Smart heparin-based bioconjugates synthesized by a combination of ATRP and click chemistry

Abstract

This article describes the synthesis of novel well defined polysaccharide–polymer bioconjugates. Alkyne-containing bioconjugates were prepared using Cu(I) catalyzed azide–alkyne [3 + 2] dipolar cycloaddition, i.e. ‘click’ chemistry between an alkyne functionalized low molecular weight heparin (LMWH) and α-azide functionalized stimuli-responsive copolymers synthesized by atom transfer radical polymerization using Activators Generated by Electron Transfer (AGET). The alkyne functionality was incorporated into the heparin by conducting a high yield amidation of the polysaccharide using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride. The structure and composition of the novel bioconjugates were confirmed by FTIR, NMR and thermogravimetric analysis (TGA).