2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

Bioorg Med Chem Lett. 2010 Apr 1;20(7):2275-8. doi: 10.1016/j.bmcl.2010.02.007. Epub 2010 Feb 6.

Abstract

2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride (CDDO anhydride) has been synthesized, which is the first example of an oleanane triterpenoid anhydride. CDDO anhydride shows potency similar to or higher than the corresponding acid (CDDO) in various in vitro and in vivo assays related to inflammation and carcinogenesis. Notably, preliminary phamacokinetics studies show that CDDO anhydride levels are higher than CDDO levels in mouse tissues and blood. Further evaluation of CDDO anhydride is in progress.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anhydrides / chemistry
  • Anhydrides / pharmacokinetics
  • Anhydrides / pharmacology
  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / pharmacokinetics
  • Anti-Inflammatory Agents / pharmacology*
  • Cell Line, Tumor
  • Cytoprotection / drug effects
  • Heme Oxygenase-1 / metabolism
  • Mice
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / metabolism
  • Nitric Oxide Synthase Type II / metabolism
  • Oleanolic Acid / chemistry*
  • Oleanolic Acid / pharmacokinetics
  • Oleanolic Acid / pharmacology*
  • Triterpenes / chemistry
  • Triterpenes / pharmacokinetics
  • Triterpenes / pharmacology

Substances

  • Anhydrides
  • Anti-Inflammatory Agents
  • Triterpenes
  • Nitric Oxide
  • Oleanolic Acid
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse
  • Heme Oxygenase-1