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

Autores
Borosky, Gabriela Leonor
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
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; Argentina
Materia
Dna Adducts
Heteroaromatic Amines
Mutagenicity
Noncovalent Interactions
Quantum Chemistry
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/60994
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/60994
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
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 Técnicas2025-09-29T09:49:35Zoai: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:34982025-09-29 09:49:35.299CONICET 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
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
topic Dna Adducts
Heteroaromatic Amines
Mutagenicity
Noncovalent Interactions
Quantum Chemistry
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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.
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; Argentina
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
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
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 13.070432

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