The effect of alkoxy substituents on the mutagenicity of some aminoazobenzene dyes and their reductive-cleavage products

Esancy, James F.; Freeman, Harold S.; Claxton, Larry D.

doi:10.1016/0165-1110(90)90036-b

Cited by 29 publications

(6 citation statements)

References 17 publications

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“…Azo dye toxicity also depends on the nature and position of the aromatic rings and the amino nitrogen atom. For example, 2-methoxy-4-aminoazobenzene is an extremely weak mutagen, whereas 3-methoxy-4-aminoazobenzene is a strong hepatocarcinogen and mutagen (Esancy et al, 1990;Garg et al, 2002). Likewise, the presence of sulphonic groups on aromatic amines decreases their mutagenicity whereas the acetoxy Aromatic amines formed during anoxic conditions Dafale et al (2010) (COCH 3 ) substituent increases their mutagenic effects (Pasha et al, 2008;Roy et al, 2006).…”

Section: Dye Structure-associated Toxicitymentioning

confidence: 99%

Bacterial diversity and composition in major fresh produce growing soils affected by physiochemical properties and geographic locations

Ibekwe

Yang

et al. 2016

Science of The Total Environment

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Azo dyes and their intermediate degradation products are common contaminants of soil and groundwater in developing countries where textile and leather dye products are produced. The toxicity of azo dyes is primarily associated with their molecular structure, substitution groups and reactivity. To avoid contamination of natural resources and to minimize risk to human health, this wastewater requires treatment in an environmentally safe manner. This manuscript critically reviews biological treatment systems and the role of bacterial reductive and oxidative enzymes/processes in the bioremediation of dye-polluted wastewaters. Many studies have shown that a variety of culturable bacteria have efficient enzymatic systems that can carry out complete mineralization of dye chemicals and their metabolites (aromatic compounds) over a wide range of environmental conditions. Complete mineralization of azo dyes generally involves a two-step process requiring initial anaerobic treatment for decolorization, followed by an oxidative process that results in degradation of the toxic intermediates that are formed during the first step. Molecular studies have revealed that the first reductive process can be carried out by two classes of enzymes involving flavin-dependent and flavin-free azoreductases under anaerobic or low oxygen conditions. The second step that is carried out by oxidative enzymes that primarily involves broad specificity peroxidases, laccases and tyrosinases. This review focuses, in particular, on the characterization of these enzymes with respect to their enzyme kinetics and the environmental conditions that are necessary for bioreactor systems to treat azo dyes contained in wastewater.

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Section: Dye Structure-associated Toxicitymentioning

confidence: 99%

Bacterial diversity and composition in major fresh produce growing soils affected by physiochemical properties and geographic locations

Ibekwe

Yang

et al. 2016

Science of The Total Environment

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“…Several dyes from this group have shown mutagenic responses in Salmonella and mammalian assay systems, and it is clear that their potencies depend on the nature and position of the substituents with respect to both the aromatic rings and the amino nitrogen atom. For instance, 3‐methoxy‐4‐aminoazobenzene is a potent hepatocarcinogen in rats and a strong mutagen in bacteria, whereas 2‐methoxy‐4‐aminoazobenzene is apparently noncarcinogenic and an extremely weak mutagen in bacteria (Hashimoto et al, 1977; Esancy et al, 1990). The dyes Acid Red 18 and Acid Red 27 are nonmutagenic, whereas the structurally similar dye Acid Red 26 is reported to be carcinogenic just because of the incorporation of a methyl group and alteration of the position of the sodium sulfonate (Freeman et al, 1990).…”

Section: Introductionmentioning

confidence: 99%

Differential toxicity of Disperse Red 1 and Disperse Red 13 in the Ames test, HepG2 cytotoxicity assay, and Daphnia acute toxicity test

Ferraz¹,

Umbuzeiro²,

de-Almeida³

et al. 2011

Environmental Toxicology

126

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Azo dyes are of environmental concern due to their degradation products, widespread use, and low-removal rate during conventional treatment. Their toxic properties are related to the nature and position of the substituents with respect to the aromatic rings and amino nitrogen atom. The dyes Disperse Red 1 and Disperse Red 13 were tested for Salmonella mutagenicity, cell viability by annexin V, and propidium iodide in HepG2 and by aquatic toxicity assays using daphnids. Both dyes tested positive in the Salmonella assay, and the suggestion was made that these compounds induce mainly frame-shift mutations and that the enzymes nitroreductase and O-acetyltransferase play an important role in the observed effect. In addition, it was shown that the presence of the chlorine substituent in Disperse Red 13 decreased the mutagenicity about 14 times when compared with Disperse Red 1, which shows the same structure as Disperse Red 13, but without the chlorine substituent. The presence of this substituent did not cause cytotoxicity in HepG2 cells, but toxicity to the water flea Daphnia similis increased in the presence of the chlorine substituent. These data suggest that the insertion of a chlorine substituent could be an alternative in the design of dyes with low-mutagenic potency, although the ecotoxicity should be carefully evaluated.

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“…Among the synthetic dyes, the textile azo dyes with synthetic intermediates as contaminant and its products have undoubtedly attracted attention with regard to their potentiality to form toxic aromatic products with carcinogenicity and mutagenicity properties [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. The Ecological and Toxicological Association of the Dyestuff Manufacturing Industry (ETAD) have reported that the highest rates of toxicity (LD50) were found amongst azo dyes [15].…”

Section: Introductionmentioning

confidence: 99%

Photoelectrocatalytic oxidation of remazol turquoise blue and toxicological assessment of its oxidation products

Osugi

Umbuzeiro²,

Castro³

et al. 2006

Journal of Hazardous Materials

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The effect of alkoxy substituents on the mutagenicity of some aminoazobenzene dyes and their reductive-cleavage products

Cited by 29 publications

References 17 publications

Bacterial diversity and composition in major fresh produce growing soils affected by physiochemical properties and geographic locations

Bacterial diversity and composition in major fresh produce growing soils affected by physiochemical properties and geographic locations

Differential toxicity of Disperse Red 1 and Disperse Red 13 in the Ames test, HepG2 cytotoxicity assay, and Daphnia acute toxicity test

Photoelectrocatalytic oxidation of remazol turquoise blue and toxicological assessment of its oxidation products

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