Comparative investigations of genotoxic activity of five nitriles in the comet assay and the Ames test

Wu, Jong-C.; Hseu, You Cheng; Chen, Chin-H.; Wang, Shu Hui; Chen, Ssu. C.

doi:10.1016/j.jhazmat.2009.03.121

Cited by 24 publications

(8 citation statements)

References 32 publications

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“…Finally, there is no evidence in the literature to indicate that the cyano group is itself a major structural alert for mutagenicity. Benzonitrile (cyanobenzene) gave negative results [Wu et al, ; Bhatia et al, ] as did the fungicide chlorothalonil (2,4,5,6‐tetrachloroiso‐phthalonitrile; 1,3‐dicyano‐2,4,5,6‐tetrachlorobenzene) [Wei, ]. Overall, there is no obvious explanation for the potent mutagenicity of CNNA and CNCNNA in terms of the individual contributions of the nitro, amino, and cyano substituents on the benzene ring; it appears that the genotoxicity of the compounds depends on the interaction of all of these contributing functional groups.…”

Section: Discussionmentioning

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: Discussionmentioning

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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“…This is supported further by the Ames test, which indicated mutagenicity for some of the supernatants but not for single substances. This comes at little surprise as the Ames is known to be less sensitive particularly for substances with low solubility (Lah et al 2008; Wu et al 2009). Meanwhile when used at their peak concentrations, the toxicity of the overall metabolite mixture in the comet assay came close to that of the original bacterial supernatants.…”

Section: Discussionmentioning

confidence: 99%

Toxification of polycyclic aromatic hydrocarbons by commensal bacteria from human skin

et al. 2017

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The ubiquitous occurrence of polycyclic aromatic hydrocarbons (PAHs) leads to constant human exposure at low levels. Toxicologically relevant are especially the high-molecular weight substances due to their (pro-)carcinogenic potential. Following ingestion or uptake, the eukaryotic phase I metabolism often activates these substances to become potent DNA binders, and unsurprisingly metabolism and DNA-adduct formation of model substances such as benzo[a]pyrene (B[a]P) are well studied. However, apart from being subjected to eukaryotic transformations PAHs are also carbon and energy sources for the myriads of commensal microbes inhabiting man’s every surface. Yet, we know little about the microbiome’s PAH-metabolism capacity and its potentially adverse impact on the human host. This study now shows that readily isolable skin commensals transform B[a]P into a range of highly cyto- and genotoxic metabolites that are excreted in toxicologically relevant concentrations during growth. The respective bacterial supernatants contain a mixture of established eukaryotic as well as hitherto unknown prokaryotic metabolites, the combination of which leads to an increased toxicity. Altogether we show that PAH metabolism of the microbiome has to be considered a potential hazard.Electronic supplementary materialThe online version of this article (doi:10.1007/s00204-017-1964-3) contains supplementary material, which is available to authorised users.

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“…This result is different from the degradation of AFB 1 in water and acetonitrile solution under UV irradiation, as detected in our previous articles. [21,22] A postulated mechanism for this reaction could involve a cleavage of the double bond on AFB 1 , as a consequence of the EBI treatment (Fig. 5).…”

Section: Degradation Products Of Afb 1 In Peanut Mealmentioning

confidence: 99%

Degradation of aflatoxin B₁ in peanut meal by electron beam irradiation

Liu

Wang

et al. 2018

International Journal of Food Properties

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The effects and safety of electron beam irradiation (EBI) treatment on the detoxification of aflatoxin B 1 (AFB 1) in the peanut meal were evaluated in this article. The AFB 1 degradation was predominantly affected by both initial AFB 1 and water concentrations. The degradation of AFB 1 in the selected concentrations (0.5-5 ppm) was proven to follow pseudo firstorder reaction kinetics (R 2 > 0.95). The AFB 1 degradation was faster when the initial concentration was 5 ppm and the moisture content was 21.47%, in comparison with the initial concentration of 1 ppm and 0.5 ppm and the moisture content of 14.32% and 8.74%, respectively. The Ames and cytotoxicity tests were employed to evaluate the residual toxicity of EBI-treated peanut meal. The mutagenic activity of EB-treated samples was completely lost compared with that of untreated samples and the degradation products in peanut meal has almost no cell toxicity.

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Comparative investigations of genotoxic activity of five nitriles in the comet assay and the Ames test

Cited by 24 publications

References 32 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

Toxification of polycyclic aromatic hydrocarbons by commensal bacteria from human skin

Degradation of aflatoxin B₁ in peanut meal by electron beam irradiation

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Comparative investigations of genotoxic activity of five nitriles in the comet assay and the Ames test

Cited by 24 publications

References 32 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

Toxification of polycyclic aromatic hydrocarbons by commensal bacteria from human skin

Degradation of aflatoxin B1 in peanut meal by electron beam irradiation

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Degradation of aflatoxin B₁ in peanut meal by electron beam irradiation