6%, 11%, 13%, and 18% higher stability than MnO2-GO/CFP, MnO2/CFP, rGO/CFP, and GO/CFP, resp. It is believed that the ultrahigh performance of MnO2-rGO/CFP is possibly due to high cond. of rGO, high active surface area of tiny MnO2, and high porosity between each MnO2-rGO nanosheet coated on porous CFP. An as-fabricated all-solid-state prototype MnO2-rGO/CFP supercapacitor (2 × 14 cm) can spin up a 3 V motor for ∼6 min.
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    Jayakumar, K.; Camarada, M. B.; Venkataraman, D.; Rajendiran, R.; Rengarajan, V.; Huangxian, J.; Mahalingam, M.; Abhishek, R.; Sudipta, R. B.; Yangping, W. Layer-by-Layer-Assembled AuNPs-Decorated First-Generation Poly (amidoamine) Dendrimer with Reduced Graphene Oxide Core as Highly Sensitive Biosensing Platform with Controllable 3D Nanoarchitecture for Rapid Voltammetric Analysis of Ultratrace DNA Hybridization. ACS Appl. Mater. Interfaces 2018, 10, 21541– 21555,  DOI: 10.1021/acsami.8b03236
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    Layer-by-Layer-Assembled AuNPs-Decorated First-Generation Poly(amidoamine) Dendrimer with Reduced Graphene Oxide Core as Highly Sensitive Biosensing Platform with Controllable 3D Nanoarchitecture for Rapid Voltammetric Analysis of Ultratrace DNA Hybridization
    Jayakumar, Kumarasamy; Camarada, Maria Belen; Dharuman, Venkataraman; Rajesh, Rajendiran; Venkatesan, Rengarajan; Ju, Huangxian; Maniraj, Mahalingam; Rai, Abhishek; Barman, Sudipta Roy; wen, Yangping
    ACS Applied Materials & Interfaces (2018), 10 (25), 21541-21555CODEN: AAMICK; ISSN:1944-8244. (American Chemical Society)
    The structure and electrochem. properties of layer-by-layer-assembled gold nanoparticles (AuNPs)-decorated first-generation (G1) poly(amidoamine) dendrimer (PD) with reduced graphene oxide (rGO) core as a highly sensitive and label-free biosensing platform with a controllable three-dimensional (3D) nanoarchitecture for the rapid voltammetric anal. of DNA hybridization at ultratrace levels were characterized. Mercaptopropinoic acid (MPA) was self-assembled onto Au substrate, then GG1PD formed by the covalent functionalization between the amino terminals of G1PD and carboxyl terminals of rGO was covalently linked onto MPA, and finally AuNPs were decorated onto GG1PD by strong physicochem. interaction between AuNPs and -OH of rGO in GG1PD, which was characterized through different techniques and confirmed by computational calcn. This 3D controllable thin-film electrode was optimized and evaluated using [Fe(CN)6]3-/4- as the redox probe and employed to covalently immobilize thiol-functionalized single-stranded DNA as biorecognition element to form the DNA nanobiosensor, which achieved fast, ultrasensitive, and high-selective differential pulse voltammetric anal. of DNA hybridization in a linear range from 1 × 10-6 to 1 × 10-13 g m-1 with a low detection limit of 9.07 × 10-14 g m-1. This work will open a new pathway for the controllable 3D nanoarchitecture of the layer-by-layer-assembled metal nanoparticles-functionalized lower-generation PD with two-dimensional layered nanomaterials as cores that can be employed as ultrasensitive and label-free nanobiodevices for the fast diagnosis of specific genome diseases in the field of biomedicine.
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  32. 32
    Karthik, P.; Vinoth, R.; Zhang, P.; Wonyong, C.; Balaraman, E.; Neppolian, B. π–π Interaction Between Metal–Organic Framework and Reduced Graphene Oxide for Visible-Light Photocatalytic H2 Production. ACS Appl. Energy Mater. 2018, 1, 1913– 1923,  DOI: 10.1021/acsaem.7b00245
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    π-π Interaction Between Metal-Organic Framework and Reduced Graphene Oxide for Visible-Light Photocatalytic H2 Production
    Karthik, Peramaiah; Vinoth, Ramalingam; Zhang, Peng; Choi, Wonyong; Balaraman, Ekambaram; Neppolian, Bernaurdshaw
    ACS Applied Energy Materials (2018), 1 (5), 1913-1923CODEN: AAEMCQ; ISSN:2574-0962. (American Chemical Society)
    Solar water splitting provides a promising path for sustainable hydrogen prodn. and solar energy storage. In recent times, metal-org. frameworks (MOFs) have received considerable attention as promising materials for diverse solar energy conversion applications. However, their photocatalytic performance is poor and rarely explored due to rapid electron-hole recombination. Herein, we have developed a material MOF@rGO that exhibits highly enhanced visible-light photocatalytic activity. A real-time investigation reveals that a strong π-π interaction between MOF and rGO is responsible for efficient sepn. of electron-hole pairs, and thereby enhances the photocatalytic hydrogen prodn. activity. Surprisingly, MOF@rGO showed ∼9.1-fold enhanced photocatalytic hydrogen prodn. activity compared to that of pristine MOF. In addn., it is worth mentioning here that remarkable apparent quantum efficiency (0.66%) is achieved by π-π interaction mediated charge carrier sepn.
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  33. 33
    Srinivasan, V.; Mariadoss, A. J.; Kathiresan, M.; Arunkumar, K. Nanostructured Graphene Oxide Dots: Synthesis, Characterization, Photoinduced Electron Transfer Studies, and Detection of Explosives/Biomolecules. ACS Omega 2018, 3, 9096– 9104,  DOI: 10.1021/acsomega.8b01180
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    Nanostructured Graphene Oxide Dots: Synthesis, Characterization, Photoinduced Electron Transfer Studies, and Detection of Explosives/Biomolecules
    Srinivasan, Venkatesan; Asha Jhonsi, Mariadoss; Kathiresan, Murugavel; Kathiravan, Arunkumar
    ACS Omega (2018), 3 (8), 9096-9104CODEN: ACSODF; ISSN:2470-1343. (American Chemical Society)
    Herein, the authors are reporting the prepn. of graphene oxide dots (GO dots) by fine-tuning the carbonization degree of citric acid. The structure of GO dots was characterized by absorption spectroscopy, FTIR anal., Raman spectroscopy, as well as HR-SEM and TEM analyses. The typical particle size of the GO dots was 42 nm. Fluorescent characteristics of GO dots were analyzed by fluorescence spectroscopy. Once excited at 360 nm, the GO dots were fluorescent at 450-550 nm which was dependent on the excitation wavelength. Further GO dots were effectively used for multifarious applications such as photoinduced electron transfer, detection of explosives and biomols. The emission property of GO dots was competently quenched by viologens, picric acid and bilirubin. The mechanism of quenching by viologens and explosives/biomols. are light induced electron transfer and internal filter effect, resp. Intriguingly, the detection min. of picric acid is in the nano molar level. Towards the commercialization, the economic test strips also were introduced for the identification of picric acid. Also, the GO dots were applied as an efficient luminescent bio-probe for a selective and perceptive finding of bilirubin.
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    Dong, X. C.; Xu, H.; Wang, X. W.; Huang, Y. X.; Chan-Park, M. B.; Zhang, H.; Wang, L. H.; Huang, W.; Chen, P. 3D Graphene–Cobalt Oxide Electrode for High Performance Supercapacitor and Enzymeless Glucose Detection. ACS Nano 2012, 6, 3206– 3213,  DOI: 10.1021/nn300097q
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    3D Graphene-Cobalt Oxide Electrode for High-Performance Supercapacitor and Enzymeless Glucose Detection
    Dong, Xiao-Chen; Xu, Hang; Wang, Xue-Wan; Huang, Yin-Xi; Chan-Park, Mary B.; Zhang, Hua; Wang, Lian-Hui; Huang, Wei; Chen, Peng
    ACS Nano (2012), 6 (4), 3206-3213CODEN: ANCAC3; ISSN:1936-0851. (American Chemical Society)
    Using a simple hydrothermal procedure, cobalt oxide (Co3O4) nanowires were in situ synthesized on three-dimensional (3D) graphene foam grown by chem. vapor deposition. The structure and morphol. of the resulting 3D graphene/Co3O4 composites were characterized by SEM, TEM, x-ray diffraction, and Raman spectroscopy. The 3D graphene/Co3O4 composite was used as the monolithic free-standing electrode for supercapacitor application and for enzymeless electrochem. detection of glucose. The authors demonstrate that it is capable of delivering high specific capacitance of ∼1100 F g-1 at a c.d. of 10 A g-1 with excellent cycling stability, and it can detect glucose with a ultrahigh sensitivity of 3.39 mA mM-1 cm-2 and a remarkable lower detection limit of <25 nM (S/N = 8.5).
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    Yang, Y.; Wang, Z.; Yang, M.; Li, J.; Zheng, F.; Shen, G.; Yu, R. Electrical Detection of Deoxyribonuclic acid Hybridization Based on Carbon-Nanotubes/Nanozirconium Dioxide/Chaitozen-Modified Electrode. Anal. Chim. Acta. 2007, 584, 268– 274,  DOI: 10.1016/j.aca.2006.11.055
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    Chen, A.; Zhou, Y.; Ta, N.; Li, Y.; Shen, W. Redox Properties and Catalytic Performance of Ceria–Zirconia Nanorods. Catal. Sci. Technol. 2015, 5, 4184– 4192,  DOI: 10.1039/C5CY00564G
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    Redox properties and catalytic performance of ceria-zirconia nanorods
    Chen, Aling; Zhou, Yan; Ta, Na; Li, Yong; Shen, Wenjie
    Catalysis Science & Technology (2015), 5 (8), 4184-4192CODEN: CSTAGD; ISSN:2044-4753. (Royal Society of Chemistry)
    The redox properties and catalytic performance of Ce1-xZrxO2 (0 ≤ x ≤ 0.2) nanorods, mainly exposing {110} and {100} planes, were comparatively examd. with spherical Ce1-xZrxO2 nanoparticles that predominantly exposed {111} planes. The CeO2 nanorods had a superior redox property and much higher activity towards CO oxidn. than the CeO2 nanoparticles, primarily because of the preferential exposure of the reactive {110} planes. However, this shape effect was weakened considerably in Ce1-xZrxO2 (x = 0.05-0.20) nanomaterials. ZrO2-doping promoted the reducibility of the nanoparticles more significantly than that of the nanorods, involving different rate-detg. steps in the redn. process. The activity for CO oxidn. enhanced with increasing ZrO2 content on the nanoparticles but decreased over the nanorods. These results demonstrate that the shape effect of Ce1-xZrxO2 nanomaterials is assocd. with the amt. of zirconia that is incorporated into the ceria lattice.
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    Kumar, S.; Kumar, S.; Srivastava, S.; Yadav, B. K.; Lee, S. H.; Sharma, J. G.; Doval, D. C.; Malhotra, B. D. Reduced Graphene Oxide Modified Smart Conducting Paper for Cancer Biosensor. Biosens. Bioelectron. 2015, 73, 114– 122,  DOI: 10.1016/j.bios.2015.05.040
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    Reduced graphene oxide modified smart conducting paper for cancer biosensor
    Kumar, Saurabh; Kumar, Suveen; Srivastava, Saurabh; Yadav, Birendra K.; Lee, Seung H.; Sharma, Jai G.; Doval, Dinesh C.; Malhotra, Bansi D.
    Biosensors & Bioelectronics (2015), 73 (), 114-122CODEN: BBIOE4; ISSN:0956-5663. (Elsevier B.V.)
    We report results of the studies relating to the fabrication of a paper based sensor comprising of poly (3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) and reduced graphene oxide (RGO) composite. The effect of various solvents like methanol, ethylene glycol and H2SO4 on the elec. cond. of PEDOT:PSS coated Whatman paper has been investigated. The cond. of this soln. processed conducting paper significantly increases from ∼1.16×10-4 S cm-1 up to ∼3.57×10-2 S cm-1 (∼300 times) on treatment with ethylene glycol. The obsd. significant increase in elec. cond. is due to conformational rearrangement in the polymer and is due to strong non-covalent cooperative interaction between PEDOT and the cellulose mols. Further, incorporation of RGO into the conducting paper results in improved electrochem. performance and signal stability. This paper electrode is a promising alternative over the expensive conventional electrodes (ITO, gold and glassy carbon), that are known to have limited application in smart point-of-care (POC) devices. This low cost, flexible and environment friendly conducting paper based biosensor utilized for cancer biomarker (carcinoembryonic antigen, CEA) detection reveals high sensitivity of 25.8 μA ng-1 mL cm-2 in the physiol. range, 1-10 ng mL-1.
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    Zhao, N.; Pan, D.; Nie, W.; Ji, X. Two-Phase Synthesis of Shape-Controlled Colloidal Zirconia Nanocrystals and their Characterization. J. Am. Chem. Soc. 2006, 128, 10118– 10124,  DOI: 10.1021/ja0612145
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    Two-Phase Synthesis of Shape-Controlled Colloidal Zirconia Nanocrystals and Their Characterization
    Zhao, Nana; Pan, Daocheng; Nie, Wei; Ji, Xiangling
    Journal of the American Chemical Society (2006), 128 (31), 10118-10124CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
    We have developed a two-phase approach for the synthesis of shape-controlled colloidal zirconia nanocrystals, including spherical-, teardrop-, rod-, and rice grain-shaped particles. We found that the key factors for controlling the shape were the reaction time, the nature of the capping agent, and the monomer concn. We have analyzed the morphologies, crystallinity, optical properties, and structural features of the as-prepd. ZrO2 nanoparticles by using TEM, high-resoln. TEM, X-ray powder diffraction, and UV-vis absorption and fluorescence spectroscopy. The possible nucleation and growth process is also discussed.
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    Vilian, A. T. E.; Chen, S. M.; Huang, L. H. Simultaneous Determination of Catechol and Hydroquinone Using a Pt/ZrO2-rGO/GCE Composite Modified Glassy Carbon Electrode. Electrochim. Acta 2014, 125, 503– 509,  DOI: 10.1016/j.electacta.2014.01.092
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    Kumar, S.; Sharma, J. G.; Maji, S.; Malhotra, B. D. Nanostructured Zirconia Decorated Reduced Graphene Oxide Based Efficient Biosensing Platform for Non-Invasive Oral Cancer Detection. Biosens. Bioelectron. 2016, 78, 497– 504,  DOI: 10.1016/j.bios.2015.11.084
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    Nanostructured zirconia decorated reduced graphene oxide based efficient biosensing platform for non-invasive oral cancer detection
    Kumar, Suveen; Sharma, Jai Gopal; Maji, Sagar; Malhotra, Bansi Dhar
    Biosensors & Bioelectronics (2016), 78 (), 497-504CODEN: BBIOE4; ISSN:0956-5663. (Elsevier B.V.)
    We report results of the studies relating to fabrication of a non-invasive, label-free and an efficient biosensing platform for detection of the oral cancer biomarker (CYFRA-21-1). One step hydrothermal process was used for uniform decoration of nanostructured zirconia (av. particle size 13 nm) on reduced graphene oxide (ZrO2-RGO) to avoid coagulation of the zirconia nanoparticles and to obtain enhanced electrochem. performance of ZrO2-RGO nanocomposite based biosensor. Further, ZrO2-RGO has been functionalized using 3-aminopropyl triethoxy saline (APTES) and electrophoretically deposited on the indium tin oxide coated glass substrate at a low DC potential. The APTES/ZrO2-RGO/ITO electrode exhibits improved heterogeneous electron transfer (more than two times) with respect to that of the APTES/ZrO2/ITO electrode indicating faster electron transfer kinetics. The -NH2 contg. APTES/ZrO2-RGO/ITO platform is further biofunctionalized with anti-CYFRA-21-1. The structural and morphol. investigations of the ZrO2-RGO based biosensing platform have been accomplished using X-ray diffraction (XRD), electrochem., transmission electron microscopy (TEM), at. force microscopy (AFM) and Fourier transform IR spectroscopy (FT-IR) studies. The obsd. results have been validated via enzyme linked immunosorbent assay (ELISA).
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    Gupta, P. K.; Sachchidanand, T.; Zishan, H. K.; Pratima, S. R. Amino Acid Functionalized ZrO2 Nanoparticles Decorated Reduced Graphene Oxide Based Immunosensor. J. Mater. Chem. B 2017, 5, 2019– 2033,  DOI: 10.1039/C6TB02594C
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    Amino acid functionalized ZrO2 nanoparticles decorated reduced graphene oxide based immunosensor
    Gupta, Pramod K.; Tiwari, Sachchidanand; Khan, Zishan H.; Solanki, Pratima R.
    Journal of Materials Chemistry B: Materials for Biology and Medicine (2017), 5 (10), 2019-2033CODEN: JMCBDV; ISSN:2050-7518. (Royal Society of Chemistry)
    Here, a study is reported on a simple, one-step method for the synthesis of a zirconium dioxide-reduced graphene oxide (ZrO2-RGO) nanocomposite involving the redn. of graphene oxide (GO) and in situ growth of ZrO2 NPs using hydrazine as a reducer. This ZrO2-RGO nanocomposite was functionalized with L-methionine (Meth) for immunosensor application. Morphol. and structural studies clearly indicated that ZrO2 NPs (6 nm) were decorated onto the RGO sheets, and enhanced exfoliation, thereby preventing the restacking of the RGO sheets. RGO improved the electrochem. properties of the ZrO2-RGO nanocomposite and minimized the aggregation of ZrO2 NPs. FTIR studies confirmed the functionalization of the ZrO2-RGO nanocomposite with Meth and biomols. (anti-OTA and BSA). The Meth functionalized ZrO2-RGO nanocomposite had enhanced biocompatibility and wettability as confirmed by MTT assay and contact angle studies, resp. Furthermore, a uniform thin film of the Meth/ZrO2-RGO nanocomposite was electrophoretically deposited onto an indium tin oxide (ITO) coated glass substrate and utilized for covalent immobilization of monoclonal antibodies specific to ochratoxin A (anti-OTA) for the detection of ochratoxin A (OTA). The fabricated BSA/anti-OTA/Meth/ZrO2-RGO/ITO immunoelectrode exhibited a wide linear detection range of 1-20 ng mL-1 with a sensitivity of 4.8 μA ng-1 mL cm-2 and a detection limit of 0.079 ng mL-1 for OTA detection.
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    Raj, M.; Gupta, P.; Goyal, R. N.; Shim, Y. B. Graphene/Conducting Polymer Nano-Composite Loaded Screen-Printed Carbon Sensor for Simultaneous Determination of Dopamine and 5-Hydroxytryptamine. Sens. Actuators, B 2017, 239, 993– 1002,  DOI: 10.1016/j.snb.2016.08.083
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    Graphene/conducting polymer nano-composite loaded screen printed carbon sensor for simultaneous determination of dopamine and 5-hydroxytryptamine
    Raj, Mamta; Gupta, Pankaj; Goyal, Rajendra N.; Shim, Yoon-Bo
    Sensors and Actuators, B: Chemical (2017), 239 (), 993-1002CODEN: SABCEB; ISSN:0925-4005. (Elsevier B.V.)
    A novel and sensitive electrochem. method has been developed for the simultaneous detn. of dopamine (DA) and 5-hydroxytryptamine (5-HT) using graphene (GR) and poly 4-amino-3-hydroxy-1-naphthalenesulfonic acid modified screen printed carbon sensor. The electrochem. measurements were studied using cyclic voltammetry, square wave voltammetry, whereas the surface morphol. of the modified sensor was characterized by Electrochem. Impedance Spectroscopy and Field Emission SEM. The fabricated sensor facilitated the anal. of DA and 5-HT in the concn. range 0.05-100μM and 0.05-150μM with the detection limit of 2 nM and 3 nM resp. The fabricated sensor has been explored for the detn. of 5-HT in the plasma samples and the selectivity of the proposed work has been proved by the anal. of DA and 5-HT in the presence of common metabolites present in biol. fluids. The anal. applicability of the fabricated sensor has also been successfully demonstrated for the simultaneous detection of DA and 5-HT in the pharmacol. formulations, human urine and blood samples.
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    https://chemport.cas.org/services/resolver?origin=ACS&resolution=options&coi=1%3ACAS%3A528%3ADC%252BC28XhsVWjtr3O&md5=bafa1aab34b94d004b44a697e61494f9
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    Simultaneous Voltammetric Determination of Acetaminophen and Isoniazid (Hepatotoxicity-Related Drugs) Utilizing Bismuth Oxide Nanorod Modified Screen-Printed Electrochemical Sensing Platforms
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    To overcome the recent outbreaks of hepatotoxicity related-drugs, a new anal. tool for the continuously detn. of these drugs in human fluids is required. Electrochem. based anal. methods offer an effective, rapid and simple tool for on-site detn. of various org. and inorg. species. However, the design of a sensitive, selective, stable and reproducible sensor is still a major challenge. In the present manuscript, a facile, one-pot hydrothermal synthesis of bismuth oxide (Bi2O2.33) nanostructures (nanorods) was developed. These BiO nanorods were cast onto mass disposable graphite screen-printed electrodes (BiO-SPEs) allowing the ultrasensitive detn. of acetaminophen (APAP) in the presence of it's the common interference isoniazid (INH) which are both found in drug samples. The simultaneous electroanal. sensing using BiO-SPEs exhibited strong electrocatalytic activity towards the sensing of APAP and INH with an enhanced anal. signal (voltammetric peak) over that achievable at unmodified (bare) SPEs. The electroanal. sensing of APAP and INH are possible with accessible linear ranges from 0.5 to 1250 μM and 5 to 1760 μM with limits of detection (3σ) of 30 nM and 1.85 μM, resp. The stability, reproducibility and repeatability of BiO-SPE were also investigated. The BiO-SPEs were evaluated towards the sensing of APAP and INH in human serum, urine, saliva and tablet samples. The results presented in this paper demonstrate that BiO-SPEs sensing platforms provide a potential candidate for the accurate detn. of APAP and INH within human fluids and pharmaceutical formulations.
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    The equation of a linear potential sweep voltammogram is derived for any degree of reversibility of the electrochem. reaction for the following methods:surface voltammetry when both the oxidized and the reduced froms are strongly adsorbed, and a Langmuir isotherm is obeyed, thin-layer voltammetry, and linear potential sweep coulometry. The results are expressed in a math. form valid for the 3 cases. The transfer coeff. and the rate const. of the electrochem. reaction can be deduced from an exptl. study of the variations of the peak potentials as a function of the sweep rate.
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    Electrochemical behavior and voltammetric determination of paracetamol on Nafion/TiO2-graphene modified glassy carbon electrode
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    Electrochemical determination of acetaminophen based on TiO2-graphene/poly(methyl red) composite film modified electrode
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https://doi.org/10.1021/acsomega.8b02129
Published November 1, 2018

