Studies on the reactivity of CDDO, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action.
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.
Couch
Robin D
RD
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA.
Browning
R Greg
RG
Honda
Tadashi
T
Gribble
Gordon W
GW
Wright
Dennis L
DL
Sporn
Michael B
MB
Anderson
Amy C
AC
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
C116817:2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid; D009569:Nitric Oxide; D009828:Oleanolic Acid; D004229:Dithiothreitol