In vitro genotoxicity of para-phenylenediamine and its N-monoacetyl or N,N′-diacetyl metabolites

Garrigue, Jean-Luc; Ballantyne, Mark; Kumaravel, T. S.; Lloyd, Mel; Nohynek, Gerhard J.; Kirkland, David; Toutain, Hervé

doi:10.1016/j.mrgentox.2006.05.001

Cited by 46 publications

(33 citation statements)

References 24 publications

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“…From the studies by Mann [1], Barnes [42] and Smith [43] on the electrochemical oxidation of primary amines and from previous studies we made on the electrochemical oxidation of aliphatic diamines [24,25], we took the anodic oxidation of pPD the mechanism described in Figure 9. The first step is the adsorption of pPD on the surface electrode.…”

Section: Discussionmentioning

confidence: 99%

“…Fixing of Poly-pPD on a platinum electrode using cyclic voltammetry Polymerization of pPD on the platinum electrode: The results of the study of the anodic oxidation of pPD on the platinum electrode were published in 2013 [42]. The decrease of the oxidation peaks with repeated potential cycling between 0.8 and 1.35 V/ECS show a second oxidation of the pPD accompanied by fixation of pPD on the electrode (or polymerization) until saturation Pt pPD sites ( Figure 5).…”

Section: Physicochemical Testsmentioning

confidence: 99%

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confidence: 99%

“…potential scan rate of 200 mVs-1, two voltametric waves on the platen; which corresponds to two successive and reversible processes to a single electron, leading to the formation of a diamine [24].…”

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confidence: 99%

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Chemical and Biological Analyses of the Role of the Poly- Para- Phenylenediamine in the Erythrocytes Resistance in Hypotonic Environment

Srhayri¹,

Naimi²,

Takky³

et al. 2016

J Membra Sci Technol

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potential scan rate of 200 mVs-1, two voltametric waves on the platen; which corresponds to two successive and reversible processes to a single electron, leading to the formation of a diamine [24].Moreover, the genotoxicity studies in vitro have shown that pPD, like several other aromatic amines which belong to the aniline family can react with DNA and cause breaks . Picardo et al. have shown that pPD at high concentrations and for long exposure time induced cell cycle block and toxicity, but at low concentrations (10 µg/mL)and for shorter periods exposure (30 min) increased keratinocyte proliferation [39]. Habti et al. [6] have shown that pPD at low concentrations (5µg/mL) and for 2h exposure time gives RBC temporary resistance to hemolysis in hypotonic blend, the mechanism remains unexplained till now [6]. The aim of our study is to contribute to elucidate the molecular mechanism responsible for this temporary resistance. Material and Methods Collection of human blood sampleBlood samples from volunteer donors, and healthy aged 25-35 years were collected in tubes of 7 mL containing EDTA. Blood donors were nonsmokers and had no history of allergic reaction to pPD or AbstractThe high chemical and biological reactivity of para-phenylenediamine (pPD) has been illustrated in several studies, including polymerization genotoxicity and oxidative stress at the level of the plasma membrane cells. However, its reactivity with red blood cells (RBC) was rarely explored.The aim of this study is to help expound the molecular actions of para-phenylenediamine in hypotonic environment of human red blood cells by conducting biological tests for the globular resistance and physicochemical cyclic voltammetry and UV-visible spectroscopy.Our results show that the para-phenylenediamine at low concentration gives red blood cells temporary resistance (30 min) against hemolysis in hypotonic environment with 4.5 g/L NaCl. Spectrometry results for UVvisible and cyclic voltammetry suggest that membrane stability is due to the presence of the polymer poly-paraphenylenediamine (poly-pPD).

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Section: Discussionmentioning

confidence: 99%

Section: Physicochemical Testsmentioning

confidence: 99%

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Chemical and Biological Analyses of the Role of the Poly- Para- Phenylenediamine in the Erythrocytes Resistance in Hypotonic Environment

Srhayri¹,

Naimi²,

Takky³

et al. 2016

J Membra Sci Technol

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“…7) Moreover, it is reported that N-oxidation of arylamines like PPD occurs in the liver and is generally considered to involve cytochrome P450. 8) Furthermore, N-acetylated PPD metabolites are less toxic and they are excreted in urine.…”

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The Effects of Tungstate on Skin Lesions Caused by PPD in Rats

