Alpha-cyano-beta-hydroxy-beta-methyl-N-[4-(trifluoromethoxy)phenyl] propenamide: an inhibitor of the epidermal growth factor receptor tyrosine kinase with potent cytotoxic activity against breast cancer cells

Clin Cancer Res. 1998 Nov;4(11):2657-68.

Abstract

Epidermal growth factor receptor (EGF-R) tyrosine kinase is known to be overexpressed in several malignancies and is an important target for anticancer drug design. We constructed a homology model to represent the structure of EGF-R and propose that this model can be used to design potent inhibitors of EGF-R. We used our EGF-R model and a docking procedure to rationally design compounds predicted to bind favorably to EGF-R. This approach led to the successful design of a leflunomide metabolite analogue, which was found to have an IC50 value of 1.7 microM in EGF-R inhibition assays and killed >99% of human breast cancer cells in vitro by triggering apoptosis. The reported studies may provide the basis for the development of a new class of potent and clinically useful anti-breast cancer agents.

MeSH terms

  • Aniline Compounds / chemical synthesis
  • Aniline Compounds / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Apoptosis
  • Breast Neoplasms / drug therapy*
  • Breast Neoplasms / enzymology
  • Breast Neoplasms / pathology
  • Cell Line
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology
  • ErbB Receptors / antagonists & inhibitors*
  • Humans
  • Isoxazoles / metabolism
  • Isoxazoles / pharmacology
  • Leflunomide
  • Microscopy, Confocal
  • Models, Molecular
  • Nitriles / chemical synthesis
  • Nitriles / pharmacology*
  • Protein Conformation
  • Tumor Cells, Cultured
  • Tumor Stem Cell Assay

Substances

  • Aniline Compounds
  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Isoxazoles
  • LFM A12
  • Nitriles
  • ErbB Receptors
  • Leflunomide