Photoresponsive Supramolecular Hydrogel Co-assembled from Fmoc-Phe-OH and 4,4′-Azopyridine for Controllable Dye Release
- Corresponding author: Chuan-Liang Feng, clfeng@sjtu.edu.cn Holger Schönherr, schoenherr@chemie.uni-siegen.de
Citation:
Xiao-Qiu Dou, Chang-Li Zhao, Nabila Mehwish, Ping Li, Chuan-Liang Feng, Holger Schönherr. Photoresponsive Supramolecular Hydrogel Co-assembled from Fmoc-Phe-OH and 4,4′-Azopyridine for Controllable Dye Release[J]. Chinese Journal of Polymer Science,
;2019, 37(5): 437-443.
doi:
10.1007/s10118-019-2223-2
Dou, X. Q.; Feng, C. L. Amino acids and peptide-based supramolecular hydrogels for three-dimensional cell culture. Adv. Mater. 2017, 29, 1604062.
doi: 10.1002/adma.201604062
Du, X. W.; Zhou, J.; Shi, J. F.; Xu, B. Supramolecular hydrogelators and hydrogels: from soft matter to molecular biomaterials. Chem. Rev. 2015, 115, 13165-13307.
doi: 10.1021/acs.chemrev.5b00299
Wang, Y. C.; Shim, M. S.; Levinson, N. S.; Sung, H. W.; Xia, Y. N. Stimuli-responsive materials for controlled release of theranostic agents. Adv. Funct. Mater. 2014, 24, 4206-4220.
doi: 10.1002/adfm.v24.27
Zhang, W. M.; Zhang, J.; Qiao, Z.; Yin, J. Functionally oriented tumor microenvironment responsive polymeric nanoassembly: engineering and applications. Chinese J. Polym. Sci. 2018, 36, 273-287.
doi: 10.1007/s10118-018-2035-9
Samai, S.; Sapsanis, C.; Patil, S. P.; Ezzeddine, A.; Moosa, B. A.; Omran, H.; Emwas, A. H.; Salama, K. N.; Khashab, N. M. A light responsive two-component supramolecular hydrogel: A sensitive platform for the fabrication of humidity sensors, Soft Matter 2016, 12, 2842-2845
doi: 10.1039/c6sm00272b
He, M. T.; Li, J. B.; Tan, S.; Wang, R. Z.; Zhang, Y. Photodegradable supramolecular hydrogels with fluorescence turn-on reporter for photomodulation of cellular microenvironments. J. Am. Chem. Soc. 2013, 135, 18718-18721.
doi: 10.1021/ja409000b
Chen, Q.; Lv, Y. X.; Zhang, D. Q.; Zhang, G. X.; Liu, C. Y.; Zhu, D. B. Cysteine and pH-responsive hydrogel based on a saccharide derivative with an aldehyde group. Langmuir 2010, 26, 3165-3168.
doi: 10.1021/la903102z
Sarkar, K.; Dastidar, P. Supramolecular hydrogel derived from a c3-symmetric boronic acid derivative for stimuli-responsive release of insulin and doxorubicin. Langmuir 2018, 34, 685-692.
doi: 10.1021/acs.langmuir.7b03326
Wang, F.; Feng, C. L. Metal-ion-mediated supramolecular chirality of L-phenylalanine based hydrogels. Angew. Chem. Int. Ed. 2018, 57, 5655-5659.
doi: 10.1002/anie.201800251
Cheng, C.; Tang, M. C.; Wu, C. S.; Simon, T.; Ko, F. H. New synthesis route of hydrogel through a bioinspired supramolecular approach: Gelatin, binding interaction, and in vitro dressing. ACS Appl. Mater. Interfaces 2015, 7, 19306-19315.
doi: 10.1021/acsami.5b05360
Kuddushi, M.; Patel, N. K.; Rajputt, S.; Shah, A.; EI Seoud, O. A.; Malek, N. I. Thermo-switchable de novo ionic liquid-based gelators with dye absorbing and drug encapsulating characteristics. ACS Omega 2018, 3, 12068-12078.
