{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,29]],"date-time":"2025-10-29T03:44:07Z","timestamp":1761709447614,"version":"3.41.2"},"reference-count":58,"publisher":"Frontiers Media SA","content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Pharmacol."],"DOI":"10.3389\/fphar.2018.00116","type":"journal-article","created":{"date-parts":[[2018,2,19]],"date-time":"2018-02-19T04:22:26Z","timestamp":1519014146000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":15,"title":["Sulfur-Containing Monoterpenoids as Potential Antithrombotic Drugs: Research in the Molecular Mechanism of Coagulation Activity Using Pinanyl Sulfoxide as an Example"],"prefix":"10.3389","volume":"9","author":[{"given":"Liliya E.","family":"Nikitina","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sergei V.","family":"Kiselev","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Valeriya A.","family":"Startseva","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrei V.","family":"Bodrov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zulfiya R.","family":"Azizova","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Olga T.","family":"Shipina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Inna V.","family":"Fedyunina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sergei V.","family":"Boichuk","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Olga A.","family":"Lodochnikova","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vladimir V.","family":"Klochkov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Leisan F.","family":"Galiullina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Aliya V.","family":"Khaliullina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1965","published-online":{"date-parts":[[2018,2,19]]},"reference":[{"key":"B1","unstructured":"AbrahamM. J.\n            van der SpoelD.\n            LindahlE.\n            HessB.\n          GROMACS User Manual version 5.0.12014"},{"key":"B2","doi-asserted-by":"publisher","first-page":"873","DOI":"10.1007\/s11224-008-9353-4","article-title":"First examples of the cocrystallization of diastereomers of chiral phosphorus compounds","volume":"19","author":"Alfonsov","year":"2008","journal-title":"Struct. Chem"},{"key":"B3","doi-asserted-by":"publisher","first-page":"2109","DOI":"10.1021\/cg0603265","article-title":"When Z' = 2 Is better than Z' = 1 supramolecular centrosymmetric hydrogen-bonded dimers in chiral systems","volume":"6","author":"Anderson","year":"2006","journal-title":"Cryst. Growth Des"},{"key":"B4","doi-asserted-by":"publisher","first-page":"1013","DOI":"10.1016\/S0040-4020(01)90039-0","article-title":"Synthesis of configurationally stable allylic sulphoxides via diastereoselective oxidation","volume":"43","author":"Annunziata","year":"1987","journal-title":"Tetrahedron Lett"},{"key":"B5","doi-asserted-by":"publisher","first-page":"1983","DOI":"10.1021\/jo00006a005","article-title":"Powerful dienophiles for asymmetric Diels-Alder reactions:.alpha.-(2-exo-hydroxy-10-bornylsulfinyl)maleimides","volume":"56","author":"Arai","year":"1991","journal-title":"Org. Chem"},{"key":"B6","doi-asserted-by":"publisher","first-page":"79","DOI":"10.3998\/ark.5550190.0003.b09","article-title":"Synthesis and Diels-Alder reactivity of sulfinyl homo- and hetero- dienes obtained via enantio-pure sulfenic acids","volume":"17","author":"Aversa","year":"2002","journal-title":"ARKIVOC"},{"volume-title":"Herbal Medicine","year":"1994","author":"Balick","key":"B7"},{"key":"B8","doi-asserted-by":"crossref","first-page":"331","DOI":"10.1007\/978-94-015-7658-1_21","article-title":"Interaction models for water in relation to protein hydration","volume-title":"Intermolecular