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  • Abstract

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    Scheme 1

    Scheme 1. Synthesis of the ZrO2/rGO Nanocomposite for the Electrochemical Sensing of REG
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    Figure 1

    Figure 1. TEM, HRTEM, and SAED images of (a–c) pristine ZrO2 and (d–f) ZrO2/rGO nanocomposite.

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    Figure 2

    Figure 2. Cyclic voltammograms recorded in 0.1 M PBS, pH 7.0, at the scan rate of 100 mV s–1 (a) blank and bare GCE electrode without REG, (b) bare GCE in the presence of 0.01 mM REG, (c) ZrO2-modified GC electrode in the presence of 0.01 mM REG, and (d) ZrO2/rGO/GCE in the presence of 0.01 mM REG.

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    Figure 3

    Figure 3. (a) DPV voltammograms obtained with the ZrO2/rGO/GCE in an electrolyte solution at different pH values, with 0.01 mM REG. (b) Calibration plot of the anodic peak current (curve-I) and the anodic peak potential (curve-II) vs the pH of the 0.1 M PBS solution, during the electro-oxidation of 0.01 mM REG, at a scan rate of 100 mV s–1.

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    Scheme 2

    Scheme 2. Electrochemical Redox Process of REG by ZrO2/rGO/GCE
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    Figure 4

    Figure 4. (a) Cyclic voltammograms recorded at the ZrO2/rGO/GCE in the electrolyte solution at different scan rates from 10 to 100 mV s–1. (b) Calibration plot of the anodic and cathode peak currents versus the square root of the scan rate, during the electro-oxidation of 0.01 mM REG in the presence of 0.1 M PBS, pH 7.0.

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    Figure 5

    Figure 5. (a) Differential pulse voltammograms recorded at the ZrO2/rGO/GCE over an REG concentration of 11–343 nM in 0.1 M PBS at pH 7.0. (b) Linear calibration plot of the anodic peak current versus REG concentration.

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    Figure 6

    Figure 6. DPVs recorded on the ZrO2/rGO/GCE during simultaneous determination of 0.32–0.66 μM REG, 0.58–1.26 μM AA, and 0.08–0.52 μM UA in 0.1 M PBS, pH 7.0. Insets: plots of the anodic peak currents against concentrations of REG, AA, and UA.

