A facile synthetic approach to L- and P-selectin blockers via copolymerization of vinyl monomers constructing the key carbohydrate modules of Sialyl Lewisx mimics

Yoshihiro Nishida, Hirotaka Uzawa, Tadashi Toba, Kenji Sasaki, Hirosato Kondo, Kazukiyo Kobayashi

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34 Citations (Scopus)

Abstract

A highly practical synthetic approach is described for artificial L- and P-selectin blockers. The synthesis involves radical bi- and terpolymerizations of p-(N-acrylamido)phenyl 3- or/and 6-sulfo-β-D-galactoside with allyl α-L-fucoside in the presence of acrylamide. Each of the two glycosyl monomers constructs a key carbohydrate module responsible for selectins/sulfated sialyl Lewisx (sLex) bindings. Whereas an acrylamide copolymer carrying 3-sulfo-galactoside showed no activity for any selectins, the fucosylated terpolymer showed a potent activity to block both of P- and L-selectins/sLex binding at a concentration of a few micrograms per milliliter. The enhanced activity is apparently ascribed to the cooperative binding effects of the fucoside and the 3-sulfo-galactoside residues.

Original languageEnglish
Pages (from-to)68-74
Number of pages7
JournalBiomacromolecules
Volume1
Issue number1
Publication statusPublished - Mar 1 2000
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Bioengineering
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry

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