Literature DB >> 15837296

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

Robin D Couch1, R Greg Browning, Tadashi Honda, Gordon W Gribble, Dennis L Wright, Michael B Sporn, Amy C Anderson.   

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.

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Year:  2005        PMID： 15837296     DOI： 10.1016/j.bmcl.2005.03.031

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  33 in total

1.  CDDO-methyl ester delays breast cancer development in BRCA1-mutated mice.

Authors:  Eun-Hee Kim; Chuxia Deng; Michael B Sporn; Darlene B Royce; Renee Risingsong; Charlotte R Williams; Karen T Liby
Journal:  Cancer Prev Res (Phila)       Date:  2011-09-20

2.  In Vitro Biotransformation of the Nrf2 Activator Bardoxolone: Formation of an Epoxide Metabolite That Undergoes Two Novel Glutathione-Mediated Metabolic Pathways: Epoxide Reduction and Oxidative Elimination of Nitrile Moiety.

Authors:  Amin M Kamel; Stephen Bowlin; Ban Anwar; Holly Reichard; Joe Argus; Ian A Blair
Journal:  Chem Res Toxicol       Date:  2019-10-25       Impact factor: 3.739

3.  Design and synthesis of novel antimicrobials with activity against Gram-positive bacteria and mycobacterial species, including M. tuberculosis.

Authors:  V V N Phani Babu Tiruveedhula; Christopher M Witzigmann; Ranjit Verma; M Shahjahan Kabir; Marc Rott; William R Schwan; Sara Medina-Bielski; Michelle Lane; William Close; Rebecca L Polanowski; David Sherman; Aaron Monte; Jeffrey R Deschamps; James M Cook
Journal:  Bioorg Med Chem       Date:  2013-10-21       Impact factor: 3.641

4.  Potency ranking of triterpenoids as inducers of a cytoprotective enzyme and as inhibitors of a cellular inflammatory response via their electron affinity and their electrophilicity index.

Authors:  René V Bensasson; Vincent Zoete; Gaston Berthier; Paul Talalay; Albena T Dinkova-Kostova
Journal:  Chem Biol Interact       Date:  2010-04-28       Impact factor: 5.192

5.  Targeting Nrf2-mediated gene transcription by extremely potent synthetic triterpenoids attenuate dopaminergic neurotoxicity in the MPTP mouse model of Parkinson's disease.

Authors:  Navneet Ammal Kaidery; Rebecca Banerjee; Lichuan Yang; Natalya A Smirnova; Dmitry M Hushpulian; Karen T Liby; Charlotte R Williams; Masayuki Yamamoto; Thomas W Kensler; Rajiv R Ratan; Michael B Sporn; M Flint Beal; Irina G Gazaryan; Bobby Thomas
Journal:  Antioxid Redox Signal       Date:  2012-08-13       Impact factor: 8.401

6.  Bardoxolone Methyl and a Related Triterpenoid Downregulate cMyc Expression in Leukemia Cells.

Authors:  Un-Ho Jin; Yating Cheng; Beiyan Zhou; Stephen Safe
Journal:  Mol Pharmacol       Date:  2017-03-08       Impact factor: 4.436

7.  Human neuroblastoma cells rapidly enter cell cycle arrest and apoptosis following exposure to C-28 derivatives of the synthetic triterpenoid CDDO.

Authors:  Jennifer L Alabran; Adam Cheuk; Karen Liby; Michael Sporn; Javed Khan; John Letterio; Konstantin S Leskov
Journal:  Cancer Biol Ther       Date:  2008-05-07       Impact factor: 4.742

8.  Genetic versus chemoprotective activation of Nrf2 signaling: overlapping yet distinct gene expression profiles between Keap1 knockout and triterpenoid-treated mice.

Authors:  Melinda S Yates; Quynh T Tran; Patrick M Dolan; William O Osburn; Soona Shin; Colin C McCulloch; Jay B Silkworth; Keiko Taguchi; Masayuki Yamamoto; Charlotte R Williams; Karen T Liby; Michael B Sporn; Thomas R Sutter; Thomas W Kensler
Journal:  Carcinogenesis       Date:  2009-04-21       Impact factor: 4.944

Review 9.  Synthetic oleanane triterpenoids: multifunctional drugs with a broad range of applications for prevention and treatment of chronic disease.

Authors:  Karen T Liby; Michael B Sporn
Journal:  Pharmacol Rev       Date:  2012-09-10       Impact factor: 25.468

10.  Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo.

Authors:  Rodger E Tiedemann; Jessica Schmidt; Jonathan J Keats; Chang-Xin Shi; Yuan Xiao Zhu; Stephen E Palmer; Xinliang Mao; Aaron D Schimmer; A Keith Stewart
Journal:  Blood       Date:  2008-12-18       Impact factor: 22.113
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