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  • References

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      Purpose: Regorafenib, a multikinase inhibitor targeting the Ras/Raf/MEK/ERK pathway, has recently been approved for the treatment of metastatic colorectal cancer. However, the mechanisms of action of regorafenib in colorectal cancer cells have been unclear. We investigated how regorafenib suppresses colorectal cancer cell growth and potentiates effects of other chemotherapeutic drugs. Exptl. Design: We detd. whether and how regorafenib induces the expression of PUMA, a p53 target and a crit. mediator of apoptosis in colorectal cancer cells. We also investigated whether PUMA is necessary for the killing and chemosensitization effects of regorafenib in colorectal cancer cells. Furthermore, xenograft tumors were used to test if PUMA mediates the in vivo antitumor, antiangiogenic, and chemosensitization effects of regorafenib. Results: We found that regorafenib treatment induces PUMA in colorectal cancer cells irresp. of p53 status through the NF-κB pathway following ERK inhibition and glycogen synthase kinase 3β activation. Upregulation of PUMA is correlated with apoptosis induction in different colorectal cancer cell lines. PUMA is necessary for regorafenib-induced apoptosis in colorectal cancer cells. Chemosensitization by regorafenib is mediated by enhanced PUMA induction through different pathways. Furthermore, deficiency in PUMA abrogates the in vivo antitumor, antiangiogenic, and chemosensitization effects of regorafenib. Conclusions: Our results demonstrate a key role of PUMA in mediating the anticancer effects of regorafenib in colorectal cancer cells. They suggest that PUMA induction can be used as an indicator of regorafenib sensitivity, and also provide a rationale for manipulating the apoptotic machinery to improve the therapeutic efficacy of regorafenib and other targeted drugs. Clin Cancer Res; 20(13); 3472-84. ©2014 AACR.
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      Angiogenesis, a crit. driver of tumor development, is controlled by interconnected signaling pathways. Vascular endothelial growth factor receptor (VEGFR) 2 and tyrosine kinase with Ig and epidermal growth factor homol. domain 2 play crucial roles in the biol. of normal and tumor vasculature. Regorafenib (BAY 73-4506), a novel oral multikinase inhibitor, potently inhibits these endothelial cell kinases in biochem. and cellular kinase phosphorylation assays. Furthermore, regorafenib inhibits addnl. angiogenic kinases (VEGFR1/3, platelet-derived growth factor receptor-β and fibroblast growth factor receptor 1) and the mutant oncogenic kinases KIT, RET and B-RAF. The antiangiogenic effect of regorafenib was demonstrated in vivo by dynamic contrast-enhanced magnetic resonance imaging. Regorafenib administered once orally at 10 mg/kg significantly decreased the extravasation of Gadomer in the vasculature of rat GS9L glioblastoma tumor xenografts. In a daily (qd)×4 dosing study, the pharmacodynamic effects persisted for 48 h after the last dosing and correlated with tumor growth inhibition (TGI). A significant redn. in tumor microvessel area was obsd. in a human colorectal xenograft after qd×5 dosing at 10 and 30 mg/kg. Regorafenib exhibited potent dose-dependent TGI in various preclin. human xenograft models in mice, with tumor shrinkages obsd. in breast MDA-MB-231 and renal 786-O carcinoma models. Pharmacodynamic analyses of the breast model revealed strong redn. in staining of proliferation marker Ki-67 and phosphorylated extracellular regulated kinases 1/2. These data demonstrate that regorafenib is a well-tolerated, orally active multikinase inhibitor with a distinct target profile that may have therapeutic benefit in human malignancies.
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      Di Gion, P.; Kanefendt, F.; Lindauer, A.; Scheffler, M.; Doroshyenko, O.; Fuhr, U.; Wolf, J.; Jaehde, U. Clinical Pharmacokinetics of Tyrosine Kinase Inhibitors: Focus on Pyrimidines, Pyridines, and Pyrroles. Clin. Pharmacokinet. 2011, 50, 551– 603,  DOI: 10.2165/11593320-000000000-00000
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      Clinical pharmacokinetics of tyrosine kinase inhibitors: focus on pyrimidines, pyridines and pyrroles
      Di Gion, Paola; Kanefendt, Friederike; Lindauer, Andreas; Scheffler, Matthias; Doroshyenko, Oxana; Fuhr, Uwe; Wolf, Juergen; Jaehde, Ulrich
      Clinical Pharmacokinetics (2011), 50 (9), 551-603CODEN: CPKNDH; ISSN:0312-5963. (Wolters Kluwer Health)
      A review. Pyrimidine (imatinib, dasatinib, nilotinib and pazopanib), pyridine (sorafenib) and pyrrole (sunitinib) tyrosine kinase inhibitors (TKIs) are multi-targeted TKIs with high activity towards several families of receptor and non-receptor tyrosine kinases involved in angiogenesis, tumor growth and metastatic progression of cancer. These orally administered TKIs have quite diverse characteristics with regard to absorption from the gastrointestinal tract. Abs. bioavailability in humans has been investigated only for imatinib (almost 100%) and pazopanib (14-39%; n = 3). On the basis of human radioactivity data, dasatinib is considered to be well absorbed after oral administration (19% and 0.1% of the total radioactivity were excreted as unchanged dasatinib in the faeces and urine, resp.). Quite low abs. bioavailability under fasted conditions is assumed for nilotinib (31%), sorafenib (50%) and sunitinib (50%). Imatinib, dasatinib and sunitinib exhibit dose-proportional increases in their area under the plasma concn.-time curve values over their therapeutic dose ranges. Less than dose-proportional increases were obsd. for nilotinib at doses ≥400 mg/day and for sorafenib and pazopanib at doses ≥800 mg/day. At steady state, the accumulation ratios are 1.5-2.5 (unchanged imatinib), 2.0 (nilotinib once-daily dosing), 3.4 (nilotinib twice-daily dosing), 1.2-4.5 (pazopanib), 5.7-6.4 (sorafenib) and 3.0-4.5 (sunitinib). Concomitant intake of a high-fat meal does not alter exposure to imatinib, dasatinib and sunitinib but leads to considerably increased bioavailability of nilotinib and pazopanib and decreased bioavailability of sorafenib. With the exception of pazopanib, the TKIs described here have large apparent vols. of distribution, exceeding the vol. of body water by at least 4-fold. Very low penetration into the central nervous system in humans has been reported for imatinib and dasatinib, but there are currently no published human data for nilotinib, pazopanib, sorafenib or sunitinib. All TKIs that have been described are more than 90% bound to the plasma proteins: α1-acid glycoprotein and/or albumin. They are metabolized primarily via cytochrome P 450 (CYP) 3A4, the only exception being sorafenib, for which uridine diphosphate glucuronosyltransferase 1A9 is the other main enzyme involved. Active metabolites of imatinib and sunitinib contribute to their antitumor activity. Although some patient demographics have been identified as significant co-factors that partly explain interindividual variability in exposure to TKIs, these findings have not been regarded as sufficient to recommend age-, sex-, bodyweight- or ethnicity-specific dose adjustment. Systemic exposure to imatinib, sorafenib and pazopanib increases in patients with hepatic impairment, and redn. of the initial therapeutic dose is recommended in this subpopulation. The starting dose of imatinib should also be reduced in renally impaired subjects. Because the soly. of dasatinib is pH dependent, co-administration of histamine H2-receptor antagonists and proton pump inhibitors with dasatinib should be avoided. With the exception of sorafenib, systemic exposure to TKIs is significantly decreased/increased by co-administration of potent CYP3A4 inducers/inhibitors, and so it is strongly recommended that the TKI dose is adjusted or that such co-administration is avoided. Caution is also recommended for co-administration of CYP3A4 substrates with TKIs, esp. for those with a narrow therapeutic index. However, current recommendations with regard to dose adjustment of TKIs need to be validated in clin. studies. Further investigations are needed to explain the large interindividual variability in the pharmacokinetics of these drugs and to assess the clin. relevance of their interaction potential and inhibitory effects on metabolizing enzymes and transporters.
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      Josephs, Debra H.; Fisher, Danielle S.; Spicer, James; Flanagan, Robert J.
      Therapeutic Drug Monitoring (2013), 35 (5), 562-587CODEN: TDMODV; ISSN:0163-4356. (Lippincott Williams & Wilkins)
      A review. The treatment of many malignancies has been improved in recent years by the introduction of mol. targeted therapies. These drugs interact preferentially with specific targets that are mutated and/or overexpressed in malignant cells. A group of such targets are the tyrosine kinases, against which a no. of inhibitors (tyrosine kinase inhibitors, TKIs) have been developed. Imatinib, a TKI with targets that include the breakpoint cluster region-Abelson (bcr-abl) fusion protein kinase and mast/stem cell growth factor receptor kinase (c-Kit), was the first clin. successful drug of this type and revolutionized the treatment and prognosis of chronic myeloid leukemia and gastrointestinal stromal tumors. This success paved the way for the development of other TKIs for the treatment of a range of hematol. malignancies and solid tumors. To date, 14 TKIs have been approved for clin. use and many more are under investigation. All these agents are given orally and are substrates of a range of drug transporters and metabolizing enzymes. In addn., some TKIs are capable of inhibiting their own transporters and metabolizing enzymes, making their disposition and metab. at steady-state unpredictable. A given dose can therefore give rise to markedly different plasma concns. in different patients, favoring the selection of resistant clones in the case of subtherapeutic exposure, and increasing the risk of toxicity if dosage is excessive. The aim of this review was to summarize current knowledge of the clin. pharmacokinetics and known adverse effects of the TKIs that are available for clin. use and to provide practical guidance on the implications of these data in patient management, in particular with respect to therapeutic drug monitoring.
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    5. 5
      Ly, J. Q.; Messick, K.; Qin, A.; Takahashi, R. H.; Choo, E. F. Utility of CYP3A4 and PXR-CAR-CYP3A4/3A7 Transgenic Mouse Models to Assess the Magnitude of CYP3A4 Mediated Drug–Drug Interactions. Mol. Pharmaceutics 2017, 14, 1754– 1759,  DOI: 10.1021/acs.molpharmaceut.7b00006
      5
      Utility of CYP3A4 and PXR-CAR-CYP3A4/3A7 Transgenic Mouse Models To Assess the Magnitude of CYP3A4 Mediated Drug-Drug Interactions
      Ly, Justin Q.; Messick, Kirsten; Qin, Ann; Takahashi, Ryan H.; Choo, Edna F.
      Molecular Pharmaceutics (2017), 14 (5), 1754-1759CODEN: MPOHBP; ISSN:1543-8384. (American Chemical Society)
      Species differences in the expression, activity, regulation, and substrate specificity of metabolizing enzymes preclude the use of animal models to predict clin. drug-drug interactions (DDIs). The objective of this work is to det. if the transgenic (Tg) Cyp3a-/-Tg-3A4Hep/Int and Nr1i2/Nr1i3-/--Cyp3a-/-Tg-PXR-CAR-3A4/3A7Hep/Int (PXR-CAR-CYP3A4/3A7) mouse models could be used to predict in vivo DDI of 10 drugs; alprazolam, bosutinib, crizotinib, dasatinib, gefitinib, ibrutinib, regorafenib, sorafenib, triazolam, and vandetinib (as victims); with varying magnitudes of reported CYP3A4 clin. DDI. As an assessment of the effect of CYP3A4 inhibition, these drugs were coadministered to Cyp3a-/-Tg-3A4Hep/Int mice with the CYP3A inhibitor, itraconazole. For crizotinib, regorafenib, sorafenib, and vandetanib, there was no significant increase of AUC obsd.; with alprazolam, bosutinib, ibrutinib, dasatinib, and triazolam, pretreatment with itraconazole resulted in a 2-, 4-, 17-, 7-, and 15-fold increase in AUC, resp. With the exception of gefinitib for which the DDI effect was overpredicted (12-fold in Tg-mice vs 2-fold in the clinic), the magnitude of AUC increase obsd. in this study was consistent (within 2-fold) with the clin. DDI obsd. following administration with itraconazole/ketoconazole. As an assessment of CYP3A4 induction, following rifampin pretreatment to PXR-CAR-3A4/3A7Hep/Int mice, an 8% decrease in vandetanib mean AUC was obsd.; 39-52% redn. in AUC were obsd. for dasatinib, ibrutinib, regorafenib, and sorafenib compared to vehicle treated mice. The greatest effect of rifampin induction was obsd. with alprazolam, bosutinib, crizotinib, gefitinib, and triazolam where 72-91% decrease in AUC were obsd. With the exception of vandetanib for which rifampin induction was under-predicted, the magnitude of induction obsd. in this study was consistent (within 2-fold) with clin. observations. These data sets suggest that, with two exceptions, these transgenic mice models were able to exclude or capture the magnitude of CYP3A4 clin. inhibition and induction. Data generated in transgenic mice may be used to gain confidence and complement in vitro and in silico methods for assessing DDI potential/liability.
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    6. 6
