Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids
Genotoxic permanent hair dye precursors p-aminophenol and p-toluenediamine electrochemical oxidation mechanisms and evaluation in biological fluids
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DOI：
10.1016/j.jelechem.2019.113509
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发表时间：
2020-01-15
影响因子：
4.5
通讯作者：
Oliveira-Brett, Ana Maria
中科院分区：
文献类型：
--
作者：
de Souza, Joao Carlos;Boldrin Zanoni, Maria Valnice;Oliveira-Brett, Ana Maria
本文采用循环伏安法、微分脉冲伏安法和方波伏安法，在玻碳电极上，在较宽的pH范围内，研究了持久性染发剂中广泛使用的遗传毒性前体物质对甲苯二胺（PTD）和对氨基苯酚（PAP）在生物体液中的电化学机理和评价。PTD和PAP的氧化都是可逆的。PTD的两电子两质子转移扩散控制反应发生在胺基中的分子氮原子上。PAP的氧化也是一个两个电子和两个质子转移扩散控制的反应，并发生在分子中的氮和氧原子上的胺和羟基基团。提出了PTD和PAP的电化学氧化机理。测定了PTD和PAP的扩散系数，PTD的D-PTD = 1.57 x 10（-5）cm（2）s（-1），PAP的D-PAP = 1.03 x 10（-5）cm（2）s（-1）。在0.10-1.00 μ M浓度范围内的电化学定量显示，PTD和PAP的检测限分别为0.12 μ M和0.17 μ M。建立了测定胎牛血清生物液和人工尿样中PTD和PAP的微分脉冲伏安法。
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.