Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid

Org Biomol Chem. 2010 Feb 7;8(3):632-9. doi: 10.1039/b918846k. Epub 2009 Dec 8.

Abstract

A series of nitric oxide (NO)-releasing glycosyl derivatives () of oleanolic acid were synthesized to improve the aqueous solubility and cytotoxicity of the parent compound . Derivative exhibited better solubility and strong cytotoxicity against human hepatocellular carcinoma (HCC) in vitro. Furthermore, displayed low acute toxicity to mice and significantly inhibited the growth of HCC tumors in vivo, indicating that may be a promising candidate for the treatment of human HCC.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / therapeutic use
  • Antineoplastic Agents / toxicity
  • Carcinoma, Hepatocellular / drug therapy
  • Carcinoma, Hepatocellular / pathology*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Discovery
  • Female
  • Glycosylation
  • Humans
  • Liver Neoplasms / drug therapy
  • Liver Neoplasms / pathology*
  • Male
  • Mice
  • Nitric Oxide / chemistry*
  • Oleanolic Acid / chemical synthesis*
  • Oleanolic Acid / pharmacology*
  • Oleanolic Acid / therapeutic use
  • Oleanolic Acid / toxicity
  • Solubility
  • Structure-Activity Relationship
  • Water / chemistry
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Water
  • Nitric Oxide
  • Oleanolic Acid