Forces","author":"Berendsen","year":"1981"},{"key":"B9","doi-asserted-by":"publisher","first-page":"6381","DOI":"10.1016\/S0040-4039(01)84604-9","article-title":"Preparation of stable, camphor-derived, optically active allylic sulfoxides","volume":"26","author":"Binns","year":"1985","journal-title":"Tetrahedron Lett"},{"key":"B10","doi-asserted-by":"publisher","first-page":"927","DOI":"10.1038\/194927b0","article-title":"Aggregation of blood platelets by adenosine diphosphate and its reversal","volume":"194","author":"Born","year":"1962","journal-title":"Nature"},{"key":"B11","doi-asserted-by":"publisher","first-page":"3788","DOI":"10.1021\/jp013616z","article-title":"Molecular dynamics simulation of sodium dodecyl sulfate micelle in water: micellar structural characteristics and counterion distribution","volume":"106","author":"Bruce","year":"2002","journal-title":"J. Phys. Chem"},{"key":"B12","doi-asserted-by":"publisher","first-page":"2091","DOI":"10.1016\/j.bbamem.2013.05.014","article-title":"Evaluation of membrane models and their composition for islet amyloidpolypeptide-membrane aggregation","volume":"1828","author":"Caillon","year":"2013","journal-title":"Biochim. Biophys. Acta"},{"key":"B13","doi-asserted-by":"publisher","first-page":"6129","DOI":"10.1039\/b908043k","article-title":"Enantiopure sulfoxides: recent applications in asymmetric synthesis","volume":"41","author":"Carreno","year":"2009","journal-title":"Chem. Commun"},{"key":"B14","doi-asserted-by":"publisher","first-page":"7453","DOI":"10.1021\/bi00444a045","article-title":"A new model to describe extrinsic protein binding to phospholipid membranes of varying composition: application to human coagulation proteins","volume":"28","author":"Cutsforth","year":"1989","journal-title":"Biochemistry"},{"key":"B15","doi-asserted-by":"publisher","first-page":"940","DOI":"10.1002\/hlca.201100484","article-title":"Synthesis and asymmetric oxidation of caranylsulfanylimidazoles","volume":"5","author":"Demakova","year":"","journal-title":"Helv. Chim. Acta"},{"key":"B16","doi-asserted-by":"publisher","first-page":"113","DOI":"10.1134\/S1070428012010186","article-title":"Reaction of 1-methyl-2-terpenylsulfanylimidazoles with chlorine dioxide","volume":"1","author":"Demakova","year":"","journal-title":"Russ. J. Org. Chem"},{"key":"B17","doi-asserted-by":"publisher","first-page":"137","DOI":"10.1039\/c39880000137","article-title":"A simple route to (R)-(+)-4-t-butoxycyclopent-2-enone","author":"Eschler","year":"1988","journal-title":"Chem. Soc. Chem. Commun"},{"key":"B18","doi-asserted-by":"publisher","first-page":"934","DOI":"10.1016\/j.ijcard.2012.10.046","article-title":"Mortality from ischemic heart disease by country, region, and age: statistics from World Health Organisation and United Nations","volume":"168","author":"Finegold","year":"2013","journal-title":"Int. J. Cardiol"},{"key":"B19","doi-asserted-by":"publisher","first-page":"880","DOI":"10.1021\/cg901224f","article-title":"Hydrogen bonding is not everything: extensive polymorphism in a system with conserved hydrogen bonded synthons","volume":"10","author":"Fucke","year":"2010","journal-title":"Cryst. Growth Des"},{"key":"B20","unstructured":"Investigation of cholesterol+model of biological membrane complex by NMR spectroscopy12204\n            GaliullinaL. F.\n            BlokhinD. S.\n            AganovA. V.\n            KlochkovV. V.\n          MRSej142012"},{"key":"B21","doi-asserted-by":"publisher","first-page":"110","DOI":"10.1002\/mrc.4146","article-title":"Structure of pravastatin and its complex with sodium dodecyl sulfate micelles studied by NMR spectroscopy","volume":"53","author":"Galiullina","year":"2015","journal-title":"Magn. Reson. Chem."