ACS Publications. Most Trusted. Most Cited. Most Read
Modular Design of Redox-Responsive Stabilizers for Nanocrystals

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Nano 2013, 7, 9, 8243-8250
    Article

    Modular Design of Redox-Responsive Stabilizers for Nanocrystals
    Click to copy article linkArticle link copied!

    View Author Information
    Institute of Pharmaceutical Sciences, Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology Zurich (ETH Zürich), Wolfgang-Pauli-Straße 10, 8093 Zurich, Switzerland
    *Address correspondence to [email protected]
    Other Access OptionsSupporting Information (1)

    ACS Nano

    Cite this: ACS Nano 2013, 7, 9, 8243–8250
    Click to copy citationCitation copied!
    https://doi.org/10.1021/nn4037317
    Published August 22, 2013
    Copyright © 2013 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Many potent drugs are difficult to administer intravenously due to poor aqueous solubility. A common approach for addressing this issue is to process them into colloidal dispersions known as “nanocrystals” (NCs). However, NCs possess high-energy surfaces that must be stabilized with surfactants to prevent aggregation. An optimal surfactant should have high affinity for the nanocrystal’s surface to stabilize it, but may also include a trigger mechanism that could offer the possibility of altering size distribution and uptake of the NC. This study presents a modular and systematic strategy for optimizing the affinity of polymeric stabilizers for drug nanocrystals both before and after oxidation (i.e., the selected trigger), thus allowing for the optimal responsiveness for a given application to be identified. A library of 10 redox-responsive polymer stabilizers was prepared by postpolymerization modification, using the thiol–yne reaction, of two parent block copolymers. The stabilizing potential of these polymers for paclitaxel NCs is presented as well as the influence of oxidation on size and dissolution following exposure to reactive oxygen species (ROS), which are strongly associated with chronic inflammation and cancer. Owing to the versatility of postpolymerization modification, this contribution provides general tools for preparing triggered-sheddable stabilizing coatings for nanoparticles.

    Copyright © 2013 American Chemical Society

    Subjects

    what are subjects

    Keywords

    what are keywords

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Supporting SEC chromatograms, 1H NMR and correlation spectra, MALDI TOF MS and FTIR spectra, additional size stability and dissolution figures. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 40 publications.