      Cheng, A. L.; Kang, Y. K.; Lin, D. Y.; Park, J. W.; Kudo, M.; Qin, S.; Chung, H. C.; Song, X.; Xu, J.; Poggi, G.; Omata, M.; Pitman Lowenthal, S.; Lanzalone, S.; Yang, L.; Lechuga, M. J.; Raymond, E. Sunitinib Versus Sorafenib in Advanced Hepatocellular Cancer: Results of a Randomized Phase III Trial. J. Clin. Oncol. 2013, 31, 4067– 4075,  DOI: 10.1200/JCO.2012.45.8372
      6
      Sunitinib versus sorafenib in advanced hepatocellular cancer: results of a randomized phase III trial
      Cheng, Ann-Lii; Kang, Yoon-Koo; Lin, Deng-Yn; Park, Joong-Won; Kudo, Masatoshi; Qin, Shukui; Chung, Hyun-Cheol; Song, Xiangqun; Xu, Jianming; Poggi, Guido; Omata, Masao; Lowenthal, Susan Pitman; Lanzalone, Silvana; Yang, Liqiang; Lechuga, Maria Jose; Raymond, Eric
      Journal of Clinical Oncology (2013), 31 (32), 4067-4075CODEN: JCONDN; ISSN:0732-183X. (American Society of Clinical Oncology)
      Purpose Open-label, phase III trial evaluating whether sunitinib was superior or equiv. to sorafenib in hepatocellular cancer. Patients and Methods Patients were stratified and randomly assigned to receive sunitinib 37.5 mg once per day or sorafenib 400 mg twice per day. Primary end point was overall survival (OS). Results Early trial termination occurred for futility and safety reasons. A total of 1,074 patients were randomly assigned to the study (sunitinib arm, n = 530; sorafenib arm, n = 544). For sunitinib and sorafenib, resp., median OS was 7.9 vs. 10.2 mo (hazard ratio [HR], 1.30; one-sided P = .9990; two-sided P = .0014); median progression-free survival (PFS; 3.6 v 3.0 mo; HR, 1.13; one-sided P = .8785; two-sided P = .2286) and time to progression (TTP; 4.1 v 3.8 mo; HR, 1.13; one-sided P = .8312; two-sided P = .3082) were comparable. Median OS was similar among Asian (7.7 v 8.8 mo; HR, 1.21; one-sided P = .9829) and hepatitis B-infected patients (7.6 v 8.0 mo; HR, 1.10; one-sided P = .8286), but was shorter with sunitinib in hepatitis C-infected patients (9.2 v 17.6 mo; HR, 1.52; one-sided P = .9835). Sunitinib was assocd. with more frequent and severe adverse events (AEs) than sorafenib. Common grade 3/4 AEs were thrombocytopenia (29.7%) and neutropenia (25.7%) for sunitinib; hand-foot syndrome (21.2%) for sorafenib. Discontinuations owing to AEs were similar (sunitinib, 13.3%; sorafenib, 12.7%). Conclusion OS with sunitinib was not superior or equiv. but was significantly inferior to sorafenib. OS was comparable in Asian and hepatitis B-infected patients. OS was superior in hepatitis C-infected patients who received sorafenib. Sunitinib-treated patients reported more frequent and severe toxicity.
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    7. 7
      Cheng, A. L.; Kang, Y. K.; Chen, A. L.; Tsao, Z.; Qin, C. J.; Kim, S.; Luo, J. S.; Feng, R.; Ye, J.; Yang, S.; Xu, T. S.; Sun, J.; Liang, Y.; Liu, H.; Wang, J.; Tak, J.; Pan, W. Y.; Burock, H.; Zou, K.; Voliotis, J.; Guan, D. Z. Efficacy, and Safety of Sorafenib in Patients in the Asia-Pacific Region with Advanced Hepatocellular Carcinoma: A Phase III Randomized, Double-Blind, Placebo-Controlled Trial. Lancet Oncol. 2009, 10, 25– 34,  DOI: 10.1016/S1470-2045(08)70285-7
      7
      Efficacy and safety of sorafenib in patients in the Asia-Pacific region with advanced hepatocellular carcinoma: a phase III randomized, double-blind, placebo-controlled trial
      Cheng, Ann-Lii; Kang, Yoon-Koo; Chen, Zhendong; Tsao, Chao-Jung; Qin, Shukui; Kim, Jun Suk; Luo, Rongcheng; Feng, Jifeng; Ye, Shenglong; Yang, Tsai-Sheng; Xu, Jianming; Sun, Yan; Liang, Houjie; Liu, Jiwei; Wang, Jiejun; Tak, Won Young; Pan, Hongming; Burock, Karin; Zou, Jessie; Voliotis, Dimitris; Guan, Zhongzhen
      Lancet Oncology (2009), 10 (1), 25-34CODEN: LOANBN; ISSN:1470-2045. (Elsevier Ltd.)
      Most cases of hepatocellular carcinoma occur in the Asia-Pacific region, where chronic hepatitis B infection is an important etiol. factor. Assessing the efficacy and safety of new therapeutic options in an Asia-Pacific population is thus important. We did a multinational phase III, randomized, double-blind, placebo-controlled trial to assess the efficacy and safety of sorafenib in patients from the Asia-Pacific region with advanced (unresectable or metastatic) hepatocellular carcinoma. Between Sept 20, 2005, and Jan 31, 2007, patients with hepatocellular carcinoma who had not received previous systemic therapy and had Child-Pugh liver function class A, were randomly assigned to receive either oral sorafenib (400 mg) or placebo twice daily in 6-wk cycles, with efficacy measured at the end of each 6-wk period. Eligible patients were stratified by the presence or absence of macroscopic vascular invasion or extrahepatic spread (or both), Eastern Cooperative Oncol. Group performance status, and geog. region. Randomization was done centrally and in a 2:1 ratio by means of an interactive voice-response system. There was no predefined primary endpoint; overall survival, time to progression (TTP), time to symptomatic progression (TTSP), disease control rate (DCR), and safety were assessed. Efficacy analyses were done by intention to treat. This trial is registered with, no. Two hundred and seventy-one 271 patients from 23 centers in China, South Korea, and Taiwan were enrolled in the study. Of these, 226 patients were randomly assigned to the exptl. group (n=150) or to the placebo group (n=76). Median overall survival was 6.5 mo (95% CI 5.56-7.56) in patients treated with sorafenib, compared with 4.2 mo (3.75-5.46) in those who received placebo (hazard ratio [HR] 0.68 [95% CI 0.50-0.93]; p=0.014). Median TTP was 2.8 mo (2.63-3.58) in the sorafenib group compared with 1.4 mo (1.35-1.55) in the placebo group (HR 0.57 [0.42-0.79]; p=0.0005). The most frequently reported grade 3/4 drug-related adverse events in the 149 assessable patients treated with sorafenib were hand-foot skin reaction (HFSR; 16 patients [10.7%]), diarrhea (nine patients [6.0%]), and fatigue (five patients [3.4%]). The most common adverse events resulting in dose redns. were HFSR (17 patients [11.4%]) and diarrhea (11 patients [7.4%]); these adverse events rarely led to discontinuation. Sorafenib is effective for the treatment of advanced hepatocellular carcinoma in patients from the Asia-Pacific region, and is well tolerated. Taken together with data from the Sorafenib Hepatocellular Carcinoma Assessment Randomized Protocol (SHARP) trial, sorafenib seems to be an appropriate option for the treatment of advanced hepatocellular carcinoma. Funding: Bayer HealthCare Pharmaceuticals and Onyx Pharmaceuticals, Inc.
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    8. 8
      Hutson, T. E.; Escudier, B.; Esteban, E.; Bjarnason, G. A.; Lim, H. Y.; Pittman, K. B.; Senico, P.; Niethammer, A.; Lu, D. R.; Hariharan, S.; Motzer, R. J. Randomized Phase III Trial of Temsirolimus versus Sorafenib as Second-Line Therapy after Sunitinib in Patients with Metastatic Renal Cell Carcinoma. J. Clin. Oncol. 2014, 32, 760– 767,  DOI: 10.1200/JCO.2013.50.3961
      8
      Randomized phase III trial of temsirolimus versus sorafenib as second-line therapy after sunitinib in patients with metastatic renal cell carcinoma
      Hutson, Thomas E.; Escudier, Bernard; Esteban, Emilio; Bjarnason, Georg A.; Lim, Ho Yeong; Pittman, Kenneth B.; Senico, Peggy; Niethammer, Andreas; Lu, Dongrui Ray; Hariharan, Subramanian; Motzer, Robert J.
      Journal of Clinical Oncology (2014), 32 (8), 760-767CODEN: JCONDN; ISSN:0732-183X. (American Society of Clinical Oncology)
      Purpose This international phase III trial (Investigating Torisel As Second-Line Therapy [INTORSECT]) compared the efficacy of temsirolimus (mammalian target of rapamycin inhibitor) and sorafenib (vascular endothelial growth factor receptor [VEGFR] tyrosine kinase inhibitor) as second-line therapy in patients with metastatic renal cell carcinoma (mRCC) after disease progression on sunitinib. Patients and Methods In total, 512 patients were randomly assigned 1:1 to receive i.v. temsirolimus 25 mg once weekly (n = 259) or oral sorafenib 400 mg twice per day (n = 253), with stratification according to duration of prior sunitinib therapy (≤ or > 180 days), prognostic risk, histol. (clear cell or non-clear cell), and nephrectomy status. The primary end point was progression-free survival (PFS) by independent review committee assessment. Safety, objective response rate (ORR), and overall survival (OS) were secondary end points. Results Primary anal. revealed no significant difference between treatment arms for PFS (stratified hazard ratio [HR], 0.87; 95% CI, 0.71 to 1.07; two-sided P = .19) or ORR. Median PFS in the temsirolimus and sorafenib arms were 4.3 and 3.9 mo, resp. There was a significant OS difference in favor of sorafenib (stratified HR, 1.31; 95% CI, 1.05 to 1.63; two-sided P = .01). Median OS in the temsirolimus and sorafenib arms was 12.3 and 16.6 mo, resp. Safety profiles of both agents were consistent with previous studies. Conclusion In patients with mRCC and progression on sunitinib, second-line temsirolimus did not demonstrate a PFS advantage compared with sorafenib. The longer OS obsd. with sorafenib suggests sequenced VEGFR inhibition may benefit patients with mRCC.
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    9. 9
      Grothey, A.; Van Cutsem, E.; Sobrero, A.; Siena, S.; Falcone, A.; Ychou, M.; Humblet, Y.; Bouché, O.; Mineur, L.; Barone, C.; Adenis, A.; Tabernero, J.; Yoshino, T.; Lenz, H. J.; Goldberg, R. M.; Sargent, D. J.; Cihon, F.; Cupit, L.; Wagner, A.; Laurent, D. Correct Study Group, Regorafenib Monotherapy for Previously Treated Metastatic Colorectal Cancer (Correct): An International, Multicentre, Randomised, Placebo-Controlled, Phase III Trial. Lancet 2013, 381, 303– 312,  DOI: 10.1016/S0140-6736(12)61900-X
      There is no corresponding record for this reference.
    10. 10
      Escudier, B.; Eisen, T.; Stadle, W. M.; Szczylik, C.; Oudard, S.; Siebels, M.; Negrier, S.; Chevreau, C.; Solska, E.; Desai, A. A. Sorafenib in Advanced Clear-Cell Renal-Cell Carcinoma. N. Engl. J. Med. 2007, 356, 125– 134,  DOI: 10.1056/NEJMoa060655
      10
      Sorafenib in advanced clear-cell renal-cell carcinoma
      Escudier, Bernard; Eisen, Tim; Stadler, Walter M.; Szczylik, Cezary; Oudard, Stephane; Siebels, Michael; Negrier, Sylvie; Chevreau, Christine; Solska, Ewa; Desai, Apurva A.; Rolland, Frederic; Demkow, Tomasz; Hutson, Thomas E.; Gore, Martin; Freeman, Scott; Schwartz, Brian; Shan, Minghua; Simantov, Ronit; Bukowski, Ronald M.; Blajman, C.; Fein, L.; Martin, C.; Taber, R.; Boyer, M.; Davis, I.; Gurney, H.; Hovey, E.; Leong, D.; Steer, C.; DeGreve, J.; Gil, T.; Barrios, C.; David, W.; Skare, N. G.; Notari, A.; Schwartsmann, G.; Gunnar, N.; Ernst, S.; Hotte, S.; Miller, W.; Moore, M.; North, S.; Fodor, M.; Caty, A.; Chevreau, C.; Duclos, B.; Gravis, G.; Negrier, S.; Oudard, S.; Ravaud, A.; Rolland, F.; Sevin, E.; Grimm, M. O.; Gschwennd, J.; Heinzer, H.; Jager, E.; Krause, S.; Michel, M.-S.; Rohde, D.; Siebels, M.; Siegsmund, M.; Staehler, M.; Wirth, M.; Baki, M.; Bodrogi, I.; Cseh, J.; Ruzsa, A.; Toth, C.; Ben-Yosef, R.; Gez, E.; Bajetta, E.; Boni, C.; Bracarda, S.; Cognetti, F.; Conte, P.; Porta, C.; Spronsen, D. J.; Blasinka-Morawiec, M.; Dernkow, T.; Lorenz, J.; Mazurkiewicz, M.; Roslki, J.; Sikorski, A.; Solska, E.; Tomczak, P.; Bolotina, L.; Karlov, P.; Karyakin, O.; Khasanov, R.; Lichinitser, M.; Lubennikov, V.; Moiseenko, V.; Sherman, N.; Abratt, R.; Coetzee, L.; Cohen, G.; Heyns, C.; Jordaan, J.; Ruff, P.; Wentzel, S.; Bellmunt, J.; Climent, M. A.; Gonzalez, J. L.; Lopez, G.; Bashtan, V.; Dumamsky, Y.; Klimenko, I.; Pilipenko, N.; Shparik, Y.; Hawkins, R.; McMenemin, R.; Nathan, P.; Porfiri, E.; Savage, P.; White, J.; Anderson, C.; Bains, Y.; Bleickardt, E.; Bradof, J.; Brooks, D.; Cardi, G.; Cervera, A.; Davis, N.; Desai, A.; Drabkin, H.; Dudek, A.; Dutcher, J.; Formanek, G.; Gabrail, N.; Gorss, H.; Haung, Y.; Henderson, C.; Hutson, T.; Jonasch, E.; Lara, P.; McCracken, J.; McDermott, D.; Mena, R.; Middleton, R.; Petrylak, D.; Picus, D.; Quinn, D.; Rausch, P.; Rinaldi, D.; Ryan, C.; Tchekmedyian, N.; Vuky, J.
      New England Journal of Medicine (2007), 356 (2), 125-134CODEN: NEJMAG; ISSN:0028-4793. (Massachusetts Medical Society)
      We conducted a phase 3, randomized, double-blind, placebo-controlled trial of sorafenib, a multikinase inhibitor of tumor-cell proliferation and angiogenesis, in patients with advanced clear-cell renal-cell carcinoma. From Nov. 2003 to Mar. 2005, we randomly assigned 903 patients with renal-cell carcinoma that was resistant to std. therapy to receive either continuous treatment with oral sorafenib (at a dose of 400 mg twice daily) or placebo; 451 patients received sorafenib and 452 received placebo. The primary end point was overall survival. A single planned anal. of progression-free survival in Jan. 2005 showed a statistically significant benefit of sorafenib over placebo. Consequently, crossover was permitted from placebo to sorafenib, beginning in May 2005. At the Jan. 2005 cutoff, the median progression-free survival was 5.5 mo in the sorafenib group and 2.8 mo in the placebo group (hazard ratio for disease progression in the sorafenib group, 0.44; 95% confidence interval [CI], 0.35 to 0.55). The 1st interim anal. of overall survival in May 2005 showed that sorafenib reduced the risk of death, as compared with placebo (hazard ratio, 0.72; 95% CI, 0.54 to 0.94), although this benefit was not statistically significant according to the O'Brien-Fleming threshold. Partial responses were reported as the best response in 10% of patients receiving sorafenib and in 2% of those receiving placebo. Diarrhea, rash, fatigue, and hand-foot skin reactions were the most common adverse events assocd. with sorafenib. Hypertension and cardiac ischemia were rare serious adverse events that were more common in patients receiving sorafenib than in those receiving placebo. As compared with placebo, treatment with sorafenib prolongs progression-free survival in patients with advanced clear-cell renal-cell carcinoma in whom previous therapy has failed; however, treatment is assocd. with increased toxic effects. (ClinicalTrials.gov no., NCT00073307).
