Degradation of Azo Dyes by Laccase and Ultrasound Treatment

Tauber, Michael Marco; Guebitz, Georg M.; Rehorek, Astrid

doi:10.1128/aem.71.5.2600-2607.2005

Cited by 67 publications

(27 citation statements)

References 45 publications

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“…Specific features that contribute to mutagenicity of azo dyes are related to differences in substitution sites, and the number and position of hydroxyl and sulpho groups adjacent to the azo bond (Table 1). For example, dyes containing a hydroxyl group at the ortho position are more toxic than those containing a hydroxyl group at the para position (Tauber et al, 2005). Likewise, differences in biodegradability are associated with particular features.…”

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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“…Moreover, degradation of azo dyes by reduction in water produces several aromatic amines, which are more toxic and carcinogenic than are the dyes themselves. The permissible concentration of aromatic amines in waste water is regulated by legislation, especially in developed countries (Tauber et al 2005). Aromatic amines enter the human body through the environmental chain and are next converted to acyloxyamine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Degradation of the synthetic dye amaranth by the fungus Bjerkandera adusta Dec 1: inference of the degradation pathway from an analysis of decolorized products

et al. 2011

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We examined the degradation of amaranth, a representative azo dye, by Bjerkandera adusta Dec 1. The degradation products were analyzed by high performance liquid chromatography (HPLC), visible absorbance, and electrospray ionization time-of-flight mass spectroscopy (ESI-TOF-MS). At the primary culture stage (3 days), the probable reaction intermediates were 1-aminonaphthalene-2,3,6-triol, 4-(hydroxyamino) naphthalene-1-ol, and 2-hydroxy-3-[2-(4-sulfophenyl) hydrazinyl] benzenesulfonic acid. After 10 days, the reaction products detected were 4-nitrophenol, phenol, 2-hydroxy-3-nitrobenzenesulfonic acid, 4-nitrobenzene sulfonic acid, and 3,4'-disulfonyl azo benzene, suggesting that no aromatic amines were created. Manganese-dependent peroxidase activity increased sharply after 3 days culture. Based on these results, we herein propose, for the first time, a degradation pathway for amaranth. Our results suggest that Dec 1 degrades amaranth via the combined activities of peroxidase and hydrolase and reductase action.

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“…It is known that laccases can catalyze the polymerization of various halogen-, alkyl-, and alkoxy-substituted anilines (15). In the literature, there is a large number of papers reporting on the decolorization of azo dyes; however, the fate of the products of azo dye laccase reactions and their possible polymerization have been ignored (7,16,25,28). Therefore, the purpose of this work was the study of azo dye degradation products in the presence of laccase.…”

mentioning

confidence: 99%

Degradation of Azo Dyes by Trametes villosa Laccase over Long Periods of Oxidative Conditions

Zille

Górnacka

Rehorek

et al. 2005

Appl Environ Microbiol

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149

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Trametes villosa laccase was used for direct azo dye degradation, and the reaction products that accumulated after 72 h of incubation were analyzed. Liquid chromatography-mass spectrometry (LC-MS) analysis showed the formation of phenolic compounds during the dye oxidation process as well as a large amount of polymerized products that retain azo group integrity. The amino-phenol reactions were also investigated by 13 C-nuclear magnetic resonance and LC-MS analysis, and the polymerization character of laccase was shown. This study highlights the fact that laccases polymerize the reaction products obtained during long-term batch decolorization processes with azo dyes. These polymerized products provide unacceptable color levels in effluents, limiting the application of laccases as bioremediation agents.The chemical structure of dyes is comprised of a conjugated system of double bonds and aromatic rings. The major classes of dyes have antroquinoid, indigoid, and azo aromatic structures. All of these structures allow strong -* transitions in the UV-visible (UV-Vis) area, with high extinction coefficients that allow us to consider these structures dye chromophores. Of all of these structures, the azo aromatic one is the most widespread dye class in the industry. The main drawback of this class of dyes is that they are not easily degraded by aerobic bacteria, and with the action of anaerobic or microaerobic reductive bacteria, they can form toxic and/or mutagenic compounds such as aromatic amines (9, 10, 34). There is a great environmental concern about the fate of these dyes, with special emphasis on reactive dyeing of cellulosic fibers, where large amounts of unbound dye are discharged in the effluent (24).Laccases have been extensively studied for their degradation of azo dyes (1,5,8,17,19,21,23,33). These enzymes are multicopper phenol oxidases that decolorize azo dyes through a highly nonspecific free radical mechanism forming phenolic compounds, thereby avoiding the formation of toxic aromatic amines (8,35). Over long periods of time, there can be a coupling between the reaction products, and even polymerization. It is known that laccases can catalyze the polymerization of various halogen-, alkyl-, and alkoxy-substituted anilines (15). In the literature, there is a large number of papers reporting on the decolorization of azo dyes; however, the fate of the products of azo dye laccase reactions and their possible polymerization have been ignored (7,16,25,28). Therefore, the purpose of this work was the study of azo dye degradation products in the presence of laccase. Direct azo dye laccase degradation and amino-phenol polymerization were performed for several days. The formed soluble products were studied by liquid chromatography-mass spectrometry (LC-MS), and the polymerized insoluble products were studied by 13 C-nuclear magnetic resonance ( 13 C-NMR). MATERIALS AND METHODSDyes, reagents, and enzymes. The investigated dyes, 3-(4-dimethylamino-1-phenylazo) benzenesulfonic acid (dye I) and 3-(2-hydroxy-1-naphthyl...

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Degradation of Azo Dyes by Laccase and Ultrasound Treatment

Cited by 67 publications

References 45 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

Degradation of the synthetic dye amaranth by the fungus Bjerkandera adusta Dec 1: inference of the degradation pathway from an analysis of decolorized products

Degradation of Azo Dyes by Trametes villosa Laccase over Long Periods of Oxidative Conditions

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