doi: 10.1021/acsomega.8b01984
Shankar, B. V.; Patnaik, A. A New pH and thermo-responsive chiral hydrogel for stimulated release. J. Phys. Chem. B 2007, 111, 9294-9300.
doi: 10.1021/jp073275a
Lu, X. J.; Yang, X. Y.; Meng, Y.; Li, S. Z. Temperature and pH dually-responsive poly(β-amino ester) nanoparticles for drug delivery. Chinese J. Poly. Sci. 2017, 35, 534-546.
doi: 10.1007/s10118-017-1916-7
Ji, W.; Liu, G. F.; Xu, M. X.; Feng, C. L. A redox-responsive supramolecular hydrogel for controllable dye release. Macromol. Chem. Phys. 2015, 216, 1945-1951.
doi: 10.1002/macp.201500210
Wojciechowski, J. P.; Martin, A. D.; Thordarson, P. Kinetically controlled lifetimes in redox-responsive transient supramolecular hydrogels. J. Am. Chem. Soc. 2018, 140, 2869-2874.
doi: 10.1021/jacs.7b12198
Yao, L.; Krause, S. Electromechanical responses of strong acid polymer gels in DC electric fields. Macromolecules 2003, 36, 2055-2065.
doi: 10.1021/ma021326q
Ji, W.; Liu, G. F.; Wang, F.; Zhu, Z.; Feng, C. L. Galactose-decorated light-responsive hydrogelator precursors for selectively killing cancer cells. Chem. Commun. 2016, 52, 12574-12577.
doi: 10.1039/C6CC05707A
Ji, W.; Qin, M. G.; Feng, C. L. Photoresponsive coumarin-based supramolecular hydrogel for controllable dye release. Macromol. Chem. Phys. 2018, 219, 1700398.
doi: 10.1002/macp.v219.2
Roth-Konforti, M. E.; Comune, M.; Halperin-Sternfeld, M.; Grigoriants, I.; Shabat, D.; Adler-Abramovich, L. UV Light-responsive peptide-based supramolecular hydrogel for controlled drug delivery. Macromol. Rapid Commun. 2018, 1800588.
Yang, Q. F.; Wang, P.; Zhao, C. Z.; Wang, W. Q.; Yang, J. F.; Liu, Q. Light-switchable self-healing hydrogel based on host-guest macro-crosslinking. Macromol. Rapid Commun. 2017, 38, 1600741.
doi: 10.1002/marc.v38.6
Liu, G. F.; Ji, W.; Wang, W. L.; Feng, C. L. Azobenzene derivatives as 3d scaffolds for photoguiding cell adhesion and release. ACS Appl. Mater. Interfaces 2015, 7, 301-307.
doi: 10.1021/am506202s
Wang, W.; Gao, F.; Yao, Y.; Lin, S. L. Directional photo-manipulation of self-assembly patterned microstructures. Chinese J. Polym. Sci. 2018, 36, 297-305.
doi: 10.1007/s10118-018-2087-x
Muraoka, T.; Koh, C. Y.; Cui, H. G.; Stupp, S. I. Light-triggered bioactivity in three dimensions. Angew. Chem. Int. Ed. 2009, 48, 5946-5949.
doi: 10.1002/anie.v48:32
Komatsu, H.; Tsukiji, S.; Ikeda, M.; Hamachi, I. Stiff, multistimuli-responsive supramolecular hydrogels as unique molds for 2D/3D microarchitectures of live cells. Chem. Asian J. 2001, 6, 2368-2375.
