Literature DB >> 11909709

A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production.

Tadashi Honda1, Yukiko Honda, Frank G Favaloro, Gordon W Gribble, Nanjoo Suh, Andrew E Place, Mara H Rendi, Michael B Sporn.   

Abstract

New oleanane triterpenoids with various substituents at the C-17 position of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO) and methyl 2-carboxy-3,12-dioxooleana-1,9(11)-dien-28-oate were synthesized. Among them, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile shows extremely high inhibitory activity (IC(50)=1 pM level) against production of nitric oxide induced by interferon-gamma in mouse macrophages. This potency is about 100 times and 30 times more potent than CDDO and dexamethasone, respectively.

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Year:  2002        PMID： 11909709     DOI： 10.1016/s0960-894x(02)00105-1

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


  53 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.  Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A.

Authors:  Tadashi Honda; Karen T Liby; Xiaobo Su; Chitra Sundararajan; Yukiko Honda; Nanjoo Suh; Renee Risingsong; Charlotte R Williams; Darlene B Royce; Michael B Sporn; Gordon W Gribble
Journal:  Bioorg Med Chem Lett       Date:  2006-09-25       Impact factor: 2.823

3.  AN EFFICIENT SYNTHESIS OF TRICYCLIC COMPOUNDS, (+/-)-(4abeta8abeta10aalpha)-1,2,3,4,4a,6,7,8,8a,9,10,10a-DODECAHYDRO-1,1,4a-TRIMETHYL-2-OXOPHENANTHRENE-8a-CARBOXYLIC ACID, ITS METHYL ESTER, AND (+/-)-(4abeta,8abeta10aalpha)-3,4,4a,6,7,8,8a,9,10,10a-DECAHYDRO-8a-HYDROXYMETHYL-1,1,4a-TRIMETHYLPHENANTHREN-2(1H)-ONE.

Authors:  Tadashi Honda; Yukiko Honda; Hidenori Yoshizawa; Gordon W Gribble
Journal:  Org Prep Proced Int       Date:  2005-12       Impact factor: 1.628

4.  Synthetic triterpenoids can protect against toxicity without reducing the efficacy of treatment with Carboplatin and Paclitaxel in experimental lung cancer.

Authors:  Karen T Liby
Journal:  Dose Response       Date:  2013-08-01       Impact factor: 2.658

5.  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

Review 6.  Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents.

Authors:  Reen-Yen Kuo; Keduo Qian; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Nat Prod Rep       Date:  2009-08-13       Impact factor: 13.423

7.  Triterpenoids CDDO-methyl ester or CDDO-ethyl amide and rexinoids LG100268 or NRX194204 for prevention and treatment of lung cancer in mice.

Authors:  Karen Liby; Renee Risingsong; Darlene B Royce; Charlotte R Williams; Tian Ma; Mark M Yore; Michael B Sporn
Journal:  Cancer Prev Res (Phila)       Date:  2009-12-01

8.  Triterpenoid CDDO-methylamide improves memory and decreases amyloid plaques in a transgenic mouse model of Alzheimer's disease.

Authors:  Magali Dumont; Elizabeth Wille; Noel Y Calingasan; Davide Tampellini; Charlotte Williams; Gunnar K Gouras; Karen Liby; Michael Sporn; Carl Nathan; M Flint Beal; Michael T Lin
Journal:  J Neurochem       Date:  2009-02-07       Impact factor: 5.372

9.  Bardoxolone methyl (CDDO-Me or RTA402) induces cell cycle arrest, apoptosis and autophagy via PI3K/Akt/mTOR and p38 MAPK/Erk1/2 signaling pathways in K562 cells.

Authors:  Xin-Yu Wang; Xue-Hong Zhang; Li Peng; Zheng Liu; Yin-Xue Yang; Zhi-Xu He; Hong-Wan Dang; Shu-Feng Zhou
Journal:  Am J Transl Res       Date:  2017-10-15       Impact factor: 4.060

10.  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
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