Rapid access to new bioconjugates of betulonic acid via click chemistry

Rapid access to new bioconjugates of betulonic acid via click chemistry Full article

Journal

Bioorganic and Medicinal Chemistry Letters
ISSN: 0960-894X , E-ISSN: 1464-3405

Output data

Year: 2011, Volume: 21, Number: 1, Pages: 62-65 Pages count : DOI: 10.1016/j.bmcl.2010.11.072

Tags

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

Authors

Vasilevsky Sergey F. ² , Govdi Anastasiya I. ² , Sorokina Irina V. ³ , Tolstikova Tatyana G. ³ , Baev Dmitry S. ³ , Tolstikov Genrikh A. ³ , Mamatuyk Victor I. ³ , Alabugin Igor V. ¹

Affiliations

1	(Данные Web of science) Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
2	(Данные Web of science) Russian Acad Sci, Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia

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 immuno-modulating 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. (C) 2010 Elsevier Ltd. All rights reserved.

Vasilevsky S.F. , Govdi A.I. , Sorokina I.V. , Tolstikova T.G. , Baev D.S. , Tolstikov G.A. , Mamatuyk V.I. , Alabugin I.V.
Rapid access to new bioconjugates of betulonic acid via click chemistry
Bioorganic and Medicinal Chemistry Letters. 2011. V.21. N1. P.62-65. DOI: 10.1016/j.bmcl.2010.11.072 WOS Scopus РИНЦ

Published print:

Jan 1, 2011

Web of science	WOS:000285544400008
Scopus	2-s2.0-78650512271
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