Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids

Autor(es)

de Souza, Joao Carlos ^{[1, 2]} ; Boldrin Zanoni, Maria Valnice ^[2] ; Oliveira-Brett, Ana Maria ^[1]

Afiliação do(s) autor(es)

^[1] Univ Coimbra, Fac Sci & Technol, Dept Chem, P-3004535 Coimbra - Portugal

^[2] Sao Paulo State Univ, UNESP, Natl Inst Alternat Technol Detect Toxicol Assessm, Dept Analyt Chem, Inst Chem, BR-14800060 Araraquara, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: JOURNAL OF ELECTROANALYTICAL CHEMISTRY; v. 857, JAN 15 2020.
• Citações Web of Science: 0

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, D-PTD = 1.57 x 10(-5) cm(2) s(-1) for PTD, and D-PAP = 1.03 x 10(-5) cm(2) s(-1) for PAP, were determined. The electrochemical quantification in 0.10-1.00 mu M concentration range showed a detection limit of 0.12 mu M for PTD and 0.17 mu M 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. (AU)

• Processo FAPESP: 14/50945-4 - INCT 2014: Instituto Nacional de Tecnologias Alternativas para Detecção, Avaliação Toxicológica e Remoção de Micropoluentes e Radioativos
• Beneficiário: Maria Valnice Boldrin
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 18/12449-6 - Estudo do comportamento eletroquímico da queratina e sua interação com p-toluenodiamina e p-aminofenol e seus produtos de oxidação mimetizando reações de tintura permanente de cabelo
• Beneficiário: João Carlos de Souza
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado
• Processo FAPESP: 15/12998-1 - Métodos cromatográficos e eletroanalíticos aplicados na determinação de p-toluenodiamina e p-aminofenol em meio oxidativo usados em tintura permanente de cabelos.
• Beneficiário: João Carlos de Souza
• Modalidade de apoio: Bolsas no Brasil - Doutorado