Dual Photo/Thermo-Responsive Polypeptoids

Yu-Xuan Zhang; Jie Huang; Jun Zhang; Ning Ren; Gang-Sheng Tong; Xin-Yuan Zhu

doi:10.1007/s10118-022-2837-7

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Dual Photo/Thermo-Responsive Polypeptoids

RESEARCH ARTICLE | Updated：2022-12-19

- Dual Photo/Thermo-Responsive Polypeptoids
- Chinese Journal of Polymer Science Vol. 41, Issue 1, Pages: 24-31(2023)
- Affiliations：
  
  School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Research Institute of Polymer Materials, Shanghai Jiao Tong University, Shanghai 200240, China
- Author bio：
  
  ningren@sjtu.edu.cn (N.R.)
  xyzhu@sjtu.edu.cn (X.Y.Z)
- Funds：
- DOI：10.1007/s10118-022-2837-7
  CLC：
- Received：31 May 2022，
  
  Revised：2022-6-30，
  
  Accepted：04 July 2022，
  
  Online First：08 October 2022，
  
  Published：01 January 2023
- Accepted：
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Zhang, Y. X.; Huang, J.; Zhang, J.; Ren, N.; Tong, G. S.; Zhu, X. Y. Dual photo/thermo-responsive polypeptoids. Chinese J. Polym. Sci. 2023, 41, 24–31

Yu-Xuan Zhang, Jie Huang, Jun Zhang, et al. Dual Photo/Thermo-Responsive Polypeptoids[J]. Chinese Journal of Polymer Science, 2023, 41(1): 24-31.
Zhang, Y. X.; Huang, J.; Zhang, J.; Ren, N.; Tong, G. S.; Zhu, X. Y. Dual photo/thermo-responsive polypeptoids. Chinese J. Polym. Sci. 2023, 41, 24–31 DOI： 10.1007/s10118-022-2837-7.

Yu-Xuan Zhang, Jie Huang, Jun Zhang, et al. Dual Photo/Thermo-Responsive Polypeptoids[J]. Chinese Journal of Polymer Science, 2023, 41(1): 24-31. DOI： 10.1007/s10118-022-2837-7.

摘要

The synthesis of dual photo/thermo-responsive polypeptoid via ring-opening polymerization of a NNCA monomer bearing both Azo group and OEG segment.

Abstract

A series of polypeptoids with dual photo/thermo-responsiveness were prepared by incorporating both azobenzene (Azo) group and oligo(ethylene glycol) (OEG) segment into the side chains. Firstly

the

-substituted-

-carboxyanhydride (NNCA) monomers with different Azo and OEG groups were synthesized

and then a single NNCA ring-openning polymerization was performed to afford dual-responsive polypeptoids without any post-polymerization modification. The ultra-violet/visible (UV/Vis) photo-responsive behaviors of the polypeptoids were achieved by

cis

trans

photoisomerization of the Azo group and confirmed by both

H-NMR and UV/Vis spectroscopy. The thermo-responsive behaviors were realized by both OEG segment and Azo group and confirmed by UV/Vis spectroscopy and dynamic light scattering. This work demonstrated the synthetic pathway for dual responsive polypeptoids using NNCA monomers with two responsive groups and revealed the potential of polypeptoids as smart materials that could respond to different environmental stimuli.

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Keywords

references

Yu, D.; Yang, J.; Wang, L.; Chen, M.; Yang, R.; Zheng, J . Engineering a dual-responsive, exosome-surface anchored DNA nanosensor for microenvironment monitoring in vivo . Chem. Commun. , 2022 . 58 3661 - 3664 . DOI: 10.1039/D1CC07070C http://doi.org/10.1039/D1CC07070C .

Xue, Y.; Bai, S.; Wang, L.; Luo, S.; Zhang, Z.; Gong, T.; Zhang, L . A dual-responsive nanoplatform with feedback amplification improves antitumor efficacy of photodynamic therapy . Nanoscale , 2022 . 14 2758 - 2770 . DOI: 10.1039/D1NR06875J http://doi.org/10.1039/D1NR06875J .