    1. Murtada A. Oshi, Juho Lee, Muhammad Naeem, Nurhasni Hasan, Jihyun Kim, Hak Jin Kim, Eun Hee Lee, Yunjin Jung, Jin-Wook Yoo. Curcumin Nanocrystal/pH-Responsive Polyelectrolyte Multilayer Core–Shell Nanoparticles for Inflammation-Targeted Alleviation of Ulcerative Colitis. Biomacromolecules 2020, 21 (9) , 3571-3581. https://doi.org/10.1021/acs.biomac.0c00589
    2. Feiyang Deng, Hua Zhang, Xing Wang, Yuan Zhang, Hongxiang Hu, Siyang Song, Wenbing Dai, Bing He, Ying Zheng, Xueqing Wang, and Qiang Zhang . Transmembrane Pathways and Mechanisms of Rod-like Paclitaxel Nanocrystals through MDCK Polarized Monolayer. ACS Applied Materials & Interfaces 2017, 9 (7) , 5803-5816. https://doi.org/10.1021/acsami.6b15151
    3. Weiwei Kong, Shuang Guo, Shaoqi Wu, Xuefeng Liu, and Yongmin Zhang . Redox-Controllable Interfacial Properties of Zwitterionic Surfactant Featuring Selenium Atoms. Langmuir 2016, 32 (38) , 9846-9853. https://doi.org/10.1021/acs.langmuir.6b02616
    4. Eda Gungor and Andrea M. Armani . Photocleavage of Covalently Immobilized Amphiphilic Block Copolymer: From Bilayer to Monolayer. Macromolecules 2016, 49 (16) , 5773-5781. https://doi.org/10.1021/acs.macromol.6b01609
    5. Kathrin Fuhrmann, Marc A. Gauthier, and Jean-Christophe Leroux . Targeting of Injectable Drug Nanocrystals. Molecular Pharmaceutics 2014, 11 (6) , 1762-1771. https://doi.org/10.1021/mp5001247
    6. Chenglin Liang, Ge Zhang, Linlin Guo, Xinyi Ding, Heng Yang, Hongling Zhang, Zhenzhong Zhang, Lin Hou. Spatiotemporal transformable nano-assembly for on-demand drug delivery to enhance anti-tumor immunotherapy. Asian Journal of Pharmaceutical Sciences 2024, 19 (1) , 100888. https://doi.org/10.1016/j.ajps.2024.100888
    7. Tao Sun, Chufeng Li, Xuwen Li, Haolin Song, Boyu Su, Haoyu You, Tongyu Zhang, Chen Jiang. Pharmaceutical Nanotechnology. 2023, 179-283. https://doi.org/10.1007/978-981-16-8984-0_10
    8. Dipak Kumar Gupta, Asad Ali, Abdul Ahad, Ayesha Waheed, Mohd. Aqil, Fahad I. Al-Jenoobi, Abdullah M. Al-Mohizea. Functionalized Nanocrystals and Theranostic Applications. 2023, 331-359. https://doi.org/10.1007/978-981-99-0538-6_14
    9. Thashree Marimuthu, Lisa C. du Toit, Yahya E. Choonara. Nanocrystals as a versatile platform for theranostic applications. 2023, 209-239. https://doi.org/10.1016/B978-0-323-85785-7.00021-8
    10. Paramita Saha, Himanshu Kathuria, Murali Monohar Pandey. Nose-to-brain delivery of rotigotine redispersible nanosuspension: In vitro and in vivo characterization. Journal of Drug Delivery Science and Technology 2023, 79 , 104049. https://doi.org/10.1016/j.jddst.2022.104049
    11. Huamin Liang, Fengming Zou, Liyi Fu, Qingwang Liu, Beilei Wang, Xiaofei Liang, Jing Liu, Qingsong Liu. PEG-Bottlebrush Stabilizer-Based Worm-like Nanocrystal Micelles with Long-Circulating and Controlled Release for Delivery of a BCR-ABL Inhibitor against Chronic Myeloid Leukemia (CML). Pharmaceutics 2022, 14 (8) , 1662. https://doi.org/10.3390/pharmaceutics14081662
    12. Tao Sun, Chufeng Li, Xuwen Li, Haolin Song, Boyu Su, Haoyu You, Tongyu Zhang, Chen Jiang. Pharmaceutical Nanotechnology. 2022, 1-106. https://doi.org/10.1007/978-981-13-9374-7_10-1
    13. Shashi Kiran Misra, Kamla Pathak. Drug nanocrystals as drug delivery systems. 2022, 153-178. https://doi.org/10.1016/B978-0-12-824024-3.00026-9
    14. Fengmei Lv, Jun Wang, Haini Chen, Li Sui, Linglin Feng, Zhepeng Liu, Yu Liu, Gang Wei, Weiyue Lu. Enhanced mucosal penetration and efficient inhibition efficacy against cervical cancer of PEGylated docetaxel nanocrystals by TAT modification. Journal of Controlled Release 2021, 336 , 572-582. https://doi.org/10.1016/j.jconrel.2021.07.008
