Electrochemical study of methyl 2-[p-nitrophenyl(hydroxy)methyl]acrylate -

dc.creatorGoulart, MOF
dc.creatorde Souza, AA
dc.creatorde Abreu, FC
dc.creatorde Paula, FS
dc.creatorSales, EM
dc.creatorAlmeida, WP
dc.creatorBuriez, O
dc.creatorAmatore, C
dc.date2007
dc.date2014-11-18T12:54:42Z
dc.date2015-11-26T17:50:27Z
dc.date2014-11-18T12:54:42Z
dc.date2015-11-26T17:50:27Z
dc.date.accessioned2018-03-29T00:33:40Z
dc.date.available2018-03-29T00:33:40Z
dc.identifierJournal Of The Electrochemical Society. Electrochemical Soc Inc, v. 154, n. 11, n. P121, n. P129, 2007.
dc.identifier0013-4651
dc.identifierWOS:000249787900089
dc.identifier10.1149/1.2773535
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/65194
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/65194
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/65194
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1289684
dc.descriptionElectrochemical experiments with methyl 2-[p-nitrophenyl(hydroxy)methyl]acrylate (1) were performed in protic (EtOH+phosphate buffer 1:9, 0.1 mol L(-1), pH 6.9; EtOH+phosphate buffer+NaOH 1:9, 0.1 mol L(-1) or 0.2 mol L(-1), pH 9.4 and EtOH+NaHCO(3)+NaOH 2:8, 0.18 mol L(-1), pH 9.6) and aprotic [dimethylformamide (DMF)+tetrabutylammonium perchlorate (TBAP), 0.1 mol L(-1)] media. The primary reduction behavior in aprotic medium was typical of nitroaromatics along with an additional wave related to the reduction of the acrylate function. Kinetic analysis carried out in aprotic and aqueous basic media pointed out to the high stability of the electrogenerated nitro radical anion, especially in DMF+TBAP. Reduced (GSH) and oxidized (GSSG) gluthatione in phosphate buffer influenced the reduction behavior of 1, due mainly to protonation effects. Direct reduction of 1, in the presence of GSH, led to a transient nitroso-GS adduct. In the presence of GSSG, hydrogen-bonding-associated GSSG-hydroxylamine was the main product. Electrochemical studies of 1, in the presence of oxygen, showed no chemical reactivity between O(2) and 1(-center dot). These electrochemical results help in the understanding of the anticancer activity of 1 that can be considered a bioreductive agent with a glutathione depleting function. (c) 2007 The Electrochemical Society.
dc.description154
dc.description11
dc.descriptionP121
dc.descriptionP129
dc.languageen
dc.publisherElectrochemical Soc Inc
dc.publisherPennington
dc.publisherEUA
dc.relationJournal Of The Electrochemical Society
dc.relationJ. Electrochem. Soc.
dc.rightsaberto
dc.sourceWeb of Science
dc.subjectGlutathione Synthesis
dc.subjectNitro-compounds
dc.subjectRadical-anion
dc.subjectDrugs
dc.subjectReactivity
dc.subjectAnalogs
dc.titleElectrochemical study of methyl 2-[p-nitrophenyl(hydroxy)methyl]acrylate -
dc.typeArtículos de revistas


Este ítem pertenece a la siguiente institución