Controlled/Living ab Initio Emulsion Polymerization via a Glucose RAFTstab: Degradable Cross-Linked Glyco-Particles for Concanavalin A/FimH Conjugations to Cluster E. coli Bacteria

Abstract

Glyco-particles bearing glucose units have been prepared via a one-step controlled/living ab initio cross-linking emulsion polymerization of styrene based on self-assembly via a glucose RAFTstab (reversible addition−fragmentation chain transfer colloidal stabilizer). The RAFTstab was synthesized from the monomer 2-(methacrylamido)glucopyranose (MAG) and the hydrophobic trithiocarbonate RAFT agent S-methoxycarbonylphenylmethyl dodecyltrithiocarbonate (MCPDT). In order to obtain glyco-particles stable for biomedical applications, a degradable bis(2-acryloyloxyethyl) disulfide cross-linker (disulfide diacrylate, DSDA) was employed in the emulsion polymerization. The cross-linked glyco-particles were stable in N,N-dimethylacetamide (DMAc), in contrast to the corresponding non-cross-linked glyco-particles which disintegrate to form linear glycopolymers in solution. The cross-linked particles underwent reductive degradation into the constituent linear (primary) chains upon treatment with 1,4-dithiothreitol (DDT...