Enzyme Sensitive Synthetic Polymer Micelles Based on the Azobenzene Motif
Abstract
In this study, we investigate the potential of an artificial structural motif, azobenzene, in the preparation of enzyme sensitive polymeric nanostructures. For this purpose, an azobenzene linkage is established at the copolymer junction of an amphiphilic diblock copolymer. This polymer assembles into a micellar structure in water. Treatment with the enzyme azoreductase, in the presence of coenzyme NADPH, results in the cleavage of the azo-based copolymer junction and disruption of the micellar assembly. These results suggest that azobenezene is a useful non-natural structural motif for the preparation of enzyme responsive polymer nanoparticles. Due to the presence of azoreductase in the human intestine, such nanomaterials are anticipated to find applicability in the arena of colon-specific delivery systems.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Hyaluronidase, γ-Glutamyltranspeptidase, prostate-specific antigen, Trysin, β-galactosidase, Azoreductase, etc. are also used in enzyme-stimulated response smart nano-delivery systems.
“In addition, hyaluronidase, γ-Glutamyltranspeptidase, prostate-specific antigen, Trysin, β-galactosidase, Azoreductase, etc. are also used in enzyme-stimulated response smart nano-delivery systems.157–162”
From Smart nanoparticles for cancer therapy (2023) · cites this paper as [162]
Cites
Atom Transfer Radical Polymerization
Matyjaszewski, K. A., & Xia, J. (2001) · Chemical Reviews · doi:10.1021/cr940534g · Cited by 7,646 · see citing works
Wang, J.-S., & Matyjaszewski, K. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00125a035 · Cited by 4,622 · see citing works
N-Heterocyclic Carbenes: A New Concept in Organometallic Catalysis
Herrmann, W. A. (2002) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20020415)41:8 · Cited by 3,764 · see citing works
Micellar Nanocarriers: Pharmaceutical Perspectives
Torchilin, V. P. (2006) · Pharmaceutical Research · doi:10.1007/s11095-006-9132-0 · Cited by 1,910 · see citing works
Matyjaszewski, K. A., Patten, T. E., & Xia, J. (1997) · Journal of the American Chemical Society · doi:10.1021/ja963361g · Cited by 886 · see citing works
Polymers with Very Low Polydispersities from Atom Transfer Radical Polymerization
Patten, T. E., Xia, J., Abernathy, T., & Matyjaszewski, K. A. (1996) · Science · doi:10.1126/science.272.5263.866 · Cited by 864 · see citing works
Multi-Stimuli Sensitive Amphiphilic Block Copolymer Assemblies
Klaikherd, A., Nagamani, C., & Thayumanavan, S. (2009) · Journal of the American Chemical Society · doi:10.1021/ja809475a · Cited by 594 · see citing works
Stimuli-Responsive Supramolecular Assemblies of Linear-Dendritic Copolymers
Gillies, E. R., Jonsson, T. B., & Fréchet, J. M. J. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0463738 · Cited by 549 · see citing works
Kim, S., Shi, Y., Kim, J. Y., Park, K., & Cheng, J. (2009) · Expert Opinion on Drug Delivery · doi:10.1517/17425240903380446 · Cited by 549 · see citing works
Voltage-Responsive Vesicles Based on Orthogonal Assembly of Two Homopolymers
Yan, Q., Yuan, J., Cai, Z., Xin, Y., Kang, Y., & Yin, Y. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1027502 · Cited by 511 · see citing works
Design and development of polymeric micelles with cleavable links for intracellular drug delivery
Wei, H., Zhuo, R., & Zhang, X. (2012) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2012.07.002 · Cited by 475 · see citing works
A New Approach to the Oral Administration of Insulin and Other Peptide Drugs
Saffran, M., Kumar, G. S., Savariar, C. M., Burnham, J. C., Williams, F. E., & Neckers, D. C. (1986) · Science · doi:10.1126/science.3526553 · Cited by 469 · see citing works
A New Design for Light-Breakable Polymer Micelles
