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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Franco, Jefferson Honorio [1] ; da Silva, Bianca F. [1] ; Dias, Elisangela Franciscon G. [2] ; de Castro, Alexandre A. [3] ; Ramalho, Teodorico C. [3] ; Zanoni, Maria Valnice Boldrin [1]
Total Authors: 6
Affiliation:
[1] State Univ Julio de Mesquita Filho UNESP, Inst Chem, Sao Paulo - Brazil
[2] Univ Campinas UNICAMP, Sch Technol, Sao Paulo - Brazil
[3] Fed Univ Lavras UFLA, Dept Chem, Lavras, Minas Gerais - Brazil
Total Affiliations: 3
Document type: Journal article
Source: ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY; v. 160, p. 114-126, SEP 30 2018.
Web of Science Citations: 4
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 colt (E. cob) 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. (AU)

FAPESP's process: 15/18109-4 - Contribution of Nanostructured Materials in Electroanalysis of pharmaceuticals and dyes, in the oxidation and reduction photoeletrocatalytic process of Inorganic and Organic Pollutants and Water Disinfection.
Grantee:Maria Valnice Boldrin
Support Opportunities: Regular Research Grants
FAPESP's process: 08/10449-7 - Assessment of occurrence, toxicity/genotoxicity and degradation processes of dyes in effluents and surface water
Grantee:Maria Valnice Boldrin
Support Opportunities: Research Projects - Thematic Grants