Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density

Autores
Angelina, Emilio Luis; Andujar, Sebastian Antonio; Tosso, Rodrigo David; Enriz, Ricardo Daniel; Peruchena, Nelida Maria
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this paper, we reported the results obtained by charge density analysis of the network of non-covalent interactions (NCI) established in the binding pocket of a receptor, in relevant conformations of ligand – receptor complexes. Starting with strong and moderate hydrogen bonds, moving on to weaker polar interactions and ending with stacking and T-shape like interactions between aromatic rings, all of them have been investigated within the framework of the density functional theory and the quantum theory of atoms in molecules. Also, natural bond orbital analysis was carried out, in order to evaluate quantitatively the electronic population of the aromatic rings. The analysis of our “case study” shows that the interactions of the catechol OH groups of the ligand, in the different conformations of the dopamine (DA) – D2 receptor complex, determine the decrease or increase of the electron density on the aromatic ring of DA. In turn, the electronic population of the aromatic ring of DA defines its orientation within the binding site and the type of interactions that it establishes with the aromatic rings of the receptor. Although the approach used here was traditionally applied to the study of NCI in small molecules complexes in gas phase, we show through this work that this methodology is also a very powerful tool for the study of biomolecular complexes, providing a very detailed description of the binding event.
Fil: Angelina, Emilio Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Andujar, Sebastian Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Tosso, Rodrigo David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Peruchena, Nelida Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Química. Laboratorio de Estructura Molecular y Propiedades; Argentina
Materia
Dft
D2-Dopamine Receptor
Nbo
Qtaim
Stacking Interaction
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:11336/35831
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge densityAngelina, Emilio LuisAndujar, Sebastian AntonioTosso, Rodrigo DavidEnriz, Ricardo DanielPeruchena, Nelida MariaDftD2-Dopamine ReceptorNboQtaimStacking Interactionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this paper, we reported the results obtained by charge density analysis of the network of non-covalent interactions (NCI) established in the binding pocket of a receptor, in relevant conformations of ligand – receptor complexes. Starting with strong and moderate hydrogen bonds, moving on to weaker polar interactions and ending with stacking and T-shape like interactions between aromatic rings, all of them have been investigated within the framework of the density functional theory and the quantum theory of atoms in molecules. Also, natural bond orbital analysis was carried out, in order to evaluate quantitatively the electronic population of the aromatic rings. The analysis of our “case study” shows that the interactions of the catechol OH groups of the ligand, in the different conformations of the dopamine (DA) – D2 receptor complex, determine the decrease or increase of the electron density on the aromatic ring of DA. In turn, the electronic population of the aromatic ring of DA defines its orientation within the binding site and the type of interactions that it establishes with the aromatic rings of the receptor. Although the approach used here was traditionally applied to the study of NCI in small molecules complexes in gas phase, we show through this work that this methodology is also a very powerful tool for the study of biomolecular complexes, providing a very detailed description of the binding event.Fil: Angelina, Emilio Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Andujar, Sebastian Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Tosso, Rodrigo David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Peruchena, Nelida Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Química. Laboratorio de Estructura Molecular y Propiedades; ArgentinaWiley2013-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/35831Angelina, Emilio Luis; Andujar, Sebastian Antonio; Tosso, Rodrigo David; Enriz, Ricardo Daniel; Peruchena, Nelida Maria; Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density; Wiley; Journal Of Physical Organic Chemistry; 27; 2; 11-2013; 971-9820894-32301099-1395CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/poc.3250/abstractinfo:eu-repo/semantics/altIdentifier/doi/10.1002/poc.3250info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:50:58Zoai:ri.conicet.gov.ar:11336/35831instacron: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:34982025-09-03 09:50:58.889CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density
title Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density
spellingShingle Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density
Angelina, Emilio Luis
Dft
D2-Dopamine Receptor
Nbo
Qtaim
Stacking Interaction
title_short Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density
title_full Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density