Jiang, J., Tong, X., & Zhao, Y. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0521019 · Cited by 460 · see citing works
Light‐Induced Reversible Formation of Polymeric Micelles
Lee, H., Wu, W., Oh, J. K., Mueller, L., Sherwood, G. A., Peteanu, L. A., Kowalewski, T., & Matyjaszewski, K. A. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200604278 · Cited by 400 · see citing works
Synthetic Micelle Sensitive to IR Light via a Two-Photon Process
Goodwin, A. P., Mynar, J. L., Ma, Y., Fleming, G. R., & Fréchet, J. M. J. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0523035 · Cited by 352 · see citing works
Enzyme responsive materials: design strategies and future developments
Zelzer, M., Todd, S. J., Hirst, A. R., McDonald, T. O., & Ulijn, R. V. (2012) · Biomaterials Science · doi:10.1039/c2bm00041e · Cited by 306 · see citing works
A new approach towards acid sensitive copolymer micelles for drug delivery
Gillies, E. R., & Fréchet, J. M. J. (2003) · Chemical Communications · doi:10.1039/b304251k · Cited by 252 · see citing works
Chen, H., Hopper, S. L., & Cerniglia, C. E. (2005) · Microbiology · doi:10.1099/mic.0.27805-0 · Cited by 235 · see citing works
An Enzyme‐Responsive Polymeric Superamphiphile
Wang, C., Chen, Q., Wang, Z., & Zhang, X. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201004253 · Cited by 209 · see citing works
Enzyme-Triggered Disassembly of Dendrimer-Based Amphiphilic Nanocontainers
Azagarsamy, M. A., Sokkalingam, P., & Thayumanavan, S. (2009) · Journal of the American Chemical Society · doi:10.1021/ja906162u · Cited by 201 · see citing works
Polymeric nanovehicles for anticancer drugs with triggering release mechanisms
Oh, K. T., Yin, H., Lee, E. S., & Bae, Y. H. (2007) · Journal of Materials Chemistry · doi:10.1039/b707142f · Cited by 196 · see citing works
Controlling and Switching the Morphology of Micellar Nanoparticles with Enzymes
Ku, T., Chien, M., Thompson, M. P., Sinkovits, R. S., Olson, N. H., Baker, T. S., & Gianneschi, N. C. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2004736 · Cited by 172 · see citing works
Enzymatically Triggered Self-Assembly of Block Copolymers
Amir, R. J., Zhong, S., Pochan, D. J., & Hawker, C. J. (2009) · Journal of the American Chemical Society · doi:10.1021/ja9060917 · Cited by 158 · see citing works
A polymeric drug for treatment of inflammatory bowel disease
BROWN, J. P., McGarraugh, G. V., Parkinson, T. M., WINGARD, R. E. J., & Onderdonk, A. B. (1983) · Journal of Medicinal Chemistry · doi:10.1021/jm00363a015 · Cited by 150 · see citing works
Knox, R. J., Boland, M. P., Friedlos, F., Coles, B., Southan, C., & Roberts, J. J. (1988) · Biochemical Pharmacology · doi:10.1016/0006-2952(88)90336-x · Cited by 146 · see citing works
Almutairi, A., Guillaudeu, S. J., Berezin, M. Y., Achilefu, S. A., & Fréchet, J. M. J. (2007) · Journal of the American Chemical Society · doi:10.1021/ja078147e · Cited by 120 · see citing works
Hydrogels for Site-Specific Drug Delivery to the Colon: In Vitro and in Vivo Degradation
BRØNDSTED, H. V., & Kopec̆ek, J. (1992) · Pharmaceutical Research · doi:10.1023/a:1015847921435 · Cited by 119 · see citing works
In vitro degradation of pH-sensitive hydrogels containing aromatic azo bonds
Ghandehari, H., Kopečková, P., & Kopec̆ek, J. (1997) · Biomaterials · doi:10.1016/s0142-9612(97)00007-0 · Cited by 106 · see citing works
Triggered structural and property changes in polymeric nanomaterials
Spruell, J. M., & Hawker, C. J. (2010) · Chemical Science · doi:10.1039/c0sc00426j · Cited by 99 · see citing works
Enzyme-activated nanoconjugates for tunable release of doxorubicin in hepatic cancer cells
Medina, S. H., Chevliakov, M. V., Tiruchinapally, G., Durmaz, Y. Y., Kuruvilla, S. P., & ElSayed, M. E. H. (2013) · Biomaterials · doi:10.1016/j.biomaterials.2013.02.070 · Cited by 90 · see citing works
