Mutagenicity evaluation of the commercial product CI Disperse Blue 291 using different protocols of the Salmonella assay

Umbuzeiro, Gisela de Aragão; Freeman, Harold S.; Warren, Sarah H.; Kummrow, Fábio; Claxton, Larry D.

doi:10.1016/j.fct.2004.08.011

Cited by 82 publications

(9 citation statements)

References 25 publications

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“…Some commercial preparations of disperse azo dyes are known to be mutagenic in the Ames ( Salmonella typhimurium histidine reversion) assay. For example, de Aragão Umbuzeiro et al reported positive test results for Disperse Blue 291 in bacterial strains sensitive to frameshift and base pair substitution mutations [de Aragão Umbuzeiro et al, ] and Chequer et al found Disperse Red 1 and Disperse Red 13 to be Ames test‐positive frameshift mutagens [Chequer et al, ; Ferraz et al, ].…”

Section: Introductionmentioning

confidence: 99%

Potent mutagenicity in the Ames test of 2‐cyano‐4‐nitroaniline and 2,6‐dicyano‐4‐nitroaniline, components of disperse dyes

Josephy

Zahid

Dhanoa

et al. 2015

Environ and Mol Mutagen

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Genotoxicity data on commercial azo dyes and their components remain sparse, despite their widespread use. We have tested the mutagenicity of 2-cyano-4-nitroaniline (CNNA) and 2,6-dicyano-4-nitroaniline (CNCNNA), components of azo dyes such as Disperse Blue 165 and Disperse Red 73, in Ames test strains. Both compounds are extraordinarily potent frameshift mutagens, with much greater activity than structurally similar dihalonitroanilines and halodinitroanilines. Analysis of the responses of strains over-expressing or deficient in bioactivation enzymes shows that bacterial nitroreductase and acetyl CoA: arylamine N-acetyltransferase are important mediators of the mutagenicity of CNNA and CNCNNA. Environ. Mol. Mutagen. 57:10-16, 2016. V C 2015 Wiley Periodicals, Inc.Key words: Ames test; nitroanilines; cyanoaromatics; disperse dyes INTRODUCTIONThe history of the synthetic dye industry is interwoven with the development of organic chemistry, toxicology, and occupational safety. Azo dyes continue to comprise more than half of the worldwide production volume of dyes. Azo compounds are found in many functional classes of dyes, including acid, basic, disperse, reactive, and solvent dyes [Freeman, 2013]. The European Commission has banned the use of any azo dyes which, upon reduction, might liberate any of 22 designated aromatic amines, including benzidine, 4-aminobiphenyl, 2-naphthylamine, and other proven or suspected carcinogens [Ahlstr€ om et al., 2005]. However, absence from this list is not proof of safety. Regulatory agencies have conducted major research studies and risk-assessment reviews of azo dyes and their aromatic amine precursors, notably the "Benzidine Dye Initiative" of the National Toxicology Program, USA [Morgan et al., 1994] and the recent "Aromatic Azo and Benzidinebased Substance Grouping" component of the "Substance Groupings Initiative" conducted by Environment Canada and Health Canada. The chemical structures of many of these dyes include "structural alerts" for mutagenicity, such as nitroaromatic and arylamine functional groups. Nevertheless, there are many knowledge gaps in the toxicology and genotoxicology data for azo dyes and their components. One major reason for this is simply the very large number of synthetic dyes; Weaver states that nearly 100,000 different dyes were produced at the Eastman Kodak Co. alone, through 1986[Weaver, 2003.Besides the possible toxicity of azo dyes per se [Yadav et al., 2013;Fernandes et al., 2015], these dyes can also present hazards mediated by their constituent aromatic Abbreviations: BrBrNA, 2,6-dibromo-4-nitroaniline; BrDNA, 2-bromo-4,6-dinitroaniline; ClBrNA, 2-bromo-6-chloro-4-nitroaniline; ClClNA, 2,6-dichloro-4-nitroaniline; ClDNA, 2-chloro-4,6-dinitroaniline; CNCNNA, 2,6-dicyano-4-nitroaniline; CNCNNB, 1,3-dicyano-5-nitrobenzene; CNCNPPD, 2,6-dicyano-p-phenylenediamine; CNNA, 2-cyano-4-nitroaniline. All authors declare that there are no conflicts of interest. Environmental and Molecular Mutagenesis 57:10^16 (2016) amines. Residues of the amines used i...

