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Journal of Molecular Liquids, volume 301, pages 112366

Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes

Startseva Valeriya A 1, 2
Kiselev Sergei V 2
Galiullina Leisan F 3
Aganova Oksana V 3
Timerova Ayzira F 3
Azizova Zulfiya R 2
Klochkov V V 3
Huster Daniel 4
Khodov Ilya A. 3, 5
Scheidt Holger A 4
Publication typeJournal Article
Publication date2020-03-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor6
ISSN01677322, 18733166
Materials Chemistry
Electronic, Optical and Magnetic Materials
Physical and Theoretical Chemistry
Spectroscopy
Atomic and Molecular Physics, and Optics
Condensed Matter Physics
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.

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Nikitina L. E. et al. Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes // Journal of Molecular Liquids. 2020. Vol. 301. p. 112366.
GOST all authors (up to 50) Copy
Nikitina L. E., Pavelyev R. S., Startseva V. A., Kiselev S. V., Galiullina L. F., Aganova O. V., Timerova A. F., Boichuk S., Azizova Z. R., Klochkov V. V., Huster D., Khodov I. A., Scheidt H. A. Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes // Journal of Molecular Liquids. 2020. Vol. 301. p. 112366.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.molliq.2019.112366
UR - https://doi.org/10.1016%2Fj.molliq.2019.112366
TI - Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes
T2 - Journal of Molecular Liquids
AU - Nikitina, Liliya E.
AU - Pavelyev, Roman S.
AU - Startseva, Valeriya A
AU - Kiselev, Sergei V
AU - Galiullina, Leisan F
AU - Aganova, Oksana V
AU - Timerova, Ayzira F
AU - Boichuk, Sergei
AU - Azizova, Zulfiya R
AU - Klochkov, V V
AU - Huster, Daniel
AU - Khodov, Ilya A.
AU - Scheidt, Holger A
PY - 2020
DA - 2020/03/01 00:00:00
PB - Elsevier
SP - 112366
VL - 301
SN - 0167-7322
SN - 1873-3166
ER -
BibTex
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BibTex Copy
@article{2020_Nikitina
author = {Liliya E. Nikitina and Roman S. Pavelyev and Valeriya A Startseva and Sergei V Kiselev and Leisan F Galiullina and Oksana V Aganova and Ayzira F Timerova and Sergei Boichuk and Zulfiya R Azizova and V V Klochkov and Daniel Huster and Ilya A. Khodov and Holger A Scheidt},
title = {Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes},
journal = {Journal of Molecular Liquids},
year = {2020},
volume = {301},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016%2Fj.molliq.2019.112366},
pages = {112366},
doi = {10.1016/j.molliq.2019.112366}
}
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