    15. Mike Geven, Richard d'Arcy, Zulfiye Yesim Turhan, Farah El-Mohtadi, Aws Alshamsan, Nicola Tirelli. Sulfur-based oxidation-responsive polymers. Chemistry, (chemically selective) responsiveness and biomedical applications. European Polymer Journal 2021, 149 , 110387. https://doi.org/10.1016/j.eurpolymj.2021.110387
    16. Roni Sverdlov Arzi, Asaf Kay, Yulia Raychman, Alejandro Sosnik. Excipient-Free Pure Drug Nanoparticles Fabricated by Microfluidic Hydrodynamic Focusing. Pharmaceutics 2021, 13 (4) , 529. https://doi.org/10.3390/pharmaceutics13040529
    17. Cristian Vergallo, Muhammad Nadeem Hafeez, Dalila Iannotta, Hélder A. Santos, Nicola D’Avanzo, Luciana Dini, Felisa Cilurzo, Massimo Fresta, Luisa Di Marzio, Celia Christian. Conventional Nanosized Drug Delivery Systems for Cancer Applications. 2021, 3-27. https://doi.org/10.1007/978-3-030-58174-9_1
    18. Haotian Shi, Teng Qiu, H. Daniel Ou-Yang, Huangbing Xu, Qingchuan Lu, Ying Zheng, Kexin Liu, Lifan He, Longhai Guo, Xiaoyu Li. ABA-type triblock copolymer micellar system with lower critical solution temperature-type sol-gel transition. Journal of Colloid and Interface Science 2019, 545 , 220-230. https://doi.org/10.1016/j.jcis.2019.03.039
    19. Zhi-gang Huang, Feng-mei Lv, Jun Wang, Shui-juan Cao, Zhe-peng Liu, Yu Liu, Wei-yue Lu. RGD-modified PEGylated paclitaxel nanocrystals with enhanced stability and tumor-targeting capability. International Journal of Pharmaceutics 2019, 556 , 217-225. https://doi.org/10.1016/j.ijpharm.2018.12.023
    20. Farah El‐Mohtadi, Richard d'Arcy, Nicola Tirelli. Oxidation‐Responsive Materials: Biological Rationale, State of the Art, Multiple Responsiveness, and Open Issues. Macromolecular Rapid Communications 2019, 40 (1) https://doi.org/10.1002/marc.201800699
    21. Chien-Kai Wang, Hsiao-Chien Chen, Sheng-Uei Fang, Chia-Wen Ho, Cheng-Jeng Tai, Chih-Ping Yang, Yu-Chuan Liu. Innovatively Therapeutic Strategy on Lung Cancer by Daily Drinking Antioxidative Plasmon-Induced Activated Water. Scientific Reports 2018, 8 (1) https://doi.org/10.1038/s41598-018-24752-x
    22. Roni Sverdlov Arzi, Alejandro Sosnik. Electrohydrodynamic atomization and spray-drying for the production of pure drug nanocrystals and co-crystals. Advanced Drug Delivery Reviews 2018, 131 , 79-100. https://doi.org/10.1016/j.addr.2018.07.012
    23. Xiangliang Lv, Lian Liu, Xuefeng Liu, Zan Ge, Kai Zhong. Reversibly Redox‐Switchable Anionic Surfactant Contains Two Selenium Atoms. Journal of Surfactants and Detergents 2018, 21 (3) , 295-301. https://doi.org/10.1002/jsde.12026
    24. Imran Shair Mohammad, Wei He, Lifang Yin. A Smart Paclitaxel-Disulfiram Nanococrystals for Efficient MDR Reversal and Enhanced Apoptosis. Pharmaceutical Research 2018, 35 (4) https://doi.org/10.1007/s11095-018-2370-0
    25. Leena Peltonen, Jouni Hirvonen. Drug nanocrystals – Versatile option for formulation of poorly soluble materials. International Journal of Pharmaceutics 2018, 537 (1-2) , 73-83. https://doi.org/10.1016/j.ijpharm.2017.12.005
    26. Ana R. Fernandes, João Dias-Ferreira, Classius Ferreira-da-Silva, Patrícia Severino, Carlos Martins-Gomes, Amélia M. Silva, Eliana B. Souto. Drug nanocrystals. 2018, 239-253. https://doi.org/10.1016/B978-0-12-813741-3.00011-X
    27. Yike Xie, Baokui Shi, Fei Xia, Jianping Qi, Xiaochun Dong, Weili Zhao, Tonglei Li, Wei Wu, Yi Lu. Epithelia transmembrane transport of orally administered ultrafine drug particles evidenced by environment sensitive fluorophores in cellular and animal studies. Journal of Controlled Release 2018, 270 , 65-75. https://doi.org/10.1016/j.jconrel.2017.11.046
