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
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.envpol.2018.07.054 http://hdl.handle.net/11449/180169 |
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-nitrobenzonitrile, 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. To sum up, the results point out that both the original textile dyes and their degradation products may pose serious risks to human health and the environment at large. |
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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 DNABiotransformationDisperse dyes degradationEnzyme immobilized onto magnetiteNitroreductaseThe 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-nitrobenzonitrile, 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. To sum up, the results point out that both the original textile dyes and their degradation products may pose serious risks to human health and the environment at large.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Institute of Chemistry - São Paulo State University “Julio de Mesquita Filho”-UNESP-Avenida Professor Francisco Degni, 55, QuitandinhaDepartment of Chemistry Federal University of LavrasGroup of Sensors and Biosensors Autonomous University of BarcelonaInstitute of Chemistry - São Paulo State University “Julio de Mesquita Filho”-UNESP-Avenida Professor Francisco Degni, 55, QuitandinhaCNPq: 200309/2015-3 400459/2012-4FAPESP: 2008/10449-7FAPESP: 2015/18109-4Universidade Estadual Paulista (Unesp)Federal University of LavrasAutonomous University of BarcelonaFranco, Jefferson Honorio [UNESP]da Silva, Bianca F. [UNESP]de Castro, Alexandre A.Ramalho, Teodorico C.Pividori, María IsabelZanoni, Maria Valnice Boldrin [UNESP]2018-12-11T17:38:27Z2018-12-11T17:38:27Z2018-11-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article863-871application/pdfhttp://dx.doi.org/10.1016/j.envpol.2018.07.054Environmental Pollution, v. 242, p. 863-871.1873-64240269-7491http://hdl.handle.net/11449/18016910.1016/j.envpol.2018.07.0542-s2.0-850530714892-s2.0-85053071489.pdfScopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengEnvironmental Pollution1,6151,615info:eu-repo/semantics/openAccess2023-12-17T06:17:42Zoai:repositorio.unesp.br:11449/180169Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T20:32:52.133305Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
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 |
title |
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 |
spellingShingle |
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 Franco, Jefferson Honorio [UNESP] Biotransformation Disperse dyes degradation Enzyme immobilized onto magnetite Nitroreductase |
title_short |
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 |
title_full |
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 |
title_fullStr |
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 |
title_full_unstemmed |
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 |
title_sort |
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 |
author |
Franco, Jefferson Honorio [UNESP] |
author_facet |
Franco, Jefferson Honorio [UNESP] da Silva, Bianca F. [UNESP] de Castro, Alexandre A. Ramalho, Teodorico C. Pividori, María Isabel Zanoni, Maria Valnice Boldrin [UNESP] |
author_role |
author |
author2 |
da Silva, Bianca F. [UNESP] de Castro, Alexandre A. Ramalho, Teodorico C. Pividori, María Isabel Zanoni, Maria Valnice Boldrin [UNESP] |
author2_role |
author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) Federal University of Lavras Autonomous University of Barcelona |
dc.contributor.author.fl_str_mv |
Franco, Jefferson Honorio [UNESP] da Silva, Bianca F. [UNESP] de Castro, Alexandre A. Ramalho, Teodorico C. Pividori, María Isabel Zanoni, Maria Valnice Boldrin [UNESP] |
dc.subject.por.fl_str_mv |
Biotransformation Disperse dyes degradation Enzyme immobilized onto magnetite Nitroreductase |
topic |
Biotransformation Disperse dyes degradation Enzyme immobilized onto magnetite Nitroreductase |
description |
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-nitrobenzonitrile, 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. To sum up, the results point out that both the original textile dyes and their degradation products may pose serious risks to human health and the environment at large. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-12-11T17:38:27Z 2018-12-11T17:38:27Z 2018-11-01 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.envpol.2018.07.054 Environmental Pollution, v. 242, p. 863-871. 1873-6424 0269-7491 http://hdl.handle.net/11449/180169 10.1016/j.envpol.2018.07.054 2-s2.0-85053071489 2-s2.0-85053071489.pdf |
url |
http://dx.doi.org/10.1016/j.envpol.2018.07.054 http://hdl.handle.net/11449/180169 |
identifier_str_mv |
Environmental Pollution, v. 242, p. 863-871. 1873-6424 0269-7491 10.1016/j.envpol.2018.07.054 2-s2.0-85053071489 2-s2.0-85053071489.pdf |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Environmental Pollution 1,615 1,615 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
863-871 application/pdf |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808129218427486208 |