Azo Dyes and Their Metabolites: Does the Discharge of the Azo Dye into Water Bodies Represent Human and Ecological Risks?

Chequer, Farah Maria Drumond; Dorta, Daniel Junqueira; Oliveira, Danielle Palma de

doi:10.5772/19872

Cited by 36 publications

(20 citation statements)

References 124 publications

(166 reference statements)

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“…The CYP P450 enzymes belong to a superfamily of heme proteins that are present in all living organisms, mainly in the liver, and they are involved in the metabolism of a wide variety of chemical compounds (Livingstone, 1998;Kleinow et al, 1987). Chequer et al (Chequer et al, 2011) studied the products formed by the oxidation and reduction of the Disperse Red 1 by the reaction with cytochrome P450 isoenzymes using the methodologies of HPLC-DAD and GC-MS and evaluated the mutagenic potential of these products using two different methods: the Salmonella/microsome test with the strains TA 98 and YG 1041 in the absence of exogenous metabolic activation (S9) and the rat lymphoma assay (MLA). The work concluded that azo dye Disperse Red 1 can be metabolized by hepatic enzymes that generate mutagenic compounds, such as nitrobenzene, which is a mutagenic product and should be used with precaution.…”

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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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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show abstract

“…Most waste generated by the textile industry [1], is composed of organic and inorganic compounds generated during textile dyeing [2,3]. These compounds are difficult to eliminate by traditional effluent treatment processes [2,[4][5][6], due to the excessive content of suspended solids, and the presence of surfactants, detergents, and dyes [7]. The textile sector is also characterized by high competition, stimulated by economic, consumerism, and globalization factors, seeking improvements to reduce its expenses and costs, maintaining the quality of the product and contributing to sustainability [8].…”

Section: Introductionmentioning

confidence: 99%

Surface Modification of Polyester Fabrics by Ozone and Its Effect on Coloration Using Disperse Dyes

et al. 2021

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Polyester fibers (PES) are the most consumed textile fibers due to their low water absorption; non-ionic character and high crystallinity. However, due to their chemical structure, the chemical interactions between polyester, finishing products, and dyes are quite challenging. We report on the use of ozone to modify the surface of polyester fibers with the goal of improving the interaction of the modified surface with finishing compounds and dyes. We used C.I. Disperse Yellow 211 to dye ozone-treated polyester fabrics and evaluated the effects of ozone treatment using FTIR-ATR, Raman spectroscopy, SEM imaging, rubbing tests, and capillarity measurements. We evaluated the dyeing performance via color analysis, and determined the dyeing kinetics. Experimental results indicate that the modification of polyester fabrics with ozone is a feasible pre-treatment that improves dyeing efficiency allowing better solidity of color and a decrease in the amount of dye required.

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“…Genotoxic effects can be a result of progressive DNA damage which is partially mediated by reactive oxygen species and has a potential to lead to mutation and development of cancer [11]. Free radicals can be generated by the dye molecule itself, during reductive biotransformation of the azo bond or by products obtained after oxidation [12].…”

Section: Introductionmentioning

confidence: 99%

Acidic horseradish peroxidase activity abolishes genotoxicity of common dyes

Janović

Collins

Vujčić

et al. 2017

Journal of Hazardous Materials

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The aim of this study was to investigate the impact of dyes on DNA before and after enzymatic decolorization by acidic horseradish peroxidase (HRP-A). The comet assay is easy and feasible method widely used to measure DNA damage and repair. The medium-throughput comet assay was employed for assessment of genotoxic effects of 8 dyes in BEAS-2B cells. We have incorporated a digestion with bacterial endonuclease (formamidopyrimidine DNA glycosylase, FPG) to detect oxidized bases in the case of single and double azo dyes, Orange II (OR2) and Amido Black 10B (AB), respectively. This allowed detection 8-oxo-7,8-dihydroguanine, one of most abundant oxidized bases in nuclear DNA. In the case of AB there was no indication of DNA damage, either strand brakes or FPG-sensitive sites before and after decolorization. The OR2 induced DNA damage (in terms of percentage of DNA in comet tails). Also, the frequency of FPG-sensitive sites increased with OR2 concentration. After decolorization no DNA damaging effects was seen at all. The interaction studies of OR2 and AB, before and after decolorization, with calf thymus DNA has been investigated by absorption and fluorescence spectroscopy. The results provide support for the idea that in some cases enzymatic decolorization contributes to lower genotoxicity potential.

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Azo Dyes and Their Metabolites: Does the Discharge of the Azo Dye into Water Bodies Represent Human and Ecological Risks?

Cited by 36 publications

References 124 publications

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

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

Surface Modification of Polyester Fabrics by Ozone and Its Effect on Coloration Using Disperse Dyes

Acidic horseradish peroxidase activity abolishes genotoxicity of common dyes

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