Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling

Autores
Zoppi, Ariana; Quevedo, Mario Alfredo; Longhi, Marcela Raquel
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The main objective of this work was to study an inclusion complex between enalapril (ENA), and B-cyclodextrin (B-CD). From nuclear magnetic resonance (NMR) we determined that the complex showed a 1:1 stoichiometry, with an apparent formation constant (KC) of 439 and 290 M1 for the cis and trans isomers, respectively. The molecular modeling and NMR techniques demonstrated that the aromatic moiety of ENA was inserted into the hydrophobic cavity of B-CD. When studying the chemical stability of ENA complexed to B-CD, a clear stabilizing effect was observed in both the aqueous solution and solid state.
Fil: Zoppi, Ariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Longhi, Marcela Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Materia
Enalapril maleate
B-cyclodextrin
Drug stability
NMR sprectroscopy
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:11336/242182

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network_name_str CONICET Digital (CONICET)
spelling Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modelingZoppi, ArianaQuevedo, Mario AlfredoLonghi, Marcela RaquelEnalapril maleateB-cyclodextrinDrug stabilityNMR sprectroscopyhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The main objective of this work was to study an inclusion complex between enalapril (ENA), and B-cyclodextrin (B-CD). From nuclear magnetic resonance (NMR) we determined that the complex showed a 1:1 stoichiometry, with an apparent formation constant (KC) of 439 and 290 M1 for the cis and trans isomers, respectively. The molecular modeling and NMR techniques demonstrated that the aromatic moiety of ENA was inserted into the hydrophobic cavity of B-CD. When studying the chemical stability of ENA complexed to B-CD, a clear stabilizing effect was observed in both the aqueous solution and solid state.Fil: Zoppi, Ariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Longhi, Marcela Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaPergamon-Elsevier Science Ltd2008-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/242182Zoppi, Ariana; Quevedo, Mario Alfredo; Longhi, Marcela Raquel; Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 16; 18; 9-2008; 8403-84120968-0896CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0968089608007621info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2008.08.032info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:20:31Zoai:ri.conicet.gov.ar:11336/242182instacron: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 10:20:31.412CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling
title Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling
spellingShingle Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling
Zoppi, Ariana
Enalapril maleate
B-cyclodextrin
Drug stability
NMR sprectroscopy
title_short Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling
title_full Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling
title_fullStr Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling
title_full_unstemmed Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling
title_sort Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling
dc.creator.none.fl_str_mv Zoppi, Ariana
Quevedo, Mario Alfredo
Longhi, Marcela Raquel
author Zoppi, Ariana
author_facet Zoppi, Ariana
Quevedo, Mario Alfredo
Longhi, Marcela Raquel
author_role author
author2 Quevedo, Mario Alfredo
Longhi, Marcela Raquel
author2_role author
author
dc.subject.none.fl_str_mv Enalapril maleate
B-cyclodextrin
Drug stability
NMR sprectroscopy
topic Enalapril maleate
B-cyclodextrin
Drug stability
NMR sprectroscopy
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The main objective of this work was to study an inclusion complex between enalapril (ENA), and B-cyclodextrin (B-CD). From nuclear magnetic resonance (NMR) we determined that the complex showed a 1:1 stoichiometry, with an apparent formation constant (KC) of 439 and 290 M1 for the cis and trans isomers, respectively. The molecular modeling and NMR techniques demonstrated that the aromatic moiety of ENA was inserted into the hydrophobic cavity of B-CD. When studying the chemical stability of ENA complexed to B-CD, a clear stabilizing effect was observed in both the aqueous solution and solid state.
Fil: Zoppi, Ariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Longhi, Marcela Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
description The main objective of this work was to study an inclusion complex between enalapril (ENA), and B-cyclodextrin (B-CD). From nuclear magnetic resonance (NMR) we determined that the complex showed a 1:1 stoichiometry, with an apparent formation constant (KC) of 439 and 290 M1 for the cis and trans isomers, respectively. The molecular modeling and NMR techniques demonstrated that the aromatic moiety of ENA was inserted into the hydrophobic cavity of B-CD. When studying the chemical stability of ENA complexed to B-CD, a clear stabilizing effect was observed in both the aqueous solution and solid state.
publishDate 2008
dc.date.none.fl_str_mv 2008-09
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/11336/242182
Zoppi, Ariana; Quevedo, Mario Alfredo; Longhi, Marcela Raquel; Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 16; 18; 9-2008; 8403-8412
0968-0896
CONICET Digital
CONICET
url http://hdl.handle.net/11336/242182
identifier_str_mv Zoppi, Ariana; Quevedo, Mario Alfredo; Longhi, Marcela Raquel; Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 16; 18; 9-2008; 8403-8412
0968-0896
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0968089608007621
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2008.08.032
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
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science 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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