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

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 RA FT,slab 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). The bioactivity of the glucose moieties on the surface of the particles was examined using two classes of lectins, namely plant lectin (Concanavalin A, Canavalia ensiformis) and bacteria lectin (fimH, from Escherichia coli). Successful binding was demonstrated, thus illustrating, that these particles have potential as smart materials in biological systems.