title: Rapid access to new bioconjugates of betulonic acid via click chemistry.
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.
authors.affiliation: Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 Institutskaya str, 630090 Novosibirsk, Russian Federation.
authors.forename: Sergey F
authors.initials: SF
authors.lastname: Vasilevsky
authors.forename: Anastasiya I
authors.initials: AI
authors.lastname: Govdi
authors.forename: Irina V
authors.initials: IV
authors.lastname: Sorokina
authors.forename: Tatyana G
authors.initials: TG
authors.lastname: Tolstikova
authors.forename: Dmitry S
authors.initials: DS
authors.lastname: Baev
authors.forename: Genrikh A
authors.initials: GA
authors.lastname: Tolstikov
authors.forename: Victor I
authors.initials: VI
authors.lastname: Mamatuyk
authors.forename: Igor V
authors.initials: IV
authors.lastname: Alabugin
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D057930:Click Chemistry; D051379:Mice; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D012984:Software; D013329:Structure-Activity Relationship; D000094062:Betulinic Acid
chemical_list: D000480:Alkynes; D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D000998:Antiviral Agents; D009828:Oleanolic Acid; C118308:betulonic acid; D000094062:Betulinic Acid