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Chiral enantioresolution of cathinone derivatives present in “legal highs”, and enantioselectivity evaluation on cytotoxicity of 3,4-methylenedioxypyrovalerone (MDPV)

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dc.contributor.authorSilva, Bárbara
dc.contributor.authorFernandes, Carla
dc.contributor.authorTiritan, Maria Elizabeth
dc.contributor.authorPinto, Madalena M.M.
dc.contributor.authorValente, Maria João
dc.contributor.authorCarvalho, Márcia
dc.contributor.authorGuedes de Pinho, Paula
dc.contributor.authorRemião, Fernando
dc.date.accessioned2021-07-02T14:41:27Z
dc.date.available2021-07-02T14:41:27Z
dc.date.issued2016
dc.description.abstractRecently, great interest has been focused on synthetic cathinones since their consumption has increased exponentially. All synthetic cathinones exist as chiral molecules; the biological and/or toxicological properties of cathinones generally differ according to the enantiomers in human body. In this study, a chiral liquid chromatography method was developed to separate and determine the enantiomeric ratio of synthetic cathinones present in "legal highs" acquired in old smart shops or over the Internet. All the synthetic cathinones were efficiently enantio-separated with α and Rs ranging from 1.24 to 3.62 and from 1.24 to 10.52, respectively, using polysaccharide-based chiral stationary phases. All synthetic cathinones, with the exception of 4-methylethcathinone (4-MEC), were present in the commercialized "legal highs" in an enantiomeric proportion of 50:50. One of the studied chiral compounds was 3,4-methylenedioxypyrovalerone (MDPV), one of the most consumed cathinone derivative worldwide. Our research group has recently reported its hepatotoxicity in the racemic form. Thus, the analytical enantioresolution of the MDPV was scaled up to multi-milligram using a semi-preparative amylose tris-3,5-dimethylphenylcarbamate column (20 cm × 7.0 mm ID, 7 µm particle size). Both enantiomers were isolated with high enantiomeric purity (enantiomeric excess > 99 %). The toxicity of S-(-)-MDPV and R-(+)-MDPV was evaluated, for the first time, using primary cultures of rat hepatocytes. It was also possible to verify that MDPV enantiomers showed hepatotoxicity in a concentration-dependent manner, but displayed no enantioselective toxicity in this cell culture model.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1007/s11419-016-0324-ypt_PT
dc.identifier.eissn1860-8973
dc.identifier.issn1860-8965
dc.identifier.urihttp://hdl.handle.net/10284/10034
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherSpringerpt_PT
dc.relation2013 - Strategic Project
dc.relationInterdisciplinary Centre of Marine and Environmental Research
dc.subject‘‘Legal highs’’pt_PT
dc.subjectSynthetic cathinonespt_PT
dc.subjectEnantioresolutionpt_PT
dc.subjectMDPV enantiomerpt_PT
dc.subjectCytotoxicity according to enantiomerspt_PT
dc.titleChiral enantioresolution of cathinone derivatives present in “legal highs”, and enantioselectivity evaluation on cytotoxicity of 3,4-methylenedioxypyrovalerone (MDPV)pt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitle2013 - Strategic Project
oaire.awardTitleInterdisciplinary Centre of Marine and Environmental Research
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6820 - DCRRNI ID/PEst-C%2FEQB%2FLA0006%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FMulti%2F04423%2F2013/PT
oaire.citation.endPage385pt_PT
oaire.citation.startPage372pt_PT
oaire.citation.titleForensic Toxicologypt_PT
oaire.citation.volume34pt_PT
oaire.fundingStream6820 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameCarvalho
person.givenNameMarcia
person.identifier2017111
person.identifier.ciencia-id8B10-171E-E63E
person.identifier.orcid0000-0001-9884-4751
person.identifier.ridD-5999-2013
person.identifier.scopus-author-id7201413997
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
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relation.isAuthorOfPublication.latestForDiscovery3837b828-ba57-47f7-a811-cce65e4922c6
relation.isProjectOfPublicationd95a62fe-3df1-48d6-b300-1ec7283d043b
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