Xu, X.; Ran, Y.; Huang, C.; Yin, Z . Glucose and H 2 O 2 dual-responsive nanocomplex grafted with insulin prodrug for blood glucose regulation . Biomacromolecules , 2022 . 23 1765 - 1776 . DOI: 10.1021/acs.biomac.2c00016 http://doi.org/10.1021/acs.biomac.2c00016 .

Wu, L.; Pan, H.; Huang, W.; Hu, Z.; Wang, M.; Zhang, F . pH and redox dual-responsive mesoporous silica nanoparticle as nanovehicle for improving fungicidal efficiency . Materials , 2022 . 15 2207 DOI: 10.3390/ma15062207 http://doi.org/10.3390/ma15062207 .

Shen, Z.; Ma, N.; Wang, F.; Ren, J.; Hou, C.; Chao, S.; Pei, Y.; Pei, Z. . pH- and H 2 O 2 -sensitive drug delivery system based on sodium xanthate: dual-responsive supramolecular vesicles from one functional group . Chin. Chem. Lett. , 2022 . 10.1016/j.cclet.2022.01.069 DOI: 10.1016/j.cclet.2022.01.069 http://doi.org/10.1016/j.cclet.2022.01.069 .

Reifarth, M.; Bekir, M.; Bapolisi, A. M.; Titov, E.; Nusshardt, F.; Nowaczyk, J.; Grigoriev, D.; Sharma, A.; Saalfrank, P.; Santer, S.; Hartlieb, M.; Boker, A . A dual pH- and light-responsive spiropyrane-based surfactant: investigations on its switching behavior and remote control over emulsion stability . Angew. Chem. Int. Ed. , 2022 . 61 e202114687 DOI: 10.1002/anie.202114687 http://doi.org/10.1002/anie.202114687 .

Miao, Z.; Chen, Z.; Wang, L.; Zhang, L.; Zhou, J . Dual-responsive zwitterion-modified nanopores: a mesoscopic simulation study . J. Mater. Chem. B , 2022 . 10 2740 - 2749 . DOI: 10.1039/D1TB02416G http://doi.org/10.1039/D1TB02416G .

Liu, P.; Wang, Z.; Hu, J.; Zhao, Y . Topology-directed multi-tunable self-assembly of linear and tadpole-shaped amorphous-responsive-crystalline terpolymers . Polym. Chem. , 2022 . 13 1986 - 1996 . DOI: 10.1039/D2PY00137C http://doi.org/10.1039/D2PY00137C .

Liang, Y.; Li, M.; Yang, Y.; Qiao, L.; Xu, H.; Guo, B . pH/glucose dual responsive metformin release hydrogel dressings with adhesion and self-healing via dual-dynamic bonding for athletic diabetic foot wound healing . ACS Nano , 2022 . 16 3194 - 3207 . DOI: 10.1021/acsnano.1c11040 http://doi.org/10.1021/acsnano.1c11040 .

Li, J. J.; Meng, X. Y.; Men, Z. N.; Chen, X.; Shen, T.; Liu, J. S . Electric and reactive oxygen species dual-responsive polymeric micelles improve the therapeutic efficacy of lamotrigine in pentylenetetrazole kindling rats . Colloids Surf. A , 2022 . 642 128628 DOI: 10.1016/j.colsurfa.2022.128628 http://doi.org/10.1016/j.colsurfa.2022.128628 .

Hsieh, P. H.; Huang, W. Y.; Wang, H. C.; Kuan, C. H.; Shiue, T. Y.; Chen, Y.; Wang, T. W . Dual-responsive polypeptide nanoparticles attenuate tumor-associated stromal desmoplasia and anticancer through programmable dissociation . Biomaterials , 2022 . 284 121469 DOI: 10.1016/j.biomaterials.2022.121469 http://doi.org/10.1016/j.biomaterials.2022.121469 .