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    11. 11
      Mross, K.; Frost, A.; Steinbild, S.; Hedbom, S.; Buchert, M.; Fasol, U.; Unger, C.; Kratzschmar, J.; Heinig, R.; Boix, O.; Christensen, O. A Phase I Dose-Escalation Study of Regorafenib (BAY 73–4506), an Inhibitor of Oncogenic, Angiogenic, and Stromal Kinases, in Patients with Advanced Solid Tumors. Clin. Cancer Res. 2012, 18, 2658– 2667,  DOI: 10.1158/1078-0432.CCR-11-1900
      11
      A Phase I Dose-Escalation Study of Regorafenib (BAY 73-4506), an Inhibitor of Oncogenic, Angiogenic, and Stromal Kinases, in Patients with Advanced Solid Tumors
      Mross, Klaus; Frost, Annette; Steinbild, Simone; Hedbom, Susanne; Buechert, Martin; Fasol, Ulrike; Unger, Clemens; Kraetzschmar, Joern; Heinig, Roland; Boix, Oliver; Christensen, Olaf
      Clinical Cancer Research (2012), 18 (9), 2658-2667CODEN: CCREF4; ISSN:1078-0432. (American Association for Cancer Research)
      PURPOSE: Regorafenib is a novel oral multikinase inhibitor of angiogenic (VEGFR1-3, TIE2), stromal (PDGFR-β, FGFR), and oncogenic kinases (KIT, RET, and RAF). This first-in-man, phase I dose-escalation study assessed the safety, pharmacokinetic, pharmacodynamic, and efficacy profiles of regorafenib in patients with advanced solid tumors. PATIENTS AND METHODS: Patients aged 18 years or older with advanced solid tumors refractory to std. treatment were recruited. Regorafenib was administered orally for 21 days on/seven days off in repeating cycles, until discontinuation due to toxicity or tumor progression. Adverse events (AE) were assessed using National Cancer Institute Common Terminol. Criteria for Adverse Events v3.0. Pharmacokinetic profiles were measured after a single dose and on day 21. Pharmacodynamic and efficacy evaluations included tumor perfusion assessment using dynamic contrast-enhanced MRI, plasma cytokines, and tumor response using RECIST (v1.0). RESULTS: Fifty-three patients were enrolled into eight cohorts at dose levels from 10 to 220 mg daily. The recommended dose for future studies was detd. to be 160 mg daily, with a treatment schedule of 21 days on/seven days off in repeating 28-day cycles. The most common drug-related grade 3 or 4 AEs were dermatol. AEs (hand-foot skin reaction, rash), hypertension, and diarrhea. Pharmacokinetic anal. revealed a similar exposure at steady state for the parent compd. and two pharmacol. active metabolites. Tumor perfusion and plasma cytokine anal. showed biol. activity of regorafenib. Three of 47 evaluable patients achieved a partial response (renal cell carcinoma, colorectal carcinoma, and osteosarcoma). CONCLUSION: Regorafenib showed an acceptable safety profile and preliminary evidence of antitumor activity in patients with solid tumors. Clin Cancer Res; 18(9); 2658-67.
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    12. 12
      Crona, D. J.; Keisler, M. D.; Walko, C. M. Regorafenib: A Novel Multitargeted Tyrosinekinase Inhibitor for Colorectal Cancer and Gastrointestinal Stromal Tumors. Ann. Pharmacother. 2013, 47, 1685– 1696,  DOI: 10.1177/1060028013509792
      There is no corresponding record for this reference.
    13. 13
      Fujita, K.; Miura, M.; Shibata, H. Quantitative Determination of Regorafenib and its Two Major Metabolites in Human Plasma with High-Performance Liquid Chromatography and Ultraviolet Detection. Biomed. Chromatogr. 2016, 30, 1611– 1617,  DOI: 10.1002/bmc.3730
      13
      Quantitative determination of regorafenib and its two major metabolites in human plasma with high-performance liquid chromatography and ultraviolet detection
      Fujita, Kazuma; Miura, Masatomo; Shibata, Hiroyuki
      Biomedical Chromatography (2016), 30 (10), 1611-1617CODEN: BICHE2; ISSN:0269-3879. (John Wiley & Sons Ltd.)
      A simple, highly sensitive and specific high-performance liq. chromatog. (HPLC) method was developed for the simultaneous quantitation of regorafenib, N-oxidemetabolite (M-2) and the desmethyl N-oxide metabolite (M-5) in human plasma. Regorafenib, M-2, M-5 and the internal std. sorafenib were sepd. using a mobile phase of 0.5% KH2PO4 (pH 3.5)-acetonitrile (30:70, vol./vol.), on a Capcell PAK MG II column at a flow rate of 0.5 mL/min and measurement at UV 260 nm. The lower limits of quantification for regorafenib, M-2 and M-5 were 10 ng/mL for each analyte. A procedure using solid-phase extn. required only a small amt. of plasma (100 μL) for one anal. while providing high extn. recovery (>81% for all compds.) and good selectivity. Coeffs. of variation for intra- and inter-day assays were <12.2% for regorafenib, <12.3% for M-2 and <15.1% for M-5. Accuracies for intra- and inter-day assays were <9.4% for regorafenib, <8.0% for M-2 and <12.8% for M-5 over a linear range from 10 to 10,000 ng/mL. This HPLC assay is suitable for clin. pharmacokinetic studies of regorafenib. The present HPLC method is currently in use for our observational studies of patients under treatment.
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    14. 14
      Luethi, D.; Durmus, S.; Schinkel, A. H.; Schellens, J. H. M.; Beijnen, J. H.; Sparidans, R. W. Liquid Chromatography–Tandem Mass Spectrometric Assay for the Multikinase Inhibitor Regorafenib in Plasma. Biomed. Chromatogr. 2014, 28, 1366– 1370,  DOI: 10.1002/bmc.3176
      14
      Liquid chromatography-tandem mass spectrometric assay for the multikinase inhibitor regorafenib in plasma
      Luethi, Dino; Durmus, Selvi; Schinkel, Alfred H.; Schellens, Jan H. M.; Beijnen, Jos H.; Sparidans, Rolf W.
      Biomedical Chromatography (2014), 28 (10), 1366-1370CODEN: BICHE2; ISSN:0269-3879. (John Wiley & Sons Ltd.)
      Regorafenib has recently been approved for the treatment of colorectal cancer. A bioanal. liq. chromatog.-tandem mass spectrometric assay for this multikinase inhibitor was developed and validated in plasma. The concn. range of the assay was 25-25,000 ng/mL. Protein pptn. with acetonitrile was used as sample pre-treatment with sorafenib as internal std. The ext. was dild. with methanol (25%, vol./vol.) and then injected onto the sub-2 μm particle, bridged ethylsilicia hybrid trifunctional bonded C18 column. Isocratic elution using 0.02% (vol./vol.) formic acid in a methanol-water mixt. was used. Compds. were monitored by a triple quadrupole mass spectrometer in the selected reaction monitoring mode after pos. electrospray ionization. Double logarithmic calibration was used; within-day precisions, between-day precisions, and accuracies were 3.2-9.2, 4.1-12.3 and 94.8-103.0%, resp. High drug stability was obsd. under all relevant storage conditions. The assay was used to measure drug concns. in a pharmacokinetic study in wild-type FVB mice. Copyright © 2014 John Wiley & Sons, Ltd.
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    15. 15
      van Erp, N. P.; Wit, D. D.; Guchelaar, H. J.; Gelderblom, H.; Hessing, T. J.; Hartigh, J. D. A Validated Assay for the Simultaneous Quantification of Six Tyrosine Kinase Inhibitors and Two Active Metabolites in Human Serum Using Liquid Chromatography Coupled with Tandem Mass Spectrometry. J. Chromatogr. B 2013, 937, 33– 43,  DOI: 10.1016/j.jchromb.2013.08.013
      15
      A validated assay for the simultaneous quantification of six tyrosine kinase inhibitors and two active metabolites in human serum using liquid chromatography coupled with tandem mass spectrometry
      van Erp, Nielka P.; de Wit, Djoeke; Guchelaar, Henk-Jan; Gelderblom, Hans; Hessing, Trees J.; den Hartigh, Jan
      Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences (2013), 937 (), 33-43CODEN: JCBAAI; ISSN:1570-0232. (Elsevier B.V.)
      A sensitive, sophisticated and practical bioanal. assay for the simultaneous detn. of six tyrosine kinase inhibitors (imatinib, sunitinib, nilotinib, dasatinib, pazopanib, regorafenib) and two active metabolites (N-desmethyl imatinib and N-desethyl sunitinib) was developed and validated. For the quant. assay, a mixt. of three stable isotopes as internal stds. was added to human serum, stds. and controls. Thereafter, samples were pre-treated using protein pptn. with methanol. The supernatant was dild. with water and injected into an ultra pressure liq. chromatog. system with an Acquity TQ tandem mass spectrometry detector. The compds. were sepd. on an Acquity BEH C18 anal. column (100 mm × 2.1 mm ID, 1.7 μm particle size) and eluted with a linear gradient system. The ions were detected in the multiple reaction monitoring mode. The lower limit of quantification and the linearity of all compds. generously met with the concns. that are to be expected in clin. practice. The developed bioanal. assay can be used for guiding TKI therapy in daily clin. practice as well as for investigator-initiated research.
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    16. 16
      Hafner, F.-T.; Werner, D.; Kaiser, M. Determination of Regorafenib (Bay 73- 4506) and its Major Human Metabolites Bay 75-7495 (M-2) and Bay 81-8752 (M-5) in Human Plasma by Stable-Isotope Dilution Liquid Chromatography–Tandem Ms. Bioanalysis 2014, 6, 1923– 1937,  DOI: 10.4155/bio.14.52
      There is no corresponding record for this reference.
    17. 17
      Merienne, C.; Rousset, M.; Ducint, D.; Castaing, N.; Titier, K.; Molimard, M.; Bouchet, S. High Throughput Routine Determination of 17 Tyrosine Kinase Inhibitors by LC-MS/MS. J. Pharm. Biomed. Anal. 2018, 150, 112– 120,  DOI: 10.1016/j.jpba.2017.11.060
      17
      High throughput routine determination of 17 tyrosine kinase inhibitors by LC-MS/MS
      Merienne, Camille; Rousset, Marine; Ducint, Dominique; Castaing, Nadege; Titier, Karine; Molimard, Mathieu; Bouchet, Stephane
      Journal of Pharmaceutical and Biomedical Analysis (2018), 150 (), 112-120CODEN: JPBADA; ISSN:0731-7085. (Elsevier B.V.)
      Several studies have shown that therapeutic drug monitoring of tyrosine kinase inhibitors (TKI) can improve their benefit in cancer. An anal. tool has been developed in order to quantify 17 tyrosine kinase inhibitors and 2 metabolites in human plasma (afatinib, axitinib, bosutinib, crizotinib, dabrafenib, dasatinib, erlotinib, gefitinib, imatinib, lapatinib, nilotinib, ponatinib, regorafenib, regorafenib M2, regorafenib M5, ruxolitinib, sorafenib, sunitinib, vandetanib). Drugs were arranged in four groups, according to their plasma concn. range: 0.1-200 ng/mL, 1-200 ng/mL, 4-800 ng/mL and 25-5000 ng/mL. Solid phase extn. was used and sepn. was performed with HPLC using a gradient system on a solid core particle C18 column (5 × 2.1 mm, 1.6 μm). Ions were detected with a triple quadrupole mass spectrometry system. This assay allows rapid detn. of 19 TKI in less than 5 min per run. This high throughput routine method will be useful to adjust doses of oral anticancer drugs in order to improve treatments efficacy.
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    18. 18
      Pang, Y. Y.; Tan, Y. L.; Ho, H. K. Investigation of the Effect of Plasma Albumin Levels on Regorafenib-Induced Hepatotoxicity Using A Validated Liquid Chromatography-Tandem Mass Spectrometry Method. J. Chromatogr. B 2017, 1061–1062, 220– 224,  DOI: 10.1016/j.jchromb.2017.07.023
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      Investigation of the effect of plasma albumin levels on regorafenib-induced hepatotoxicity using a validated liquid chromatography-tandem mass spectrometry method
      Pang, Yi Yun; Tan, Yeong Lan; Ho, Han Kiat
      Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences (2017), 1061-1062 (), 220-224CODEN: JCBAAI; ISSN:1570-0232. (Elsevier B.V.)
      Regorafenib is an oral multikinase inhibitor indicated for metastatic colorectal cancer and gastrointestinal stromal tumor. Due to its extensive plasma protein binding and low calcd. hepatic extn. ratio, the hepatotoxicity obsd. with usage of the drug may be related to its plasma exposure. To investigate the highly dynamic free:bound drug concn. for regorafenib in the plasma, a bioanal. liq. chromatog.-tandem mass spectrometric assay was developed and validated in human plasma. The concn. range of the assay was 2-1000 ng/mL. Sample prepn. was via protein pptn. using acetonitrile with sorafenib as the internal std. The supernatant was injected into an ultra-performance liq. chromatog. system coupled to a triple quadrupole mass spectrometer. The analytes were sepd. on an AQUITY UPLC BEH C18 column (120 Å, 1.7 μm, 2.1 mm × 50 mm) and eluted with a gradient elution system. The ions were detected in multiple reaction monitoring mode. The linearity, lower limit of quantification, intraday and interday precision and accuracy conformed to FDA guidelines. The validated method was successfully applied to det. the effect of albumin levels in plasma on the extent of protein binding of regorafenib. The results indicated that physiol.-relevant levels of albumin were found to have no significant effect on the extent of protein binding of regorafenib, hence imposing minimal effect on drug disposition.
