Studies on the reactivity of CDDO, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action

Bioorg Med Chem Lett. 2005 May 2;15(9):2215-9. doi: 10.1016/j.bmcl.2005.03.031.


CDDO, a semi-synthetic triterpenoid derived from oleanolic acid, has the potential to be used as a chemopreventive and chemotherapeutic agent. The structure of CDDO contains two alpha,beta-unsaturated carbonyl moieties, suggesting a mechanism of action involving a conjugate nucleophilic addition. Spectroscopic evaluation with thiol nucleophiles illustrates that an addition does indeed occur, but this addition is selective and reversible.

Publication types

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

MeSH terms

  • Dithiothreitol
  • Kinetics
  • Molecular Conformation
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemical synthesis
  • Oleanolic Acid / pharmacology
  • Spectrophotometry, Ultraviolet


  • 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid
  • Nitric Oxide
  • Oleanolic Acid
  • Dithiothreitol