},{"key":"B22","doi-asserted-by":"publisher","first-page":"1829","DOI":"10.1016\/j.jacc.2007.11.080","article-title":"The role of aspirin in cardiovascular prevention: implications of aspirin resistance","volume":"51","author":"Gasparyan","year":"2008","journal-title":"J. Am. Coll. Cardiol."},{"key":"B23","doi-asserted-by":"publisher","first-page":"126","DOI":"10.1007\/s11094-010-0413-x","article-title":"Synthesis and antifungal activity of sulfides, sulfoxides, and sulfones based on (1S)-(\u2013)-\u03b2-pinene","volume":"44","author":"Gavrilov","year":"2010","journal-title":"Pharm. Chem. J"},{"key":"B24","first-page":"1","article-title":"Theory and origin of polymorphism","volume-title":"Polymorphism in Pharmaceutical Solids","author":"Grant","year":"1999"},{"key":"B25","doi-asserted-by":"publisher","first-page":"515","DOI":"10.1016\/S0076-6879(94)39020-7","article-title":"Methods to study membrane protein structure in solution","volume":"239","author":"Henry","year":"1994","journal-title":"Meth. Enzymol"},{"key":"B26","doi-asserted-by":"publisher","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","article-title":"VMD - Visual Molecular Dynamics","volume":"14","author":"Humphrey","year":"1996","journal-title":"J. Mol. Graph"},{"key":"B27","doi-asserted-by":"publisher","first-page":"22","DOI":"10.1007\/s10600-014-0862-7","article-title":"Sulfurcontaining derivatives of mono- and bicyclic natural monoterpenoids","volume":"50","author":"Ishmuratov","year":"2014","journal-title":"Chem. Nat. Compd"},{"key":"B28","doi-asserted-by":"publisher","first-page":"49","DOI":"10.1016\/j.jim.2012.12.001","article-title":"A heparin-based method for flow cytometric analysis of microparticles directly from platelet-poor plasma in calcium containing buffer","volume":"388","author":"Iversen","year":"2013","journal-title":"J. Immunol. Methods"},{"key":"B29","doi-asserted-by":"publisher","first-page":"78","DOI":"10.1007\/s11094-017-1611-6","article-title":"Hemocoagulation activity of sulfur-containing pinane-type terpenoids","volume":"51","author":"Kiselev","year":"2017","journal-title":"Pharm. Chem. J"},{"key":"B30","doi-asserted-by":"publisher","first-page":"4529","DOI":"10.1021\/jo00069a009","article-title":"Catalytic Asymmetric oxidation of sulfides with tret-Butyl hydroperoxide using binaphthol as a chiral auxiliary","volume":"58","author":"Komatsu","year":"1993","journal-title":"J. Org. Chem"},{"key":"B31","first-page":"23","article-title":"Tissue factor structure and coagulation","volume-title":"Thrombosis and Inflammation in Acute Coronary Syndromes","author":"Krudysz-Amblo","year":"2015"},{"key":"B32","doi-asserted-by":"publisher","first-page":"206","DOI":"10.1111\/j.1423-0410.2008.01151.x","article-title":"Microparticle sizng by dynamic light scattering in freshfrozen plasma","volume":"96","author":"Lawrie","year":"2009","journal-title":"Vox Sang"},{"key":"B33","doi-asserted-by":"publisher","first-page":"1883","DOI":"10.1111\/j.1538-7836.2011.04478.x","article-title":"Platelet membrane phospholipid asymmetry: from the characterization of a scramblase activity to the indentification of an essential protein mutated in Scott syndrome","volume":"9","author":"Lhermusier","year":"2011","journal-title":"J. Thromb. Haemost"},{"key":"B34","doi-asserted-by":"publisher","first-page":"2222","DOI":"10.1080\/10426507.2015.1072185","article-title":"S = O\u2026S = O interactions as a driving force for low-temperature conformational rearrangement of stable H-bonding {S(O)-CH2-CH2-OH\u2219\u2219\u2219}2 synthon in two modifications of diastereomeric pinanyl sulfoxides