Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/12872
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dc.contributor.authorMilhazes, Nuno-
dc.contributor.authorCunha-Oliveira, Teresa-
dc.contributor.authorMartins, Pedro-
dc.contributor.authorGarrido, Jorge-
dc.contributor.authorOliveira, Catarina-
dc.contributor.authorRego, A. Cristina-
dc.contributor.authorBorges, Fernanda-
dc.date.accessioned2010-03-12T12:32:08Z-
dc.date.available2010-03-12T12:32:08Z-
dc.date.issued2006-10-
dc.identifier.citationChemical Research in Toxicology. 19:10 (2006) 1294-1304en_US
dc.identifier.issn0893-228X-
dc.identifier.urihttp://hdl.handle.net/10316/12872-
dc.description.abstractThe toxicological and redox profiles of MDMA and its major metabolites (MDA, α-methyldopamine, N-methyl-α-methyldopamine, 6-hydroxy-α-methyldopamine, 3-methoxy-α-methyldopamine) were studied to establish a structure-toxicity relationship and determine their individual contribution to cell death induction by apoptosis and/or necrosis. The results of the comparative toxicity study, using undifferentiated PC12 cells, strongly suggest that the metabolites possessing a catecholic group are more toxic to the cells than MDMA and metabolites with at least one protected phenolic group. Redox studies reveal that an oxidative mechanism seems to play an important role in metabolite cytotoxicity. Nuclear features of apoptosis and/or necrosis show that most of the metabolites, particularly N-methyl-α-methyldopamine, induce cell death by apoptosis, largely accompanied by necrotic features. No significant differences were found between MDMA and the metabolites, concerning overall characteristics of cell death. These results may be useful to ascertain the contribution of metabolism in MDMA neurotoxicity molecular mechanismsen_US
dc.language.isoengen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsopenAccessen_US
dc.titleSynthesis and Cytotoxic Profile of 3,4-Methylenedioxymethamphetamine (“Ecstasy”) and Its Metabolites on Undifferentiated PC12 Cells: A Putative Structure−Toxicity Relationshipen_US
dc.typearticleen_US
dc.identifier.doi10.1021/tx060123i-
item.languageiso639-1en-
item.fulltextCom Texto completo-
item.grantfulltextopen-
crisitem.author.deptCNC - Center for Neuroscience and Cell Biology-
crisitem.author.deptFaculty of Medicine-
crisitem.author.deptFaculty of Medicine-
crisitem.author.parentdeptUniversity of Coimbra-
crisitem.author.parentdeptUniversity of Coimbra-
crisitem.author.researchunitCNC - Center for Neuroscience and Cell Biology-
crisitem.author.researchunitCNC - Center for Neuroscience and Cell Biology-
crisitem.author.orcid0000-0002-5171-0454-
crisitem.author.orcid0000-0002-7382-0339-
crisitem.author.orcid0000-0001-8981-231X-
crisitem.author.orcid0000-0001-6942-4328-
crisitem.author.orcid0000-0003-0700-3776-
Appears in Collections:FMUC Medicina - Artigos em Revistas Internacionais
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