Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.jelechem.2019.113509 http://hdl.handle.net/11449/199788 |
Resumo: | The p-toluenediamine (PTD) and p-aminophenol (PAP), genotoxic precursor agents widely used in permanent hair dyeing formulations, electrochemical mechanisms and evaluation in biological fluids, at a glassy carbon electrode, in a wide pH range, by cyclic, differential pulse, and square wave voltammetry, were investigated. The oxidation of both PTD and PAP is reversible. The PTD two electrons and two protons transfer diffusion-controlled reaction occurs at the molecule nitrogen atoms in the amine groups. Also PAP oxidation is a two electrons and two protons transfer diffusion-controlled reactions, and occur at the nitrogen and oxygen atoms of the molecule amine and hydroxyl groups. An electrochemical oxidation mechanism for PTD and PAP is proposed. The PTD and PAP diffusion coefficients, DPTD = 1.57 × 10−5 cm2 s−1 for PTD, and DPAP = 1.03 × 10−5 cm2 s−1 for PAP, were determined. The electrochemical quantification in 0.10–1.00 μM concentration range showed a detection limit of 0.12 μM for PTD and 0.17 μM PAP. A new electroanalytical method for the determination of PTD and PAP in fetal bovine serum biological fluid, and in artificial urine samples, using differential pulse voltammetry, was also developed. |
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Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluidsElectrochemical oxidationGenotoxic precursorsGlassy carbon electrodeHair dyesP-aminophenolP-toluenediamineThe p-toluenediamine (PTD) and p-aminophenol (PAP), genotoxic precursor agents widely used in permanent hair dyeing formulations, electrochemical mechanisms and evaluation in biological fluids, at a glassy carbon electrode, in a wide pH range, by cyclic, differential pulse, and square wave voltammetry, were investigated. The oxidation of both PTD and PAP is reversible. The PTD two electrons and two protons transfer diffusion-controlled reaction occurs at the molecule nitrogen atoms in the amine groups. Also PAP oxidation is a two electrons and two protons transfer diffusion-controlled reactions, and occur at the nitrogen and oxygen atoms of the molecule amine and hydroxyl groups. An electrochemical oxidation mechanism for PTD and PAP is proposed. The PTD and PAP diffusion coefficients, DPTD = 1.57 × 10−5 cm2 s−1 for PTD, and DPAP = 1.03 × 10−5 cm2 s−1 for PAP, were determined. The electrochemical quantification in 0.10–1.00 μM concentration range showed a detection limit of 0.12 μM for PTD and 0.17 μM PAP. A new electroanalytical method for the determination of PTD and PAP in fetal bovine serum biological fluid, and in artificial urine samples, using differential pulse voltammetry, was also developed.Programa Operacional Temático Factores de CompetitividadeFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Fundação para a Ciência e a TecnologiaDepartment of Chemistry Faculty of Sciences and Technology University of CoimbraInstitute of Chemistry Department of Analytical Chemistry National Institute of Alternative Technologies for Detection Toxicological Assessment and Removal of Micropollutants and Radioactive (INCT-DATREM) São Paulo State University (UNESP)Institute of Chemistry Department of Analytical Chemistry National Institute of Alternative Technologies for Detection Toxicological Assessment and Removal of Micropollutants and Radioactive (INCT-DATREM) São Paulo State University (UNESP)University of CoimbraUniversidade Estadual Paulista (Unesp)de Souza, João Carlos [UNESP]Zanoni, Maria Valnice Boldrin [UNESP]Oliveira-Brett, Ana Maria2020-12-12T01:49:18Z2020-12-12T01:49:18Z2020-01-15info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.jelechem.2019.113509Journal of Electroanalytical Chemistry, v. 857.1572-6657http://hdl.handle.net/11449/19978810.1016/j.jelechem.2019.1135092-s2.0-85076237131Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Electroanalytical Chemistryinfo:eu-repo/semantics/openAccess2021-10-23T09:49:05Zoai:repositorio.unesp.br:11449/199788Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T16:13:35.915590Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids |
title |
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids |
spellingShingle |
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids de Souza, João Carlos [UNESP] Electrochemical oxidation Genotoxic precursors Glassy carbon electrode Hair dyes P-aminophenol P-toluenediamine |
title_short |
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids |
title_full |
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids |
title_fullStr |
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids |
title_full_unstemmed |
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids |
title_sort |
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids |
author |
de Souza, João Carlos [UNESP] |
author_facet |
de Souza, João Carlos [UNESP] Zanoni, Maria Valnice Boldrin [UNESP] Oliveira-Brett, Ana Maria |
author_role |
author |
author2 |
Zanoni, Maria Valnice Boldrin [UNESP] Oliveira-Brett, Ana Maria |
author2_role |
author author |
dc.contributor.none.fl_str_mv |
University of Coimbra Universidade Estadual Paulista (Unesp) |
dc.contributor.author.fl_str_mv |
de Souza, João Carlos [UNESP] Zanoni, Maria Valnice Boldrin [UNESP] Oliveira-Brett, Ana Maria |
dc.subject.por.fl_str_mv |
Electrochemical oxidation Genotoxic precursors Glassy carbon electrode Hair dyes P-aminophenol P-toluenediamine |
topic |
Electrochemical oxidation Genotoxic precursors Glassy carbon electrode Hair dyes P-aminophenol P-toluenediamine |
description |
The p-toluenediamine (PTD) and p-aminophenol (PAP), genotoxic precursor agents widely used in permanent hair dyeing formulations, electrochemical mechanisms and evaluation in biological fluids, at a glassy carbon electrode, in a wide pH range, by cyclic, differential pulse, and square wave voltammetry, were investigated. The oxidation of both PTD and PAP is reversible. The PTD two electrons and two protons transfer diffusion-controlled reaction occurs at the molecule nitrogen atoms in the amine groups. Also PAP oxidation is a two electrons and two protons transfer diffusion-controlled reactions, and occur at the nitrogen and oxygen atoms of the molecule amine and hydroxyl groups. An electrochemical oxidation mechanism for PTD and PAP is proposed. The PTD and PAP diffusion coefficients, DPTD = 1.57 × 10−5 cm2 s−1 for PTD, and DPAP = 1.03 × 10−5 cm2 s−1 for PAP, were determined. The electrochemical quantification in 0.10–1.00 μM concentration range showed a detection limit of 0.12 μM for PTD and 0.17 μM PAP. A new electroanalytical method for the determination of PTD and PAP in fetal bovine serum biological fluid, and in artificial urine samples, using differential pulse voltammetry, was also developed. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-12-12T01:49:18Z 2020-12-12T01:49:18Z 2020-01-15 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.jelechem.2019.113509 Journal of Electroanalytical Chemistry, v. 857. 1572-6657 http://hdl.handle.net/11449/199788 10.1016/j.jelechem.2019.113509 2-s2.0-85076237131 |
url |
http://dx.doi.org/10.1016/j.jelechem.2019.113509 http://hdl.handle.net/11449/199788 |
identifier_str_mv |
Journal of Electroanalytical Chemistry, v. 857. 1572-6657 10.1016/j.jelechem.2019.113509 2-s2.0-85076237131 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Electroanalytical Chemistry |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808128620752797696 |