ChemInform Abstract: Design and Synthesis of 2‐Cyano‐3,12‐dioxoolean‐1,9‐dien‐28‐oic Acid, a Novel and Highly Active Inhibitor of Nitric Oxide Production in Mouse Macrophages.

Honda, Tadashi; Rounds, BarbieAnn V.; Gribble, Gordon W.; Suh, Nanjoo; Wang, Y.; Sporn, Michael B.

doi:10.1002/chin.199908191

ChemInform

1999

DOI: 10.1002/chin.199908191

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ChemInform Abstract: Design and Synthesis of 2‐Cyano‐3,12‐dioxoolean‐1,9‐dien‐28‐oic Acid, a Novel and Highly Active Inhibitor of Nitric Oxide Production in Mouse Macrophages.

Tadashi Honda

BarbieAnn V. Rounds

Gordon W. Gribble

et al.

Abstract: Design and Synthesis of 2-Cyano-3,12-dioxoolean-1,9-dien-28-oic Acid, a Novel and Highly Active Inhibitor of Nitric Oxide Production in Mouse Macrophages.-Several new derivatives with electronwithdrawing substituents at the C-2 position of 3-oxoolean-1-en-28-oic acid are prepared and tested as inhibitors of the production of nitric oxide induced by interferon-γ in mouse macrophages. Among the compounds prepared, (VII) is the most effective one. The potency of (VII) is similar to that of dexamethasone though it… Show more

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Unifying Mechanisms of Action of the Anticancer Activities of Triterpenoids and Synthetic Analogs

Safe¹,

Prather²,

Brents³

et al. 2012

ACAMC

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Triterpenoids such as betulinic acid (BA) and synthetic analogs of oleanolic acid [2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO)] and glycyrrhetinic acid [2-cyano-3,11-dioxo-18β-oleana-1,12-dien-30-oc acid (CDODA)] are potent anticancer agents that exhibit antiproliferative, antiangiogenic, anti-inflammatory and pro-apoptotic activities. Although their effects on multiple pathways have been reported, unifying mechanisms of action have not been reported. Studies in this laboratory have now demonstrated that several triterpenoids including BA and some derivatives, celastrol, methyl ursolatee, β-boswellic acid derivatives, and the synthetic analogs CDDO, CDODA and their esters decreased expression of specificity protein (Sp) transcription factors and several pro-oncogenic Sp-regulated genes in multiple cancer cell lines. The mechanisms of this response are both compound- and cell context-dependent and include activation of both proteasome-dependent and -independent pathways. Triterpenoid-mediated induction of reactive oxygen species (ROS) has now been characterized as an important proteasome-independent pathway for downregulation of Sp transcription factors. ROS decreases expression of microRNA-27a (miR-27a) and miR-20a/miR-17-5p and this results in the induction of the transcriptional “Sp-repressors” ZBTB10 and ZBTB4, respectively, which in turn downregulate Sp and Sp-regulated genes. Triterpenoids also activate or deactive nuclear receptors and G-protein coupled receptors, and these pathways contribute to their antitumorigenic activity and may also play a role in targeting Sp1, Sp3 and Sp4 which are highly overexpressed in multiple cancers and appear to be important for maintaining the cancer phenotype.

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Unifying Mechanisms of Action of the Anticancer Activities of Triterpenoids and Synthetic Analogs

Safe¹,

Prather²,

Brents³

et al. 2012

ACAMC

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show abstract

Dietary terpenoids and prostate cancer chemoprevention

Rabi

Gupta²

2008

Front Biosci

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Cancer chemoprevention by phytochemicals may be one of the most feasible approaches for cancer control. Phytochemicals obtained from vegetables, fruits, spices, teas, herbs and medicinal plants, such as terpenoids and other phenolic compounds, have been proven to suppress experimental carcinogenesis in various organs in pre-clinical models. Recent studies have indicated that mechanisms underlying chemopreventive potential may be a combination of antioxidant, anti-inflammatory, immune-enhancing, and hormone modulation effects, with modification of drug metabolizing enzymes, influence on cell cycle and cell differentiation, induction of apoptosis, suppression of proliferation and angiogenesis playing roles in the initiation and secondary modification stages of neoplastic development. Specific features of prostate cancer, such as high prevalence and long latency period provides ample opportunities for chemopreventive agents to work at various stages of disease progression. Finally, suitable populations with appropriate risk factors, including the presence of pre-malignant lesions and genetic predispositions, need to be well characterized for future chemopreventive interventions. Here we review naturally occurring dietary terpenoids as useful agents for prostate cancer chemoprevention with reference to their classes and sources.

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ChemInform Abstract: Design and Synthesis of 2‐Cyano‐3,12‐dioxoolean‐1,9‐dien‐28‐oic Acid, a Novel and Highly Active Inhibitor of Nitric Oxide Production in Mouse Macrophages.

Cited by 2 publications

References 1 publication

Unifying Mechanisms of Action of the Anticancer Activities of Triterpenoids and Synthetic Analogs

Unifying Mechanisms of Action of the Anticancer Activities of Triterpenoids and Synthetic Analogs

Dietary terpenoids and prostate cancer chemoprevention

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