Hemocoagulation Activity of Sulfur-Containing Pinane-Type Terpenoids

Киселев, С. В.; Никитина, Л. Е.; Старцева, В. А.; Artemova, N. P.; Бодров, А. В.; Boichuk, Sergei; Vorontsova, M. M.; Рахматуллина, А. А.; Turaev, R G; Клочков, В. В.

doi:10.1007/s11094-017-1611-6

Cited by 10 publications

(4 citation statements)

References 9 publications

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“…Moreover, we also demonstrated the anti-fungal, anti-inflammatory, anti-helicobacter, antimicrobial and other types of activities of sulfur-containing monoterpenoids (Nikitina et al, 2009 , 2010 , 2012a , b ; Gavrilov et al, 2010 ). Coagulation activity of these compounds has already been described in our previous publications (Kiselev et al, 2017 ; Nikitina et al, 2017a , b ). We observed that all synthesized sulfur-containing monoterpenoids have a low toxicity, whereas mutagenic and genotoxic effects were not found (Nikitina et al, 2011 ).…”

Section: Introductionmentioning

confidence: 52%

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Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example

et al. 2018

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In this article we present the synthesis of enantiomerically pure sulfoxide and study the influence of this compound on hemostasis. Detailed NMR studies and molecular dynamics simulations using sodium dodecyl sulfate (SDS) membrane models indicated that the bicyclic fragment of sulfoxide was embedded into the SDS micelle whereas the -SO(CH2)2OH fragment remained on the surface of the micelle and was in contact with the solvent. We also found that the pro-coagulative activity of sulfoxide was due to its ability to inhibit platelet activation and inhibited the catalytic activity of phospholipid surface which was involved in formation of coagulation clotting factor complexes.

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Section: Introductionmentioning

confidence: 52%

“…Recent studies have shown that sulfur-containing monoterpenoids have membranotropic properties (Kiselev et al, 2017 ). Therefore, in present study we examined the possibility of using sulfoxide 2a as a platelet concentrate stabilizer.…”

Section: Resultsmentioning

confidence: 99%

Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example

et al. 2018

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“…NMR spectroscopy was used to evaluate the interaction between compounds 3–5 and the model cell membrane. The interaction of monoterpenoids with the cell membrane has already been investigated in our previous studies [ 27 , 28 , 29 ]. Here, the dodecyl phosphocholine (DPC) micelles solution in water were used as model systems mimicking the surface of the cell membrane.…”

Section: Resultsmentioning

confidence: 99%

Unraveling the Mechanism of Platelet Aggregation Suppression by Monoterpenoids

et al. 2022

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Platelet aggregation causes various diseases and therefore challenges the development of novel antiaggregatory drugs. In this study, we report the possible mechanism of platelet aggregation suppression by newly synthesized myrtenol-derived monoterpenoids carrying different heteroatoms (sulphur, oxygen, or nitrogen). Despite all tested compounds suppressed the platelet aggregation in vitro, the most significant effect was observed for the S-containing compounds. The molecular docking confirmed the putative interaction of all tested compounds with the platelet’s P2Y12 receptor suggesting that the anti-aggregation properties of monoterpenoids are implemented by blocking the P2Y12 function. The calculated binding force depended on heteroatom in monoterpenoids and significantly decreased with the exchanging of the sulphur atom with oxygen or nitrogen. On the other hand, in NMR studies on dodecyl phosphocholine (DPC) as a membrane model, only S-containing compound was found to be bound with DPC micelles surface. Meanwhile, no stable complexes between DPC micelles with either O- or N-containing compounds were observed. The binding of S-containing compound with cellular membrane reinforces the mechanical properties of the latter, thereby preventing its destabilization and subsequent clot formation on the phospholipid surface. Taken together, our data demonstrate that S-containing myrtenol-derived monoterpenoid suppresses the platelet aggregation in vitro via both membrane stabilization and blocking the P2Y12 receptor and, thus, appears as a promising agent for hemostasis control.

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“…It has been shown that thioterepenoids also have anti-helicobacter, antiaggregatory, and anticoagulant effects. In addition, this class of compounds is characterized by low toxicity, mutagenic, and genotoxic effects [34][35][36][37]. In 2018 and 2019, the authors of [38,39] presented a first paper dealing with the fluorescence labeling of terpenes by BODIPYs.…”

Section: Bodipy Conjugates With Terpenesmentioning

confidence: 99%

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

et al. 2022

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Fluorescent dyes absorbing and emitting in the visible and near-IR regions are promising for the development of fluorescent probes for labeling and bio-visualization of body cells. The ability to absorb and emit in the long-wavelength region increases the efficiency of recording the spectral signals of the probes due to the higher permeability of the skin layers. Compared to other fluorescent dyes, BODIPYs are attractive due to their excellent photophysical properties–narrow absorption and emission, intense fluorescence, simple signal modulation for the practical applications. As part of conjugates with biomolecules, BODIPY could act as a biomarker, but as therapeutic agent, which allows solving several problems at once-labeling or bioimaging and treatment based on the suppression of pathogenic microflora and cancer cells, which provides a huge potential for practical application of BODIPY conjugates in medicine. The review is devoted to the discussion of the recent, promising directions of BODIPY application in the field of conjugation with biomolecules. The first direction is associated with the development of BODIPY conjugates with drugs, including compounds of platinum, paclitaxel, chlorambucil, isoxazole, capsaicin, etc. The second direction is devoted to the labeling of vitamins, hormones, lipids, and other biomolecules to control the processes of their transport, localization in target cells, and metabolism. Within the framework of the third direction, the problem of obtaining functional optically active materials by conjugating BODIPY with other colored and fluorescent particles, in particular, phthalocyanines, is being solved.

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Hemocoagulation Activity of Sulfur-Containing Pinane-Type Terpenoids

Cited by 10 publications

References 9 publications

Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example

Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example

Unraveling the Mechanism of Platelet Aggregation Suppression by Monoterpenoids

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

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