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    19. 19
      Allard, M.; Khoudour, N.; Rousseau, B.; Joly, C.; Costentin, C.; Blanchet, B.; Tournigand, C.; Hulin, A. Simultaneous Analysis of Regorafenib and Sorafenib and Three of their Metabolites in Human Plasma Using LC–MS/MS. J. Pharm. Biomed. Anal. 2017, 142, 42– 48,  DOI: 10.1016/j.jpba.2017.04.053
      19
      Simultaneous analysis of regorafenib and sorafenib and three of their metabolites in human plasma using LC-MS/MS
      Allard, Marie; Khoudour, Nihel; Rousseau, Benoit; Joly, Charlotte; Costentin, Charlotte; Blanchet, Benoit; Tournigand, Christophe; Hulin, Anne
      Journal of Pharmaceutical and Biomedical Analysis (2017), 142 (), 42-48CODEN: JPBADA; ISSN:0731-7085. (Elsevier B.V.)
      A new liq. chromatog.-tandem mass spectrometry (LC-MS/MS) method, performed by electrospray ionization in pos. mode using a triple quadrupole mass spectrometry, has been developed and validated for the simultaneous detn. of regorafenib (REGO), its two metabolites regorafenib-M2 and regorafenib-M5, sorafenib (SORA), and its N-oxide metabolite in human plasma. Sepn. is achieved on an Hypersil Gold column using a gradient elution of 10 mM ammonium formate contg. 0.1% formic acid (A) and acetonitrile contg. 0.1% formic acid (B) at a flow rate of 0.3 mL/min. After addn. of two internal stds. and a protein pptn., the supernatant is dild. two-fold in a 0.1% (vol./vol.) formic acid soln. Two selected reaction monitoring transitions are used, for each analyte, one for quantitation and the second one for confirmation. The std. curves are ranged from 50 to 5 000 ng/mL for REGO and its metabolites and 80 to 5 000 ng/mL for SORA and its metabolite and were fitted to a 1/x weighted linear regression model. The method also showed satisfactory results in terms of sensitivity, specificity, precision (intra- and inter-day CV from 2.4 to 10.2%), accuracy (from 91.0 to 111.7%), recovery as well as stability of the analytes under various conditions. The method is usually used in clin. practice to improve the SORA treatment for renal carcinoma, REGO treatment for colorectal cancer and both for hepatocellular carcinoma.
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    20. 20
      Albayrak, M. Development and Validation of a New Spectrophotometric Method for the Determination of Regorafenib in Pure and Tablet Dosage Form. Lat. Am. J. Pharm. 2018, 37, 1349– 1353
      There is no corresponding record for this reference.
    21. 21
      Ma, Z.; Chen, P.; Cheng, W.; Yan, K.; Pan, L.; Shi, Y.; Guihua, Y. Highly Sensitive, Printable Nanostructured Conductive Polymer Wireless Sensor for Food Spoilage Detection. Nano Lett. 2018, 18, 4570– 4575,  DOI: 10.1021/acs.nanolett.8b01825
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      Highly Sensitive, Printable Nanostructured Conductive Polymer Wireless Sensor for Food Spoilage Detection
      Ma, Zhong; Chen, Ping; Cheng, Wen; Yan, Kun; Pan, Lijia; Shi, Yi; Yu, Guihua
      Nano Letters (2018), 18 (7), 4570-4575CODEN: NALEFD; ISSN:1530-6984. (American Chemical Society)
      Near-field communication (NFC) labeling technol. has been recently used to endow smartphones with nonline-of-sight sensing functions to improve the environment, human health, and quality of life. For applications in detecting food spoilage, the development of a sensor with high enough sensitivity to act as a switch for an NFC tag remains a challenge. In this Letter, we developed a nanostructured conductive polymer-based gas sensor with high sensitivity of ΔR/R0 = 225% toward 5 ppm ammonia NH3 and unprecedented sensitivities of 46% and 17% toward 5 ppm putrescine and cadaverine, resp. The gas sensor plays a crit. role as a sensitive switch in the circuit of the NFC tag and enables a smartphone to readout meat spoilage when the concn. of biogenic amines is over a preset threshold. We envision the broad potential use of such intelligent sensing for food status monitoring applications in daily life, storage and supply chains.
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    22. 22
      Ngo, Y. H.; Brothers, M.; Martin, J. A.; Grigsby, C. C.; Fullerton, K.; Naik, R. R.; Kim, S. S. Chemically Enhanced Polymer-Coated Carbon Nanotube Electronic Gas Sensor for Isopropyl Alcohol Detection. ACS Omega 2018, 3, 6230– 6236,  DOI: 10.1021/acsomega.8b01039
      22
      Chemically Enhanced Polymer-Coated Carbon Nanotube Electronic Gas Sensor for Isopropyl Alcohol Detection
      Ngo, Yen H.; Brothers, Michael; Martin, Jennifer A.; Grigsby, Claude C.; Fullerton, Kathy; Naik, Rajesh R.; Kim, Steve S.
      ACS Omega (2018), 3 (6), 6230-6236CODEN: ACSODF; ISSN:2470-1343. (American Chemical Society)
      Breathing-air quality within com. airline cabins has come under increased scrutiny because of the identification of volatile org. compds. (VOCs) from the engine bleed air used to provide O to cabins. Ideally, a sensor would be placed within the bleed air pipe itself, enabling detection before it permeated through and contaminated the entire cabin. Current gas-phase sensors suffer from issues with selectivity, do not have the appropriate form factor, or are too complex for com. deployment. Here, we chose iso-Pr alc. (IPA), a main component of de-icer spray used in the aerospace community, as a target analyte: IPA exposure has been hypothesized to be a key component of aerotoxic syndrome in pre, during, and postflight. IPAs proposed mechanism of action is that of an anesthetic and central nervous system depressant. Here, we describe IPA sensor development by showing: (1) the integration of a polymer as an IPA capture matrix, (2) the adoption of a redox chem. additives as an IPA oxidizer, and (3) the application of C nanotubes as an electronic sensing conduit. We demonstrate the ability to not only detect IPA at 100-10,000 ppm in unfiltered, lab. air but also discriminate among IPA, isoprene, and acetone, esp. in comparison to a typical photoionization detector. Overall, we show an electronic device that operates at room temp. and responds preferentially to IPA, where the increase in the resistance corresponds directly to the concn. of IPA. Ultimately, this study opens up the pathway to selective electronic sensors that can enable real-time monitoring in a variety of environments for the force health prevention and protection, and the potential through future work to enable low ppm and possibly high ppb selective detection of gas-phase VOCs of interest.
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    23. 23
      Hou, H.; Tingting, X.; Yang, W.; Shengjun, L.; Chu, R.; Zhang, J.; Liu, B. Conductive and Chiral Polymer-Modified Metal–Organic Framework for Enantioselective Adsorption and Sensing. ACS Appl. Mater. Interfaces 2018, 10, 26365– 26371,  DOI: 10.1021/acsami.8b06540
      23
      Conductive and Chiral Polymer-Modified Metal-Organic Framework for Enantioselective Adsorption and Sensing
      Hou, Xudong; Xu, Tingting; Wang, Yang; Liu, Shengjun; Chu, Runrun; Zhang, Junxiang; Liu, Bo
      ACS Applied Materials & Interfaces (2018), 10 (31), 26365-26371CODEN: AAMICK; ISSN:1944-8244. (American Chemical Society)
      The authors reported integration of cond., chirality, and porosity into MIL-101@chiral-PANI composite for synchronous chiral recognition, adsorption, and sensing toward enantiomers. The core-shell structure of MIL-101@chiral-PANI was characterized in detail by FTIR and CD spectroscopy as well as SEM and TEM. Adsorption behaviors of carvone enantiomers over chiral PANI and MIL-101@chiral-PANI are satisfied with pseudo-first-order fitting. In comparison with chiral PANI, MIL-101@c-PANI exhibits a better enantioselectivity and much higher (>5-fold) adsorption amt. over L-carvone than D-carvone. And MIL-101@c-PANI is able to recognize the chirality of carvone via electrochem. sensing, taking advantage of the elec. cond. of chiral PANI. Result demonstrated the feasibility of applying achiral MOF for enantioselective sensing and adsorption via installing chiral and conductive gates. And this chiral polymer modification strategy represents a universal way to entitle achiral MOFs with chiral functions.
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    24. 24
      Reddy, Y. V. M.; Sravani, B.; Fernandes, D. M.; Madhuri, Ch.; Subramanyam Sarma, L.; Madhavi, G. Facile One-Pot Synthesis of Bimetallic Pd-Ag/Reduced Graphene Oxide Nanocomposite as an Electrochemical Sensor for Sensitive Detection of Antihypotensive Drug. Colloids Surf., A 2018, 546, 293– 300,  DOI: 10.1016/j.colsurfa.2018.03.032
      There is no corresponding record for this reference.
    25. 25
      Reddy, Y. V. M.; Bathinapatla, S.; Łuczak, T.; Osinska, M.; Maseed, H.; Ragavendhra, P.; Sarma, L. S.; Srikanth, V. V. S. S.; Madhavi, G. An Ultra-Sensitive Electrochemical Sensor for the Detection of Acetaminophen in the Presence of Etilefrine using Bimetallic Pd–Ag/Reduced Graphene Oxide Nanocomposites. New J. Chem. 2018, 42, 3137– 3146,  DOI: 10.1039/C7NJ04775D
      There is no corresponding record for this reference.
    26. 26
      Reddy, Y. V. M.; Sravani, B.; Agarwal, S.; Guptha, V. K.; Madhavi, G. Electrochemical Sensor for Detection of Uric acid in the Presence of Ascorbic acid and Dopamine Using the Poly (Dpa)/Sio2@Fe3o4 Modified Carbon Paste Electrode. J. Electroanal. Chem. 2018, 820, 168– 75,  DOI: 10.1016/j.jelechem.2018.04.059
      There is no corresponding record for this reference.
    27. 27
      Sağlam, Ş.; Aysem, U. Z.; Erol, E.; Resat, A. Electrochemical Determination of TNT, DNT, RDX, and HMX with Gold Nanoparticles/Poly (Carbazole-Aniline) Film-Modified Glassy Carbon Sensor Electrodes Imprinted for Molecular Recognition of Nitroaromatics and Nitramines. Anal. Chem. 2018, 90, 7364– 7370,  DOI: 10.1021/acs.analchem.8b00715
      There is no corresponding record for this reference.
    28. 28
      Li, L.; Chen, M.; Huang, G.; Yang, N.; Zhang, L.; Wang, H.; Liu, Y.; Wang, W.; Gao, J. A Green Method to Prepare Pd–Ag Nanoparticles Supported on Reduced Graphene Oxide and Their Electrochemical Catalysis of Methanol and Ethanol Oxidation. J. Power Sources 2014, 263, 13– 21,  DOI: 10.1016/j.jpowsour.2014.04.021
      28
      A green method to prepare Pd-Ag nanoparticles supported on reduced graphene oxide and their electrochemical catalysis of methanol and ethanol oxidation
      Li, Lingzhi; Chen, Mingxi; Huang, Guanbo; Yang, Nian; Zhang, Li; Wang, Huan; Liu, Yu; Wang, Wei; Gao, Jianping
      Journal of Power Sources (2014), 263 (), 13-21CODEN: JPSODZ; ISSN:0378-7753. (Elsevier B.V.)
      Bimetallic palladium-silver nanoparticles (NPs) supported on reduced oxide graphene (RGO) with different Pd/Ag ratios (Pd-Ag/RGO) were prepd. by an easy green method which did not use any addnl. reducing agents or a dispersing agent. During the process, simultaneous redox reactions between AgNO3, K2PdCl4, and graphene oxide (GO) led to bimetallic Pd-Ag NPs. The morphol. and compn. of the Pd-Ag/RGO were characterized by transmission electron microscopy, X-ray diffraction, XPS, thermogravimetric anal., and Raman spectroscopy. Cyclic voltammetry and chronoamperometry were used to investigate the electrochem. activities and stabilities of these Pd-Ag/RGO catalysts for the electro-oxidn. of methanol and ethanol in alk. media. Among the different Pd/Ag ratios, the Pd-Ag (1:1)/RGO had the best catalytic activities and stability. So it is a promising catalyst for direct alc. fuel cell applications.
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    29. 29
      Mazloum-Ardakani, M.; Hosseinzadeh, L.; Taleat, Z. Synthesis and Electrocatalytic Effect of Ag@Pt Core–Shell Nanoparticles Supported on Reduced Graphene Oxide for Sensitive and Simple Label-Free Electrochemical Aptasensor. Biosens. Bioelectron. 2015, 74, 30– 36,  DOI: 10.1016/j.bios.2015.05.072
      There is no corresponding record for this reference.
    30. 30
      Sawangphruk, M.; Srimuk, P.; Chio-chan, P.; Krittayavathananon, A.; Luanwuthi, S.; Limtrakul, J. Limtrakul. the High-Performance Supercapacitor of Manganese Oxide/Reduced Graphene Oxide Nanocomposite Coated on Flexible Carbon Fiber Paper. Carbon 2013, 60, 109– 116,  DOI: 10.1016/j.carbon.2013.03.062
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      High-performance supercapacitor of manganese oxide/reduced graphene oxide nanocomposite coated on flexible carbon fiber paper
      Sawangphruk, Montree; Srimuk, Pattarachai; Chiochan, Poramane; Krittayavathananon, Atiweena; Luanwuthi, Santamon; Limtrakul, Jumras
      Carbon (2013), 60 (), 109-116CODEN: CRBNAH; ISSN:0008-6223. (Elsevier Ltd.)
