CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III

Detalhes bibliográficos
Autor(a) principal: Zanoni, Thalita Boldrin
Data de Publicação: 2013
Outros Autores: Lizier, Thiago M. [UNESP], Assis, Marilda das Dores, Zanoni, Maria Valnice Boldrin [UNESP], De Oliveira, Danielle Palma
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1016/j.fct.2013.03.035
http://hdl.handle.net/11449/75764
Resumo: This work describes the mutagenic response of Sudan III, an adulterant food dye, using Salmonella typhimurium assay and the generation of hazardous aromatic amines after different oxidation methods of this azo dye. For that, we used metabolic activation by S9, catalytic oxidation by ironporphyrin and electrochemistry oxidation in order to simulate endogenous oxidation conditions. The oxidation reactions promoted discoloration from 65% to 95% of Sudan III at 1×10-4molL-1 and generation of 7.6×10-7molL-1 to 0.31×10-4molL-1 of aniline, o-anisidine, 2-methoxi-5-methylaniline, 4-aminobiphenyl, 4,4'-oxydianiline; 4,4'-diaminodiphenylmethane and 2,6-dimethylaniline. The results were confirmed by LC-MS-MS experiments. We also correlate the mutagenic effects of Sudan III using S. typhimurium with the strain TA1535 in the presence of exogenous metabolic activation (S9) with the metabolization products of this compound. Our findings clearly indicate that aromatic amines are formed due to oxidative reactions that can be promoted by hepatic cells, after the ingestion of Sudan III. Considering that, the use of azo compounds as food dyestuffs should be carefully controlled. © 2013 Elsevier Ltd.
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spelling CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan IIIAromatic aminesBiomimetical modelsElectrochemical oxidationIronporphyrinsOxidative metabolismSudan dyes2 methoxy 5 methylaniline2,6 dimethylaniline4 biphenylamine4,4' diaminodiphenyl ether4,4' methylenedianilineanisidinearomatic amineironporphyrinoil scarletporphyrinunclassified drugbase pairingcatalysiselectrochemistryframeshift mutationliquid chromatographymass spectrometrymetabolic activationmutagenic activityoxidationSalmonella typhimuriumThis work describes the mutagenic response of Sudan III, an adulterant food dye, using Salmonella typhimurium assay and the generation of hazardous aromatic amines after different oxidation methods of this azo dye. For that, we used metabolic activation by S9, catalytic oxidation by ironporphyrin and electrochemistry oxidation in order to simulate endogenous oxidation conditions. The oxidation reactions promoted discoloration from 65% to 95% of Sudan III at 1×10-4molL-1 and generation of 7.6×10-7molL-1 to 0.31×10-4molL-1 of aniline, o-anisidine, 2-methoxi-5-methylaniline, 4-aminobiphenyl, 4,4'-oxydianiline; 4,4'-diaminodiphenylmethane and 2,6-dimethylaniline. The results were confirmed by LC-MS-MS experiments. We also correlate the mutagenic effects of Sudan III using S. typhimurium with the strain TA1535 in the presence of exogenous metabolic activation (S9) with the metabolization products of this compound. Our findings clearly indicate that aromatic amines are formed due to oxidative reactions that can be promoted by hepatic cells, after the ingestion of Sudan III. Considering that, the use of azo compounds as food dyestuffs should be carefully controlled. © 2013 Elsevier Ltd.Faculdade de Ciências Farmacêuticas de Ribeirão Preto Departamento de Análises Clínicas Toxicológicas e Bromatológicas Universidade de São Paulo, Avenida do Café, s/n, 14040-903 Ribeirão Preto, SPInstituto de Química Departamento de Química Analítica Universidade Estadual Paulista - UNESP, Rua Professor Francisco Degni, 55 Quitandinha, 14800-900 Araraquara, SPFaculdade de Filosofia, Ciências e Letras de Ribeirão Preto Departamento de Química Universidade de São Paulo, Av. Bandeirantes 3900, 14040-901 Ribeirão Preto, SPInstituto de Química Departamento de Química Analítica Universidade Estadual Paulista - UNESP, Rua Professor Francisco Degni, 55 Quitandinha, 14800-900 Araraquara, SPUniversidade de São Paulo (USP)Universidade Estadual Paulista (Unesp)Zanoni, Thalita BoldrinLizier, Thiago M. [UNESP]Assis, Marilda das DoresZanoni, Maria Valnice Boldrin [UNESP]De Oliveira, Danielle Palma2014-05-27T11:29:48Z2014-05-27T11:29:48Z2013-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article217-226application/pdfhttp://dx.doi.org/10.1016/j.fct.2013.03.035Food and Chemical Toxicology, v. 57, p. 217-226.0278-69151873-6351http://hdl.handle.net/11449/7576410.1016/j.fct.2013.03.035WOS:0003204983000282-s2.0-848767993822-s2.0-84876799382.pdf0000-0002-2296-1393Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengFood and Chemical Toxicology3.9771,144info:eu-repo/semantics/openAccess2023-12-25T06:21:28Zoai:repositorio.unesp.br:11449/75764Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T21:16:14.992738Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III
title CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III
spellingShingle CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III
Zanoni, Thalita Boldrin
Aromatic amines
Biomimetical models
Electrochemical oxidation
Ironporphyrins
Oxidative metabolism
Sudan dyes
2 methoxy 5 methylaniline
2,6 dimethylaniline
4 biphenylamine
4,4' diaminodiphenyl ether
4,4' methylenedianiline
anisidine
aromatic amine
ironporphyrin
oil scarlet
porphyrin
unclassified drug
base pairing
catalysis
electrochemistry
frameshift mutation
liquid chromatography
mass spectrometry
metabolic activation
mutagenic activity
oxidation
Salmonella typhimurium
title_short CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III
title_full CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III
title_fullStr CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III
title_full_unstemmed CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III
title_sort CYP-450 isoenzymes catalyze the generation of hazardous aromatic amines after reaction with the azo dye Sudan III
author Zanoni, Thalita Boldrin
author_facet Zanoni, Thalita Boldrin
Lizier, Thiago M. [UNESP]
Assis, Marilda das Dores
Zanoni, Maria Valnice Boldrin [UNESP]
De Oliveira, Danielle Palma
author_role author
author2 Lizier, Thiago M. [UNESP]
Assis, Marilda das Dores
Zanoni, Maria Valnice Boldrin [UNESP]
De Oliveira, Danielle Palma
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Universidade de São Paulo (USP)
Universidade Estadual Paulista (Unesp)
dc.contributor.author.fl_str_mv Zanoni, Thalita Boldrin
Lizier, Thiago M. [UNESP]
Assis, Marilda das Dores
Zanoni, Maria Valnice Boldrin [UNESP]
De Oliveira, Danielle Palma
dc.subject.por.fl_str_mv Aromatic amines
Biomimetical models
Electrochemical oxidation
Ironporphyrins
Oxidative metabolism
Sudan dyes
2 methoxy 5 methylaniline
2,6 dimethylaniline
4 biphenylamine
4,4' diaminodiphenyl ether
4,4' methylenedianiline
anisidine
aromatic amine
ironporphyrin
oil scarlet
porphyrin
unclassified drug
base pairing
catalysis
electrochemistry
frameshift mutation
liquid chromatography
mass spectrometry
metabolic activation
mutagenic activity
oxidation
Salmonella typhimurium
topic Aromatic amines
Biomimetical models
Electrochemical oxidation
Ironporphyrins
Oxidative metabolism
Sudan dyes
2 methoxy 5 methylaniline
2,6 dimethylaniline
4 biphenylamine
4,4' diaminodiphenyl ether
4,4' methylenedianiline
anisidine
aromatic amine
ironporphyrin
oil scarlet
porphyrin
unclassified drug
base pairing
catalysis
electrochemistry
frameshift mutation
liquid chromatography
mass spectrometry
metabolic activation
mutagenic activity
oxidation
Salmonella typhimurium
description This work describes the mutagenic response of Sudan III, an adulterant food dye, using Salmonella typhimurium assay and the generation of hazardous aromatic amines after different oxidation methods of this azo dye. For that, we used metabolic activation by S9, catalytic oxidation by ironporphyrin and electrochemistry oxidation in order to simulate endogenous oxidation conditions. The oxidation reactions promoted discoloration from 65% to 95% of Sudan III at 1×10-4molL-1 and generation of 7.6×10-7molL-1 to 0.31×10-4molL-1 of aniline, o-anisidine, 2-methoxi-5-methylaniline, 4-aminobiphenyl, 4,4'-oxydianiline; 4,4'-diaminodiphenylmethane and 2,6-dimethylaniline. The results were confirmed by LC-MS-MS experiments. We also correlate the mutagenic effects of Sudan III using S. typhimurium with the strain TA1535 in the presence of exogenous metabolic activation (S9) with the metabolization products of this compound. Our findings clearly indicate that aromatic amines are formed due to oxidative reactions that can be promoted by hepatic cells, after the ingestion of Sudan III. Considering that, the use of azo compounds as food dyestuffs should be carefully controlled. © 2013 Elsevier Ltd.
publishDate 2013
dc.date.none.fl_str_mv 2013-07-01
2014-05-27T11:29:48Z
2014-05-27T11:29:48Z
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.fct.2013.03.035
Food and Chemical Toxicology, v. 57, p. 217-226.
0278-6915
1873-6351
http://hdl.handle.net/11449/75764
10.1016/j.fct.2013.03.035
WOS:000320498300028
2-s2.0-84876799382
2-s2.0-84876799382.pdf
0000-0002-2296-1393
url http://dx.doi.org/10.1016/j.fct.2013.03.035
http://hdl.handle.net/11449/75764
identifier_str_mv Food and Chemical Toxicology, v. 57, p. 217-226.
0278-6915
1873-6351
10.1016/j.fct.2013.03.035
WOS:000320498300028
2-s2.0-84876799382
2-s2.0-84876799382.pdf
0000-0002-2296-1393
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Food and Chemical Toxicology
3.977
1,144
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 217-226
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
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