Comb-Shaped Glycopolymer/Peptide Bioconjugates by Combination of RAFT Polymerization and Thiol-Ene "Click" Chemistry

Abstract

Comb-shaped glycopolymer/peptide bioconjugates are constructed by grafting reduced glutathione (GSH) onto acrylate-functional block glycocopolymers via thiol-ene click chemistry. In aqueous solution, the glycopolymer/GSH bioconjugate self-assembles to sugar-installed spherical micelles. The size of micelles decreases with increasing pH, demonstrating pH-responsive character. The isoelectric point (IEP) of the PMAGlc/GSH bioconjugate is estimated to be 3.43. The micelles show a specific interaction with the protein Concanavalin A. At endosomal pH, the PMAGlc/GSH bioconjugate can gradually degrade. These pH-responsive glycopolymer/peptide micelles with biological recognition and degradation can be used as multifunctional nanocarriers for targeted drug delivery. Tripeptide reduced glutathione (GSH) is conjugated to acrylate-functional block glycocopolymers through an acid-labile β-thiopropionate linkage. The glycopolymer/GSH bioconjugate self-assembles to sugar-installed spherical micelles with pH-sensitive, degradation, and biological recognition characteristics. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.