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Rapid access to new bioconjugates of betulonic acid via click chemistry

Authors
Journal
Bioorganic & Medicinal Chemistry Letters
0960-894X
Publisher
Elsevier
Publication Date
Volume
21
Issue
1
Identifiers
DOI: 10.1016/j.bmcl.2010.11.072
Keywords
  • Bioconjugates
  • Click Chemistry
  • Terpenoids
  • Lupanes
  • Oleanes
  • Cycloaddition
  • Triazoles
  • Anti-Oxidant Activity
  • Anti-Inflammatory Activity
Disciplines
  • Biology
  • Medicine

Abstract

Abstract Plant-derived pentacyclic triterpenoids of lupane and oleanane families provide a versatile structural platform for the discovery of new biologically active compounds. A number of semisynthetic derivatives of these molecules, possess high medical efficiency including antiviral (HIV-1), anticancer and immunomodulating activity. Even small structural changes in these triterpenoid derivatives were reported to lead to significant changes in their activity, making a convincing case for a systematic study of structure–activity relationships in this class of compounds. Our earlier work opened synthetic access to alkynes derived from the betulonic scaffold and enabled the development of a new family of biohybrids using Click Chemistry (CC). The computer-aided prediction of several types of biological activity were performed with program PASS (Prediction Activity Spectra of Substances. Experimental studies based on mouse models verified the SAR predictions obtained by the PASS program. The observed correlation between the anti-inflammatory and antioxidant activity indicates substantial contribution of the latter in the mechanism of anti-inflammatory effect of the triazole derivatives of betulonic acid.

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