Structural details on the interaction of biologically active sulfur-containing monoterpenoids with lipid membranes
| Autor: | Ilya A. Khodov, Ayzira F. Timerova, Holger A. Scheidt, Roman S. Pavelyev, Daniel Huster, S V Kiselev, Liliya E. Nikitina, Vladimir V. Klochkov, Oksana V. Aganova, V. A. Startseva, Zulfiya R. Azizova, Sergei Boichuk, L. F. Galiullina |
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| Rok vydání: | 2020 |
| Předmět: |
Chemistry
Sodium Phospholipid Thio chemistry.chemical_element Biological activity 02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology Condensed Matter Physics 01 natural sciences Combinatorial chemistry Atomic and Molecular Physics and Optics 0104 chemical sciences Electronic Optical and Magnetic Materials Acetic acid chemistry.chemical_compound Membrane Bornane Materials Chemistry Physical and Theoretical Chemistry Solubility 0210 nano-technology Spectroscopy |
| Zdroj: | Journal of Molecular Liquids. 301:112366 |
| ISSN: | 0167-7322 |
| DOI: | 10.1016/j.molliq.2019.112366 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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