Polymers prepared using cleavable initiators: Synthesis, characterization and degradation
Rikkou‐Kalourkoti, M., & Patrickios, C. S. (2011) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2011.01.004 · Cited by 76 · see citing works
Rationally Designed Polymer Hosts of Fullerene
Stuparu, M. C. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201303032 · Cited by 72 · see citing works
den Mooter, G. V., Samyn, C., & Kinget, R. D. (1994) · Pharmaceutical Research · doi:10.1023/a:1018911316021 · Cited by 68 · see citing works
Kimura, Y., Makita, Y., KUMAGAI, T., Yamane, H., KITAO, T., Sasatani, H., & Kim, S. I. (1992) · Polymer · doi:10.1016/0032-3861(92)90814-d · Cited by 63 · see citing works
Skelly, J. V., Sanderson, M. R., Suter, D. A., Baumann, U., Read, M. A., Gregory, D. S., Bennett, M. S., Hobbs, S. M., & Neidle, S. (1999) · Journal of Medicinal Chemistry · doi:10.1021/jm991060m · Cited by 54 · see citing works
Systematic Study of Absorption Spectra of Donor–Acceptor Azobenzene Mesogenic Structures
Hrozhyk, U. A., Serak, S. V., Tabiryan, N. V., Hoke, L., Steeves, D. M., Kimball, B. R., & Kedziora, G. S. (2008) · Molecular Crystals and Liquid Crystals · doi:10.1080/15421400802218959 · Cited by 46 · see citing works
Rao, J., De, S., & Khan, A. (2012) · Chemical Communications · doi:10.1039/c2cc17397b · Cited by 35 · see citing works
Self-citationSynthesizing amphiphilic block copolymers through macromolecular azo-coupling reaction
He, Y., He, W., Wei, R., Chen, Z., & Wang, X. (2011) · Chemical Communications · doi:10.1039/c1cc16362k · Cited by 34 · see citing works
Rao, J., & Khan, A. (2013) · Polymer Chemistry · doi:10.1039/c3py00200d · Cited by 14 · see citing works
Self-citation
Flagged first, then by citations
Cited by
Sorted by citations
Kamaly, N., Yameen, B., Wu, J., & Farokhzad, O. C. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00346 · Cited by 3,070 · see citing works
Smart nanoparticles for cancer therapy
Sun, L., Liu, H., Ye, Y., Lei, Y., Islam, R., Tan, S., Tong, R., Miao, Y.-B., & Cai, L. (2023) · Signal Transduction and Targeted Therapy · doi:10.1038/s41392-023-01642-x · Cited by 1,073 · see citing works
Dai, Y., Xu, C., Sun, X., & Chen, X. S. (2017) · Chemical Society Reviews · doi:10.1039/c6cs00592f · Cited by 931 · see citing works
Stimuli-responsive nanocarriers for drug delivery, tumor imaging, therapy and theranostics
Mi, P. (2020) · Theranostics · doi:10.7150/thno.38069 · Cited by 865 · see citing works
Enzyme-responsive nanomaterials for controlled drug delivery
Hu, Q., Katti, P. S., & Gu, Z. (2014) · Nanoscale · doi:10.1039/c4nr04249b · Cited by 683 · see citing works
Advances and opportunities in the exciting world of azobenzenes
Jerca, F. A., Jerca, V. V., & Hoogenboom, R. (2021) · Nature Reviews Chemistry · doi:10.1038/s41570-021-00334-w · Cited by 531 · see citing works
Boyer, C. A., Corrigan, N. A., Jung, K., Nguyen, D., Nguyen, T., Adnan, N. N. M., Oliver, S., Shanmugam, S., & Yeow, J. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00396 · Cited by 483 · see citing works
Recent advances in polymeric micelles for anti-cancer drug delivery
Biswas, S., Kumari, P., Lakhani, P. M., & Ghosh, B. (2015) · European Journal of Pharmaceutical Sciences · doi:10.1016/j.ejps.2015.12.031 · Cited by 475 · see citing works
Development of endogenous enzyme-responsive nanomaterials for theranostics
Mu, J., Lin, J., Huang, P., & Chen, X. S. (2018) · Chemical Society Reviews · doi:10.1039/c7cs00663b · Cited by 394 · see citing works
Light: A Magical Tool for Controlled Drug Delivery
Tao, Y., Chan, H. F., Shi, B., Li, M., & Leong, K. W. (2020) · Advanced Functional Materials · doi:10.1002/adfm.202005029 · Cited by 314 · see citing works
