Detection and Determination of Aromatic Amines as Products of Reductive Splitting from Selected Azo Dyes

Pielesz, Anna; Baranowska, Irena; Rybak, Aurelia; Włochowicz, A.

doi:10.1006/eesa.2002.2191

Cited by 150 publications

(74 citation statements)

References 9 publications

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“…Aromatic amines are released after cleavage of azo bonds by microflora containing azoreductases (Prasad & Aikat, 2014). Moreover, aromatic amines are also produced when azo dyes come in contact with sweat, saliva or gastric juices of living organisms (Pielesz, 1999;Pielesz et al, 2002). Similarly, ingested azo dyes can be reduced to constitutive aromatic amines by the action of anaerobic intestinal microflora or by mammalian azoreductases that are produced in the intestinal wall or liver (Chequer et al, 2011).…”

Section: Aromatic Amines/intermediate-linked 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: Aromatic Amines/intermediate-linked 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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“…Sudan II also induced mutation in Salmonella typhimurium TA 1538 in the presence of a rat liver preparation [40]. Concerns about the safety of Sudan III have been raised due to potential metabolic cleavage of Sudan III to yield 4-aminoazobenzene and aniline by skin bacteria [41]. Sudan IV required chemical reduction and microsomal activation to be mutagenic [42].…”

Section: Azo Colorants and Their Applicationsmentioning

confidence: 99%

Recent Advances in Azo Dye Degrading Enzyme Research

Chen¹

2006

CPPS

218

125

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Azo dyes, which are characterized by one or more azo bonds, are a predominant class of colorants used in tattooing, cosmetics, foods, and consumer products. These dyes are mainly metabolized by bacteria to colorless aromatic amines, some of which are carcinogenic, by azoreductases that catalyze a NAD(P)H-dependent reduction. The resulting amines are further degraded aerobically by bacteria. Some bacteria have the ability to degrade azo dyes both aerobically and anaerobically. Plant-degrading white rot fungi can break down azo dyes by utilizing a number of oxidases and peroxidases as well. In yeast, a ferric reductase system participates in the extracellular reduction of azo dyes. Recently, two types of azoreductases have been discovered in bacteria. The first class of azoreductases is monomeric flavin-free enzymes containing a putative NAD(P)H binding motif at their N-termini; the second class is polymeric flavin dependent enzymes which are studied more extensively. Azoreductases from bacteria represent novel families of enzymes with little similarity to other reductases. Dissociation and reconstitution of the flavin dependent azoreductases demonstrate that the non-covalent bound flavin prosthetic group is required for the enzymatic functions. In this review, structures and carcinogenicity of azo colorants, protein structure, enzymatic function, and substrate specificity, as well as application of the azo dyes and azoreductases will be discussed.

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“…Sudan I is considered a possible human carcinogen and mutagen [4], and it is classified as a category 3 carcinogen by the International Agency for Research on Cancer (IARC) [5]. Moreover, Sudan II has been shown to cause a high frequency of bladder carcinomas in mice [6].…”

Section: Introductionmentioning

confidence: 99%

Determination of banned Sudan dyes in food samples by molecularly imprinted solid phase extraction‐high performance liquid chromatography

Baggiani¹,

Anfossi

Baravalle

et al. 2009

J of Separation Science

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Original PaperDetermination of banned Sudan dyes in food samples by molecularly imprinted solid phase extraction-high performance liquid chromatography A method for molecularly imprinted SPE of banned Sudan azo-dyes from food samples was investigated. The molecularly imprinted polymer was obtained by suspension polymerization using 1-(4-chlorophenyl)azonaphthalen-2-ol as the mimic template. The molecular recognition properties of imprinted beads were evaluated for use as a SPE sorbent, in order to develop a selective extraction protocol for the Sudan class of dyes. The optimized extraction protocol resulted in a reliable molecularly imprinted SPE (MISPE) method suitable for HPLC analysis. It was selective for the main analyte, Sudan I, and the related azo-dyes Sudan II, III, IV, Sudan Red B, and Sudan Red 7B, while the permitted azo-dyes Allura Red AC, Neococcin, and Sunset Yellow FCF were not extracted. The method was tested for Sudan I, II, III, and IV in five different food samples (hot chilli pepper, hot chilli tomato sauce, sausage, tomato sauce, and hard boiled egg yolk) at three concentration levels (15, 100, and 300 lg/g). It demonstrated itself to be insensitive to the presence of different complex matrices, precise, accurate, and with good recovery rates (85 -101%). The LOD and LOQ were satisfactory for most analytical determinations.

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Detection and Determination of Aromatic Amines as Products of Reductive Splitting from Selected Azo Dyes

Cited by 150 publications

References 9 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

Recent Advances in Azo Dye Degrading Enzyme Research

Determination of banned Sudan dyes in food samples by molecularly imprinted solid phase extraction‐high performance liquid chromatography

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