Antifouling Glycocalyx-Mimetic Peptoids

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• 作者：Hyun Ok Ham ; Sung Hyun Park ; Josh W. Kurutz ; Igal G. Szleifer ; Phillip B. Messersmith
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：September 4, 2013
• 年：2013
• 卷：135
• 期：35
• 页码：13015-13022
• 全文大小：507K
• 年卷期：v.135,no.35(September 4, 2013)
• ISSN：1520-5126

文摘

The glycocalyx of the cell is composed of highly hydrated saccharidic groups conjugated to protein and lipid cores. Although components of the glycocalyx are important in cell鈥揷ell interactions and other specific biological recognition events, a fundamental role of the glycocalyx is the inhibition of nonspecific interactions at the cell surface. Inspired by glycoproteins present in the glycocalyx, we describe a new class of synthetic antifouling polymer composed of saccharide containing N-substituted polypeptide (glycopeptoid). Grafting of glycopeptoids to a solid surface resulted in a biomimetic shielding layer that dramatically reduced nonspecific protein, fibroblast, and bacterial cell attachment. All-atom molecular dynamics simulation of grafted glycopeptoids revealed an aqueous interface enriched in highly hydrated saccharide residues. In comparison to saccharide-free peptoids, the interfacial saccharide residues of glycopeptoids formed a higher number of hydrogen bonds with water molecules. Moreover, these hydrogen bonds displayed a longer persistence time, which we believe contributed to fouling resistance by impeding interactions with biomolecules. Our findings suggest that the fouling resistance of glycopeptoids can be explained by the presence of both a 鈥榳ater barrier鈥?effect associated with the hydrated saccharide residues as well as steric hindrance from the polymer backbone.