Syntheses of sulfo-glycodendrimers using click chemistry and their biological evaluation

Yoshiko Miura, Shunsuke Onogi, Tomohiro Fukuda

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Abstract

A series of novel glycol-clusters containing sulfonated N-acetyl-D-glucosamine (GlcNAc) have been synthesized using click chemistry. Three dendrimers with aromatic dendrons were synthesized using chlorination, azidation and click chemistries. The resulting dendrimers were modified with azide-terminated sulfonated GlcNAc using click chemistry. The sulfonated dendrimers showed affinity for proteins, including the lectin wheat germ agglutinin and amyloid beta peptide (1-42). The dendrimers of G1 and G2 in particular showed the largest affinity for the proteins. The addition of the sulfonated GlcNAc dendrimers of G1 and G2 exhibited an inhibition effect on the aggregation of the amyloid beta peptide, reduced the β-sheet conformation, and led to a reduction in the level of nanofiber formation.

Original languageEnglish
Pages (from-to)11877-11896
Number of pages20
JournalMolecules
Volume17
Issue number10
DOIs
Publication statusPublished - Oct 1 2012

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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