Rational design, synthesis and characterization of potent, non-peptidic Smac mimics/XIAP inhibitors as proapoptotic agents for cancer therapy

Bioorg Med Chem. 2009 Aug 15;17(16):5834-56. doi: 10.1016/j.bmc.2009.07.009. Epub 2009 Jul 10.

Abstract

Novel proapoptotic Smac mimics/IAPs inhibitors have been designed, synthesized and characterized. Computational models and structural studies (crystallography, NMR) have elucidated the SAR of this class of inhibitors, and have permitted further optimization of their properties. In vitro characterization (XIAP BIR3 and linker-BIR2-BIR3 binding, cytotox assays, early ADMET profiling) of the compounds has been performed, identifying one lead for further in vitro and in vivo evaluation.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / toxicity
  • Apoptosis Regulatory Proteins
  • Bridged Bicyclo Compounds / chemical synthesis
  • Bridged Bicyclo Compounds / chemistry*
  • Bridged Bicyclo Compounds / toxicity
  • Cell Line, Tumor
  • Computer Simulation
  • Crystallography, X-Ray
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Humans
  • Intracellular Signaling Peptides and Proteins / chemistry*
  • Intracellular Signaling Peptides and Proteins / metabolism
  • Mitochondrial Proteins / chemistry*
  • Mitochondrial Proteins / metabolism
  • Neoplasms / drug therapy*
  • Protein Structure, Tertiary
  • Structure-Activity Relationship
  • X-Linked Inhibitor of Apoptosis Protein / antagonists & inhibitors*
  • X-Linked Inhibitor of Apoptosis Protein / chemistry
  • X-Linked Inhibitor of Apoptosis Protein / metabolism

Substances

  • Antineoplastic Agents
  • Apoptosis Regulatory Proteins
  • Bridged Bicyclo Compounds
  • DIABLO protein, human
  • Intracellular Signaling Peptides and Proteins
  • Mitochondrial Proteins
  • X-Linked Inhibitor of Apoptosis Protein
  • bicyclo(5.3.0)decane