Discovery and biological activity of 6BrCaQ as an inhibitor of the Hsp90 protein folding machinery

ChemMedChem. 2011 May 2;6(5):804-15. doi: 10.1002/cmdc.201000489. Epub 2011 Mar 4.

Abstract

Heat shock protein 90 (Hsp90) is a significant target in the development of rational cancer therapy, due to its role at the crossroads of multiple signaling pathways associated with cell proliferation and viability. Here, a novel series of Hsp90 inhibitors containing a quinolein-2-one scaffold was synthesized and evaluated in cell proliferation assays. Results from these structure-activity relationships studies enabled identification of the simplified 3-aminoquinolein-2-one analogue 2 b (6BrCaQ), which manifests micromolar activity against a panel of cancer cell lines. The molecular signature of Hsp90 inhibition was assessed by depletion of standard known Hsp90 client proteins. Finally, processing and activation of caspases 7, 8, and 9, and the subsequent cleavage of PARP by 6BrCaQ, suggest stimulation of apoptosis through both extrinsic and intrinsic pathways.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / toxicity
  • Apoptosis
  • Cell Line, Tumor
  • Drug Evaluation, Preclinical
  • HSP90 Heat-Shock Proteins / antagonists & inhibitors*
  • HSP90 Heat-Shock Proteins / metabolism
  • Humans
  • Novobiocin / toxicity
  • Proteasome Endopeptidase Complex / metabolism
  • Protein Folding
  • Quinolones / chemical synthesis
  • Quinolones / chemistry*
  • Quinolones / toxicity

Substances

  • 3-aminoquinolein-2-one
  • Antineoplastic Agents
  • HSP90 Heat-Shock Proteins
  • Quinolones
  • Novobiocin
  • Proteasome Endopeptidase Complex