Fan, X.; Gu, S.; Lei, J.; Gu, S.; Yang, L . Controlled release of insulin based on temperature and glucose dual responsive biomicrocapsules . Molecules , 2022 . 27 1686 DOI: 10.3390/molecules27051686 http://doi.org/10.3390/molecules27051686 .

Carrod, A. J.; Graglia, F.; Male, L.; Le Duff, C.; Simpson, P.; Elsherif, M.; Ahmed, Z.; Butt, H.; Xu, G. X.; Kam-Wing Lo, K.; Bertoncello, P.; Pikramenou, Z . Photo- and electrochemical dual-responsive iridium probe for saccharide detection . Chem. Eur. J. , 2022 . 28 e202103541 DOI: 10.1002/chem.202103541 http://doi.org/10.1002/chem.202103541 .

Wang, Z.; Li, Y.; Wang, X.; Pi, M.; Yan, B.; Ran, R . A rapidly responsive, controllable, and reversible photo-thermal dual response hydrogel . Polymer , 2021 . 237 124344 DOI: 10.1016/j.polymer.2021.124344 http://doi.org/10.1016/j.polymer.2021.124344 .

Wang, F.; Sha, X.; Song, X.; Bai, M.; Tian, X.; Liu, L . A dual-responsive peptide-based smart biointerface with biomimetic adhesive behaviors for bacterial isolation . Langmuir , 2021 . 37 14638 - 14645 . DOI: 10.1021/acs.langmuir.1c02357 http://doi.org/10.1021/acs.langmuir.1c02357 .

Tian, M.; Xin, F.; Gao, Y.; Nie, J.; Sun, F . Design of a near-infrared-triggered photo/thermal dual-responsive composite carrier with excellent biocompatibility for controllable drug release . J. Appl. Polym. Sci. , 2022 . 139 e52029 DOI: 10.1002/app.52029 http://doi.org/10.1002/app.52029 .

Lei, B.; Sun, M.; Chen, M.; Xu, S.; Liu, H . pH and temperature double-switch hybrid micelles for controllable drug release . Langmuir , 2021 . 37 14628 - 14637 . DOI: 10.1021/acs.langmuir.1c02298 http://doi.org/10.1021/acs.langmuir.1c02298 .

Sun, Y. J.; Cheng, X. X.; Miao, T. F.; Ma, H. T.; Zhang, W.; Zhu, X. L . Reversible CO 2 -, photo- and thermo-triple responsive supramolecular chirality of azo-containing block copolymer assemblies prepared by polymerization-induced chiral self-assembly . Chinese J. Polym. Sci. , 2022 . 40 56 - 66 . DOI: 10.1007/s10118-021-2647-3 http://doi.org/10.1007/s10118-021-2647-3 .

Cheng, X. X.; Miao, T. F.; Yin, L.; Zhang, Wei, Zhu, X. L . Construction of supramolecular chirality in polymer systems: Chiral induction, transfer and application . Chinese J. Polym. Sci. , 2021 . 39 1357 - 1375 . DOI: 10.1007/s10118-021-2561-8 http://doi.org/10.1007/s10118-021-2561-8 .

Liang, S. F.; Nie, C.; Yan, J.; Zhang, Q. J.; Wu, S . Photoinduced reversible solid-to-liquid transitions and directional photofluidization of azobenzene-containing polymers . Chinese J. Polym. Sci. , 2021 . 39 1225 - 1234 . DOI: 10.1007/s10118-021-2519-x http://doi.org/10.1007/s10118-021-2519-x .

Zegota, M. M.; Mueller, M. A.; Lantzberg, B.; Kizilsavas, G.; Coelho, J. A. S.; Moscariello, P.; Martinez-Negro, M.; Morsbach, S.; Gois, P. M. P.; Wagner, M.; Ng, D. Y. W.; Kuan, S. L.; Weil, T . Dual stimuli-responsive dynamic covalent peptide tags: toward sequence-controlled release in tumor-like microenvironments . J. Am. Chem. Soc. , 2021 . 143 17047 - 17058 . DOI: 10.1021/jacs.1c06559 http://doi.org/10.1021/jacs.1c06559 .