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Section: Introductionmentioning

confidence: 99%

Potent mutagenicity in the Ames test of 2‐cyano‐4‐nitroaniline and 2,6‐dicyano‐4‐nitroaniline, components of disperse dyes

Josephy

Zahid

Dhanoa

et al. 2015

Environ and Mol Mutagen

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“…These dyes and their degradation products when released into water, even at very low concentrations, could be toxic, inducing carcinogenic, mutagenic or teratogenic effects to various organisms, including aquatic organisms and humans. Toxicological risks of these compounds are closely related to biotransformation processes (Umbuzeiro et al, 2005b;Umbuzeiro et al, 2005a), considering that changes to their chemical structure induced by different biological reactions, such as reduction, oxidation, acetylation and chlorination reactions may produce harmful compounds to the environment and human health (Novotný et al, 2006).…”

Section: G R a P H I C A L Abstractmentioning

confidence: 99%

Identification of biotransformation products of disperse dyes with rat liver microsomes by LC-MS/MS and theoretical studies with DNA: Structure-mutagenicity relationship using Salmonella/microsome assay

Franco

Silva

Oliveira³

et al. 2018

Science of The Total Environment

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Azo dyes are known as a group of substances with DNA damage potential that depend on the nature and number of azo groups connected to aromatic rings (benzene and naphthalene), chemical properties, e.g. solubility and reactive functional groups, which significantly affect their toxicological and ecological risks. In this paper, we used in vitro models to evaluate the metabolism of selected textile dyes: Disperse Red 73 (DR 73), Disperse Red 78 (DR 78) and Disperse Red 167 (DR 167). To evaluate the mutagenic potential of the textile dyes, the Salmonella mutagenicity assay (Ames test) with strains TA 98 and TA 100 in the presence and absence of the exogenous metabolic system (S9) was used. DR73 was considered the most mutagenic compound, inducing both replacement base pairs (TA 100) and also changing frameshift (TA 98) mutations that are reduced in the presence of the S9 mixture. Furthermore, we used rat liver microsomes in the same experimental conditions of the S9 mixture to metabolize the dyes and the resultant solutions were analyzed using a liquid chromatography coupled to a quadrupole linear ion trap mass spectrometry (LC-MS/MS) to investigate the metabolites formed by the in vitro biotransformation. Based on this experiment, we detected and identified two biotransformation products for each textile dye substrate analyzed. Furthermore, to evaluate the interaction and reactivity of these compounds with DNA, theoretical calculations were also carried out. The results showed that the chemical reaction occurred preferentially at the azo group and the nitro group, indicating that there was a reduction in these groups by the CYP P450 enzymes presented in the rat microsomal medium. Our results clearly demonstrated that the reduction of these dyes by biological systems is a great environmental concern due to increased genotoxicity for the body of living beings, especially for humans.

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“…Depending on the quality of the chemicals used for the coloring, as well as on the coloring/washing procedures, the remaining chemical impurities of the dye’s formulation present in the textile may constitute a health risk if taken up by and passing through the human skin. In vitro mutagenicity and cytotoxicity studies have been conducted to assess the risk of chronic exposure to fabric dyes (de Aragão Umbuzeiro 2005 ; Tsuboy 2007 ; Ferraz 2012 ). In the production step of natural fabrics (e.g., cotton), several pesticides are often used during storage (Thompson 2015 ; Zhang 2008 ), or to improve the technical characteristics of the final product, obtaining an anti-bug cloth (Holme 2007 ).…”

Section: Introductionmentioning

confidence: 99%

Chemicals from textiles to skin: an in vitro permeation study of benzothiazole

Iadaresta

Manniello

Östman

et al. 2018

Environ Sci Pollut Res

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Despite the possible impact on human health, few studies have been conducted to assess the penetration and accumulation of contaminants in the skin after a prolonged contact with textile materials. In previous studies, we have shown that benzothiazole and its derivatives, as well as other potentially hazardous chemicals, often are present as textile contaminants in clothes available on the retail market. Since benzothiazole is a common contaminant in clothes, these can be a possible route for human chemical exposure, both systemic and onto the skin. To investigate this potential exposure, Franz-type and flow-through cells were used for the permeation studies together with a Strat-M® artificial membranes. Experiments were performed using solutions of benzothiazole, as well as contaminated textile samples in the donor chamber. Benzothiazole was demonstrated to penetrate through, as well as being accumulated in the membrane mimicking the skin. After 24 h, up to 62% of benzothiazole was found in the acceptor cell, while up to 37% was found absorbed in the skin mimicking membrane. It also was shown that there was release and permeation from contaminated fabrics. The results indicate that benzothiazole can be released from textile materials, penetrate through the skin, and further enter the human body. This will possibly also apply to other chemical contaminants in textiles, and the results of this study indicate that the presence of these textile contaminants entails potential health risks. A rough risk assessment was made for clothing textiles according to Environmental Protection Agency (EPA) and European regulations for carcinogenic and non-carcinogenic compounds, using literature data for benzothiazole.Electronic supplementary materialThe online version of this article (10.1007/s11356-018-2448-6) contains supplementary material, which is available to authorized users.

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Mutagenicity evaluation of the commercial product CI Disperse Blue 291 using different protocols of the Salmonella assay

Cited by 82 publications

References 25 publications

Potent mutagenicity in the Ames test of 2‐cyano‐4‐nitroaniline and 2,6‐dicyano‐4‐nitroaniline, components of disperse dyes

Potent mutagenicity in the Ames test of 2‐cyano‐4‐nitroaniline and 2,6‐dicyano‐4‐nitroaniline, components of disperse dyes

Identification of biotransformation products of disperse dyes with rat liver microsomes by LC-MS/MS and theoretical studies with DNA: Structure-mutagenicity relationship using Salmonella/microsome assay

Chemicals from textiles to skin: an in vitro permeation study of benzothiazole

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