      Although supercapacitors have higher power d. than batteries, they are still limited by low energy d. and low capacity retention. Here the authors report a high-performance supercapacitor electrode of Mn oxide/reduced graphene oxide nanocomposite coated on flexible C fiber paper (MnO2-rGO/CFP). MnO2-rGO nanocomposite was produced using a colloidal mixing of rGO nanosheets and 1.8 ± 0.2 nm MnO2 nanoparticles. MnO2-rGO nanocomposite was coated on CFP using a spray-coating technique. MnO2-rGO/CFP exhibited ultrahigh specific capacitance and stability. The specific capacitance of MnO2-rGO/CFP detd. by a galvanostatic charge-discharge method at 0.1 A g-1 is ∼393 F g-1, which is 1.6-, 2.2-, 2.5-, and 7.4-fold higher than those of MnO2-GO/CFP, MnO2/CFP, rGO/CFP, and GO/CFP, resp. The capacity retention of MnO2-rGO/CFP is over 98.5% of the original capacitance after 2000 cycles. This electrode has comparatively 6%, 11%, 13%, and 18% higher stability than MnO2-GO/CFP, MnO2/CFP, rGO/CFP, and GO/CFP, resp. It is believed that the ultrahigh performance of MnO2-rGO/CFP is possibly due to high cond. of rGO, high active surface area of tiny MnO2, and high porosity between each MnO2-rGO nanosheet coated on porous CFP. An as-fabricated all-solid-state prototype MnO2-rGO/CFP supercapacitor (2 × 14 cm) can spin up a 3 V motor for ∼6 min.
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    31. 31
      Jayakumar, K.; Camarada, M. B.; Venkataraman, D.; Rajendiran, R.; Rengarajan, V.; Huangxian, J.; Mahalingam, M.; Abhishek, R.; Sudipta, R. B.; Yangping, W. Layer-by-Layer-Assembled AuNPs-Decorated First-Generation Poly (amidoamine) Dendrimer with Reduced Graphene Oxide Core as Highly Sensitive Biosensing Platform with Controllable 3D Nanoarchitecture for Rapid Voltammetric Analysis of Ultratrace DNA Hybridization. ACS Appl. Mater. Interfaces 2018, 10, 21541– 21555,  DOI: 10.1021/acsami.8b03236
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      Layer-by-Layer-Assembled AuNPs-Decorated First-Generation Poly(amidoamine) Dendrimer with Reduced Graphene Oxide Core as Highly Sensitive Biosensing Platform with Controllable 3D Nanoarchitecture for Rapid Voltammetric Analysis of Ultratrace DNA Hybridization
      Jayakumar, Kumarasamy; Camarada, Maria Belen; Dharuman, Venkataraman; Rajesh, Rajendiran; Venkatesan, Rengarajan; Ju, Huangxian; Maniraj, Mahalingam; Rai, Abhishek; Barman, Sudipta Roy; wen, Yangping
      ACS Applied Materials & Interfaces (2018), 10 (25), 21541-21555CODEN: AAMICK; ISSN:1944-8244. (American Chemical Society)
      The structure and electrochem. properties of layer-by-layer-assembled gold nanoparticles (AuNPs)-decorated first-generation (G1) poly(amidoamine) dendrimer (PD) with reduced graphene oxide (rGO) core as a highly sensitive and label-free biosensing platform with a controllable three-dimensional (3D) nanoarchitecture for the rapid voltammetric anal. of DNA hybridization at ultratrace levels were characterized. Mercaptopropinoic acid (MPA) was self-assembled onto Au substrate, then GG1PD formed by the covalent functionalization between the amino terminals of G1PD and carboxyl terminals of rGO was covalently linked onto MPA, and finally AuNPs were decorated onto GG1PD by strong physicochem. interaction between AuNPs and -OH of rGO in GG1PD, which was characterized through different techniques and confirmed by computational calcn. This 3D controllable thin-film electrode was optimized and evaluated using [Fe(CN)6]3-/4- as the redox probe and employed to covalently immobilize thiol-functionalized single-stranded DNA as biorecognition element to form the DNA nanobiosensor, which achieved fast, ultrasensitive, and high-selective differential pulse voltammetric anal. of DNA hybridization in a linear range from 1 × 10-6 to 1 × 10-13 g m-1 with a low detection limit of 9.07 × 10-14 g m-1. This work will open a new pathway for the controllable 3D nanoarchitecture of the layer-by-layer-assembled metal nanoparticles-functionalized lower-generation PD with two-dimensional layered nanomaterials as cores that can be employed as ultrasensitive and label-free nanobiodevices for the fast diagnosis of specific genome diseases in the field of biomedicine.
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    32. 32
      Karthik, P.; Vinoth, R.; Zhang, P.; Wonyong, C.; Balaraman, E.; Neppolian, B. π–π Interaction Between Metal–Organic Framework and Reduced Graphene Oxide for Visible-Light Photocatalytic H2 Production. ACS Appl. Energy Mater. 2018, 1, 1913– 1923,  DOI: 10.1021/acsaem.7b00245
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      π-π Interaction Between Metal-Organic Framework and Reduced Graphene Oxide for Visible-Light Photocatalytic H2 Production
      Karthik, Peramaiah; Vinoth, Ramalingam; Zhang, Peng; Choi, Wonyong; Balaraman, Ekambaram; Neppolian, Bernaurdshaw
      ACS Applied Energy Materials (2018), 1 (5), 1913-1923CODEN: AAEMCQ; ISSN:2574-0962. (American Chemical Society)
      Solar water splitting provides a promising path for sustainable hydrogen prodn. and solar energy storage. In recent times, metal-org. frameworks (MOFs) have received considerable attention as promising materials for diverse solar energy conversion applications. However, their photocatalytic performance is poor and rarely explored due to rapid electron-hole recombination. Herein, we have developed a material MOF@rGO that exhibits highly enhanced visible-light photocatalytic activity. A real-time investigation reveals that a strong π-π interaction between MOF and rGO is responsible for efficient sepn. of electron-hole pairs, and thereby enhances the photocatalytic hydrogen prodn. activity. Surprisingly, MOF@rGO showed ∼9.1-fold enhanced photocatalytic hydrogen prodn. activity compared to that of pristine MOF. In addn., it is worth mentioning here that remarkable apparent quantum efficiency (0.66%) is achieved by π-π interaction mediated charge carrier sepn.
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    33. 33
      Srinivasan, V.; Mariadoss, A. J.; Kathiresan, M.; Arunkumar, K. Nanostructured Graphene Oxide Dots: Synthesis, Characterization, Photoinduced Electron Transfer Studies, and Detection of Explosives/Biomolecules. ACS Omega 2018, 3, 9096– 9104,  DOI: 10.1021/acsomega.8b01180
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      Nanostructured Graphene Oxide Dots: Synthesis, Characterization, Photoinduced Electron Transfer Studies, and Detection of Explosives/Biomolecules
      Srinivasan, Venkatesan; Asha Jhonsi, Mariadoss; Kathiresan, Murugavel; Kathiravan, Arunkumar
      ACS Omega (2018), 3 (8), 9096-9104CODEN: ACSODF; ISSN:2470-1343. (American Chemical Society)
      Herein, the authors are reporting the prepn. of graphene oxide dots (GO dots) by fine-tuning the carbonization degree of citric acid. The structure of GO dots was characterized by absorption spectroscopy, FTIR anal., Raman spectroscopy, as well as HR-SEM and TEM analyses. The typical particle size of the GO dots was 42 nm. Fluorescent characteristics of GO dots were analyzed by fluorescence spectroscopy. Once excited at 360 nm, the GO dots were fluorescent at 450-550 nm which was dependent on the excitation wavelength. Further GO dots were effectively used for multifarious applications such as photoinduced electron transfer, detection of explosives and biomols. The emission property of GO dots was competently quenched by viologens, picric acid and bilirubin. The mechanism of quenching by viologens and explosives/biomols. are light induced electron transfer and internal filter effect, resp. Intriguingly, the detection min. of picric acid is in the nano molar level. Towards the commercialization, the economic test strips also were introduced for the identification of picric acid. Also, the GO dots were applied as an efficient luminescent bio-probe for a selective and perceptive finding of bilirubin.
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    34. 34
      Dong, X. C.; Xu, H.; Wang, X. W.; Huang, Y. X.; Chan-Park, M. B.; Zhang, H.; Wang, L. H.; Huang, W.; Chen, P. 3D Graphene–Cobalt Oxide Electrode for High Performance Supercapacitor and Enzymeless Glucose Detection. ACS Nano 2012, 6, 3206– 3213,  DOI: 10.1021/nn300097q
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      3D Graphene-Cobalt Oxide Electrode for High-Performance Supercapacitor and Enzymeless Glucose Detection
      Dong, Xiao-Chen; Xu, Hang; Wang, Xue-Wan; Huang, Yin-Xi; Chan-Park, Mary B.; Zhang, Hua; Wang, Lian-Hui; Huang, Wei; Chen, Peng
      ACS Nano (2012), 6 (4), 3206-3213CODEN: ANCAC3; ISSN:1936-0851. (American Chemical Society)
      Using a simple hydrothermal procedure, cobalt oxide (Co3O4) nanowires were in situ synthesized on three-dimensional (3D) graphene foam grown by chem. vapor deposition. The structure and morphol. of the resulting 3D graphene/Co3O4 composites were characterized by SEM, TEM, x-ray diffraction, and Raman spectroscopy. The 3D graphene/Co3O4 composite was used as the monolithic free-standing electrode for supercapacitor application and for enzymeless electrochem. detection of glucose. The authors demonstrate that it is capable of delivering high specific capacitance of ∼1100 F g-1 at a c.d. of 10 A g-1 with excellent cycling stability, and it can detect glucose with a ultrahigh sensitivity of 3.39 mA mM-1 cm-2 and a remarkable lower detection limit of <25 nM (S/N = 8.5).
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    35. 35
      Yang, Y.; Wang, Z.; Yang, M.; Li, J.; Zheng, F.; Shen, G.; Yu, R. Electrical Detection of Deoxyribonuclic acid Hybridization Based on Carbon-Nanotubes/Nanozirconium Dioxide/Chaitozen-Modified Electrode. Anal. Chim. Acta. 2007, 584, 268– 274,  DOI: 10.1016/j.aca.2006.11.055
      There is no corresponding record for this reference.
    36. 36
      Chen, A.; Zhou, Y.; Ta, N.; Li, Y.; Shen, W. Redox Properties and Catalytic Performance of Ceria–Zirconia Nanorods. Catal. Sci. Technol. 2015, 5, 4184– 4192,  DOI: 10.1039/C5CY00564G
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      Redox properties and catalytic performance of ceria-zirconia nanorods
      Chen, Aling; Zhou, Yan; Ta, Na; Li, Yong; Shen, Wenjie
      Catalysis Science & Technology (2015), 5 (8), 4184-4192CODEN: CSTAGD; ISSN:2044-4753. (Royal Society of Chemistry)
      The redox properties and catalytic performance of Ce1-xZrxO2 (0 ≤ x ≤ 0.2) nanorods, mainly exposing {110} and {100} planes, were comparatively examd. with spherical Ce1-xZrxO2 nanoparticles that predominantly exposed {111} planes. The CeO2 nanorods had a superior redox property and much higher activity towards CO oxidn. than the CeO2 nanoparticles, primarily because of the preferential exposure of the reactive {110} planes. However, this shape effect was weakened considerably in Ce1-xZrxO2 (x = 0.05-0.20) nanomaterials. ZrO2-doping promoted the reducibility of the nanoparticles more significantly than that of the nanorods, involving different rate-detg. steps in the redn. process. The activity for CO oxidn. enhanced with increasing ZrO2 content on the nanoparticles but decreased over the nanorods. These results demonstrate that the shape effect of Ce1-xZrxO2 nanomaterials is assocd. with the amt. of zirconia that is incorporated into the ceria lattice.
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    37. 37
      Kumar, S.; Kumar, S.; Srivastava, S.; Yadav, B. K.; Lee, S. H.; Sharma, J. G.; Doval, D. C.; Malhotra, B. D. Reduced Graphene Oxide Modified Smart Conducting Paper for Cancer Biosensor. Biosens. Bioelectron. 2015, 73, 114– 122,  DOI: 10.1016/j.bios.2015.05.040
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      Reduced graphene oxide modified smart conducting paper for cancer biosensor
      Kumar, Saurabh; Kumar, Suveen; Srivastava, Saurabh; Yadav, Birendra K.; Lee, Seung H.; Sharma, Jai G.; Doval, Dinesh C.; Malhotra, Bansi D.
      Biosensors & Bioelectronics (2015), 73 (), 114-122CODEN: BBIOE4; ISSN:0956-5663. (Elsevier B.V.)
      We report results of the studies relating to the fabrication of a paper based sensor comprising of poly (3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) and reduced graphene oxide (RGO) composite. The effect of various solvents like methanol, ethylene glycol and H2SO4 on the elec. cond. of PEDOT:PSS coated Whatman paper has been investigated. The cond. of this soln. processed conducting paper significantly increases from ∼1.16×10-4 S cm-1 up to ∼3.57×10-2 S cm-1 (∼300 times) on treatment with ethylene glycol. The obsd. significant increase in elec. cond. is due to conformational rearrangement in the polymer and is due to strong non-covalent cooperative interaction between PEDOT and the cellulose mols. Further, incorporation of RGO into the conducting paper results in improved electrochem. performance and signal stability. This paper electrode is a promising alternative over the expensive conventional electrodes (ITO, gold and glassy carbon), that are known to have limited application in smart point-of-care (POC) devices. This low cost, flexible and environment friendly conducting paper based biosensor utilized for cancer biomarker (carcinoembryonic antigen, CEA) detection reveals high sensitivity of 25.8 μA ng-1 mL cm-2 in the physiol. range, 1-10 ng mL-1.
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    38. 38
      Zhao, N.; Pan, D.; Nie, W.; Ji, X. Two-Phase Synthesis of Shape-Controlled Colloidal Zirconia Nanocrystals and their Characterization. J. Am. Chem. Soc. 2006, 128, 10118– 10124,  DOI: 10.1021/ja0612145
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      Two-Phase Synthesis of Shape-Controlled Colloidal Zirconia Nanocrystals and Their Characterization
