Design, synthesis, and evaluation of potent, nonpeptidic mimetics of second mitochondria-derived activator of caspases

J Med Chem. 2009 Feb 12;52(3):593-6. doi: 10.1021/jm801101z.

Abstract

A series of new Smac mimetics have been designed, synthesized, and evaluated. The most potent compound 10 binds to XIAP, cIAP-1, and cIAP-2 BIR3 proteins with K(i) of 3.9, 0.37, and 0.25 nM, respectively. Compound 10 antagonizes XIAP in a cell-free functional assay and induces rapid cIAP-1 degradation in cancer cells. Compound 10 inhibits cell growth in the MDA-MB-231 cancer cell line with an IC(50) of 8.9 nM.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Alanine / pharmacology
  • Apoptosis / drug effects
  • Apoptosis Regulatory Proteins
  • Breast Neoplasms
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Cell Line, Tumor
  • Humans
  • Inhibitor of Apoptosis Proteins / chemical synthesis
  • Inhibitor of Apoptosis Proteins / chemistry*
  • Intracellular Signaling Peptides and Proteins / chemical synthesis*
  • Mitochondrial Proteins / chemical synthesis*
  • X-Linked Inhibitor of Apoptosis Protein / metabolism

Substances

  • Apoptosis Regulatory Proteins
  • Bridged Bicyclo Compounds, Heterocyclic
  • DIABLO protein, human
  • DM-28 compound
  • Inhibitor of Apoptosis Proteins
  • Intracellular Signaling Peptides and Proteins
  • Mitochondrial Proteins
  • X-Linked Inhibitor of Apoptosis Protein
  • Alanine