title: Studies on the reactivity of CDDO, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action.
abstract: 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.
authors.affiliation: Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA.
authors.forename: Robin D
authors.initials: RD
authors.lastname: Couch
authors.forename: R Greg
authors.initials: RG
authors.lastname: Browning
authors.forename: Tadashi
authors.initials: T
authors.lastname: Honda
authors.forename: Gordon W
authors.initials: GW
authors.lastname: Gribble
authors.forename: Dennis L
authors.initials: DL
authors.lastname: Wright
authors.forename: Michael B
authors.initials: MB
authors.lastname: Sporn
authors.forename: Amy C
authors.initials: AC
authors.lastname: Anderson
mesh_terms: D004229:Dithiothreitol; D007700:Kinetics; D008968:Molecular Conformation; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet
chemical_list: C116817:2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid; D009569:Nitric Oxide; D009828:Oleanolic Acid; D004229:Dithiothreitol