Powerful probes for glycosidases: novel, fluorescently tagged glycosidase inhibitors

Bioorg Med Chem Lett. 2001 May 21;11(10):1339-42. doi: 10.1016/s0960-894x(01)00209-8.

Abstract

Amino-1,2,5-trideoxy-2,5-imino-D-mannitol was fluorescently tagged by reaction with dansyl chloride at N-1 or by attachment of a dansyl amide bearing spacer to this centre. Compounds obtained are highly potent inhibitors of beta-glucosidase exhibiting Ki values in the single figure nanomolar range. The 1-N-dansyl substituted inhibitor was successfully exploited for binding studies with beta-glucosidase from Agrobacterium sp. employing fluorescence spectrometric methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding, Competitive
  • Dansyl Compounds / chemistry
  • Dose-Response Relationship, Drug
  • Electrophoresis, Polyacrylamide Gel / methods
  • Enzyme Inhibitors* / chemical synthesis
  • Enzyme Inhibitors* / metabolism
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / metabolism
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Mannitol / chemical synthesis
  • Mannitol / metabolism
  • Molecular Probes / chemical synthesis
  • Molecular Probes / metabolism
  • Protein Binding
  • Rhizobium / enzymology

Substances

  • Dansyl Compounds
  • Enzyme Inhibitors
  • Fluorescent Dyes
  • Molecular Probes
  • Mannitol
  • Glycoside Hydrolases
  • dansyl chloride