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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 RAFT stab (reversible addition−fragmentation chain transfer colloidal stabilizer). The RAFT stab 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 ( fim H, from Escherichia coli ). Successful binding was demonstrated, thus illustrating that these particles have potential as “smart” materials in biological systems.
Ting et al. (Mon,) studied this question.