Tweaking the acid-sensitivity of transiently thermoresponsive polyacrylamides with cyclic acetal repeating units  

作　　者：Simon Van Herck Bruno G.De Geest 

机构地区：[1]Department of Pharmaceutics,Ghent University,Ghent,Belgium

出　　处：《Science China Chemistry》2020年第4期504-512,共9页中国科学（化学英文版）

基　　金：supported by Ghent University through the BOF-GOA grant scheme.

摘　　要：Merging the characteristics of thermoresponsive and stimuli-degradable polymers yields so-called transiently thermoresponsive polymers, which can find application for the design of injectable gels, nanoparticles, etc. within a biomedical context. Among these polymers, only a limited number is reported which shows selective degradation under mild acidic conditions. However,extension of the library of transiently thermoresponsive polymers is desired to broadening the biomaterials toolbox to suit specific needs. Three monomers were developed by modification of 2-hydroxyethylacrylamide(HEAm) via tetrahydropyranylation or-furanylation with 3,4-dihydro-2 H-pyran(DHP), 2,3-dihydrofuran(DHF) or 2,3-dihydro-5-methylfuran(MeDHF). The presence of an acetal or ketal bond provided the monomers a pH-dependent hydrolysis behavior ranging from minutes to days. RAFT polymerisation allowed for the construction of homopolymers with temperature responsive behavior and pH-dependent hydrolysis which was strongly influenced by nature of the monomeric repeating units.Merging the characteristics of thermoresponsive and stimuli-degradable polymers yields so-called transiently thermoresponsive polymers, which can find application for the design of injectable gels, nanoparticles, etc. within a biomedical context. Among these polymers, only a limited number is reported which shows selective degradation under mild acidic conditions. However,extension of the library of transiently thermoresponsive polymers is desired to broadening the biomaterials toolbox to suit specific needs. Three monomers were developed by modification of 2-hydroxyethylacrylamide(HEAm) via tetrahydropyranylation or-furanylation with 3,4-dihydro-2 H-pyran(DHP), 2,3-dihydrofuran(DHF) or 2,3-dihydro-5-methylfuran(MeDHF). The presence of an acetal or ketal bond provided the monomers a pH-dependent hydrolysis behavior ranging from minutes to days. RAFT polymerisation allowed for the construction of homopolymers with temperature responsive behavior and pH-dependent hydrolysis which was strongly influenced by nature of the monomeric repeating units.

关 键 词：ACETALS POLYACRYLAMIDES STIMULI-RESPONSIVE 

分 类 号：TQ460.1[化学工程—制药化工]