Anti-biofouling properties of a telomer brush with pendent glucosylurea groups.

A thiol-group-carrying telomer with pendent D-glucosylurea groups [poly(glucosylureaethyl methacrylate)-SH (PolyGUMA-SH)] was obtained by reversible addition-fragmentation chain-transfer (RAFT) polymerization of GUMA in the presence of 4,4'-azobis(4-cyanopentanoic acid) (initiator) and 4-cyanopentanoic acid dithiobenzoate (chain-transfer agent) and subsequent reduction with NaBH4. The thiol-carrying telomer was accumulated on both a gold electrode and a colloidal gold-immobilized glass substrate as proven by cyclic voltammetry using hydroquinone as a probe, and the increase in absorbance at 550 nm was ascribable to localized surface plasmon resonance (LSPR), respectively. The adsorption of various proteins to the surface of the telomer brush was examined by the LSPR method, too. The PolyGUMA brush showed a significant resistance against nonspecific adsorption of proteins, such as lysozyme, bovine serum albumin, immunoglobulin G, and fibrinogen. Furthermore, sugar-binding proteins, concanavalin A (Con A, with an affinity for mannose and glucose) and wheat germ agglutinin (WGA, with an affinity for N-acetylglucosamine), were not adsorbed to the GUMA-carrying brush, which is in contrast with the prompt and distinct binding of these proteins to the telomer brushes composed of 2-methacryloyloxyethyl D-glucopyranoside (Con A) and 1-O-(6'-methacrylamido)hexyl-2-N-acetoamido-2-deoxy-D-glucopyranoside residues (WGA). The glucosylurea-group-carrying telomer brush prepared here might be quite useful to provide a "bio-inert (anti-biofouling)" surface in biomedical fields.