Novel linear polymers bearing thiosialosides as pendant-type epitopes for influenza neuraminidase inhibitors

Bioorg Med Chem Lett. 2007 Jul 15;17(14):3826-30. doi: 10.1016/j.bmcl.2007.05.016. Epub 2007 May 13.

Abstract

A conventional synthesis of alpha-thioglycoside of sialic acid as a glycomonomer was accomplished. Radical copolymerization of the glycomonomer with vinyl acetate proceeded smoothly to afford a new class of glycopolymers having thiosialoside residues, in which all protection was removed by a combination of transesterification and saponification to provide a water-soluble thiosialoside cluster. The results of a preliminary study on biological responses against influenza virus neuraminidases using the thiosialoside polymer as a candidate for a neuraminidase inhibitor showed that the glycopolymer has potent inhibitory activity against the neuraminidases.

MeSH terms

  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Epitopes / pharmacology*
  • Magnetic Resonance Spectroscopy
  • N-Acetylneuraminic Acid / chemistry
  • N-Acetylneuraminic Acid / pharmacology*
  • Neuraminidase / antagonists & inhibitors*
  • Orthomyxoviridae / enzymology*
  • Polymers / chemistry
  • Polymers / pharmacology*
  • Spectrophotometry, Infrared

Substances

  • Enzyme Inhibitors
  • Epitopes
  • Polymers
  • Neuraminidase
  • N-Acetylneuraminic Acid