Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents

Quantum mechanical calculations were performed to elucidate the factors determining the variations in mutagenic activity within groups of isomeric heteroaromatic amines that differ in the position of methyl substituents. Formation energies for noncovalent complexes and covalent DNA adducts were eval...

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Detalhes bibliográficos
Autor: Borosky, Gabriela Leonor
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2016
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositório:CONICET Digital (CONICET)
Idioma:inglês
OAI Identifier:oai:ri.conicet.gov.ar:11336/60994
Acesso em linha:http://hdl.handle.net/11336/60994
Access Level:Acceso aberto
Palavra-chave:Dna Adducts
Heteroaromatic Amines
Mutagenicity
Noncovalent Interactions
Quantum Chemistry
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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spelling Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituentsBorosky, Gabriela LeonorDna AdductsHeteroaromatic AminesMutagenicityNoncovalent InteractionsQuantum Chemistryhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Quantum mechanical calculations were performed to elucidate the factors determining the variations in mutagenic activity within groups of isomeric heteroaromatic amines that differ in the position of methyl substituents. Formation energies for noncovalent complexes and covalent DNA adducts were evaluated by means of high level quantum chemical methods. According to the computational results in this work, covalent adduct stability is proposed to influence the relative mutagenicities of structurally related heterocyclic amines. The stability of covalent C8-dG DNA adducts was found to be mainly determined by π-stacking interactions between the fused ring system of the heteroaromatic amines and the flanking nucleobases. Relative mutagenicity of amines of very related structure is proposed to be regulated by both nitrenium ion and covalent adduct stabilities.Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaElsevier Science Inc2016-09-28info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/60994Borosky, Gabriela Leonor; Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents; Elsevier Science Inc; Journal Of Molecular Graphics & Modelling; 69; 28-9-2016; 92-1021093-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jmgm.2016.08.010info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1093326316301541info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:45:52Zoai:ri.conicet.gov.ar:11336/60994instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982024-05-08 13:45:52.511CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents
title Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents
spellingShingle Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents
Borosky, Gabriela Leonor
Dna Adducts
Heteroaromatic Amines
Mutagenicity
Noncovalent Interactions
Quantum Chemistry
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents
title_full Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents
title_fullStr Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents
title_full_unstemmed Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents
title_sort Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents
dc.creator.none.fl_str_mv Borosky, Gabriela Leonor
author Borosky, Gabriela Leonor
author_facet Borosky, Gabriela Leonor
author_role author
dc.subject.none.fl_str_mv Dna Adducts
Heteroaromatic Amines
Mutagenicity
Noncovalent Interactions
Quantum Chemistry
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Dna Adducts
Heteroaromatic Amines
Mutagenicity
Noncovalent Interactions
Quantum Chemistry
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description Quantum mechanical calculations were performed to elucidate the factors determining the variations in mutagenic activity within groups of isomeric heteroaromatic amines that differ in the position of methyl substituents. Formation energies for noncovalent complexes and covalent DNA adducts were evaluated by means of high level quantum chemical methods. According to the computational results in this work, covalent adduct stability is proposed to influence the relative mutagenicities of structurally related heterocyclic amines. The stability of covalent C8-dG DNA adducts was found to be mainly determined by π-stacking interactions between the fused ring system of the heteroaromatic amines and the flanking nucleobases. Relative mutagenicity of amines of very related structure is proposed to be regulated by both nitrenium ion and covalent adduct stabilities.
publishDate 2016
dc.date.none.fl_str_mv 2016-09-28
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/60994
Borosky, Gabriela Leonor; Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents; Elsevier Science Inc; Journal Of Molecular Graphics & Modelling; 69; 28-9-2016; 92-102
1093-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/60994
identifier_str_mv Borosky, Gabriela Leonor; Mutagenicity of heteroaromatic amines: Computational study on the influence of methyl substituents; Elsevier Science Inc; Journal Of Molecular Graphics & Modelling; 69; 28-9-2016; 92-102
1093-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jmgm.2016.08.010
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1093326316301541
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Inc
publisher.none.fl_str_mv Elsevier Science Inc
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 15,811543

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