Synthetic hydrogels formed by thiol-ene crosslinking of vinyl sulfone-functional poly(methyl vinyl ether-alt-maleic acid) with α,ω-dithio-polyethyleneglycol

被引：23

作者：

Stewart, S. A. ^{[1
]}

Coulson, M. B. ^{[1
]}

Zhou, C. ^{[1
]}

Burke, N. A. D. ^{[1
]}

Stover, H. D. H. ^{[1
]}

机构：

[1] McMaster Univ, Dept Chem & Chem Biol, Hamilton, ON L8S 4M1, Canada

来源：

SOFT MATTER | 2018年 / 14卷 / 41期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CELL ENCAPSULATION; MICHAEL ADDITION; CLICK REACTION; DRUG-DELIVERY; POLY(ETHYLENE GLYCOL); PROTEIN RELEASE; DEGRADATION; CHEMISTRY; POLYMERS; MATRIX;

D O I：

10.1039/c8sm01066h

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Polymer hydrogels formed by rapid thiol-ene coupling of macromolecular gel formers can offer access to versatile new matrices. This paper describes the efficient synthesis of cysteamine vinyl sulfone (CVS) trifluoroacetate, and its incorporation into poly(methyl vinyl ether-alt-maleic anhydride) (PMMAn) to form a series of CVS-functionalized poly(methyl vinyl ether-alt-maleic acid) polymers (PMM-CVSx) containing 10 to 30 mol% pendant vinyl sulfone groups. Aqueous mixtures of these PMM-CVS and a dithiol crosslinker, alpha,omega-dithio-polyethyleneglycol (HS-PEG-SH, M-n = 1 kDa), gelled through crosslinking by Michael addition within seconds to minutes, depending on pH, degree of functionalization, and polymer loading. Gelation efficiency, Young's modulus, equilibrium swelling and hydrolytic stability are described, and step-wise hydrogel post-functionalization with a small molecule thiol, cysteamine, was demonstrated. Cytocompatibility of these crosslinked hydrogels towards entrapped 3T3 fibroblasts was confirmed using a live/dead fluorescence assay.

引用

页码：8317 / 8324

页数：8

共 62 条

[1] Hydrogel: Preparation, characterization, and applications: A review [J].

Ahmed, Enas M. .

JOURNAL OF ADVANCED RESEARCH, 2015, 6 (02) :105-121

[2] Microfluidic Synthesis of Cell-Type-Specific Artificial Extracellular Matrix Hydrogels [J].

Allazetta, Simone ;

Hausherr, Tanja C. ;

Lutolf, Matthias P. .

BIOMACROMOLECULES, 2013, 14 (04) :1122-1131

[3] Fabrication of poly(ethylene glycol)-based cyclodextrin containing hydrogels via thiol-ene click reaction [J].

Arslan, Mehmet ;

Gevrek, Tugce Nihal ;

Sanyal, Rana ;

Sanyal, Amitav .

EUROPEAN POLYMER JOURNAL, 2015, 62 :426-434

[4] INTRAMOLECULAR CATALYSIS OF HYDROLYTIC REACTIONS .2. THE HYDROLYSIS OF PHTHALAMIC ACID [J].

BENDER, ML ;

CHOW, YL ;

CHLOUPEK, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (20) :5380-5384

[5] Selective targeting of lysosomal cysteine proteases with radiolabeled electrophilic substrate analogs [J].

Bogyo, M ;

Verhelst, S ;

Bellingard-Dubouchaud, V ;

Toba, S ;

Greenbaum, D .

CHEMISTRY & BIOLOGY, 2000, 7 (01) :27-38

[6] Matrix elasticity, cytoskeletal forces and physics of the nucleus: how deeply do cells 'feel' outside and in? [J].

Buxboim, Amnon ;

Ivanovska, Irena L. ;

Discher, Dennis E. .

JOURNAL OF CELL SCIENCE, 2010, 123 (03) :297-308

[7] An in situ-forming zwitterionic hydrogel as vitreous substitute [J].

Chang, Jing ;

Tao, Yong ;

Wang, Bin ;

Guo, Bao-hua ;

Xu, Hong ;

Jiang, Yan-rong ;

Huang, Yanbin .

JOURNAL OF MATERIALS CHEMISTRY B, 2015, 3 (06) :1097-1105

[8] Relative reactivity and selectivity of vinyl sulfones and acrylates towards the thiol-Michael addition reaction and polymerization [J].

Chatani, Shunsuke ;

Nair, Devatha P. ;

Bowman, Christopher N. .

POLYMER CHEMISTRY, 2013, 4 (04) :1048-1055

[9] Biodegradable and Biocompatible Synthetic Saccharide-Peptide Hydrogels for Three-Dimensional Stem Cell Culture [J].

Chawla, Kanika ;

Yu, Ting-Bin ;

Liao, Sophia W. ;

Guan, Zhibin .

BIOMACROMOLECULES, 2011, 12 (03) :560-567

[10] Novel hydrogels via click chemistry: Synthesis and potential biomedical applications [J].

Crescenzi, Vittorio ;

Cornelio, Lisa ;

Di Meo, Chiara ;

Nardecchia, Stefania ;

Lamanna, Raffaele .

BIOMACROMOLECULES, 2007, 8 (06) :1844-1850

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