Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies

Autores
Kogawa, A. C.; Zoppi, Ariana; Quevedo, Mario Alfredo; Longhi, Marcela Raquel; Nunes Salgado, H. R.
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Darunavir (DRV) is a protease inhibitor used in the treatment of HIVinfection, which constitutes a keystone in the therapy of patientsinfected with this virus. Unfortunately, DRV has low solubility inwater and poor bioavailability, therefore it requires administration inrelatively high doses in order to exhibit therapeutic efficacy. Acommonly applied approach to increase the solubility of drugs is theformation of complexes with macromolecules, of which molecularencapsulation with β-cyclodextrin (βCD) constitutes an alternative forthe development of new pharmaceutical dosage forms. Therefore, itwas to evaluate by theoretical (molecular modelling) and experimental(spectroscopic) approaches the possibility of obtaining an inclusioncomplex between DRV and βCD. From the results obtained by thedocking procedures, we found three clusters of conformations for the DRV:β-CD complex, corresponding to conformations in which the ligand moieties were buried into the β-CD hydrophobic cavities. Molecular modelling results were compared with spectroscopic studies, with 1H NMR studies evidencing that DRV and βCD proton resonances were modified upon complexation, thus confirming the formation of the inclusion complex. The combination of theoretical and experimental techniques confirmed the formation of the inclusion complex between DRV and βCD.
Fil: Kogawa, A. C.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
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
Fil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; 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. 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: Nunes Salgado, H. R.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Materia
Darunavir
Ciclodextrinas
Complejos
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:11336/51853
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/51853
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studiesKogawa, A. C.Zoppi, ArianaQuevedo, Mario AlfredoLonghi, Marcela RaquelNunes Salgado, H. R.DarunavirCiclodextrinasComplejoshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Darunavir (DRV) is a protease inhibitor used in the treatment of HIVinfection, which constitutes a keystone in the therapy of patientsinfected with this virus. Unfortunately, DRV has low solubility inwater and poor bioavailability, therefore it requires administration inrelatively high doses in order to exhibit therapeutic efficacy. Acommonly applied approach to increase the solubility of drugs is theformation of complexes with macromolecules, of which molecularencapsulation with β-cyclodextrin (βCD) constitutes an alternative forthe development of new pharmaceutical dosage forms. Therefore, itwas to evaluate by theoretical (molecular modelling) and experimental(spectroscopic) approaches the possibility of obtaining an inclusioncomplex between DRV and βCD. From the results obtained by thedocking procedures, we found three clusters of conformations for the DRV:β-CD complex, corresponding to conformations in which the ligand moieties were buried into the β-CD hydrophobic cavities. Molecular modelling results were compared with spectroscopic studies, with 1H NMR studies evidencing that DRV and βCD proton resonances were modified upon complexation, thus confirming the formation of the inclusion complex. The combination of theoretical and experimental techniques confirmed the formation of the inclusion complex between DRV and βCD.Fil: Kogawa, A. C.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: 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; ArgentinaFil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; 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. 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: Nunes Salgado, H. R.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilWorld Journal of Pharmacy and Pharmaceutical Sciences2014-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/51853Kogawa, A. C.; Zoppi, Ariana; Quevedo, Mario Alfredo; Longhi, Marcela Raquel; Nunes Salgado, H. R.; Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies; World Journal of Pharmacy and Pharmaceutical Sciences; World Journal of Pharmacy and Pharmaceutical Sciences; 3; 6-2014; 298-3092278-4357CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.wjpps.com/wjpps_controller/abstract_id/1383info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:07Zoai:ri.conicet.gov.ar:11336/51853instacron: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 10:33:07.959CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies
title Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies
spellingShingle Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies
Kogawa, A. C.
Darunavir
Ciclodextrinas
Complejos
title_short Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies
title_full Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies
title_fullStr Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies
title_full_unstemmed Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies
title_sort Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies
dc.creator.none.fl_str_mv Kogawa, A. C.
Zoppi, Ariana
Quevedo, Mario Alfredo
Longhi, Marcela Raquel
Nunes Salgado, H. R.
author Kogawa, A. C.
author_facet Kogawa, A. C.
