Busca avançada
Ano de início
Entree
(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Biotransformation of disperse dyes using nitroreductase immobilized on magnetic particles modified with tosyl group: Identification of products by LC-MS-MS and theoretical studies conducted with DNA

Texto completo
Autor(es):
Franco, Jefferson Honorio [1] ; da Silva, Bianca F. [1] ; de Castro, Alexandre A. [2] ; Ramalho, Teodorico C. [2] ; Isabel Pividori, Maria [3] ; Boldrin Zanoni, Maria Valnice [1]
Número total de Autores: 6
Afiliação do(s) autor(es):
[1] Sao Paulo State Univ Julio de Mesquita Filho UNES, Inst Chem, Ave Prof Francisco Degni 55, BR-14800900 Araraquara, SP - Brazil
[2] Univ Fed Lavras, Dept Chem, BR-37200000 Lavras - Brazil
[3] Autonomous Univ Barcelona, Grp Sensors & Biosensors, Barcelona - Spain
Número total de Afiliações: 3
Tipo de documento: Artigo Científico
Fonte: Environmental Pollution; v. 242, n. A, p. 863-871, NOV 2018.
Citações Web of Science: 0
Resumo

The present work evaluates the action of nitroreductase enzyme immobilized on Tosylactivated magnetic particles (MP-Tosyl) on three disperse dyes which contain nitro and azo groups. The dyes included Disperse Red 73 (DR 73), Disperse Red 78 (DR 78), and Disperse Red 167 (DR 167). The use of a magnet enabled the rapid and easy removal of the immobilized enzyme after biotransformation; this facilitated the identification of the products generated using high-performance liquid chromatography with diode array detector (HPLC-DAD) and mass spectrometry (LC-MS/MS). The main products formed by the in vitro biotransformation were identified as the product of nitro group reduction to the correspondent amine groups, which were denoted as follows: 50% of 2-(2-(4-((2-cyanoethyl)(ethyl)amino)phenyl)hydrazinyl)-5-nitrobenzonitri le, 98% of 3-((4-((4-amino-2-chlorophenyl) diazenyl)phenyl) (ethyl)amino)propanenitrile and 99% of (3-acetamido-4 - ((4-amino-2-chlorophenyl) diazenyl) phenyl) azanediyl) bis (ethane-2,1-diyl) for DR 73, DR 78 and DR 167, respectively. Based on the docking studies, the dyes investigated were found to be biotransformed by nitroreductase enzyme due to their favorable interaction with the active site of the enzyme. Theoretical results show that DR73 dye exhibits a relatively lower rate of degradation; this is attributed to the cyanide substituent which affects the electron density of the azo group. The docking studies also indicate that all the dyes presented significant reactivity towards DNA. However, Disperse Red 73 was found to exhibit a substantially higher reactivity compared to the other dyes; this implies that the dye possesses a relatively higher mutagenic power. The docking results also show that DR 73, DR 78 and DR 167 may be harmful to both humans and the environment, since the mutagenicity of nitro compounds is associated with the products formed during the reduction of nitro groups. These products can interact with biomolecules, including DNA, causing toxic and mutagenic effects. (C) 2018 Elsevier Ltd. All rights reserved. (AU)

Processo FAPESP: 08/10449-7 - Avaliação da ocorrência, toxicidade/genotoxicidade e processos para degradação de corantes em efluentes e águas superficiais
Beneficiário:Maria Valnice Boldrin
Linha de fomento: Auxílio à Pesquisa - Temático
Processo FAPESP: 15/18109-4 - Contribuição dos materiais nanoestruturados na eletroanálise de fármacos e corantes, na oxidação e redução fotoeletrocatalítica de poluentes orgânicos e inorgânicos e desinfecção de água
Beneficiário:Maria Valnice Boldrin
Linha de fomento: Auxílio à Pesquisa - Regular