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

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 embedde...

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Main Authors: Liliya E. Nikitina, Sergei V. Kiselev, Valeriya A. Startseva, Andrei V. Bodrov, Zulfiya R. Azizova, Olga T. Shipina, Inna V. Fedyunina, Sergei V. Boichuk, Olga A. Lodochnikova, Vladimir V. Klochkov, Leisan F. Galiullina, Aliya V. Khaliullina
Format: Article
Language:English
Published: Frontiers Media S.A. 2018-02-01
Series:Frontiers in Pharmacology
Subjects:
Online Access:http://journal.frontiersin.org/article/10.3389/fphar.2018.00116/full
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author Liliya E. Nikitina
Liliya E. Nikitina
Sergei V. Kiselev
Valeriya A. Startseva
Andrei V. Bodrov
Zulfiya R. Azizova
Olga T. Shipina
Inna V. Fedyunina
Sergei V. Boichuk
Olga A. Lodochnikova
Vladimir V. Klochkov
Leisan F. Galiullina
Aliya V. Khaliullina
Aliya V. Khaliullina
author_facet Liliya E. Nikitina
Liliya E. Nikitina
Sergei V. Kiselev
Valeriya A. Startseva
Andrei V. Bodrov
Zulfiya R. Azizova
Olga T. Shipina
Inna V. Fedyunina
Sergei V. Boichuk
Olga A. Lodochnikova
Vladimir V. Klochkov
Leisan F. Galiullina
Aliya V. Khaliullina
Aliya V. Khaliullina
author_sort Liliya E. Nikitina
collection DOAJ
description 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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spelling doaj.art-79a0af884b0f4e959c036c3bdc2306fa2022-12-22T01:00:04ZengFrontiers Media S.A.Frontiers in Pharmacology1663-98122018-02-01910.3389/fphar.2018.00116282691Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an ExampleLiliya E. Nikitina0Liliya E. Nikitina1Sergei V. Kiselev2Valeriya A. Startseva3Andrei V. Bodrov4Zulfiya R. Azizova5Olga T. Shipina6Inna V. Fedyunina7Sergei V. Boichuk8Olga A. Lodochnikova9Vladimir V. Klochkov10Leisan F. Galiullina11Aliya V. Khaliullina12Aliya V. Khaliullina13Department of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaMedical Physics Department, Institute of Physics, Kazan Federal University, Kazan, RussiaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaDepartment of Chemistry and Technology of Macromolecular Compounds, Kazan National Research Technological University, Kazan, RussiaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaA.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, RussiaMedical Physics Department, Institute of Physics, Kazan Federal University, Kazan, RussiaMedical Physics Department, Institute of Physics, Kazan Federal University, Kazan, RussiaDepartment of General and Organic Chemistry, Kazan State Medical University, Kazan, RussiaMedical Physics Department, Institute of Physics, Kazan Federal University, Kazan, RussiaIn 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.http://journal.frontiersin.org/article/10.3389/fphar.2018.00116/fullterpenessulfoxidesplatelets aggregationcoagulation activitymolecular mechanism of coagulation activity
spellingShingle Liliya E. Nikitina
Liliya E. Nikitina
Sergei V. Kiselev
Valeriya A. Startseva
Andrei V. Bodrov
Zulfiya R. Azizova
Olga T. Shipina
Inna V. Fedyunina
Sergei V. Boichuk
Olga A. Lodochnikova
Vladimir V. Klochkov
Leisan F. Galiullina
Aliya V. Khaliullina
Aliya V. Khaliullina
Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example
Frontiers in Pharmacology
terpenes
sulfoxides
platelets aggregation
coagulation activity
molecular mechanism of coagulation activity
title Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example
title_full Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example
title_fullStr Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example
title_full_unstemmed Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example
title_short Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example
title_sort sulfur containing monoterpenoids as potential antithrombotic drugs research in the molecular mechanism of coagulation activity using pinanyl sulfoxide as an example
topic terpenes
sulfoxides
platelets aggregation
coagulation activity
molecular mechanism of coagulation activity
url http://journal.frontiersin.org/article/10.3389/fphar.2018.00116/full
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