In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)

Autores
Borosky, Gabriela Leonor; Laali, Kenneth K.
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A computational density functional theory study on the structural and electronic properties of several polycyclic aromatic hydrocarbon (PAH) ortho-quinones was performed and the possible mechanism of DNA-adduct formation was analyzed to evaluate its thermodynamic viability. Molecular docking techniques were applied to examine the noncovalent interactions developed when a model PAH ortho-quinone intercalates between the DNA double helix. Quantum-chemical ONIOM (our Own N-layer Integrated molecular Orbital molecular Mechanics) calculations within the structure of a DNA fragment were carried out to evaluate the significant steps of noncovalent complex and covalent adduct formation. The solvent effect was also considered by employing a continuum solvation model. The present calculations suggest that initial noncovalent interactions of the PAH o-quinone within the DNA double helix could determine the feasibility of benzo[a]pyrene-7,8-dione-DNA covalent adduct formation, and that dispersion-corrected functionals are more suitable for locating the noncovalent complex. Copyright © 2012 John Wiley & Sons, Ltd.
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. University of North Florida; Estados Unidos
Fil: Laali, Kenneth K.. University of North Florida; Estados Unidos
Materia
Bioactivation Pathways
Molecular Docking
Oniom
Ortho-Quinones
Our Own N-Layer Integrated Molecular Orbital Molecular Mechanics Calculations
Polycyclic Aromatic Hydrocarbons
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:11336/62085
Acceder
id CONICETDig_87bb4acd5bc51bf086723b09c5ca355c
oai_identifier_str oai:ri.conicet.gov.ar:11336/62085
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)Borosky, Gabriela LeonorLaali, Kenneth K.Bioactivation PathwaysMolecular DockingOniomOrtho-QuinonesOur Own N-Layer Integrated Molecular Orbital Molecular Mechanics CalculationsPolycyclic Aromatic Hydrocarbonshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A computational density functional theory study on the structural and electronic properties of several polycyclic aromatic hydrocarbon (PAH) ortho-quinones was performed and the possible mechanism of DNA-adduct formation was analyzed to evaluate its thermodynamic viability. Molecular docking techniques were applied to examine the noncovalent interactions developed when a model PAH ortho-quinone intercalates between the DNA double helix. Quantum-chemical ONIOM (our Own N-layer Integrated molecular Orbital molecular Mechanics) calculations within the structure of a DNA fragment were carried out to evaluate the significant steps of noncovalent complex and covalent adduct formation. The solvent effect was also considered by employing a continuum solvation model. The present calculations suggest that initial noncovalent interactions of the PAH o-quinone within the DNA double helix could determine the feasibility of benzo[a]pyrene-7,8-dione-DNA covalent adduct formation, and that dispersion-corrected functionals are more suitable for locating the noncovalent complex. Copyright © 2012 John Wiley & Sons, Ltd.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. University of North Florida; Estados UnidosFil: Laali, Kenneth K.. University of North Florida; Estados UnidosJohn Wiley & Sons Ltd2012-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/62085Borosky, Gabriela Leonor; Laali, Kenneth K.; In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs); John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 25; 8; 8-2012; 720-7280894-3230CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/poc.2924info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.2924info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T09:41:08Zoai:ri.conicet.gov.ar:11336/62085instacron: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:34982025-11-05 09:41:08.356CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)
title In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)
spellingShingle In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)
Borosky, Gabriela Leonor
Bioactivation Pathways
Molecular Docking
Oniom
Ortho-Quinones
Our Own N-Layer Integrated Molecular Orbital Molecular Mechanics Calculations
Polycyclic Aromatic Hydrocarbons
title_short In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)
title_full In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)
title_fullStr In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)
title_full_unstemmed In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)
title_sort In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs)
dc.creator.none.fl_str_mv Borosky, Gabriela Leonor
Laali, Kenneth K.
author Borosky, Gabriela Leonor
author_facet Borosky, Gabriela Leonor
Laali, Kenneth K.
author_role author
author2 Laali, Kenneth K.
author2_role author
dc.subject.none.fl_str_mv Bioactivation Pathways
Molecular Docking
Oniom
Ortho-Quinones
Our Own N-Layer Integrated Molecular Orbital Molecular Mechanics Calculations
Polycyclic Aromatic Hydrocarbons
topic Bioactivation Pathways
Molecular Docking
Oniom
Ortho-Quinones
Our Own N-Layer Integrated Molecular Orbital Molecular Mechanics Calculations
Polycyclic Aromatic Hydrocarbons
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A computational density functional theory study on the structural and electronic properties of several polycyclic aromatic hydrocarbon (PAH) ortho-quinones was performed and the possible mechanism of DNA-adduct formation was analyzed to evaluate its thermodynamic viability. Molecular docking techniques were applied to examine the noncovalent interactions developed when a model PAH ortho-quinone intercalates between the DNA double helix. Quantum-chemical ONIOM (our Own N-layer Integrated molecular Orbital molecular Mechanics) calculations within the structure of a DNA fragment were carried out to evaluate the significant steps of noncovalent complex and covalent adduct formation. The solvent effect was also considered by employing a continuum solvation model. The present calculations suggest that initial noncovalent interactions of the PAH o-quinone within the DNA double helix could determine the feasibility of benzo[a]pyrene-7,8-dione-DNA covalent adduct formation, and that dispersion-corrected functionals are more suitable for locating the noncovalent complex. Copyright © 2012 John Wiley & Sons, Ltd.
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. University of North Florida; Estados Unidos
Fil: Laali, Kenneth K.. University of North Florida; Estados Unidos
description A computational density functional theory study on the structural and electronic properties of several polycyclic aromatic hydrocarbon (PAH) ortho-quinones was performed and the possible mechanism of DNA-adduct formation was analyzed to evaluate its thermodynamic viability. Molecular docking techniques were applied to examine the noncovalent interactions developed when a model PAH ortho-quinone intercalates between the DNA double helix. Quantum-chemical ONIOM (our Own N-layer Integrated molecular Orbital molecular Mechanics) calculations within the structure of a DNA fragment were carried out to evaluate the significant steps of noncovalent complex and covalent adduct formation. The solvent effect was also considered by employing a continuum solvation model. The present calculations suggest that initial noncovalent interactions of the PAH o-quinone within the DNA double helix could determine the feasibility of benzo[a]pyrene-7,8-dione-DNA covalent adduct formation, and that dispersion-corrected functionals are more suitable for locating the noncovalent complex. Copyright © 2012 John Wiley & Sons, Ltd.
publishDate 2012
dc.date.none.fl_str_mv 2012-08
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/11336/62085
Borosky, Gabriela Leonor; Laali, Kenneth K.; In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs); John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 25; 8; 8-2012; 720-728
0894-3230
CONICET Digital
CONICET
url http://hdl.handle.net/11336/62085
identifier_str_mv Borosky, Gabriela Leonor; Laali, Kenneth K.; In Silico study of carcinogenic o-Quinone metabolites derived from polycyclic aromatic hydrocarbons (PAHs); John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 25; 8; 8-2012; 720-728
0894-3230
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.2924
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.2924
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 John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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 13.087074

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