Synthesis and identification of new 4-arylidene curcumin analogues as potential anticancer agents targeting nuclear factor-κB signaling pathway

J Med Chem. 2010 Dec 9;53(23):8260-73. doi: 10.1021/jm1004545. Epub 2010 Nov 11.

Abstract

A series of curcumin analogues including new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized. Cell growth inhibition assays revealed that most 4-arylidene curcumin analogues can effectively decrease the growth of a panel of lung cancer cells at submicromolar and low micromolar concentrations. High content analysis technology coupled with biochemical studies showed that this new class of 4-arylidene curcumin analogues exhibits significantly improved NF-κB inhibition activity over the parent compound curcumin, at least in part by inhibiting IκB phosphorylation and degradation via IKK blockage; selected 4-arylidene curcumin analogues also reduced the tumorigenic potential of cancer cells in a clonogenic assay.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Nucleus / metabolism
  • Curcumin / analogs & derivatives*
  • Curcumin / chemical synthesis
  • Curcumin / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Lung Neoplasms / pathology
  • Magnetic Resonance Spectroscopy
  • NF-kappa B / metabolism*
  • Signal Transduction / drug effects*
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors

Substances

  • Antineoplastic Agents
  • NF-kappa B
  • Tumor Necrosis Factor-alpha
  • Curcumin