Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies

Autores
Méndez, Santiago García; Otero Espinar, Francisco J.; Alvarez, Asteria Luzardo; Longhi, Marcela Raquel; Quevedo, Mario Alfredo; Zoppi, Ariana
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
β-Cyclodextrin (β-CD) is a well-known host molecule used to prepare inclusion complexes. Considering that the three dimensional array of these complexes depends on the inclusion mode of the guest molecule within the β-CD cavity, the development of methods to elucidate their structure is highly desired. The main objective of this work aimed to shed light on the structural and energetic features related to the effect of aminoacids (AA: glycine, valine, isoleucine, arginine and glutamic acid) as third components on the complexation of benzoic acid (BA) with β-CD. In addition, hippuric acid (HA), a structure resembling a BA-glycine conjugate, was included as a model molecule to compare the effect of glycine present as a chemical moiety covalently linked to the guest molecule. Phase solubility analyses were performed to determine the relative binding affinities for binary (BA:β-CD and HA:βCD) and ternary (BA:β-CD:AA) complexes, obtaining the following results: BA:β-CD:AA > BA:β-CD: > HA:β-CD. As part of the structural elucidation of the studied complexes, their spatial configurations were determined by NMR and further characterized applying molecular modeling (i.e., molecular docking and molecular dynamics) techniques. Both approaches evidenced that BA and HA included their aromatic rings in the β-CD hydrophobic cavity, both in binary and ternary complexes. When free aminoacids were present as third components, an enhanced affinity of BA for β-CD was observed, feature that was not evidenced when the aminoacid was covalently bound to the included guest (i.e., HA). Exhaustive structural and energetic analyses are presented to rationalize and support these findings.
Fil: Méndez, Santiago García. Universidad de Santiago de Compostela; España
Fil: Otero Espinar, Francisco J.. Universidad de Santiago de Compostela; España
Fil: Alvarez, Asteria Luzardo. Universidad de Santiago de Compostela; España
Fil: Longhi, Marcela Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina
Fil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina
Fil: Zoppi, Ariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina
Materia
Benzoic Acid
Binary And Ternary Complex
Hippuric Acid
Molecular Modeling
Nmr Studies
Β-Cyclodextrin
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:11336/62959
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/62959
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studiesMéndez, Santiago GarcíaOtero Espinar, Francisco J.Alvarez, Asteria LuzardoLonghi, Marcela RaquelQuevedo, Mario AlfredoZoppi, ArianaBenzoic AcidBinary And Ternary ComplexHippuric AcidMolecular ModelingNmr StudiesΒ-Cyclodextrinhttps://purl.org/becyt/ford/2.10https://purl.org/becyt/ford/2β-Cyclodextrin (β-CD) is a well-known host molecule used to prepare inclusion complexes. Considering that the three dimensional array of these complexes depends on the inclusion mode of the guest molecule within the β-CD cavity, the development of methods to elucidate their structure is highly desired. The main objective of this work aimed to shed light on the structural and energetic features related to the effect of aminoacids (AA: glycine, valine, isoleucine, arginine and glutamic acid) as third components on the complexation of benzoic acid (BA) with β-CD. In addition, hippuric acid (HA), a structure resembling a BA-glycine conjugate, was included as a model molecule to compare the effect of glycine present as a chemical moiety covalently linked to the guest molecule. Phase solubility analyses were performed to determine the relative binding affinities for binary (BA:β-CD and HA:βCD) and ternary (BA:β-CD:AA) complexes, obtaining the following results: BA:β-CD:AA > BA:β-CD: > HA:β-CD. As part of the structural elucidation of the studied complexes, their spatial configurations were determined by NMR and further characterized applying molecular modeling (i.e., molecular docking and molecular dynamics) techniques. Both approaches evidenced that BA and HA included their aromatic rings in the β-CD hydrophobic cavity, both in binary and ternary complexes. When free aminoacids were present as third components, an enhanced affinity of BA for β-CD was observed, feature that was not evidenced when the aminoacid was covalently bound to the included guest (i.e., HA). Exhaustive structural and energetic analyses are presented to rationalize and support these findings.Fil: Méndez, Santiago García. Universidad de Santiago de Compostela; EspañaFil: Otero Espinar, Francisco J.. Universidad de Santiago de Compostela; EspañaFil: Alvarez, Asteria Luzardo. Universidad de Santiago de Compostela; EspañaFil: Longhi, Marcela Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; ArgentinaFil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; ArgentinaFil: Zoppi, Ariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; ArgentinaSpringer2016-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/62959Méndez, Santiago García; Otero Espinar, Francisco J.; Alvarez, Asteria Luzardo; Longhi, Marcela Raquel; Quevedo, Mario Alfredo; et al.; Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies ; Springer; Journal Of Inclusion Phenomena And Macrocyclic Chemistry; 85; 1-2; 6-2016; 33-480167-78611573-1111CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s10847-016-0603-6info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs10847-016-0603-6info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:41:07Zoai:ri.conicet.gov.ar:11336/62959instacron: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 09:41:07.314CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
title Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
spellingShingle Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
Méndez, Santiago García
Benzoic Acid
Binary And Ternary Complex
Hippuric Acid
Molecular Modeling
Nmr Studies
Β-Cyclodextrin
title_short Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
title_full Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
title_fullStr Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
title_full_unstemmed Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
title_sort Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
dc.creator.none.fl_str_mv Méndez, Santiago García
Otero Espinar, Francisco J.