co-crystal","volume":"190","author":"Lodochnikova","year":"2015","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"B35","doi-asserted-by":"publisher","first-page":"139","DOI":"10.1016\/j.bpc.2010.06.002","article-title":"NMR studies of new arginine vasopressin analogs modified with \u03b1-2-indanylglycine enantiomers at position 2 bound to sodium dodecyl sulfate micelles","volume":"151","author":"Lubecka","year":"2010","journal-title":"Biophys. Chem"},{"key":"B36","doi-asserted-by":"publisher","first-page":"1846","DOI":"10.1021\/j100007a011","article-title":"Molecular dynamics simulation analysis of a sodium dodecyl sulfate micelle in aqueous solution: decreased fluidity of the micelle hydrocarbon interior","volume":"99","author":"MacKerell","year":"1995","journal-title":"J. Phys. Chem"},{"key":"B37","doi-asserted-by":"publisher","first-page":"4026","DOI":"10.1021\/ct200196m","article-title":"An automated force field topology builder (ATB) and repository: version 1.0","volume":"7","author":"Malde","year":"2011","journal-title":"J. Chem. Theory Comput"},{"key":"B38","doi-asserted-by":"publisher","first-page":"20","DOI":"10.1007\/s11094-012-0727-y","article-title":"Synthesis and anti-inflammatory and antipyretic activity of 2-(1'-hydroxy-4'-isopropenyl-1'-methylcyclohexyl-2'-thio)-methylethanoate","volume":"46","author":"Nikitina","year":"","journal-title":"Pharm. Chem. J"},{"volume-title":"Natural and Thiomodified Monoterpenoids.","year":"2011","author":"Nikitina","key":"B39"},{"key":"B40","doi-asserted-by":"publisher","first-page":"811","DOI":"10.1007\/s10600-017-2131-z","article-title":"Biological activity of S-containing monoterpenoids","volume":"5","author":"Nikitina","year":"","journal-title":"Chem. Nat. Compd"},{"key":"B41","doi-asserted-by":"publisher","first-page":"1233","DOI":"10.1023\/A:1013251021230","article-title":"7,7-Dimethyl-2,10-epoxybicyclo[3.1.1]heptane. Synthesis, structure, and products of epoxide ring cleavage","volume":"8","author":"Nikitina","year":"2001","journal-title":"Russ. J. Gen. Chem"},{"key":"B42","doi-asserted-by":"publisher","first-page":"600","DOI":"10.1007\/s12668-017-0432-0","article-title":"Development of approaches to the study of the interaction of biologically active thioterpenoids with model membranes","volume":"7","author":"Nikitina","year":"","journal-title":"BioNanoScience"},{"key":"B43","doi-asserted-by":"publisher","first-page":"187","DOI":"10.1080\/10426507.2016.1255619","article-title":"Extraordinary behavior of \u03b2-hydroxy sulfoxides and sulfone of pinane series","volume":"192","author":"Nikitina","year":"","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"B44","doi-asserted-by":"publisher","first-page":"664","DOI":"10.1007\/s11094-012-0699-y","article-title":"Synthesis and antifungal activity of the carane series","volume":"45","author":"Nikitina","year":"","journal-title":"Pharm. Chem. J"},{"key":"B45","doi-asserted-by":"publisher","first-page":"178","DOI":"10.1007\/s10600-006-0072-z","article-title":"Reaction of \u03b2-pinene and thiols in the presence of Lewis acids","volume":"2","author":"Nikitina","year":"2006","journal-title":"Chem. Nat. Compd"},{"key":"B46","doi-asserted-by":"publisher","first-page":"28","DOI":"10.1007\/s10600-010-9517-5","article-title":"Antifungal activity of bicyclic monoterpenoids and terpenesulfides","volume":"46","author":"Nikitina","year":"2010","journal-title":"Chem. Nat. Compd"},{"key":"B47","doi-asserted-by":"publisher","first-page":"251","DOI":"10.1007\/s11094-009-0282-3","article-title":"Synthesis and antifungal activity of compounds of the pinane series","volume":"43","author":"Nikitina","year":"2009","journal-title":"Pharm. Chem. J"},{"key":"B48","doi-asserted-by":"publisher","first-page":"149","DOI":"10.1016\/0022-1759(90)90309-J","article-title":"Towards