Influence of auxochrome group in disperse dyes bearing azo groups as chromophore center in the biotransformation and molecular docking prediction by reductase enzyme: Implications and assessment for environmental toxicity of xenobiotics

Abstract

Synthetic azo dyes have increasingly become a matter of great concern as a result of the genotoxic and mutagenic potential of the products derived from azo dye biotransformation. This work evaluates the manner in which reducing enzymes produced by Escherichia coli (E. coli) act on three disperse dyes bearing azo groups, namely Disperse Red 73 (DR 73), Disperse Red 78 (DR 78), and Disperse Red 167 (DR 167). UV-Vis spectrophotometry, high-performance liquid chromatography with diode array detector (HPLC-DAD), and liquid chromatography mass spectrometry (LC-MS/MS) were applied towards the identification of the main products. Seven days of incubation of the azo dyes with the tested enzymes yielded a completely bleached solution. 3-4-Aminophenyl-ethyl-amino-propanitrile was detected following the biotransformation of both DR 73 and DR 78. 4-Nitroaniline and 2-chloro-4-nitroaniline were detected upon the biotransformation of DR 73 and DR 78, respectively. The main products derived from the biotransformation of DR 167 were dimethyl 3,3'-3-acetamido-4-aminophenyl-azanedyl-dipropanoate and 2-chloro-4-nitroaniline. The results imply that DR 73 lost the CN substituent during the biotransformation. Furthermore, theoretical calculations were also carried out aiming at evaluating the interaction and reactivity of these compounds with DNA. Taken together, the results indicate that DR 73, DR 78, and DR 167 pose health risks and serious threats to both human beings and the environment at large as their biotransformation produces harmful compounds such as amines, which have been widely condemned by the International Agency for Research on Cancer.

Super and Selective Adsorption of Cationic Dyes onto Carboxylate-Modified Passion Fruit Peel Biosorbent

“…And the discharge of a large amount of dye wastewater into the water body seriously threatens the ecosystem and human beings and has attracted considerable attention worldwide ( Afkhami and Moosavi, 2010 ). Furthermore, most dyes with aromatic rings are hard to be degraded by light, heat, microorganisms, and chemicals and their transformation products are carcinogenic, teratogenic, and mutagenic ( Franco et al, 2018 ). Thus, dye pollutants need to be urgently removed before the discharge of wastewater into the natural environment.…”

Characterization and Analysis of the COD Chemical Composition in the Polymer-Containing Oil Production Wastewater

“…Fig. 2 shows that the characteristics of the chromophore and auxochrome in the molecular structure were analyzed through the UV-Vis analysis [21]. The basis of the qualitative structure of the molecule was reflected by the change in the shape and position of the absorption peak.…”

Fundamentals, antibacterial, and photocatalysis properties of Ag@Se@PVDF nanocomposite membrane synthesized via laser ablation technique

“…Inhalation of methylene blue (MB) dye, which is utilized in the manufacturing, can induce digestive, respiratory, and nerve system problems. Because of their carcinogenic potential, dyes having an azo substituents caused a lot of concerns [12]. For example, to improve dye adsorption capability on the surface of the photocatalyst, the surface area is increased [13,14].…”