Tang, J., Lee, M. F. X., Zhang, W., Zhao, B., Berry, R. M., & Tam, K. C. (2014) · Biomacromolecules · doi:10.1021/bm500663w · Cited by 310 · see citing works
Wang, X., Hu, J., Liu, G., Tian, J., Wang, H., Gong, M., & Liu, S. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b10127 · Cited by 297 · see citing works
Han, S., Li, Z., Zhu, J., Han, K., Zeng, Z., Hong, W., Li, W., Jia, H.-Z., Liu, Y., Zhuo, R., et al. (2015) · Small · doi:10.1002/smll.201402865 · Cited by 269 · see citing works
Recent Advances in light-responsive on-demand drug-delivery Systems
Linsley, C. S., & Wu, B. M. (2017) · Therapeutic Delivery · doi:10.4155/tde-2016-0060 · Cited by 270 · see citing works
Hypoxia-responsive nanoparticle based drug delivery systems in cancer therapy: An up-to-date review
KUMARI, R. R., Sunil, D., & Ningthoujam, R. S. (2019) · Journal of Controlled Release · doi:10.1016/j.jconrel.2019.12.041 · Cited by 269 · see citing works
Advanced functional polymer materials
Wang, K., Amin, K., An, Z., Cai, Z., Chen, H., Chen, H., Dong, Y., Feng, X., Fu, W., Gu, J., et al. (2020) · Materials Chemistry Frontiers · doi:10.1039/d0qm00025f · Cited by 245 · see citing works
Azoreductase: a key player of xenobiotic metabolism
Misal, S. A., & Gawai, K. R. (2018) · Bioresources and Bioprocessing · doi:10.1186/s40643-018-0206-8 · Cited by 198 · see citing works
Harnoy, A. J., Rosenbaum, I., Tirosh, E., Ebenstein, Y., Shaharabani, R., Beck, R., & Amir, R. J. (2014) · Journal of the American Chemical Society · doi:10.1021/ja413036q · Cited by 191 · see citing works
Thambi, T., Park, J. H., & Lee, D. S. (2016) · Chemical Communications · doi:10.1039/c6cc02972h · Cited by 172 · see citing works
Sun, Y., & Davis, E. W. (2021) · Nanomaterials · doi:10.3390/nano11030746 · Cited by 180 · see citing works
A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging
Geng, W., Jia, S., Zheng, Z., Li, Z., Ding, D., & Guo, D. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201813397 · Cited by 166 · see citing works
Programming Stimuli-Responsive Behavior into Biomaterials
Badeau, B. A., & DeForest, C. A. (2019) · Annual Review of Biomedical Engineering · doi:10.1146/annurev-bioeng-060418-052324 · Cited by 166 · see citing works
Enzyme-Initiated Reversible Addition–Fragmentation Chain Transfer Polymerization
Zhang, B., Wang, X., Zhu, A., Ma, K., Lv, Y., Wang, X., & An, Z. (2015) · Macromolecules · doi:10.1021/acs.macromol.5b01893 · Cited by 161 · see citing works
Polymeric carriers for enhanced delivery of probiotics
Asgari, S., Pourjavadi, A., Licht, T. R., Boisen, A., & Ajalloueian, F. (2020) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2020.07.014 · Cited by 155 · see citing works
Hyaluronic Acid-Based Theranostic Nanomedicines for Targeted Cancer Therapy
Lee, S. Y., Kang, M. S., Jeong, W. Y., Han, D., & Kim, K. S. (2020) · Cancers · doi:10.3390/cancers12040940 · Cited by 149 · see citing works
Sharifi, E., Bigham, A., Yousefiasl, S., Trovato, M., Ghomi, M., Esmaeili, Y., Samadi, P., Zarrabi, A., Ashrafizadeh, M., Sharifi, S., et al. (2021) · Advanced Science · doi:10.1002/advs.202102678 · Cited by 141 · see citing works
Hyeon, L. S., Moroz, E., Castagner, B., & Leroux, J. (2014) · Journal of the American Chemical Society · doi:10.1021/ja507547w · Cited by 128 · see citing works
Stimuli-Responsive Polymers for Sensing and Reacting to Environmental Conditions
Zhang, Q. M., Zhang, Y., Wan, Y., Carvalho, W. S. P., Hu, L., & Serpe, M. J. (2021) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2021.101386 · Cited by 124 · see citing works
Liao, P., Liu, S., Feng, A., & Yuan, J. (2017) · Molecular Pharmaceutics · doi:10.1021/acs.molpharmaceut.7b00160 · Cited by 118 · see citing works
Liao, J., Zheng, H., Fei, Z., Lü, B., Zheng, H. S., Li, D., Xiong, X., & Yi, Y. (2018) · International Journal of Biological Macromolecules · doi:10.1016/j.ijbiomac.2018.03.004 · Cited by 117 · see citing works