an optimized MTT-assay","volume":"130","author":"Niks","year":"1990","journal-title":"J. Immunol. Meth"},{"key":"B49","doi-asserted-by":"publisher","first-page":"7013","DOI":"10.1016\/S0040-4020(01)89169-9","article-title":"Conjugate addition of amines to (Rs)-10-isobornyl vinyl sulfoxides","volume":"45","author":"Pyne","year":"1989","journal-title":"Tetrahedron Lett"},{"key":"B50","doi-asserted-by":"publisher","first-page":"25","DOI":"10.1016\/j.molstruc.2015.10.059","article-title":"Structural studies of pravastatin and simvastatin and their complexes with SDS micelles by NMR spectroscopy","volume":"1105","author":"Rakhmatullin","year":"2016","journal-title":"J. Mol. Struct"},{"key":"B51","doi-asserted-by":"publisher","first-page":"764","DOI":"10.1590\/S0102-695X2011005000119","article-title":"Cardiovascular effects of monoterpenes: a review","volume":"21","author":"Santos","year":"2011","journal-title":"Rev. Bras. Farmacogn"},{"volume-title":"Thrombocytic Hemostasis","year":"2000","author":"Shitikova","key":"B52"},{"key":"B53","doi-asserted-by":"publisher","first-page":"58","DOI":"10.1152\/physrev.1989.69.1.58","article-title":"Molecular mechanism of platelet activation","volume":"69","author":"Siess","year":"1989","journal-title":"Physiol. Rev"},{"key":"B54","doi-asserted-by":"publisher","first-page":"615","DOI":"10.1080\/10426507.2013.843003","article-title":"Study of \u201cRacemic Compound-Like\u201d behavior of diastereomeric mixture of pinanyl sulfoxides by X-ray diffraction, IR spectroscopy, and DFT calculations","volume":"189","author":"Startseva","year":"2014","journal-title":"Phosphorus Sulfur Silicon Relat. Elem"},{"key":"B55","doi-asserted-by":"publisher","first-page":"436","DOI":"10.1016\/j.molstruc.2013.06.043","article-title":"Solution structures of Altzheimers amyloid A\u03b213-23 peptide: NMR studies in solution and in SDS","volume":"1049","author":"Usachev","year":"2013","journal-title":"J. Mol. Struct"},{"key":"B56","doi-asserted-by":"publisher","first-page":"3297","DOI":"10.1016\/j.tetlet.2005.03.104","article-title":"Efficient and highly diastereoselective preparation of a myrtenal derived bis-sulfoxide and its preliminary evaluation as chiral acyl donor","volume":"46","author":"Vargas-D\u00edaz","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"B57","doi-asserted-by":"publisher","first-page":"4303","DOI":"10.1021\/cr900147h","article-title":"Enantioselective synthesis of sulfoxides: 2000-2009","volume":"110","author":"Wojaczynska","year":"2010","journal-title":"Chem. Rev."},{"key":"B58","doi-asserted-by":"publisher","first-page":"914","DOI":"10.1021\/jo00083a037","article-title":"Application of new camphor-derived mercapto chiral auxiliaries to the synthesis of optically active primary amines","volume":"59","author":"Yang","year":"1994","journal-title":"J. Org. Chem"}],"container-title":["Frontiers in Pharmacology"],"original-title":[],"link":[{"URL":"http:\/\/journal.frontiersin.org\/article\/10.3389\/fphar.2018.00116\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2018,2,19]],"date-time":"2018-02-19T04:22:43Z","timestamp":1519014163000},"score":1,"resource":{"primary":{"URL":"http:\/\/journal.frontiersin.org\/article\/10.3389\/fphar.2018.00116\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,2,19]]},"references-count":58,"alternative-id":["10.3389\/fphar.2018.00116"],"URL":"https:\/\/doi.org\/10.3389\/fphar.2018.00116","relation":{},"ISSN":["1663-9812"],"issn-type":[{"type":"electronic","value":"1663-9812"}],"subject":[],"published":{"date-parts":[[2018,2,19]]},"article-number":"116"}}