Clinical stage EGFR inhibitors irreversibly alkylate Bmx kinase

Bioorg Med Chem Lett. 2008 Nov 15;18(22):5916-9. doi: 10.1016/j.bmcl.2008.07.062. Epub 2008 Jul 18.

Abstract

Irreversible HER/erbB inhibitors selectively inhibit HER-family kinases by targeting a unique cysteine residue located within the ATP-binding pocket. Sequence alignment reveals that this rare cysteine is also present in ten other protein kinases including all five Tec-family members. We demonstrate that the Tec-family kinase Bmx is potently inhibited by irreversible modification at Cys496 by clinical stage EGFR inhibitors such as CI-1033. This cross-reactivity may have significant clinical implications.

MeSH terms

  • Animals
  • Cysteine / genetics
  • Cysteine / metabolism
  • ErbB Receptors / antagonists & inhibitors*
  • Mice
  • Molecular Structure
  • Morpholines / chemistry
  • Morpholines / pharmacology*
  • Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*
  • Sequence Homology, Amino Acid

Substances

  • Morpholines
  • PD168393
  • Quinazolines
  • Canertinib
  • Bmx protein, mouse
  • Tec protein-tyrosine kinase
  • ErbB Receptors
  • Protein-Tyrosine Kinases
  • Cysteine