Li, Q.; Fu, D.; Zhang, J.; Yan, H.; Wang, H.; Niu, B.; Guo, R.; Liu, Y . Dual stimuli-responsive polypeptide-calcium phosphate hybrid nanoparticles for co-delivery of multiple drugs in cancer therapy . Colloids Surf. B , 2021 . 200 111586 DOI: 10.1016/j.colsurfb.2021.111586 http://doi.org/10.1016/j.colsurfb.2021.111586 .

Kudruk, S.; Pottanam Chali, S.; Linard Matos, A. L.; Bourque, C.; Dunker, C.; Gatsogiannis, C.; Ravoo, B. J.; Gerke, V . Biodegradable and dual-responsive polypeptide-shelled cyclodextrin-containers for intracellular delivery of membrane-impermeable cargo . Adv. Sci. , 2021 . 8 2100694 DOI: 10.1002/advs.202170112 http://doi.org/10.1002/advs.202170112 .

Dong, L.; Chen, H.; Liu, T.; Zhu, J.; Yu, M.; Yuan, Q . Poly(L-cysteine) peptide amphiphile derivatives containing disulfide bonds: synthesis, self-assembly-induced β -sheet nanostructures, pH/reduction dual response, and drug release . Biomacromolecules , 2021 . 22 5374 - 5381 . DOI: 10.1021/acs.biomac.1c01324 http://doi.org/10.1021/acs.biomac.1c01324 .

Zhang, P.; Gao, Z.; Cui, J.; Hao, J . Dual-stimuli-responsive polypeptide nanoparticles for photothermal and photodynamic therapy . ACS Appl. BioMater. , 2020 . 3 561 - 569 . DOI: 10.1021/acsabm.9b00964 http://doi.org/10.1021/acsabm.9b00964 .

Zhang, X.; Yin, T.; Wang, S.; Hao, Z.; He, Y.; Li, C.; Zhao, Q.; He, H.; Gao, D . Dual stimuli-responsive peptide-based palladium nano-lychee spheres for synergistic antitumor therapy . ACS Biomater. Sci. Eng. , 2019 . 5 4474 - 4484 . DOI: 10.1021/acsbiomaterials.9b01161 http://doi.org/10.1021/acsbiomaterials.9b01161 .

Xiao, Y.; Tang, C.; Chen, Y.; Lang, M . Dual stimuli-responsive polypeptide prepared by thiol-ene click reaction of poly(L-cysteine) and N,N -dimethylaminoethyl acrylate . Biopolymers , 2019 . 110 e23318 DOI: 10.1002/bip.23318 http://doi.org/10.1002/bip.23318 .

Qu, J.; Wang, R.; Peng, S.; Shi, M. Y.; Yang, S. T.; Luo, J. B.; Lin, J.; Zhou, Q. H . Stepwise dual pH and redox-responsive cross-linked polypeptide nanoparticles for enhanced cellular uptake and effective cancer therapy . J. Mater. Chem. B , 2019 . 7 7129 - 7140 . DOI: 10.1039/c9tb01773a http://doi.org/10.1039/c9tb01773a .

Ding, Y.; Du, C.; Qian, J. W.; Dong, C. M . Zwitterionic polypeptide nanomedicine with dual NIR/reduction-responsivity for synergistic cancer photothermal-chemotherapy . Polym. Chem. , 2019 . 10 4825 - 4836 . DOI: 10.1039/C9PY00986H http://doi.org/10.1039/C9PY00986H .

Xiong, W.; Fu, X. H.; Wan, Y. M.; Sun, Y. L.; Li, Z. B.; Lu, H . Synthesis and multimodal responsiveness of poly( α -amino-acid)s bearing OEGylated azobenzene side-chains . Polym. Chem. , 2016 . 7 6375 - 6382 . DOI: 10.1039/C6PY01364C http://doi.org/10.1039/C6PY01364C .

