Thiol-alkyne chemistry for the preparation of micelles with glycopolymer corona: Dendritic surfaces versus linear glycopolymer in their ability to bind to lectins
Résumé
A poly(tert-butyl acrylate) (P(tBA)) with a glycodendric endfunctionality with eight glucose moieties was synthesised in four steps via a combination of esterification, thiol-alkyne conjugation and hetero-Diels-Alder (HDA) cycloaddition. A linear glycopolymer of similar size and composition was also synthesised in order to compare the protein binding characteristics of the polymer with glycodendritic endfunctionality to the linear glycol blockcopolymer. The two amphiphilic polymers were self-assembled in water into micelles. These particles were then tested for their ability to bind to Concanavalin A (Con A). In a turbidity assay, the polymer glycodendron exhibited a significantly faster clustering rate to the lectin as compared to the linear glycopolymer. In a precipitation assay, it is found that significantly less glucose residue is required for binding per Con A for the polymer with the glycodendritic endfunctionality. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.