Comparative Study
doi: 10.1016/s0960-894x(02)00105-1.
A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production
Affiliations
- PMID: 11909709
- DOI: 10.1016/s0960-894x(02)00105-1
Item in Clipboard
Comparative Study
A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production
Bioorg Med Chem Lett.
.
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.
Similar articles
-
Synthetic oleanane and ursane triterpenoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages.J Med Chem. 2000 Nov 2;43(22):4233-46. doi: 10.1021/jm0002230. J Med Chem. 2000. PMID: 11063620
-
Novel synthetic oleanane triterpenoids: a series of highly active inhibitors of nitric oxide production in mouse macrophages.Bioorg Med Chem Lett. 1999 Dec 20;9(24):3429-34. doi: 10.1016/s0960-894x(99)00623-x. Bioorg Med Chem Lett. 1999. PMID: 10617085
-
Design and synthesis of tricyclic compounds with enone functionalities in rings A and C: a novel class of highly active inhibitors of nitric oxide production in mouse macrophages.J Med Chem. 2002 Oct 24;45(22):4801-5. doi: 10.1021/jm025565f. J Med Chem. 2002. PMID: 12383005
-
New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress.J Nat Prod. 2011 Mar 25;74(3):537-45. doi: 10.1021/np100826q. Epub 2011 Feb 10. J Nat Prod. 2011. PMID: 21309592 Free PMC article. Review.
-
Synthesis and Anticancer Activity of CDDO and CDDO-Me, Two Derivatives of Natural Triterpenoids.Molecules. 2019 Nov 13;24(22):4097. doi: 10.3390/molecules24224097. Molecules. 2019. PMID: 31766211 Free PMC article. Review.
Cited by
-
Oleanolic acid and its analogues: promising therapeutics for kidney disease.Chin Med. 2024 May 30;19(1):74. doi: 10.1186/s13020-024-00934-w. Chin Med. 2024. PMID: 38816880 Free PMC article. Review.
-
Bardoxolone methyl inhibits the infection of rabies virus via Nrf2 pathway activation in vitro.Virol J. 2023 Nov 10;20(1):258. doi: 10.1186/s12985-023-02213-w. Virol J. 2023. PMID: 37950261 Free PMC article.
-
Cell Rearrangement and Oxidant/Antioxidant Imbalance in Huntington's Disease.Antioxidants (Basel). 2023 Feb 24;12(3):571. doi: 10.3390/antiox12030571. Antioxidants (Basel). 2023. PMID: 36978821 Free PMC article. Review.
-
Novel Soloxolone Amides as Potent Anti-Glioblastoma Candidates: Design, Synthesis, In Silico Analysis and Biological Activities In Vitro and In Vivo.Pharmaceuticals (Basel). 2022 May 14;15(5):603. doi: 10.3390/ph15050603. Pharmaceuticals (Basel). 2022. PMID: 35631429 Free PMC article.
-
A synthesized olean-28,13β-lactam targets YTHDF1-GLS1 axis to induce ROS-dependent metabolic crisis and cell death in pancreatic adenocarcinoma.Cancer Cell Int. 2022 Apr 2;22(1):143. doi: 10.1186/s12935-022-02562-6. Cancer Cell Int. 2022. PMID: 35366902 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