    28. Bingkun Yan, Yan Zhang, Chao Wei, Yue Xu. Facile synthesis of ROS-responsive biodegradable main chain poly(carbonate-thioether) copolymers. Polymer Chemistry 2018, 9 (7) , 904-911. https://doi.org/10.1039/C7PY01908D
    29. Li Yu, Mei Zhang, Fu-Sheng Du, Zi-Chen Li. ROS-responsive poly(ε-caprolactone) with pendent thioether and selenide motifs. Polymer Chemistry 2018, 9 (27) , 3762-3773. https://doi.org/10.1039/C8PY00620B
    30. Yi Lu, Jianping Qi, Xiaochun Dong, Weili Zhao, Wei Wu. The in vivo fate of nanocrystals. Drug Discovery Today 2017, 22 (4) , 744-750. https://doi.org/10.1016/j.drudis.2017.01.003
    31. Honglei Zhan, Tina Jagtiani, Jun F. Liang. Enhanced anticancer activity of drug nanoparticles formulated with β-cyclodextrin. Anti-Cancer Drugs 2017, 28 (3) , 271-280. https://doi.org/10.1097/CAD.0000000000000458
    32. Ann‐Christin Bijlard, Sarah Wald, Daniel Crespy, Andreas Taden, Frederik R. Wurm, Katharina Landfester. Functional Colloidal Stabilization. Advanced Materials Interfaces 2017, 4 (1) https://doi.org/10.1002/admi.201600443
    33. Anna Polomska, Marc A. Gauthier, Jean‐Christophe Leroux. In Vitro and In Vivo Evaluation of PEGylated Layer‐by‐Layer Polyelectrolyte‐Coated Paclitaxel Nanocrystals. Small 2017, 13 (2) https://doi.org/10.1002/smll.201602066
    34. Michael F. Cunningham, Philip G. Jessop, Ali Darabi. Stimuli-Responsive Latexes Stabilized by Carbon Dioxide Switchable Groups. 2017, 143-159. https://doi.org/10.1007/12_2017_6
    35. Wujin Sun, Quanyin Hu, Wenyan Ji, Grace Wright, Zhen Gu. Leveraging Physiology for Precision Drug Delivery. Physiological Reviews 2017, 97 (1) , 189-225. https://doi.org/10.1152/physrev.00015.2016
    36. Yi Lu, Ye Li, Wei Wu. Injected nanocrystals for targeted drug delivery. Acta Pharmaceutica Sinica B 2016, 6 (2) , 106-113. https://doi.org/10.1016/j.apsb.2015.11.005
    37. Junjie Li, Wendong Ke, Lei Wang, Mingming Huang, Wei Yin, Ping Zhang, Qixian Chen, Zhishen Ge. Self-sufficing H2O2-responsive nanocarriers through tumor-specific H2O2 production for synergistic oxidation-chemotherapy. Journal of Controlled Release 2016, 225 , 64-74. https://doi.org/10.1016/j.jconrel.2016.01.029
    38. Ali Darabi, Philip G. Jessop, Michael F. Cunningham. CO 2 -responsive polymeric materials: synthesis, self-assembly, and functional applications. Chemical Society Reviews 2016, 45 (15) , 4391-4436. https://doi.org/10.1039/C5CS00873E
    39. Wan-Xia Wu, Xian-Ling Yang, Bei-Yu Liu, Qing-Feng Deng, Miao-Miao Xun, Na Wang, Xiao-Qi Yu. Lipase-catalyzed synthesis of oxidation-responsive poly(ethylene glycol)-b-poly(β-thioether ester) amphiphilic block copolymers. RSC Advances 2016, 6 (14) , 11870-11879. https://doi.org/10.1039/C5RA21779B
    40. Hua Zhang, Hongxiang Hu, Haoran Zhang, Wenbing Dai, Xinglin Wang, Xueqing Wang, Qiang Zhang. Effects of PEGylated paclitaxel nanocrystals on breast cancer and its lung metastasis. Nanoscale 2015, 7 (24) , 10790-10800. https://doi.org/10.1039/C4NR07450E
    Download PDF
    Go to ACS Nano
    Get e-Alerts
    Get e-Alerts

    ACS Nano

    Cite this: ACS Nano 2013, 7, 9, 8243–8250
    Click to copy citationCitation copied!
    https://doi.org/10.1021/nn4037317
    Published August 22, 2013
    Copyright © 2013 American Chemical Society
    Request reuse permissions

    Article Views

    1416

    Altmetric

    -

    Citations

    40
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.