Yang, Y., Wang, Z., Peng, Y., Ding, J., & Zhou, W. (2019) · Frontiers in Pharmacology · doi:10.3389/fphar.2019.00010 · Cited by 109 · see citing works
Smart linkers in polymer–drug conjugates for tumor-targeted delivery
Chang, M., Zhang, F., Wei, T., Zuo, T., Guan, Y., Lin, G., & Shao, W. (2015) · Journal of drug targeting · doi:10.3109/1061186x.2015.1108324 · Cited by 107 · see citing works
Rao, J., Hottinger, C., & Khan, A. (2014) · Journal of the American Chemical Society · doi:10.1021/ja501632r · Cited by 104 · see citing works
Self-citationEnzyme and Redox Dual-Triggered Intracellular Release from Actively Targeted Polymeric Micelles
Zhang, L., Wang, Y., Zhang, X., Xiao, W., Xiong, X., & Zhou, S. (2017) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.6b14078 · Cited by 102 · see citing works
Thermo-triggered Drug Release from Actively Targeting Polymer Micelles
Guo, X., Li, D., Yang, G., Shi, C., Tang, Z., Wang, J., & Zhou, S. (2014) · ACS Applied Materials & Interfaces · doi:10.1021/am501422r · Cited by 97 · see citing works
Li, J., Meng, X., Deng, J., Lu, D., Zhang, X., Chen, Y., Zhu, J., Fan, A., Ding, D., Kong, D., et al. (2018) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.8b06299 · Cited by 95 · see citing works
Photopharmacology and photoresponsive drug delivery
Liu, Y., Wang, T., & Wang, W. (2025) · Chemical Society Reviews · doi:10.1039/d5cs00125k · Cited by 97 · see citing works
Ding, Y., Kang, Y., & Zhang, X. (2014) · Chemical Communications · doi:10.1039/c4cc05878j · Cited by 88 · see citing works
Zhang, Z.-T., Huang-Fu, M.-Y., Xu, W.-H., & Han, M. (2019) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/j.ejpb.2019.02.009 · Cited by 82 · see citing works
Kurakula, M., Gorityala, S., & Moharir, K. S. (2021) · Journal of Drug Delivery Science and Technology · doi:10.1016/j.jddst.2021.102579 · Cited by 82 · see citing works
Cai, D., Han, C., Liu, C., Ma, X., Qian, J., Zhou, J., Li, Y., Sun, Y., Zhang, C., & Zhu, W. (2020) · Nanoscale Research Letters · doi:10.1186/s11671-020-03351-8 · Cited by 79 · see citing works
Rezaei, A., Rafieian, F., Akbari‐Alavijeh, S., Kharazmi, M. S., & Jafari, S. M. (2022) · Advances in Colloid and Interface Science · doi:10.1016/j.cis.2022.102728 · Cited by 78 · see citing works
Untapped potential for debonding on demand: the wonderful world of azo-compounds
Mutlu, H., Geiselhart, C. M., & Barner‐Kowollik, C. (2017) · Materials Horizons · doi:10.1039/c7mh00920h · Cited by 78 · see citing works
Wu, W., Zhang, Q., Wang, J., Chen, M., Li, S., Lin, Z., & Li, J. (2014) · Polymer Chemistry · doi:10.1039/c4py00575a · Cited by 75 · see citing works
Carboxymethyl dextran-based hypoxia-responsive nanoparticles for doxorubicin delivery
Son, S., Rao, N. V., Ko, H., Shin, S., Jeon, J., Han, H. S., Nguyen, V. Q., Thambi, T., Suh, Y. D., & Park, J. H. (2017) · International Journal of Biological Macromolecules · doi:10.1016/j.ijbiomac.2017.11.048 · Cited by 74 · see citing works
Tang, Z., Zhang, L., Wang, Y., Li, D., Zhong, Z., & Zhou, S. (2016) · Acta Biomaterialia · doi:10.1016/j.actbio.2016.06.038 · Cited by 73 · see citing works
Wielding the double-edged sword: Redox drug delivery systems for inflammatory bowel disease
Chen, Y., Shui, M., Yuan, Q., Vong, C. T., Yang, Z., Chen, Z., & Wang, S. (2023) · Journal of Controlled Release · doi:10.1016/j.jconrel.2023.05.007 · Cited by 73 · see citing works
Xie, Z., Guo, W.-W., Guo, N., Huang-Fu, M.-Y., Liu, H., Lin, M., Xu, W., Chen, J., Wang, T., Wei, Q., et al. (2018) · Acta Biomaterialia · doi:10.1016/j.actbio.2018.03.013 · Cited by 71 · see citing works
Biologically activatable azobenzene polymers targeted at drug delivery and imaging applications
