Photoresponsive Supramolecular Hydrogel Co-assembled from Fmoc-Phe-OH and 4,4′-Azopyridine for Controllable Dye Release

Xiao-Qiu Dou; Chang-Li Zhao; Nabila Mehwish; Ping Li; Chuan-Liang Feng; Holger Schönherr

doi:10.1007/s10118-019-2223-2

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Photoresponsive Supramolecular Hydrogel Co-assembled from Fmoc-Phe-OH and 4,4′-Azopyridine for Controllable Dye Release

ARTICLE | Updated：2021-02-18

- Photoresponsive Supramolecular Hydrogel Co-assembled from Fmoc-Phe-OH and 4,4′-Azopyridine for Controllable Dye Release
- Chinese Journal of Polymer Science Vol. 37, Issue 5, Pages: 437-443(2019)
- Affiliations：
  
  a.Physical Chemistry I and Research Center of Micro and Nanochemistry and Engineering (Cμ), Department of Chemistry and Biology, University of Siegen, Siegen 57076, Germany
  b.State Key Lab of Metal Matrix Composites, School of Materials Science and Engineering, Shanghai Jiao Tong University, Shanghai 200240, China
- Author bio：
  
  clfeng@sjtu.edu.cn (C.L.F.)
  schoenherr@chemie.uni-siegen.de (H.S.)
- Funds：
- DOI：10.1007/s10118-019-2223-2
  CLC：
- Received：11 December 2018，
  
  Revised：2018-12-28，
  
  Accepted：07 January 2019，
  
  Online First：18 February 2019，
  
  Published：2019-05
- Accepted：
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Citation: Dou, X. Q.; Zhao, C. L.; Mehwish, N.; Li, P.; Feng, C. L.; Schönherr, H. Photoresponsive supramolecular hydrogel co-assembled from Fmoc-Phe-OH and 4,4′-azopyridine for controllable dye release. Chinese J. Polym. Sci. 2019, 37, 437–443

Xiao-Qiu Dou, Chang-Li Zhao, Nabila Mehwish, et al. 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.
Citation: Dou, X. Q.; Zhao, C. L.; Mehwish, N.; Li, P.; Feng, C. L.; Schönherr, H. Photoresponsive supramolecular hydrogel co-assembled from Fmoc-Phe-OH and 4,4′-azopyridine for controllable dye release. Chinese J. Polym. Sci. 2019, 37, 437–443 DOI： 10.1007/s10118-019-2223-2.

Xiao-Qiu Dou, Chang-Li Zhao, Nabila Mehwish, et al. 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.

摘要

Abstract

Photoresponsive hydrogels have been attractive because they can provide precise spatial and temporal control for molecule release

whereas the conventional preparation of photoresponsive hydrogels generally involves complex chemical synthesis steps or specific conditions which limits their practical applications. Herein

a new photoresponsive hydrogel is facilely prepared

via

co-assembly of two simple molecules

Fmoc-Phe-OH and Azp

without chemical synthesis. The co-assembly mechanism

morphology

and photoresponsiveness of (Fmoc-Phe-OH)-Azp hydrogel are investigated by circular dichroism (CD)

ultraviolet-visible (UV-Vis)

fluorescence

H nuclear magnetic resonance (

H-NMR)

attenuated total internal reflection Fourier transform Infrared (ATR-FTIR) spectroscopy

and scanning electron microscopy (SEM). Furthermore

the enhanced release of encapsulated sulforhodamine B (SRB) dye molecules can be achieved

via

UV light irradiation. The enhanced dye release amount can be controlled by manipulating photoirradiation time. This study provides a facile way to prepare photoresponsive hydrogel which holds great potential for controllable drug release.

关键词

Keywords

references

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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/10.1021/la903102z .

Sarkar, K.; Dastidar, P . Supramolecular hydrogel derived from a C 3 -symmetric boronic acid derivative for stimuli-responsive release of insulin and doxorubicin . Langmuir , 2018 . 34 685 - 692 . DOI: 10.1021/acs.langmuir.7b03326 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/10.1039/C5SM01888A .

Dou, X. Q.; Li, P.; Zhang, D.; Feng, C. L . C 2 -symmetric benzene-based hydrogels with unique layered structures for controllable organic dye adsorption . Soft Matter , 2012 . 8 3231 - 3238 . DOI: 10.1039/c2sm06927j http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/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 http://doi.org/10.1021/jacs.8b10024 .

Galanti, A.; Diez-Cabanes, V.; Santoro J.; Valášek, M.; Minoia, A.; Mayor, M.; Cornil, J.; Samorì, P . Electronic decoupling in C 3 -symmetrical light-responsive tris(azobenzene) scaffolds: Self-assembly and multiphotochromism . J. Am. Chem. Soc. , 2018 . 140 16062 - 16070 . DOI: 10.1021/jacs.8b06324 http://doi.org/10.1021/jacs.8b06324 .

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