title_fullStr Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density
title_full_unstemmed Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density
title_sort Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density
dc.creator.none.fl_str_mv Angelina, Emilio Luis
Andujar, Sebastian Antonio
Tosso, Rodrigo David
Enriz, Ricardo Daniel
Peruchena, Nelida Maria
author Angelina, Emilio Luis
author_facet Angelina, Emilio Luis
Andujar, Sebastian Antonio
Tosso, Rodrigo David
Enriz, Ricardo Daniel
Peruchena, Nelida Maria
author_role author
author2 Andujar, Sebastian Antonio
Tosso, Rodrigo David
Enriz, Ricardo Daniel
Peruchena, Nelida Maria
author2_role author
author
author
author
dc.subject.none.fl_str_mv Dft
D2-Dopamine Receptor
Nbo
Qtaim
Stacking Interaction
topic Dft
D2-Dopamine Receptor
Nbo
Qtaim
Stacking Interaction
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this paper, we reported the results obtained by charge density analysis of the network of non-covalent interactions (NCI) established in the binding pocket of a receptor, in relevant conformations of ligand – receptor complexes. Starting with strong and moderate hydrogen bonds, moving on to weaker polar interactions and ending with stacking and T-shape like interactions between aromatic rings, all of them have been investigated within the framework of the density functional theory and the quantum theory of atoms in molecules. Also, natural bond orbital analysis was carried out, in order to evaluate quantitatively the electronic population of the aromatic rings. The analysis of our “case study” shows that the interactions of the catechol OH groups of the ligand, in the different conformations of the dopamine (DA) – D2 receptor complex, determine the decrease or increase of the electron density on the aromatic ring of DA. In turn, the electronic population of the aromatic ring of DA defines its orientation within the binding site and the type of interactions that it establishes with the aromatic rings of the receptor. Although the approach used here was traditionally applied to the study of NCI in small molecules complexes in gas phase, we show through this work that this methodology is also a very powerful tool for the study of biomolecular complexes, providing a very detailed description of the binding event.
Fil: Angelina, Emilio Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Andujar, Sebastian Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Tosso, Rodrigo David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Peruchena, Nelida Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Química. Laboratorio de Estructura Molecular y Propiedades; Argentina
description In this paper, we reported the results obtained by charge density analysis of the network of non-covalent interactions (NCI) established in the binding pocket of a receptor, in relevant conformations of ligand – receptor complexes. Starting with strong and moderate hydrogen bonds, moving on to weaker polar interactions and ending with stacking and T-shape like interactions between aromatic rings, all of them have been investigated within the framework of the density functional theory and the quantum theory of atoms in molecules. Also, natural bond orbital analysis was carried out, in order to evaluate quantitatively the electronic population of the aromatic rings. The analysis of our “case study” shows that the interactions of the catechol OH groups of the ligand, in the different conformations of the dopamine (DA) – D2 receptor complex, determine the decrease or increase of the electron density on the aromatic ring of DA. In turn, the electronic population of the aromatic ring of DA defines its orientation within the binding site and the type of interactions that it establishes with the aromatic rings of the receptor. Although the approach used here was traditionally applied to the study of NCI in small molecules complexes in gas phase, we show through this work that this methodology is also a very powerful tool for the study of biomolecular complexes, providing a very detailed description of the binding event.
publishDate 2013
dc.date.none.fl_str_mv 2013-11
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/11336/35831
Angelina, Emilio Luis; Andujar, Sebastian Antonio; Tosso, Rodrigo David; Enriz, Ricardo Daniel; Peruchena, Nelida Maria; Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density; Wiley; Journal Of Physical Organic Chemistry; 27; 2; 11-2013; 971-982
0894-3230
1099-1395
CONICET Digital
CONICET
url http://hdl.handle.net/11336/35831
identifier_str_mv Angelina, Emilio Luis; Andujar, Sebastian Antonio; Tosso, Rodrigo David; Enriz, Ricardo Daniel; Peruchena, Nelida Maria; Non-covalent interactions in receptor-ligand complexes. A study based on the electron charge density; Wiley; Journal Of Physical Organic Chemistry; 27; 2; 11-2013; 971-982
0894-3230
1099-1395
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/poc.3250/abstract
info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.3250
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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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
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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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