Syntheses of sulfated glycopolymers and analyses of their BACE-1 inhibitory activity

Yuri Nishimura, Hiroki Shudo, Hirokazu Seto, Yu Hoshino, Yoshiko Miura

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Abstract

The glycopolymers for glycosaminoglycan mimic were synthesized, and the inhibitory effects of Alzheimer's β-secretase (BACE-1) were examined. The regio-selective sulfation was conducted on N-acetyl glucosamine (GlcNAc), and the acrylamide derivatives were synthesized with the consequent sulfated GlcNAc. The glycopolymers were synthesized with acrylamide using radical initiator. The glycopolymer with sulfated GlcNAc showed the strong inhibitory effect on BACE-1, and the inhibitory effects were dependent on the sulfation positions. Especially, glycopolymers carrying 3,4,6-O-sulfo-GlcNAc showed the strong inhibitory effect. The docking simulation suggested that glycopolymers bind to the active site of BACE-1.

Original languageEnglish
Pages (from-to)6390-6395
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number23
DOIs
Publication statusPublished - Dec 1 2013

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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