Xiong, W.; Zhang, C.; Lyu, X. L.; Zhou, H. T.; Chang, W. Y.; Bo, Y.; Chen, E. Q.; Shen, Z. H.; Lu, H . Synthesis of modifiable photo-responsive polypeptides bearing allyloxyazobenzene side-chains . Polym. Chem. , 2020 . 11 439 - 448 . DOI: 10.1039/C9PY01106D http://doi.org/10.1039/C9PY01106D .

Fu, X.; Tian, J.; Li, Z.; Sun, J.; Li, Z . Dual-responsive pegylated polypeptoids with tunable cloud point temperatures . Biopolymers , 2019 . 110 e23243 DOI: 10.1002/bip.23243 http://doi.org/10.1002/bip.23243 .

Li, Y.; Tom, J. C.; Biehl, P.; Ling, J.; Schacher, F. H . Block polypeptoids: synthesis, characterization, and response toward irradiation with UV light and temperature . Macromolecules , 2020 . 53 5218 - 5226 . DOI: 10.1021/acs.macromol.0c00654 http://doi.org/10.1021/acs.macromol.0c00654 .

Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A.; Armand, P.; Bradley, E. K.; Truong, K. T. V.; Dill, K. A.; Cohen, F. E.; Zuckermann, R. N . Sequence-specific polypeptoids: a diverse family of heteropolymers with stable secondary structure . Proc. Natl. Acad. Sci. U.S.A. , 1998 . 95 4303 - 4308 . DOI: 10.1073/pnas.95.8.4303 http://doi.org/10.1073/pnas.95.8.4303 .

Klinker, K.; Barz, M . Polypept(o)ides: hybrid systems based on polypeptides and polypeptoids . Macromol. Rapid Commun. , 2015 . 36 1943 - 1957 . DOI: 10.1002/marc.201500403 http://doi.org/10.1002/marc.201500403 .

Robinson, J. W.; Schlaad, H . A versatile polypeptoid platform based on N -allyl glycine . Chem. Commun. , 2012 . 48 7835 - 7837 . DOI: 10.1039/c2cc33881e http://doi.org/10.1039/c2cc33881e .

Rosales, A. M.; Segalman, R. A.; Zuckermann, R. N . Polypeptoids: a model system to study the effect of monomer sequence on polymer properties and self-assembly . Soft Matter , 2013 . 9 8400 - 8414 . DOI: 10.1039/c3sm51421h http://doi.org/10.1039/c3sm51421h .

Zhang, D.; Lahasky, S. H.; Guo, L.; Lee, C. U.; Lavan, M . Polypeptoid materials: current status and future perspectives . Macromolecules , 2012 . 45 5833 - 5841 . DOI: 10.1021/ma202319g http://doi.org/10.1021/ma202319g .

Zhang, Y.; Huang, J.; Zhang, J.; Zhu, X.; Tong, G . Synthesis and self-assembly of photo-responsive polypeptoid-based copolymers containing azobenzene side chains . Polym. Chem. , 2021 . 12 1823 - 1829 . DOI: 10.1039/D0PY01723J http://doi.org/10.1039/D0PY01723J .

Liu, G.; Baker, G. L . Structure-directed self-assembly of alkyl- aryl-ethylene oxide amphiphiles . Soft Matter , 2008 . 4 1094 - 1101 . DOI: 10.1039/b716041k http://doi.org/10.1039/b716041k .

Dong, R. J.; Zhu, B. S.; Zhou, Y. F.; Yan, D. Y.; Zhu, X. Y . Reversible photoisomerization of azobenzene-containing polymeric systems driven by visible light . Polym. Chem. , 2013 . 4 912 - 915 . DOI: 10.1039/C2PY21060F http://doi.org/10.1039/C2PY21060F .

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