Rapid access to new bioconjugates of betulonic acid via click chemistry

Sergey F. Vasilevsky, Anastasiya I. Govdi, Irina V. Sorokina, Tatyana G. Tolstikova, Dmitry S. Baev, Genrikh A. Tolstikov, Victor I. Mamatuyk, Igor V. Alabugin

Research output: Contribution to journalArticle

41 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)62-65
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number1
DOIs
Publication statusPublished - 1 Jan 2011
Externally publishedYes

Keywords

  • Anti-inflammatory activity
  • Anti-oxidant activity
  • Bioconjugates
  • Click chemistry
  • Cycloaddition
  • Lupanes
  • Oleanes
  • Terpenoids
  • Triazoles

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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  • Cite this

    Vasilevsky, S. F., Govdi, A. I., Sorokina, I. V., Tolstikova, T. G., Baev, D. S., Tolstikov, G. A., Mamatuyk, V. I., & Alabugin, I. V. (2011). Rapid access to new bioconjugates of betulonic acid via click chemistry. Bioorganic and Medicinal Chemistry Letters, 21(1), 62-65. https://doi.org/10.1016/j.bmcl.2010.11.072