Thioterpenoids as Potential Antithrombotic Drugs: Molecular Docking, Antiaggregant, Anticoagulant and Antioxidant Activities

Alexander A. Ksenofontov; Pavel S. Bocharov; Elena V. Antina; Oksana G. Shevchenko; Aleksandr V. Samorodov; Ilmir R. Gilfanov; Roman S. Pavelyev; Olga V. Ostolopovskaya; Valeriya A. Startseva; Inna V. Fedyunina; Zulfiya R. Azizova; Salavat I. Gaysin; Svetlana V. Pestova; Evgeniy S. Izmest’ev; Svetlana A. Rubtsova; Mohammed A. Khelkhal; Liliya E. Nikitina

doi:10.3390/biom12111599

Biomolecules (Oct 2022)

Thioterpenoids as Potential Antithrombotic Drugs: Molecular Docking, Antiaggregant, Anticoagulant and Antioxidant Activities

Alexander A. Ksenofontov,
Pavel S. Bocharov,
Elena V. Antina,
Oksana G. Shevchenko,
Aleksandr V. Samorodov,
Ilmir R. Gilfanov,
Roman S. Pavelyev,
Olga V. Ostolopovskaya,
Valeriya A. Startseva,
Inna V. Fedyunina,
Zulfiya R. Azizova,
Salavat I. Gaysin,
Svetlana V. Pestova,
Evgeniy S. Izmest’ev,
Svetlana A. Rubtsova,
Mohammed A. Khelkhal,
Liliya E. Nikitina

Affiliations

Alexander A. Ksenofontov: G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, Russia
Pavel S. Bocharov: G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, Russia
Elena V. Antina: G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Street, 153045 Ivanovo, Russia
Oksana G. Shevchenko: Center of Collective Usage «Molecular Biology», Institute of Biology, Komi Science Centre, Ural Branch of Russian Academy of Sciences, 28 Kommunisticheskaya Street, 167982 Syktyvkar, Russia
Aleksandr V. Samorodov: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Ilmir R. Gilfanov: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Roman S. Pavelyev: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Olga V. Ostolopovskaya: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Valeriya A. Startseva: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Inna V. Fedyunina: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Zulfiya R. Azizova: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Salavat I. Gaysin: General and Organic Chemistry Department, Kazan State Medical University, 49 Butlerova Street, 420012 Kazan, Russia
Svetlana V. Pestova: Medical Chemistry Laboratory, Institute of Chemistry, Komi Scientific Centre, Ural Branch of Russian Academy of Sciences, 48 Pervomaiskaya Street, 167000 Syktyvkar, Russia
Evgeniy S. Izmest’ev: Medical Chemistry Laboratory, Institute of Chemistry, Komi Scientific Centre, Ural Branch of Russian Academy of Sciences, 48 Pervomaiskaya Street, 167000 Syktyvkar, Russia
Svetlana A. Rubtsova: Medical Chemistry Laboratory, Institute of Chemistry, Komi Scientific Centre, Ural Branch of Russian Academy of Sciences, 48 Pervomaiskaya Street, 167000 Syktyvkar, Russia
Mohammed A. Khelkhal: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Liliya E. Nikitina: Biologically Active Terpenoids Laboratory, Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia

DOI: https://doi.org/10.3390/biom12111599
Journal volume & issue: Vol. 12, no. 11
p. 1599

Abstract

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Natural monoterpenes and their derivatives are widely considered as effective ingredients for the design and production of new biologically active compounds with high antioxidant, antimicrobial and anti-protozoa properties. In this study, we synthesized two series of thiotherpenoids “sulfide-sulfoxide-sulfone”, with different bicyclic monoterpene skeleton (bornane and pinane) structures. The effect of the obtained compounds on platelet aggregation was investigated by using the molecular docking technique. The obtained data revealed that all the synthesized compounds may act as potential inhibitors of platelet aggregation. Moreover, the studied sulfides have shown high antioxidant activity as revealed by lipid peroxidation (LPO) process inhibition in a non-cellular substrate containing animal lipids. The sulfides were able to inhibit erythrocyte oxidative hemolysis, to reduce the accumulation of secondary LPO products in cells and to prevent the oxidation of native oxyhemoglobin. Additionally, the corresponding sulfones and sulfoxides exhibited insignificant antioxidant activity. However, the sulfides were found to exhibit significant antiaggregant and anticoagulant effects. These findings suggest as well that the sulfides could serve as a leader compound for future research and possible practical applications.

Published in Biomolecules

ISSN: 2218-273X (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Microbiology
Website: https://www.mdpi.com/journal/biomolecules

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