Yang, R. M.; Peng, S. H.; Wan, W. B.; Hughes, T. C. Azobenzene based multistimuli responsive supramolecular hydrogels. J. Mater. Chem. C. 2014, 2, 9122-9131.
doi: 10.1039/C4TC01649A
Wang, D. S.; Wagner, M.; Butt, H. J.; Wu, S. Supramolecular hydrogels constructed by red-light-responsive host-guest interactions for photo-controlled protein release in deep tissue. Soft Matter, 2015, 11, 7656-7662.
doi: 10.1039/C5SM01888A
Dou, X. Q.; Li, P.; Zhang, D.; Feng, C. L. C2-symmetric benzene-based hydrogels with unique layered structures for controllable organic dye adsorption. Soft Matter 2012, 8, 3231-3238.
doi: 10.1039/c2sm06927j
Dou, X. Q.; Zhang, D.; Feng, C. L.; Jiang, L. Bioinspired hierarchical surface structures with tunable wettability for regulating bacteria adhesion. ACS Nano 2015, 9, 10664-10672.
doi: 10.1021/acsnano.5b04231
Liu, J. Y.; Yuan, F.; Ma, X. Y.; Auphedeous, D. Y.; Zhao, C. L.; Liu, C. T.; Shen, C. Y.; Feng, C. L. The cooperative effect of both molecular and supramolecular chirality on cell adhesion. Angew. Chem. Ind. Ed. 2018, 57, 6475-6479.
doi: 10.1002/anie.v57.22
Liu, G. F.; Zhang, D.; Feng, C. L. Control of three-dimensional cell adhesion by the chirality of nanofibers in hydrogels. Angew. Chem. Int. Ed. 2014, 53, 7789-7793.
doi: 10.1002/anie.201403249
Huang, S.; Chen, Y. X.; Ma, S. D.; Yu, H. F. Hierarchical self-assembly in liquid-crystalline block copolymers enabled by chirality transfer. Angew. Chem. Int. Ed. 2018, 57, 12524-12528.
doi: 10.1002/anie.201807379
Ryan, D. M.; Doran, T. M.; Anderson, S. B.; Nilsson, B. L. Effect of C-terminal modification on the self-assembly and hydrogelation of fluorinated Fmoc-Phe derivatives. Langmuir 2011, 27, 4029-4039.
doi: 10.1021/la1048375
Zhang, P.; Huang, Y. X.; Kwon, Y. T.; Li, S. PEGylated Fmoc-amino acid conjugates as effective nanocarriers for improved drug delivery. Mol. Pharmaceutics 2015, 12, 1680-1690.
doi: 10.1021/acs.molpharmaceut.5b00157
Dou, X. Q.; Li, P.; Lu, S. Q.; Tian, X. B.; Tang, Y. T.; Mercer-Chalmers, J. D.; Feng, C. L.; Zhang, D. Highly directional co-assembly of 2,6-pyridinedicarboxylic acid and 4-hydroxypyridine based on low molecular weight gelators. J. Mol. Liq. 2013, 180, 129-134.
doi: 10.1016/j.molliq.2013.01.005
Zhang, H. B.; Zhao, R.; Jackson, J. K.; Chiao, M.; Yu, H. F. Janus ultrathin film form multi-level self-assembly at air-water interfaces. Chem. Commun. 2014, 50, 14843-14846.
doi: 10.1039/C4CC06798C
Liu, H.; Kobayashi, T.; Yu, H. F. Easy fabrication and morphology control of supramolecular liquid-crystalline polymer microparticles. Macromol. Rapid Commun. 2011, 32, 378-383.
doi: 10.1002/marc.v32.4
Yu, H. F.; Liu, H.; Kobayashi, T. Fabrication and photoresponse of supramolecualr liquid-crystalline microparticles. ACS Appl. Mater. Interfaces 2011, 3, 1333-1340.
doi: 10.1021/am2001289
Chakraborty, P.; Mondal, S.; Khara, S.; Bairi, P.; Nandi, A. K. Integration of poly(ethylene glycol) in N-fluorenylmethoxycarbonyl-L-tryptophan hydrogel influencing mechanical, thixotropic, and release properties. J. Phys. Chem. B 2015, 119, 5933-5944.