Alvarez, Asteria Luzardo
Longhi, Marcela Raquel
Quevedo, Mario Alfredo
Zoppi, Ariana
author Méndez, Santiago García
author_facet Méndez, Santiago García
Otero Espinar, Francisco J.
Alvarez, Asteria Luzardo
Longhi, Marcela Raquel
Quevedo, Mario Alfredo
Zoppi, Ariana
author_role author
author2 Otero Espinar, Francisco J.
Alvarez, Asteria Luzardo
Longhi, Marcela Raquel
Quevedo, Mario Alfredo
Zoppi, Ariana
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Benzoic Acid
Binary And Ternary Complex
Hippuric Acid
Molecular Modeling
Nmr Studies
Β-Cyclodextrin
topic Benzoic Acid
Binary And Ternary Complex
Hippuric Acid
Molecular Modeling
Nmr Studies
Β-Cyclodextrin
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.10
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv β-Cyclodextrin (β-CD) is a well-known host molecule used to prepare inclusion complexes. Considering that the three dimensional array of these complexes depends on the inclusion mode of the guest molecule within the β-CD cavity, the development of methods to elucidate their structure is highly desired. The main objective of this work aimed to shed light on the structural and energetic features related to the effect of aminoacids (AA: glycine, valine, isoleucine, arginine and glutamic acid) as third components on the complexation of benzoic acid (BA) with β-CD. In addition, hippuric acid (HA), a structure resembling a BA-glycine conjugate, was included as a model molecule to compare the effect of glycine present as a chemical moiety covalently linked to the guest molecule. Phase solubility analyses were performed to determine the relative binding affinities for binary (BA:β-CD and HA:βCD) and ternary (BA:β-CD:AA) complexes, obtaining the following results: BA:β-CD:AA > BA:β-CD: > HA:β-CD. As part of the structural elucidation of the studied complexes, their spatial configurations were determined by NMR and further characterized applying molecular modeling (i.e., molecular docking and molecular dynamics) techniques. Both approaches evidenced that BA and HA included their aromatic rings in the β-CD hydrophobic cavity, both in binary and ternary complexes. When free aminoacids were present as third components, an enhanced affinity of BA for β-CD was observed, feature that was not evidenced when the aminoacid was covalently bound to the included guest (i.e., HA). Exhaustive structural and energetic analyses are presented to rationalize and support these findings.
Fil: Méndez, Santiago García. Universidad de Santiago de Compostela; España
Fil: Otero Espinar, Francisco J.. Universidad de Santiago de Compostela; España
Fil: Alvarez, Asteria Luzardo. Universidad de Santiago de Compostela; España
Fil: Longhi, Marcela Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina
Fil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina
Fil: Zoppi, Ariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina
description β-Cyclodextrin (β-CD) is a well-known host molecule used to prepare inclusion complexes. Considering that the three dimensional array of these complexes depends on the inclusion mode of the guest molecule within the β-CD cavity, the development of methods to elucidate their structure is highly desired. The main objective of this work aimed to shed light on the structural and energetic features related to the effect of aminoacids (AA: glycine, valine, isoleucine, arginine and glutamic acid) as third components on the complexation of benzoic acid (BA) with β-CD. In addition, hippuric acid (HA), a structure resembling a BA-glycine conjugate, was included as a model molecule to compare the effect of glycine present as a chemical moiety covalently linked to the guest molecule. Phase solubility analyses were performed to determine the relative binding affinities for binary (BA:β-CD and HA:βCD) and ternary (BA:β-CD:AA) complexes, obtaining the following results: BA:β-CD:AA > BA:β-CD: > HA:β-CD. As part of the structural elucidation of the studied complexes, their spatial configurations were determined by NMR and further characterized applying molecular modeling (i.e., molecular docking and molecular dynamics) techniques. Both approaches evidenced that BA and HA included their aromatic rings in the β-CD hydrophobic cavity, both in binary and ternary complexes. When free aminoacids were present as third components, an enhanced affinity of BA for β-CD was observed, feature that was not evidenced when the aminoacid was covalently bound to the included guest (i.e., HA). Exhaustive structural and energetic analyses are presented to rationalize and support these findings.
publishDate 2016
dc.date.none.fl_str_mv 2016-06
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/11336/62959
Méndez, Santiago García; Otero Espinar, Francisco J.; Alvarez, Asteria Luzardo; Longhi, Marcela Raquel; Quevedo, Mario Alfredo; et al.; Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies ; Springer; Journal Of Inclusion Phenomena And Macrocyclic Chemistry; 85; 1-2; 6-2016; 33-48
0167-7861
1573-1111
CONICET Digital
CONICET
url http://hdl.handle.net/11336/62959
identifier_str_mv Méndez, Santiago García; Otero Espinar, Francisco J.; Alvarez, Asteria Luzardo; Longhi, Marcela Raquel; Quevedo, Mario Alfredo; et al.; Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies ; Springer; Journal Of Inclusion Phenomena And Macrocyclic Chemistry; 85; 1-2; 6-2016; 33-48
0167-7861
1573-1111
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s10847-016-0603-6
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs10847-016-0603-6
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
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
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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