Fluorescent ligands for the hemagglutinin of influenza A: synthesis and ligand binding assays

Bioconjug Chem. 2007 Jan-Feb;18(1):231-7. doi: 10.1021/bc060178w.

Abstract

Two fluorescent conjugates of sialic acid have been prepared, with a convenient synthetic route that involves preparation of an unsaturated benzyl ester by cross-metathesis, followed by combined hydrogenation/ hydrogenolysis to provide a sialoside bearing a delta-carboxybutyl group, suitable for coupling with the chosen fluorophores. The fluorescent conjugates bound to bromelain-cleaved hemagglutinin (BHA) with affinities in the low microM range. Binding was accompanied by approximately 4.5-fold fluorescence enhancement for the dansyl conjugate 1 and approximately 3-fold fluorescence quenching for the pyrene conjugate 3.

MeSH terms

  • Fluorescent Dyes / chemistry*
  • Hemagglutinin Glycoproteins, Influenza Virus / analysis*
  • Hemagglutinin Glycoproteins, Influenza Virus / chemistry*
  • Influenza A virus / chemistry*
  • Ligands
  • Molecular Structure

Substances

  • Fluorescent Dyes
  • Hemagglutinin Glycoproteins, Influenza Virus
  • Ligands