Discovery and characterization of a cell-permeable, small-molecule c-Abl kinase activator that binds to the myristoyl binding site

Chem Biol. 2011 Feb 25;18(2):177-86. doi: 10.1016/j.chembiol.2010.12.013.

Abstract

c-Abl kinase activity is regulated by a unique mechanism involving the formation of an autoinhibited conformation in which the N-terminal myristoyl group binds intramolecularly to the myristoyl binding site on the kinase domain and induces the bending of the αI helix that creates a docking surface for the SH2 domain. Here, we report a small-molecule c-Abl activator, DPH, that displays potent enzymatic and cellular activity in stimulating c-Abl activation. Structural analyses indicate that DPH binds to the myristoyl binding site and prevents the formation of the bent conformation of the αI helix through steric hindrance, a mode of action distinct from the previously identified allosteric c-Abl inhibitor, GNF-2, that also binds to the myristoyl binding site. DPH represents the first cell-permeable, small-molecule tool compound for c-Abl activation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Binding Sites
  • Crystallography, X-Ray
  • Drug Discovery*
  • Enzyme Activation / drug effects
  • Hep G2 Cells
  • Humans
  • Hydantoins / chemistry
  • Hydantoins / metabolism*
  • Hydantoins / pharmacology*
  • Models, Molecular
  • Molecular Sequence Data
  • Permeability
  • Phosphorylation / drug effects
  • Protein Binding
  • Protein Structure, Tertiary
  • Proto-Oncogene Proteins c-abl / chemistry
  • Proto-Oncogene Proteins c-abl / metabolism*
  • Proto-Oncogene Proteins c-crk / metabolism
  • Pyrazoles / chemistry
  • Pyrazoles / metabolism*
  • Pyrazoles / pharmacology*

Substances

  • 5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-2,4-imidazolidinedione
  • Hydantoins
  • Proto-Oncogene Proteins c-crk
  • Pyrazoles
  • Proto-Oncogene Proteins c-abl

Associated data

  • PDB/3PYY