      Zhao, Nana; Pan, Daocheng; Nie, Wei; Ji, Xiangling
      Journal of the American Chemical Society (2006), 128 (31), 10118-10124CODEN: JACSAT; ISSN:0002-7863. (American Chemical Society)
      We have developed a two-phase approach for the synthesis of shape-controlled colloidal zirconia nanocrystals, including spherical-, teardrop-, rod-, and rice grain-shaped particles. We found that the key factors for controlling the shape were the reaction time, the nature of the capping agent, and the monomer concn. We have analyzed the morphologies, crystallinity, optical properties, and structural features of the as-prepd. ZrO2 nanoparticles by using TEM, high-resoln. TEM, X-ray powder diffraction, and UV-vis absorption and fluorescence spectroscopy. The possible nucleation and growth process is also discussed.
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    39. 39
      Vilian, A. T. E.; Chen, S. M.; Huang, L. H. Simultaneous Determination of Catechol and Hydroquinone Using a Pt/ZrO2-rGO/GCE Composite Modified Glassy Carbon Electrode. Electrochim. Acta 2014, 125, 503– 509,  DOI: 10.1016/j.electacta.2014.01.092
      There is no corresponding record for this reference.
    40. 40
      Kumar, S.; Sharma, J. G.; Maji, S.; Malhotra, B. D. Nanostructured Zirconia Decorated Reduced Graphene Oxide Based Efficient Biosensing Platform for Non-Invasive Oral Cancer Detection. Biosens. Bioelectron. 2016, 78, 497– 504,  DOI: 10.1016/j.bios.2015.11.084
      40
      Nanostructured zirconia decorated reduced graphene oxide based efficient biosensing platform for non-invasive oral cancer detection
      Kumar, Suveen; Sharma, Jai Gopal; Maji, Sagar; Malhotra, Bansi Dhar
      Biosensors & Bioelectronics (2016), 78 (), 497-504CODEN: BBIOE4; ISSN:0956-5663. (Elsevier B.V.)
      We report results of the studies relating to fabrication of a non-invasive, label-free and an efficient biosensing platform for detection of the oral cancer biomarker (CYFRA-21-1). One step hydrothermal process was used for uniform decoration of nanostructured zirconia (av. particle size 13 nm) on reduced graphene oxide (ZrO2-RGO) to avoid coagulation of the zirconia nanoparticles and to obtain enhanced electrochem. performance of ZrO2-RGO nanocomposite based biosensor. Further, ZrO2-RGO has been functionalized using 3-aminopropyl triethoxy saline (APTES) and electrophoretically deposited on the indium tin oxide coated glass substrate at a low DC potential. The APTES/ZrO2-RGO/ITO electrode exhibits improved heterogeneous electron transfer (more than two times) with respect to that of the APTES/ZrO2/ITO electrode indicating faster electron transfer kinetics. The -NH2 contg. APTES/ZrO2-RGO/ITO platform is further biofunctionalized with anti-CYFRA-21-1. The structural and morphol. investigations of the ZrO2-RGO based biosensing platform have been accomplished using X-ray diffraction (XRD), electrochem., transmission electron microscopy (TEM), at. force microscopy (AFM) and Fourier transform IR spectroscopy (FT-IR) studies. The obsd. results have been validated via enzyme linked immunosorbent assay (ELISA).
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    41. 41
      Gupta, P. K.; Sachchidanand, T.; Zishan, H. K.; Pratima, S. R. Amino Acid Functionalized ZrO2 Nanoparticles Decorated Reduced Graphene Oxide Based Immunosensor. J. Mater. Chem. B 2017, 5, 2019– 2033,  DOI: 10.1039/C6TB02594C
      41
      Amino acid functionalized ZrO2 nanoparticles decorated reduced graphene oxide based immunosensor
      Gupta, Pramod K.; Tiwari, Sachchidanand; Khan, Zishan H.; Solanki, Pratima R.
      Journal of Materials Chemistry B: Materials for Biology and Medicine (2017), 5 (10), 2019-2033CODEN: JMCBDV; ISSN:2050-7518. (Royal Society of Chemistry)
      Here, a study is reported on a simple, one-step method for the synthesis of a zirconium dioxide-reduced graphene oxide (ZrO2-RGO) nanocomposite involving the redn. of graphene oxide (GO) and in situ growth of ZrO2 NPs using hydrazine as a reducer. This ZrO2-RGO nanocomposite was functionalized with L-methionine (Meth) for immunosensor application. Morphol. and structural studies clearly indicated that ZrO2 NPs (6 nm) were decorated onto the RGO sheets, and enhanced exfoliation, thereby preventing the restacking of the RGO sheets. RGO improved the electrochem. properties of the ZrO2-RGO nanocomposite and minimized the aggregation of ZrO2 NPs. FTIR studies confirmed the functionalization of the ZrO2-RGO nanocomposite with Meth and biomols. (anti-OTA and BSA). The Meth functionalized ZrO2-RGO nanocomposite had enhanced biocompatibility and wettability as confirmed by MTT assay and contact angle studies, resp. Furthermore, a uniform thin film of the Meth/ZrO2-RGO nanocomposite was electrophoretically deposited onto an indium tin oxide (ITO) coated glass substrate and utilized for covalent immobilization of monoclonal antibodies specific to ochratoxin A (anti-OTA) for the detection of ochratoxin A (OTA). The fabricated BSA/anti-OTA/Meth/ZrO2-RGO/ITO immunoelectrode exhibited a wide linear detection range of 1-20 ng mL-1 with a sensitivity of 4.8 μA ng-1 mL cm-2 and a detection limit of 0.079 ng mL-1 for OTA detection.
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    42. 42
      Raj, M.; Gupta, P.; Goyal, R. N.; Shim, Y. B. Graphene/Conducting Polymer Nano-Composite Loaded Screen-Printed Carbon Sensor for Simultaneous Determination of Dopamine and 5-Hydroxytryptamine. Sens. Actuators, B 2017, 239, 993– 1002,  DOI: 10.1016/j.snb.2016.08.083
      42
      Graphene/conducting polymer nano-composite loaded screen printed carbon sensor for simultaneous determination of dopamine and 5-hydroxytryptamine
      Raj, Mamta; Gupta, Pankaj; Goyal, Rajendra N.; Shim, Yoon-Bo
      Sensors and Actuators, B: Chemical (2017), 239 (), 993-1002CODEN: SABCEB; ISSN:0925-4005. (Elsevier B.V.)
      A novel and sensitive electrochem. method has been developed for the simultaneous detn. of dopamine (DA) and 5-hydroxytryptamine (5-HT) using graphene (GR) and poly 4-amino-3-hydroxy-1-naphthalenesulfonic acid modified screen printed carbon sensor. The electrochem. measurements were studied using cyclic voltammetry, square wave voltammetry, whereas the surface morphol. of the modified sensor was characterized by Electrochem. Impedance Spectroscopy and Field Emission SEM. The fabricated sensor facilitated the anal. of DA and 5-HT in the concn. range 0.05-100μM and 0.05-150μM with the detection limit of 2 nM and 3 nM resp. The fabricated sensor has been explored for the detn. of 5-HT in the plasma samples and the selectivity of the proposed work has been proved by the anal. of DA and 5-HT in the presence of common metabolites present in biol. fluids. The anal. applicability of the fabricated sensor has also been successfully demonstrated for the simultaneous detection of DA and 5-HT in the pharmacol. formulations, human urine and blood samples.
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    43. 43
      Mahmoud, B. G.; Khairy, M.; Rashwan, A. F.; Banks, C. E. Simultaneous Voltammetric Determination of Acetaminophen and Isoniazid (Hepatotoxicity-Related Drugs) Utilizing Bismuth Oxide Nanorod Modified Screen-Printed Electrochemical Sensing Platforms. Anal. Chem. 2017, 89, 2170– 2178,  DOI: 10.1021/acs.analchem.6b05130
      43
      Simultaneous Voltammetric Determination of Acetaminophen and Isoniazid (Hepatotoxicity-Related Drugs) Utilizing Bismuth Oxide Nanorod Modified Screen-Printed Electrochemical Sensing Platforms
      Mahmoud, Bahaa G.; Khairy, Mohamed; Rashwan, Farouk A.; Banks, Craig E.
      Analytical Chemistry (Washington, DC, United States) (2017), 89 (3), 2170-2178CODEN: ANCHAM; ISSN:0003-2700. (American Chemical Society)
      To overcome the recent outbreaks of hepatotoxicity related-drugs, a new anal. tool for the continuously detn. of these drugs in human fluids is required. Electrochem. based anal. methods offer an effective, rapid and simple tool for on-site detn. of various org. and inorg. species. However, the design of a sensitive, selective, stable and reproducible sensor is still a major challenge. In the present manuscript, a facile, one-pot hydrothermal synthesis of bismuth oxide (Bi2O2.33) nanostructures (nanorods) was developed. These BiO nanorods were cast onto mass disposable graphite screen-printed electrodes (BiO-SPEs) allowing the ultrasensitive detn. of acetaminophen (APAP) in the presence of it's the common interference isoniazid (INH) which are both found in drug samples. The simultaneous electroanal. sensing using BiO-SPEs exhibited strong electrocatalytic activity towards the sensing of APAP and INH with an enhanced anal. signal (voltammetric peak) over that achievable at unmodified (bare) SPEs. The electroanal. sensing of APAP and INH are possible with accessible linear ranges from 0.5 to 1250 μM and 5 to 1760 μM with limits of detection (3σ) of 30 nM and 1.85 μM, resp. The stability, reproducibility and repeatability of BiO-SPE were also investigated. The BiO-SPEs were evaluated towards the sensing of APAP and INH in human serum, urine, saliva and tablet samples. The results presented in this paper demonstrate that BiO-SPEs sensing platforms provide a potential candidate for the accurate detn. of APAP and INH within human fluids and pharmaceutical formulations.
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    44. 44
      Laviron, E. General Expression of the Linear Potential Sweep Voltammogram in the Case of Diffusion less Electrochemical Systems. J. Electroanal. Chem. Interfacial Electrochem. 1979, 101, 19– 28,  DOI: 10.1016/S0022-0728(79)80075-3
      44
      General expression of the linear potential sweep voltammogram in the case of diffusionless electrochemical systems
      Laviron, E.
      Journal of Electroanalytical Chemistry and Interfacial Electrochemistry (1979), 101 (1), 19-28CODEN: JEIEBC; ISSN:0022-0728.
      The equation of a linear potential sweep voltammogram is derived for any degree of reversibility of the electrochem. reaction for the following methods:surface voltammetry when both the oxidized and the reduced froms are strongly adsorbed, and a Langmuir isotherm is obeyed, thin-layer voltammetry, and linear potential sweep coulometry. The results are expressed in a math. form valid for the 3 cases. The transfer coeff. and the rate const. of the electrochem. reaction can be deduced from an exptl. study of the variations of the peak potentials as a function of the sweep rate.
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    45. 45
      Fan, Y.; Liu, J. H.; Lu, H. T.; Zhang, Q. Electrochemical Behavior and Voltammetric Determination of Paracetamol on Nafion/TiO2–Graphene Modified Glassy Carbon Electrode. Colloids Surf., B 2011, 85, 289– 292,  DOI: 10.1016/j.colsurfb.2011.02.041
      45
      Electrochemical behavior and voltammetric determination of paracetamol on Nafion/TiO2-graphene modified glassy carbon electrode
      Fan, Yang; Liu, Jin-Hang; Lu, Hai-Ting; Zhang, Qin
      Colloids and Surfaces, B: Biointerfaces (2011), 85 (2), 289-292CODEN: CSBBEQ; ISSN:0927-7765. (Elsevier B.V.)
      The TiO2-graphene (TiO2-GR) nanocomposite for paracetamol electrochem. sensing is described. The electrochem. behavior of paracetamol at the Nafion/TiO2-GR composite film modified glassy carbon electrode (GCE) was investigated by cyclic voltammetry. The results showed that the incorporation of TiO2 nanoparticles with graphene significantly enhanced the electrochem. reactivity and voltammetric response of paracetamol. In addn., Nafion acts as an effective solubilizing agent and antifouling coating in the fabrication of the modified electrode. This electrochem. sensor exhibits excellent anal. performance for paracetamol detection at physiol. pH with detection limit of 2.1 × 10-7 M, linear range of 1-100 μM and reproducibility of 3.6% relative std. deviation.
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    46. 46
      Xu, C. X.; Huang, K. J.; Fan, Y.; Wu, Z. W.; Li, J. Electrochemical Determination of Acetaminophen Based on TiO2–Graphene/Poly (Methyl Red) Composite Film Modified Electrode. J. Mol. Liq. 2012, 165, 32– 37,  DOI: 10.1016/j.molliq.2011.10.006
      46
      Electrochemical determination of acetaminophen based on TiO2-graphene/poly(methyl red) composite film modified electrode
      Xu, Chun-Xuan; Huang, Ke-Jing; Fan, Yang; Wu, Zhi-Wei; Li, Jing
      Journal of Molecular Liquids (2012), 165 (), 32-37CODEN: JMLIDT; ISSN:0167-7322. (Elsevier B.V.)
      TiO2-graphene/poly(methyl red) composite film modified glassy carbon electrode (PMR/TiO2-GR/GCE) was first employed for the sensitive detn. of acetaminophen (AC). The electrochem. behavior of AC was investigated by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). The studies revealed that the oxidn. of AC was facilitated at PMR/TiO2-GR/GCE. In 0.1 M phosphate buffer (pH 7.0). The peak current for AC was found to vary linearly with its concn. in the range of 2.5 × 10-7 to 5 × 10-5 M with detection limit of 2.5 × 10-8 (S/N = 3). The modified electrode showed several advantages, such as simple prepn. procedure, high sensitivity, low detection limit, and good reproducibility. The proposed method was employed for the detn. of AC in com. pharmaceutical samples.
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