Synthesis of a cluster-forming sialylthio-D-galactose fullerene conjugate and evaluation of its interaction with influenza virus hemagglutinin and neuraminidase

Bioorg Med Chem Lett. 2014 Jun 1;24(11):2420-3. doi: 10.1016/j.bmcl.2014.04.032. Epub 2014 Apr 18.

Abstract

In order to obtain self assembling, multivalent ligand for influenza virus hemagglutinin α-N-acetylneuraminyl-(2-6)-D-galactopyranose has been synthesized and bonded to a water soluble fullerene derivative using 1,3-dipolar cycloaddition click reaction. The aggregating amphiphilic compound did not inhibit the influenza virus hemagglutinin, but it proved to be an inhibitor of its neuraminidase with a 50% inhibitory concentration of 81 μM.

Keywords: Aggregation; Antiviral activity; Fullerene; Multivalent ligand; Sialic acid; Thiodisaccharide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged-Ring Compounds / chemical synthesis
  • Bridged-Ring Compounds / chemistry
  • Bridged-Ring Compounds / pharmacology*
  • Disaccharides / chemical synthesis
  • Disaccharides / chemistry
  • Disaccharides / pharmacology*
  • Dose-Response Relationship, Drug
  • Fullerenes / chemistry
  • Fullerenes / pharmacology*
  • Hemagglutinins / metabolism*
  • Ligands
  • Molecular Structure
  • Neuraminidase / antagonists & inhibitors*
  • Neuraminidase / metabolism
  • Orthomyxoviridae / drug effects
  • Orthomyxoviridae / metabolism*
  • Structure-Activity Relationship

Substances

  • Bridged-Ring Compounds
  • Disaccharides
  • Fullerenes
  • Hemagglutinins
  • Ligands
  • Neuraminidase