Eom, T., Yoo, W., Kim, S., & Khan, A. (2018) · Biomaterials · doi:10.1016/j.biomaterials.2018.09.020 · Cited by 70 · see citing works
Self-citationLiposome technologies towards colorectal cancer therapeutics
Sang, R., Stratton, B., Engel, A. F., & Deng, W. (2021) · Acta Biomaterialia · doi:10.1016/j.actbio.2021.03.055 · Cited by 68 · see citing works
Trigger Chemistries for Better Industrial Formulations
Wang, H.-C., Zhang, Y., Casey, C. M. P., Zimmerman, S. C., Cheng, J., Moore, J. S., Harris, K., & Katz, J. S. (2015) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.5b00485 · Cited by 68 · see citing works
Polymers, responsiveness and cancer therapy
Pethe, A. M., & Yadav, K. S. (2019) · Artificial Cells Nanomedicine and Biotechnology · doi:10.1080/21691401.2018.1559176 · Cited by 66 · see citing works
Alejo, T., Usón, L., & Arruebo, M. (2019) · Journal of Controlled Release · doi:10.1016/j.jconrel.2019.10.036 · Cited by 63 · see citing works
Yang, F., Cao, Z., & Wang, G. (2015) · Polymer Chemistry · doi:10.1039/c5py01435b · Cited by 62 · see citing works
Wahlgren, M., Axenstrand, M., Håkansson, Å., Marefati, A., & Pedersen, B. L. (2019) · Pharmaceutics · doi:10.3390/pharmaceutics11020095 · Cited by 61 · see citing works
Novel drug delivery systems: Insight into self-powered and nano-enabled drug delivery systems
Ewii, U. E., Onugwu, A. L., Nwokpor, V. C., Akpaso, I.-A., Ogbulie, T. E., Aharanwa, B., Chijioke, C., Verla, N., Iheme, C. I., Ujowundu, C. O., et al. (2024) · Nano TransMed · doi:10.1016/j.ntm.2024.100042 · Cited by 61 · see citing works
Rosenbaum, I., Harnoy, A. J., Tirosh, E., Buzhor, M. G., Segal, M., Frid, L., Shaharabani, R., Avinery, R., Beck, R., & Amir, R. J. (2015) · Journal of the American Chemical Society · doi:10.1021/ja510085s · Cited by 59 · see citing works
Ma, Z., Ma, R., Wang, X., Gao, J., Zheng, Y., & Sun, Z. (2019) · European Polymer Journal · doi:10.1016/j.eurpolymj.2019.05.017 · Cited by 57 · see citing works
Design principles for bacteria-responsive antimicrobial nanomaterials
Quek, J. Y., Uroro, E. O., Goswami, N., & Vasilev, K. A. (2021) · Materials Today Chemistry · doi:10.1016/j.mtchem.2021.100606 · Cited by 56 · see citing works
Ma, Z., Ma, R., Xiao, X.-L., Zhang, Y.-H., Zhang, X., Hu, N., Gao, J., Zheng, Y., Dong, D., & Sun, Z. (2016) · Acta Biomaterialia · doi:10.1016/j.actbio.2016.08.021 · Cited by 55 · see citing works
Suzuki, H. (2019) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-019-09775-2 · Cited by 52 · see citing works
Azo Coupling Reaction Induced Macromolecular Self-Assembly in Aqueous Solution
Li, S., Wang, J., Shen, J., Wu, B., & He, Y. (2018) · ACS Macro Letters · doi:10.1021/acsmacrolett.8b00049 · Cited by 51 · see citing works
pH-triggered chitosan nanogels via an ortho ester-based linkage for efficient chemotherapy
Yang, G., Wang, X., Fu, S., Tang, R., & Wang, J. (2017) · Acta Biomaterialia · doi:10.1016/j.actbio.2017.05.003 · Cited by 49 · see citing works
Development of hypoxia-triggered prodrug micelles as doxorubicin carriers for tumor therapy
Liu, H., Zhang, R., Niu, Y., Li, Y., Qiao, C.-M., Weng, J., Li, J., Zhang, X., Xiao, Z., & Zhang, X. (2015) · RSC Advances · doi:10.1039/c4ra14875d · Cited by 48 · see citing works
“Turn‐On” Activatable AIE Dots for Tumor Hypoxia Imaging
Xue, T., Jia, X., Wang, J., Xiang, J., Wang, W., Du, J., & He, Y. (2019) · Chemistry - A European Journal · doi:10.1002/chem.201902296 · Cited by 47 · see citing works
Yue, Y., Zhang, Z., Wang, Z.-H., Ma, R., Chen, M., Ding, F., Li, H.-B., Li, J., Shi, L., Liu, Y., et al. (2022) · Small Structures · doi:10.1002/sstr.202200067 · Cited by 46 · see citing works
Frontiers in the design and synthesis of advanced nanogels for nanomedicine
Liu, G., & An, Z. (2013) · Polymer Chemistry · doi:10.1039/c3py01502e · Cited by 46 · see citing works