doi: 10.1021/acs.jpcb.5b02424
Liu, G. F.; Sheng, J. H.; Teo, W. L.; Yang, G. B.; Wu, H. W.; Li, Y. X.; Zhao, Y. L. Control on dimensions and supramolecular chirality of self-assemblies through light and metal ions. J. Am. Chem. Soc. 2018, 140, 16275-16283.
doi: 10.1021/jacs.8b10024
Galanti, A.; Diez-Cabanes, V.; Santoro J.; Valášek, M.; Minoia, A.; Mayor, M.; Cornil, J.; Samorì, P. Electronic decoupling in C3-symmetrical light-responsive tris(azobenzene) scaffolds: Self-Assembly and multiphotochromism. J. Am. Chem. Soc. 2018, 140, 16062-16070.
doi: 10.1021/jacs.8b06324
Ningning Gao , Yue Zhang , Zhenhao Yang , Lijing Xu , Kongyin Zhao , Qingping Xin , Junkui Gao , Junjun Shi , Jin Zhong , Huiguo Wang . Ba2+/Ca2+ co-crosslinked alginate hydrogel filtration membrane with high strength, high flux and stability for dye/salt separation. Chinese Chemical Letters, 2024, 35(5): 108820-. doi: 10.1016/j.cclet.2023.108820
Yutong Xiong , Ting Meng , Wendi Luo , Bin Tu , Shuai Wang , Qingdao Zeng . Molecular conformational effects on co-assembly systems of low-symmetric carboxylic acids investigated by scanning tunneling microscopy. Chinese Journal of Structural Chemistry, 2025, 44(2): 100511-100511. doi: 10.1016/j.cjsc.2025.100511
Xi Chen , Xue Zhang , Shuai Yang , Jie Wang , Tian Tang , Maling Gou . An adhesive hydrogel for the treatment of oral ulcers. Chinese Chemical Letters, 2025, 36(3): 110021-. doi: 10.1016/j.cclet.2024.110021
Ningyue Xu , Jun Wang , Lei Liu , Changyang Gong . Injectable hydrogel-based drug delivery systems for enhancing the efficacy of radiation therapy: A review of recent advances. Chinese Chemical Letters, 2024, 35(8): 109225-. doi: 10.1016/j.cclet.2023.109225
Tong Zhang , Xiaojing Liang , Licheng Wang , Shuai Wang , Xiaoxiao Liu , Yong Guo . An ionic liquid assisted hydrogel functionalized silica stationary phase for mixed-mode liquid chromatography. Chinese Chemical Letters, 2025, 36(1): 109889-. doi: 10.1016/j.cclet.2024.109889
Jia-Qi Feng , Xiang Tian , Rui-Ge Cao , Yong-Xiu Li , Wen-Long Liu , Rong Huang , Si-Yong Qin , Ai-Qing Zhang , Yin-Jia Cheng . An AIE-based theranostic nanoplatform for enhanced colorectal cancer therapy: Real-time tumor-tracking and chemical-enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(12): 109657-. doi: 10.1016/j.cclet.2024.109657
Yang Xu , Le Ma , Yang Wang , Chunmeng Shi . Engineering strategies of biomaterial-assisted exosomes for skin wound repair: Latest advances and challenges. Chinese Chemical Letters, 2025, 36(1): 109766-. doi: 10.1016/j.cclet.2024.109766
Yue Sun , Yingnan Zhu , Jiahang Si , Ruikang Zhang , Yalan Ji , Jinjie Fan , Yuze Dong . Glucose-activated nanozyme hydrogels for microenvironment modulation via cascade reaction in diabetic wound. Chinese Chemical Letters, 2025, 36(4): 110012-. doi: 10.1016/j.cclet.2024.110012
Zheyi Li , Xiaoyang Liang , Zitong Qiu , Zimeng Liu , Siyu Wang , Yue Zhou , Nan Li . Ion-interferential cell cycle arrest for melanoma treatment based on magnetocaloric bimetallic-ion sustained release hydrogel. Chinese Chemical Letters, 2024, 35(11): 109592-. doi: 10.1016/j.cclet.2024.109592
