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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/62959
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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 Técnicas2025-09-03T09:48:12Zoai: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:34982025-09-03 09:48:12.354CONICET 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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1842268909504299008 |
score |
13.13397 |