Biological Stimuli-responsive Polymer Systems: Design, Construction and Controlled Self-assembly
Xu, M., Liu, R., & Yan, Q. (2017) · Chinese Journal of Polymer Science · doi:10.1007/s10118-018-2080-4 · Cited by 46 · see citing works
Biodegradable Stimuli-Responsive Polymeric Micelles for Treatment of Malignancy
Yan, L., & Li, X. D. (2016) · Current Pharmaceutical Biotechnology · doi:10.2174/138920101703160206142821 · Cited by 45 · see citing works
Wright, D. B., Thompson, M. P., Touve, M. A., Carlini, A. S., & Gianneschi, N. C. (2018) · Macromolecular Rapid Communications · doi:10.1002/marc.201800467 · Cited by 44 · see citing works
Gu, W., Li, Q., Lu, H., Fang, L., Chen, Q., Yang, Y., & Gao, H. (2015) · Chemical Communications · doi:10.1039/c5cc00628g · Cited by 43 · see citing works
Yuan, X., Wang, Z., Li, L., Yu, J., Wang, Y., Li, H., Zhang, J., Zhang, Z., Zhou, N., & Zhu, X. (2019) · Materials Chemistry Frontiers · doi:10.1039/c8qm00672e · Cited by 42 · see citing works
Guo, W.-W., Zhang, Z., Wei, Q., Zhou, Y., Lin, M., Chen, J., Wang, T., Guo, N., Zhong, X., Lu, Y., et al. (2019) · Biomacromolecules · doi:10.1021/acs.biomac.9b01202 · Cited by 42 · see citing works
Azobenzene-aminoglycoside: Self-assembled smart amphiphilic nanostructures for drug delivery
Deka, S. R., Yadav, S., Mahato, M., & Sharma, A. K. (2015) · Colloids and Surfaces B Biointerfaces · doi:10.1016/j.colsurfb.2015.07.026 · Cited by 41 · see citing works
Emerging antitumor applications of extracellularly reengineered polymeric nanocarriers
Chen, J., Ding, J., Xiao, C., Zhuang, X., & Chen, X. (2015) · Biomaterials Science · doi:10.1039/c5bm00044k · Cited by 40 · see citing works
Green chain-shattering polymers based on a self-immolative azobenzene motif
Mutlu, H., & Barner‐Kowollik, C. (2016) · Polymer Chemistry · doi:10.1039/c5py01937k · Cited by 40 · see citing works
Zhou, Y., Wang, Z., Wang, Y., Li, L., Zhou, N., Cai, Y., Zhang, Z., & Zhu, X. (2020) · Polymer Chemistry · doi:10.1039/d0py00826e · Cited by 40 · see citing works
Hypoxia-responsive drug–drug conjugated nanoparticles for breast cancer synergistic therapy
Zhang, R., Li, Y., Zhang, M., Tang, Q., & Zhang, X. (2016) · RSC Advances · doi:10.1039/c6ra01560c · Cited by 39 · see citing works
In situ construction of a self-assembled AIE probe for tumor hypoxia imaging
Xue, T., Shao, K., Xiang, J., Pan, X., Zhu, Z., & He, Y. (2020) · Nanoscale · doi:10.1039/d0nr00444h · Cited by 39 · see citing works
Zheng, M., & Yuan, J. (2021) · Organic & Biomolecular Chemistry · doi:10.1039/d1ob01823j · Cited by 38 · see citing works
Irshad, S., Siddiqui, B., Rehman, A. U., Farooq, R. K., & Ahmed, N. (2020) · International Journal of Polymeric Materials · doi:10.1080/00914037.2020.1848829 · Cited by 37 · see citing works
Patil, N. G., Basutkar, N. B., & Ambade, A. V. (2015) · Chemical Communications · doi:10.1039/c5cc06820g · Cited by 36 · see citing works
Ji, R., Cheng, J., Yang, T., Song, C., Li, L., Du, F., & Li, Z. (2014) · Biomacromolecules · doi:10.1021/bm500711c · Cited by 36 · see citing works
Intracellular Doxorubicin Delivery of a Core Cross-linked, Redox-responsive Polymeric Micelles
Lili, Y., Ruihua, M., Li, L., Fei, L., Lin, Y., & Li, S. (2015) · International Journal of Pharmaceutics · doi:10.1016/j.ijpharm.2015.12.042 · Cited by 35 · see citing works
Liu, H., Yang, J., Yan, X., Li, C., Elsabahy, M., Chen, L., Yang, Y., & Gao, H. (2021) · Journal of Materials Chemistry B · doi:10.1039/d1tb02134f · Cited by 37 · see citing works
Structural determinants of stimuli-responsiveness in amphiphilic macromolecular nano-assemblies
Liu, H., Lu, H., Alp, Y., Wu, R., & Thayumanavan, S. (2023) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2023.101765 · Cited by 34 · see citing works
An activatable anticancer polymer–drug conjugate based on the self-immolative azobenzene motif
