Semipreparative enantioseparation of methamidophos by HPLC-UV and preliminary in vitro study of butyrylcholinesterase inhibition

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dc.contributor.authorEmerick, Guilherme Luz [UNESP]
dc.contributor.authorOliveira, Regina V.
dc.contributor.authorBelaz, Katia Roberta A.
dc.contributor.authorGoncalves, Monique [UNESP]
dc.contributor.authorDeOliveira, Georgino H. [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade Federal de São Carlos (UFSCar)
dc.date.accessioned2014-05-20T13:25:32Z
dc.date.available2014-05-20T13:25:32Z
dc.date.issued2012-02-01
dc.description.abstractMany chiral pesticides are introduced into the environment as racemates, although their pesticidal activity is usually the result of preferential reactivity of only one enantiomer, while the other enantiomer may have toxic effects against nontarget organisms. Methamidophos (O,S-dimethyl phosphoramidothioate), a chiral compound, is an insecticide widely used in agriculture in both developed and developing countries. However, this pesticide has a high toxicity not only to targeted insects but also to human and animals. In the present study, the enantiomers of methamidophos were enantiomerically separated by a semipreparative chiral liquid chromatography at the multimilligram scale on a polysaccharide-based chiral stationary phase and a preliminary evaluation of their in vitro inhibition of plasma butyrylcholinesterase (BChE) of hens was performed. In the present study, our first effort was to resolve the racemic mixture of methamidophos and to that end reversed-phase, normal-phase, and polar organic elution conditions were investigated in four different polysaccharide-based chiral phases. The best performance was achieved on a cellulose tris(3,5-dimethylphenylcarbamate) phase under normal phase. This chromatographic condition allowed the separation of 225?mg of methamidophos enantiomers with a high degree of chiral purity (>98%) in a short analysis time. Significant differences were found between the concentration that causes 50% of enzyme inhibition (IC50) of the three isoforms of methamidophos. (-)-Methamidophos showed an IC50 approximately three times larger than the (+)-enantiomer for plasma BChE of hens. Environ. Toxicol. Chem. 2012;31:239245. (C) 2011 SETACen
dc.description.affiliationUniv Estadual Paulista, Dept Nat Act Principles & Toxicol, Araraquara, Brazil
dc.description.affiliationUniversidade Federal de São Carlos (UFSCar), Dept Chem, BR-13560 São Carlos, SP, Brazil
dc.description.affiliationUnespUniv Estadual Paulista, Dept Nat Act Principles & Toxicol, Araraquara, Brazil
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipIdFAPESP: 09/51048-8
dc.description.sponsorshipIdFAPESP: 07/02872-4
dc.format.extent239-245
dc.identifierhttp://dx.doi.org/10.1002/etc.729
dc.identifier.citationEnvironmental Toxicology and Chemistry. Malden: Wiley-blackwell, v. 31, n. 2, p. 239-245, 2012.
dc.identifier.doi10.1002/etc.729
dc.identifier.issn0730-7268
dc.identifier.urihttp://hdl.handle.net/11449/8100
dc.identifier.wosWOS:000299036300003
dc.language.isoeng
dc.publisherWiley-Blackwell
dc.relation.ispartofEnvironmental Toxicology and Chemistry
dc.relation.ispartofjcr3.179
dc.relation.ispartofsjr1,178
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.subjectMethamidophosen
dc.subjectHigh-performance liquid chromatographyen
dc.subjectChiral separationen
dc.subjectPolysaccharide-based chiral phasesen
dc.subjectButyrylcholinesteraseen
dc.titleSemipreparative enantioseparation of methamidophos by HPLC-UV and preliminary in vitro study of butyrylcholinesterase inhibitionen
dc.typeArtigo
dcterms.licensehttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dcterms.rightsHolderWiley-blackwell
unesp.author.orcid0000-0002-5061-5957[2]
unesp.campusUniversidade Estadual Paulista (Unesp), Faculdade de Ciências Farmacêuticas, Araraquarapt

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