Qiang Zhou , Pingping Zhu , Wei Shao , Wanqun Hu , Xuan Lei , Haiyang Yang . Innovative Experimental Teaching Design for 3D Printing High-Strength Hydrogel Experiments. University Chemistry, 2024, 39(6): 264-270. doi: 10.3866/PKU.DXHX202310064
Qingyang Cui , Feng Yu , Zirun Wang , Bangkun Jin , Wanqun Hu , Wan Li . From Jelly to Soft Matter: Preparation and Properties-Exploring of Different Kinds of Hydrogels. University Chemistry, 2024, 39(9): 338-348. doi: 10.3866/PKU.DXHX202309046
Xiaoliu Liang , Chunliu Huang , Hui Liu , Hu Chen , Jiabao Shou , Hongwei Cheng , Gang Liu . Natural hydrogel dressings in wound care: Design, advances, and perspectives. Chinese Chemical Letters, 2024, 35(10): 109442-. doi: 10.1016/j.cclet.2023.109442
Guilong Li , Wenbo Ma , Jialing Zhou , Caiqin Wu , Chenling Yao , Huan Zeng , Jian Wang . A composite hydrogel with porous and homogeneous structure for efficient osmotic energy conversion. Chinese Chemical Letters, 2025, 36(2): 110449-. doi: 10.1016/j.cclet.2024.110449
Guanyang Zeng , Xingqiang Liu , Liangqiao Wu , Zijie Meng , Debin Zeng , Changlin Yu . Novel visible-light-driven I- doped Bi2O2CO3 nano-sheets fabricated via an ion exchange route for dye and phenol removal. Chinese Journal of Structural Chemistry, 2024, 43(12): 100462-100462. doi: 10.1016/j.cjsc.2024.100462
Jianye Kang , Xinyu Yang , Xuhao Yang , Jiahui Sun , Yuhang Liu , Shutao Wang , Wenlong Song . Carbon dots-enhanced pH-responsive lubricating hydrogel based on reversible dynamic covalent bondings. Chinese Chemical Letters, 2024, 35(5): 109297-. doi: 10.1016/j.cclet.2023.109297
Xin Li , Xuan Ding , Junkun Zhou , Hui Shi , Zhenxi Dai , Jiayi Liu , Yongcun Ma , Penghui Shao , Liming Yang , Xubiao Luo . Utilizing synergistic effects of bifunctional polymer hydrogel PAM-PAMPS for selective capture of Pb(Ⅱ) from wastewater. Chinese Chemical Letters, 2024, 35(7): 109158-. doi: 10.1016/j.cclet.2023.109158
Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616
Zhibin Ren , Shan Li , Xiaoying Liu , Guanghao Lv , Lei Chen , Jingli Wang , Xingyi Li , Jiaqing Wang . Penetrating efficiency of supramolecular hydrogel eye drops: Electrostatic interaction surpasses ligand-receptor interaction. Chinese Chemical Letters, 2024, 35(11): 109629-. doi: 10.1016/j.cclet.2024.109629
Haijun Shen , Yi Qiao , Chun Zhang , Yane Ma , Jialing Chen , Yingying Cao , Wenna Zheng . A matrix metalloproteinase-sensitive hydrogel combined with photothermal therapy for transdermal delivery of deferoxamine to accelerate diabetic pressure ulcer healing. Chinese Chemical Letters, 2024, 35(12): 110283-. doi: 10.1016/j.cclet.2024.110283
Jiajia Wang , XinXin Ge , Yajing Xiang , Xiaoliang Qi , Ying Li , Hangbin Xu , Erya Cai , Chaofan Zhang , Yulong Lan , Xiaojing Chen , Yizuo Shi , Zhangping Li , Jianliang Shen . An ionic liquid functionalized sericin hydrogel for drug-resistant bacteria-infected diabetic wound healing. Chinese Chemical Letters, 2025, 36(2): 109819-. doi: 10.1016/j.cclet.2024.109819