Eom, T., Yoo, W., Lee, Y.-D., Park, J. H., Choe, Y., Bang, J., Kim, S., & Khan, A. (2017) · Journal of Materials Chemistry B · doi:10.1039/c7tb01250k · Cited by 33 · see citing works
Self-citationYadav, S., Deka, S. R., Verma, G., Sharma, A. K., & Kumar, P. (2016) · RSC Advances · doi:10.1039/c5ra26658k · Cited by 33 · see citing works
PDEAEMA-based pH-sensitive amphiphilic pentablock copolymers for controlled anticancer drug delivery
Chen, Q., Lin, W., Wang, H., Wang, J., & Zhang, L. (2016) · RSC Advances · doi:10.1039/c6ra10757e · Cited by 32 · see citing works
Encapsulating Wall Materials for Micro-/Nanocapsules
Vijeth, S., Heggannavar, G. B., & Kariduraganavar, M. Y. (2019) · IntechOpen eBooks · doi:10.5772/intechopen.82014 · Cited by 32 · see citing works
Recent advances in biopolymer-based smart hydrogel for wound healing
Jaiswal, R. S., & Sherje, A. P. (2024) · Journal of Drug Delivery Science and Technology · doi:10.1016/j.jddst.2024.105990 · Cited by 31 · see citing works
Tarahi, M., Singh, M., Farahnaky, A., Ghasemlou, M., & Dokouhaki, M. (2026) · Advances in Colloid and Interface Science · doi:10.1016/j.cis.2026.103787 · Cited by 36 · see citing works
Liu, Y., Dong, W., Ma, Y., Dou, J., Jiang, W., Wang, L., Wang, Q., Li, M., Wang, Y., & Li, M. (2023) · Biomaterials · doi:10.1016/j.biomaterials.2023.122023 · Cited by 30 · see citing works
Host–guest interaction between fluoro-substituted azobenzene derivative and cyclodextrins
Zhang, L., Zhang, H., Gao, F., Peng, H., Ruan, Y., Xu, Y., & Weng, W. (2015) · RSC Advances · doi:10.1039/c4ra13283a · Cited by 29 · see citing works
Bioresponsive engineered nanoparticles for immunomodulation
Hegde, M., Mishra, A., Banerjee, R., Bintee, B., Alqahtani, M. S., Abbas, M., Shanmugam, M. K., Drum, C. L., Sethi, G., Liu, L., et al. (2025) · BMC Medicine · doi:10.1186/s12916-025-04305-6 · Cited by 33 · see citing works
Khafaga, D. S. R., Radwan, M. G., Muteeb, G., Aatif, M., & Farhan, M. (2023) · Catalysts · doi:10.3390/catal13111448 · Cited by 28 · see citing works
Li, Q., Cao, Z., & Wang, G. (2017) · Polymer Chemistry · doi:10.1039/c7py01822c · Cited by 28 · see citing works
Santra, S., Sk, M. A., Mondal, A. K., & Molla, M. R. (2020) · Langmuir · doi:10.1021/acs.langmuir.0c01474 · Cited by 27 · see citing works
Peroxynitrite (ONOO–) Redox Signaling Molecule-Responsive Polymersomes
Zhang, J., Hu, J., Sang, W., Wang, J., & Yan, Q. (2016) · ACS Macro Letters · doi:10.1021/acsmacrolett.6b00474 · Cited by 26 · see citing works
A Noncovalent Fluorescence Turn‐on Strategy for Hypoxia Imaging
Geng, W., Jia, S., Zheng, Z., Li, Z., Ding, D., & Guo, D. (2019) · Angewandte Chemie · doi:10.1002/ange.201813397 · Cited by 26 · see citing works
- Authors
- Rao, J., & Khan, A.
- Affiliations
- ETH Zurich (CH)
- Corresponding author
- Khan, Anzar
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-09-13
- Volume
- 135
- Issue
- 38
- Pages
- 14056-14059
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2320976673
- Cited by
- 207
- References
- 39
- Citations by year
- 2026: 6 · 2025: 11 · 2024: 7 · 2023: 17 · 2022: 12 · 2021: 18 · 2020: 25 · 2019: 23 · 2018: 18 · 2017: 18 · 2016: 19 · 2015: 19 · 2014: 13 · 2013: 1
- FWCI
- 7.88
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Biomaterials › Nanoparticle-Based Drug Delivery
- Physical Sciences › Materials Science › Materials Chemistry › Photochromic and Fluorescence Chemistry
- Keywords
- azobenzene, enzyme-responsive polymers, polymeric micelles, azoreductase, NADPH, amphiphilic diblock copolymers, colon-targeted drug delivery, polymeric nanoparticles
- MeSH terms
- Azo Compounds, Micelles, NAD, NADH, NADPH Oxidoreductases, Nitroreductases, Polyethylene Glycols, Polystyrenes
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review