Correlation of cytotoxic activity of betulinines and their hydroxy analogues

Bioorg Med Chem Lett. 2005 Oct 1;15(19):4196-200. doi: 10.1016/j.bmcl.2005.06.087.

Abstract

This research is based on intention to prepare and test 3beta-hydroxy and 3beta,28-dihydroxy analogues of new pro-apoptotic derivatives (betulinines) using selective hydrolysis procedure and strategic protective groups. The evaluation of cytotoxicity of prepared compounds on several tumor cell lines using an MTT test was our interest. It was found that hydrolysis of acetates in betulinines afforded compounds with higher cytotoxicity in case of 18-lupene-21-ones (e.g., ethyl 3beta-hydroxy-21-oxolup-18-en-28-oate), whereas hydrolysis of the 18-lupene-21,22-diones gave less active derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Hydroxylation
  • Inhibitory Concentration 50
  • Structure-Activity Relationship
  • Triterpenes / chemical synthesis*
  • Triterpenes / pharmacology

Substances

  • Antineoplastic Agents
  • Triterpenes
  • betulin