Synthesis and characterization of 5'-p-fluorosulfonylbenzoyl-2' (or 3')-(biotinyl)adenosine as an activity-based probe for protein kinases

J Biomol Screen. 2007 Feb;12(1):126-32. doi: 10.1177/1087057106296685. Epub 2006 Dec 8.

Abstract

Most of the kinase inhibitors that are approved for therapeutic uses or that are undergoing clinical trials are directed toward the adenosine triphosphate (ATP) binding site of protein kinases. 5'-Fluorosulfonylbenzoyl 5'-adenosine (FSBA) is an activitybased probe (ABP) that covalently modifies a conserved lysine present in the nucleotide binding site of most kinases. Here the authors describe synthesis of FSBA derivatives, 2'-biotinyl-FSBA and 3'-biotinyl-FSBA as kinase ABPs, and delineate a Western blot method to screen and validate ATP competitive protein kinase inhibitors using biotinyl-FSBA as a nonselective activity-based probe for protein kinases.

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / analysis
  • Adenosine / chemical synthesis
  • Adenosine / chemistry
  • Adenosine Triphosphate / pharmacology
  • Binding, Competitive / drug effects
  • Biotin / analogs & derivatives*
  • Biotin / analysis*
  • Biotin / chemical synthesis*
  • Biotin / chemistry
  • Blotting, Western
  • Chromatography, Liquid
  • Mass Spectrometry
  • Molecular Probes / analysis*
  • Molecular Probes / chemical synthesis*
  • Protein Kinase Inhibitors / pharmacology
  • Protein Kinases / metabolism*

Substances

  • Molecular Probes
  • Protein Kinase Inhibitors
  • Biotin
  • 5'-(4-fluorosulfonylbenzoyl)adenosine
  • Adenosine Triphosphate
  • Protein Kinases
  • Adenosine