Lee¹,

Cho

S³

2008

Biological & Pharmaceutical Bulletin

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Red brownish p-phenylenediamine (PPD) has been widely used as one of the ingredients in hair dyes. The use by consumers of hair dye results in exposure of the hair, scalp skin, eyes, nail, and hands to PPD. PPD studies have found that women using dye with a formulation that included PPD suffered acute sensitive responses such as headaches, dizziness, and systemic anaphylaxis for the long time after using the product.1) And in patch tests, PPD caused erythema, rash, and a burning sensation on human skin. Furthermore, workers occupationally exposed to PPD in the field suffered from the bladder cancer.2,3) Previous studies have shown that PPD application induces injury to rat skin. 4,5) It is reported that PPD is metabolized to N-acetylated adducts as the major metabolites by N-acetyltransferase in human skin and liver, 6) and rats. 7) Moreover, it is reported that N-oxidation of arylamines like PPD occurs in the liver and is generally considered to involve cytochrome P450. 8) Furthermore, N-acetylated PPD metabolites are less toxic and they are excreted in urine.9) And, lipid peroxidation was increased while glutathione was decreased in skin by PPD application.5,10) In addition, PPD toxicity is increased by MnSOD polymorphism 11) while PPD toxicity is alleviated by thiol antioxidants.12) These reports suggest that production of ROS can be related to PPD skin toxicity. However, there are ongoing controversies whether PPD induced organ toxicity or whether it is safe in animal and clinical experiment. 13,14) It is well known that xenobiotic-induced tissue damage is related to reactive metabolites as well as produced reactive oxygen species (ROS) such as superoxide, hydroxyl radical, single oxygen and hydrogen peroxide under the metabolism. 15,16) Many studies have reported an imbalance between ROS generating systems and scavenging systems such as the increasing of ROS generating enzymes and/or decreasing of scavenging enzymes and nonenzymatic antioxidants. 17,18) It is accepted that xanthine oxidase (XO), one of the ROS generating systems, is increased in the injured cells.19) It has been revealed that inhibition of XO activity by allopurinol 20) or tungstate 21) alleviates experimental tissue damage. This indicates therefore a relationship of XO to skin cell injury, which suggests that the XO plays a role in the toxicity by the exposure of xenobiotics such as cosmetics and chemicals due to relatively higher XO activity in skin tissue compared with other tissues except liver and intestine. 19,22) It is reported that oxidized PPD, imine derivatives by hydrogen peroxide 23) could induce malignant and benign tumors in the mammary gland, uterus, and soft tissues of rats.24) Moreover, it is reported that XO could generate ROS such as superoxide and hydrogen peroxide.25,26) So, we hypothesized hydrogen peroxide derived from the XO system in skin involved with PPD oxidation and produced oxidized PPD is associated with dermal tissue damage.It is well established that sodium tungstate has relatively lower toxicity than that o...

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Aromatic Amino and Nitro–Amino Compounds and Their Halogenated Derivatives

Darby

2023

Patty's Toxicology

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The fundamental aromatic hydrocarbon benzene, when substituted by one or more functional groups of the amine, nitro, or halogen classes, alone or in various combinations, provides an enormous number of compounds of immense practical value, ubiquitous presence in the industrial world, and often heightened toxicity relative to benzene itself, a notorious cause of blood cancer. This chapter begins by providing a general overview of aromatic compounds possessing amino and/or nitro substituents, with or without halogen substituents. The production and uses, exposure and biomonitoring, toxicity, and toxic mechanism of action are introduced. The remainder of the chapter focuses on specific compounds in a roughly systematic order based upon chemical structure, expanding on the same subheadings as covered in the general overview. The nomenclature of these compounds can be very confusing since many have traditional names that sometimes markedly differ from their systematized formal names. In this chapter, the same traditional names are used as were used in the previous edition of this publication, but if there is ambiguity of nomenclature, the Chemical Abstracts Service (CAS) numbers provided herein correspond to unique structures, each of which may have several names depending upon the naming convention. In general, when an aromatic compound has an amino or a nitro substituent, it is referred to as an “aniline” or a “nitrobenzene,” respectively, based upon the names of the parent compounds, even though other substituents may be present. When amino and nitro groups are present on the same benzene ring, “aniline” takes precedence, and both “aniline” and “nitrobenzene” take precedence over halogens. There are many exceptions to these general rules, however.

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In vitro genotoxicity of para-phenylenediamine and its N-monoacetyl or N,N′-diacetyl metabolites

Cited by 46 publications

References 24 publications

Chemical and Biological Analyses of the Role of the Poly- Para- Phenylenediamine in the Erythrocytes Resistance in Hypotonic Environment

Chemical and Biological Analyses of the Role of the Poly- Para- Phenylenediamine in the Erythrocytes Resistance in Hypotonic Environment

The Effects of Tungstate on Skin Lesions Caused by PPD in Rats

Aromatic Amino and Nitro–Amino Compounds and Their Halogenated Derivatives

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