Fragment-based discovery of focal adhesion kinase inhibitors

Bioorg Med Chem Lett. 2013 Oct 1;23(19):5401-9. doi: 10.1016/j.bmcl.2013.07.050. Epub 2013 Jul 31.

Abstract

Chemically diverse fragment hits of focal adhesion kinase (FAK) were discovered by surface plasmon resonance (SPR) screening of our in-house fragment library. Site specific binding of the primary hits was confirmed in a competition setup using a high-affinity ATP-site inhibitor of FAK. Protein crystallography revealed the binding mode of 41 out of 48 selected fragment hits within the ATP-site. Structural comparison of the fragment binding modes with a DFG-out inhibitor of FAK initiated first synthetic follow-up optimization leading to improved binding affinity.

Keywords: DFG-out; Focal adhesion kinase; Fragment screening; Surface plasmon resonance; X-ray structure.

MeSH terms

  • Crystallography, X-Ray
  • Drug Discovery*
  • Drug Evaluation, Preclinical
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Focal Adhesion Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Indoles / chemistry*
  • Indoles / pharmacology*
  • Inhibitory Concentration 50
  • Models, Molecular
  • Molecular Structure
  • Peptide Fragments / genetics
  • Peptide Fragments / pharmacology*
  • Small Molecule Libraries* / chemistry
  • Small Molecule Libraries* / pharmacology
  • Solubility
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology*
  • Surface Plasmon Resonance

Substances

  • Enzyme Inhibitors
  • Indoles
  • N-methyl-N-(3-((2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-5-trifluoromethyl-pyrimidin-4-ylamino)-methyl)-pyridin-2-yl)-methanesulfonamide
  • Peptide Fragments
  • Small Molecule Libraries
  • Sulfonamides
  • Focal Adhesion Protein-Tyrosine Kinases