Zoppi, Ariana
Quevedo, Mario Alfredo
Longhi, Marcela Raquel
Nunes Salgado, H. R.
author_role author
author2 Zoppi, Ariana
Quevedo, Mario Alfredo
Longhi, Marcela Raquel
Nunes Salgado, H. R.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Darunavir
Ciclodextrinas
Complejos
topic Darunavir
Ciclodextrinas
Complejos
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Darunavir (DRV) is a protease inhibitor used in the treatment of HIVinfection, which constitutes a keystone in the therapy of patientsinfected with this virus. Unfortunately, DRV has low solubility inwater and poor bioavailability, therefore it requires administration inrelatively high doses in order to exhibit therapeutic efficacy. Acommonly applied approach to increase the solubility of drugs is theformation of complexes with macromolecules, of which molecularencapsulation with β-cyclodextrin (βCD) constitutes an alternative forthe development of new pharmaceutical dosage forms. Therefore, itwas to evaluate by theoretical (molecular modelling) and experimental(spectroscopic) approaches the possibility of obtaining an inclusioncomplex between DRV and βCD. From the results obtained by thedocking procedures, we found three clusters of conformations for the DRV:β-CD complex, corresponding to conformations in which the ligand moieties were buried into the β-CD hydrophobic cavities. Molecular modelling results were compared with spectroscopic studies, with 1H NMR studies evidencing that DRV and βCD proton resonances were modified upon complexation, thus confirming the formation of the inclusion complex. The combination of theoretical and experimental techniques confirmed the formation of the inclusion complex between DRV and βCD.
Fil: Kogawa, A. C.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
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
Fil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; 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. 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: Nunes Salgado, H. R.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
description Darunavir (DRV) is a protease inhibitor used in the treatment of HIVinfection, which constitutes a keystone in the therapy of patientsinfected with this virus. Unfortunately, DRV has low solubility inwater and poor bioavailability, therefore it requires administration inrelatively high doses in order to exhibit therapeutic efficacy. Acommonly applied approach to increase the solubility of drugs is theformation of complexes with macromolecules, of which molecularencapsulation with β-cyclodextrin (βCD) constitutes an alternative forthe development of new pharmaceutical dosage forms. Therefore, itwas to evaluate by theoretical (molecular modelling) and experimental(spectroscopic) approaches the possibility of obtaining an inclusioncomplex between DRV and βCD. From the results obtained by thedocking procedures, we found three clusters of conformations for the DRV:β-CD complex, corresponding to conformations in which the ligand moieties were buried into the β-CD hydrophobic cavities. Molecular modelling results were compared with spectroscopic studies, with 1H NMR studies evidencing that DRV and βCD proton resonances were modified upon complexation, thus confirming the formation of the inclusion complex. The combination of theoretical and experimental techniques confirmed the formation of the inclusion complex between DRV and βCD.
publishDate 2014
dc.date.none.fl_str_mv 2014-06
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/11336/51853
Kogawa, A. C.; Zoppi, Ariana; Quevedo, Mario Alfredo; Longhi, Marcela Raquel; Nunes Salgado, H. R.; Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies; World Journal of Pharmacy and Pharmaceutical Sciences; World Journal of Pharmacy and Pharmaceutical Sciences; 3; 6-2014; 298-309
2278-4357
CONICET Digital
CONICET
url http://hdl.handle.net/11336/51853
identifier_str_mv Kogawa, A. C.; Zoppi, Ariana; Quevedo, Mario Alfredo; Longhi, Marcela Raquel; Nunes Salgado, H. R.; Complexation between darunavir and β-Cyclodextrin. Experimental and theoretical studies; World Journal of Pharmacy and Pharmaceutical Sciences; World Journal of Pharmacy and Pharmaceutical Sciences; 3; 6-2014; 298-309
2278-4357
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://www.wjpps.com/wjpps_controller/abstract_id/1383
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 World Journal of Pharmacy and Pharmaceutical Sciences
publisher.none.fl_str_mv World Journal of Pharmacy and Pharmaceutical Sciences
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 13.069144

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