KFU. Card publication. Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes

KAZAN
FEDERAL UNIVERSITY

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STRUCTURAL DETAILS ON THE INTERACTION OF BIOLOGICALLY ACTIVE SULFUR-CONTAINING MONOTERPENOIDS WITH LIPID MEMBRANES

Form of presentation

Articles in international journals and collections

Year of publication

2020

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Authors, employees of KFU

Aganova Oksana Vartanovna, author

Galiullina Leysan Faritovna, author

Klochkov Vladimir Vasilevich, author

Nikitina Liliya Evgenevna, author

Pavelev Roman Sergeevich, author

Starceva Valeriya Andreevna, author

Timerova Ayzira Flyusovna, author

Khodov Ilya Anatolevich, author

Other authors

Scheidt Holger A. , author

Bibliographic description in the original language

Nikitina L.E. Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes / L.E. Nikitina, R.S. Pavelyev, V.A. Startseva, S.V. Kiselev, L.F. Galiullina, O.V. Aganova, A.F. Timerova, S.V. Boichuk, Z.R. Azizova, V.V. Klochkov, D. Huster, I.A. Khodov, H.A. Scheidt, // J. Mol. Liq. – 2020. – V 301. – 112366.

Annotation

In this work, we propose the synthesis of new thioterpenoids of a bornane series and study the influence of these compounds on hemostasis. The results from this study suggest that among all investigated terpenoids, sodium ([(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]thio) acetate may be the most promising for further development due to enhanced inhibition of the spontaneous aggregation compared with isoborneol, and because of its higher solubility in water compared with ([(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]thio) acetic acid, which has approximately the same antiaggregatory and anticoagulant properties. In accordance with one hypothesis, the distribution of the studied bioactive molecules within the cellular lipid membrane can directly influence the anticoagulant properties. In the current work, the interactions of thioterpenoids with phospholipid membranes have been studied using various NMR techniques. The findings of this study indicate that sodium ([(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]thio) acetateexhibits a membrane location, which is shifted somewhat in the direction of the lipid-water interface. Such a location may shield the compound from interactions with hydrophobic lipid segments. In contrast, isoborneol is more deeply immersed in the membrane. These results represent an initial step toward developing new drugs based on the synthesized thioterpenoids in order to increase the effectiveness of treatment and prevention of several human diseases accompanying disorders in the hemostasis system.

Keywords

Thioterpenoids, Isoborneol, Coagulation activity, Platelets aggregation, 1D and 2D solution-state NMR, Solid-state NMR, Model cell membranes, Molecular mechanism of coagulation activity, NOESY, DOSY

The name of the journal

Journal of Molecular Liquids

URL

https://www.sciencedirect.com/science/article/pii/S016773221935994X?via%3Dihub

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=233316&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Aganova Oksana Vartanovna	ru_RU
dc.contributor.author	Galiullina Leysan Faritovna	ru_RU
dc.contributor.author	Klochkov Vladimir Vasilevich	ru_RU
dc.contributor.author	Nikitina Liliya Evgenevna	ru_RU
dc.contributor.author	Pavelev Roman Sergeevich	ru_RU
dc.contributor.author	Starceva Valeriya Andreevna	ru_RU
dc.contributor.author	Timerova Ayzira Flyusovna	ru_RU
dc.contributor.author	Khodov Ilya Anatolevich	ru_RU
dc.contributor.author	Scheidt Holger A.	ru_RU
dc.date.accessioned	2020-01-01T00:00:00Z	ru_RU
dc.date.available	2020-01-01T00:00:00Z	ru_RU
dc.date.issued	2020	ru_RU
dc.identifier.citation	Nikitina L.E. Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes / L.E. Nikitina, R.S. Pavelyev, V.A. Startseva, S.V. Kiselev, L.F. Galiullina, O.V. Aganova, A.F. Timerova, S.V. Boichuk, Z.R. Azizova, V.V. Klochkov, D. Huster, I.A. Khodov, H.A. Scheidt, // J. Mol. Liq. – 2020. – V 301. – 112366.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=233316&p_lang=2	ru_RU
dc.description.abstract	Journal of Molecular Liquids	ru_RU
dc.description.abstract	In this work, we propose the synthesis of new thioterpenoids of a bornane series and study the influence of these compounds on hemostasis. The results from this study suggest that among all investigated terpenoids, sodium ([(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]thio) acetate may be the most promising for further development due to enhanced inhibition of the spontaneous aggregation compared with isoborneol, and because of its higher solubility in water compared with ([(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]thio) acetic acid, which has approximately the same antiaggregatory and anticoagulant properties. In accordance with one hypothesis, the distribution of the studied bioactive molecules within the cellular lipid membrane can directly influence the anticoagulant properties. In the current work, the interactions of thioterpenoids with phospholipid membranes have been studied using various NMR techniques. The findings of this study indicate that sodium ([(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]thio) acetateexhibits a membrane location, which is shifted somewhat in the direction of the lipid-water interface. Such a location may shield the compound from interactions with hydrophobic lipid segments. In contrast, isoborneol is more deeply immersed in the membrane. These results represent an initial step toward developing new drugs based on the synthesized thioterpenoids in order to increase the effectiveness of treatment and prevention of several human diseases accompanying disorders in the hemostasis system.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	Thioterpenoids	ru_RU
dc.subject	Isoborneol	ru_RU
dc.subject	Coagulation activity	ru_RU
dc.subject	Platelets aggregation	ru_RU
dc.subject	1D and 2D solution-state NMR	ru_RU
dc.subject	Solid-state NMR	ru_RU
dc.subject	Model cell membranes	ru_RU
dc.subject	Molecular mechanism of coagulation activity	ru_RU
dc.subject	NOESY	ru_RU
dc.subject	DOSY	ru_RU
dc.title	Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes	ru_RU
dc.type	Articles in international journals and collections	ru_RU