Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution

Autores
Melo, Polyanne Nunes de; Barbosa, Euzébio Guimarães; Caland, Lília Basílio de; Carpegianni, Hugo; Garnero, Claudia; Longhi, Marcela Raquel; Fernandes Pedrosa, Matheus de Freitas; Silva Júnior, Arnóbio Antônio da
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Association of hydrophilic compounds with cyclodextrins to increase drug solubility has been extensively studied in aqueous solution. However, the mechanism of interaction among these components remains unclear. In this study, the mechanism of interaction of seven different hydrophilic polymers (HPs) and triethanolamine (TEA) in aqueous solution with beta-cyclodextrin (β-CD) to modify the aqueous solubility of benznidazole (BNZ) was well investigated using solubility diagrams, thermodynamic experiments, molecular modeling and NMR studies. Solubility diagrams in different pH values confirmed linear soluble BNZ-β-CD inclusion complexes, with 1:1 stoichiometry (AL type). A synergistic effect in the association of TEA with BCD did not occur, due to competition between TEA and BNZ β-CD cavity, which led to obtain inclusion complexes with limited solubility (B type). The increment of BNZ solubility occurred only at higher TEA concentrations by cosolvency mechanism, which was evidenced by solubility diagrams, molecular modeling and NMR studies. The association of different hydrophilic polymers with β-CD contributes thermodynamically to stabilize the formed complexes, in which POL 407 and PVA increased considerably the observed K1:1 value. An enthalpic contribution of hydrophilic polymers led to enhance the spontaneity of BNZ-β-CD interaction and a slight increasing in entropy change (ΔS) did possible to stabilize the interaction between BNZ and β-CD.
Fil: Melo, Polyanne Nunes de. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Barbosa, Euzébio Guimarães. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Caland, Lília Basílio de. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Carpegianni, Hugo. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Garnero, Claudia. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Longhi, Marcela Raquel. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Fernandes Pedrosa, Matheus de Freitas. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Silva Júnior, Arnóbio Antônio da. Universidade Federal do Rio Grande do Norte; Brasil
Materia
Benznidazole
Cyclodextrin
Multicomponent Complexes
Solubiity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/25189
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/25189
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solutionMelo, Polyanne Nunes deBarbosa, Euzébio GuimarãesCaland, Lília Basílio deCarpegianni, HugoGarnero, ClaudiaLonghi, Marcela RaquelFernandes Pedrosa, Matheus de FreitasSilva Júnior, Arnóbio Antônio daBenznidazoleCyclodextrinMulticomponent ComplexesSolubiityhttps://purl.org/becyt/ford/2.10https://purl.org/becyt/ford/2Association of hydrophilic compounds with cyclodextrins to increase drug solubility has been extensively studied in aqueous solution. However, the mechanism of interaction among these components remains unclear. In this study, the mechanism of interaction of seven different hydrophilic polymers (HPs) and triethanolamine (TEA) in aqueous solution with beta-cyclodextrin (β-CD) to modify the aqueous solubility of benznidazole (BNZ) was well investigated using solubility diagrams, thermodynamic experiments, molecular modeling and NMR studies. Solubility diagrams in different pH values confirmed linear soluble BNZ-β-CD inclusion complexes, with 1:1 stoichiometry (AL type). A synergistic effect in the association of TEA with BCD did not occur, due to competition between TEA and BNZ β-CD cavity, which led to obtain inclusion complexes with limited solubility (B type). The increment of BNZ solubility occurred only at higher TEA concentrations by cosolvency mechanism, which was evidenced by solubility diagrams, molecular modeling and NMR studies. The association of different hydrophilic polymers with β-CD contributes thermodynamically to stabilize the formed complexes, in which POL 407 and PVA increased considerably the observed K1:1 value. An enthalpic contribution of hydrophilic polymers led to enhance the spontaneity of BNZ-β-CD interaction and a slight increasing in entropy change (ΔS) did possible to stabilize the interaction between BNZ and β-CD.Fil: Melo, Polyanne Nunes de. Universidade Federal do Rio Grande do Norte; BrasilFil: Barbosa, Euzébio Guimarães. Universidade Federal do Rio Grande do Norte; BrasilFil: Caland, Lília Basílio de. Universidade Federal do Rio Grande do Norte; BrasilFil: Carpegianni, Hugo. Universidade Federal do Rio Grande do Norte; BrasilFil: Garnero, Claudia. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Longhi, Marcela Raquel. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Fernandes Pedrosa, Matheus de Freitas. Universidade Federal do Rio Grande do Norte; BrasilFil: Silva Júnior, Arnóbio Antônio da. Universidade Federal do Rio Grande do Norte; BrasilElsevier Science2013-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/25189Melo, Polyanne Nunes de; Barbosa, Euzébio Guimarães; Caland, Lília Basílio de; Carpegianni, Hugo; Garnero, Claudia; et al.; Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution; Elsevier Science; Journal of Molecular Liquids; 186; 7-2013; 147-1560167-7322CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molliq.2013.07.004info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0167732213002250info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:53:24Zoai:ri.conicet.gov.ar:11336/25189instacron: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 09:53:25.198CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution
title Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution
spellingShingle Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution
Melo, Polyanne Nunes de
Benznidazole
Cyclodextrin
Multicomponent Complexes
Solubiity
title_short Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution
title_full Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution
title_fullStr Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution
title_full_unstemmed Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution
title_sort Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution
dc.creator.none.fl_str_mv Melo, Polyanne Nunes de
Barbosa, Euzébio Guimarães
Caland, Lília Basílio de
Carpegianni, Hugo
Garnero, Claudia
Longhi, Marcela Raquel
Fernandes Pedrosa, Matheus de Freitas
Silva Júnior, Arnóbio Antônio da
author Melo, Polyanne Nunes de
author_facet Melo, Polyanne Nunes de
Barbosa, Euzébio Guimarães
Caland, Lília Basílio de
Carpegianni, Hugo
Garnero, Claudia
Longhi, Marcela Raquel
Fernandes Pedrosa, Matheus de Freitas
Silva Júnior, Arnóbio Antônio da
author_role author
author2 Barbosa, Euzébio Guimarães
Caland, Lília Basílio de
Carpegianni, Hugo
Garnero, Claudia
Longhi, Marcela Raquel
Fernandes Pedrosa, Matheus de Freitas
Silva Júnior, Arnóbio Antônio da
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Benznidazole
Cyclodextrin
Multicomponent Complexes
Solubiity
topic Benznidazole
Cyclodextrin
Multicomponent Complexes
Solubiity
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.10
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Association of hydrophilic compounds with cyclodextrins to increase drug solubility has been extensively studied in aqueous solution. However, the mechanism of interaction among these components remains unclear. In this study, the mechanism of interaction of seven different hydrophilic polymers (HPs) and triethanolamine (TEA) in aqueous solution with beta-cyclodextrin (β-CD) to modify the aqueous solubility of benznidazole (BNZ) was well investigated using solubility diagrams, thermodynamic experiments, molecular modeling and NMR studies. Solubility diagrams in different pH values confirmed linear soluble BNZ-β-CD inclusion complexes, with 1:1 stoichiometry (AL type). A synergistic effect in the association of TEA with BCD did not occur, due to competition between TEA and BNZ β-CD cavity, which led to obtain inclusion complexes with limited solubility (B type). The increment of BNZ solubility occurred only at higher TEA concentrations by cosolvency mechanism, which was evidenced by solubility diagrams, molecular modeling and NMR studies. The association of different hydrophilic polymers with β-CD contributes thermodynamically to stabilize the formed complexes, in which POL 407 and PVA increased considerably the observed K1:1 value. An enthalpic contribution of hydrophilic polymers led to enhance the spontaneity of BNZ-β-CD interaction and a slight increasing in entropy change (ΔS) did possible to stabilize the interaction between BNZ and β-CD.
Fil: Melo, Polyanne Nunes de. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Barbosa, Euzébio Guimarães. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Caland, Lília Basílio de. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Carpegianni, Hugo. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Garnero, Claudia. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Longhi, Marcela Raquel. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Fernandes Pedrosa, Matheus de Freitas. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Silva Júnior, Arnóbio Antônio da. Universidade Federal do Rio Grande do Norte; Brasil
description Association of hydrophilic compounds with cyclodextrins to increase drug solubility has been extensively studied in aqueous solution. However, the mechanism of interaction among these components remains unclear. In this study, the mechanism of interaction of seven different hydrophilic polymers (HPs) and triethanolamine (TEA) in aqueous solution with beta-cyclodextrin (β-CD) to modify the aqueous solubility of benznidazole (BNZ) was well investigated using solubility diagrams, thermodynamic experiments, molecular modeling and NMR studies. Solubility diagrams in different pH values confirmed linear soluble BNZ-β-CD inclusion complexes, with 1:1 stoichiometry (AL type). A synergistic effect in the association of TEA with BCD did not occur, due to competition between TEA and BNZ β-CD cavity, which led to obtain inclusion complexes with limited solubility (B type). The increment of BNZ solubility occurred only at higher TEA concentrations by cosolvency mechanism, which was evidenced by solubility diagrams, molecular modeling and NMR studies. The association of different hydrophilic polymers with β-CD contributes thermodynamically to stabilize the formed complexes, in which POL 407 and PVA increased considerably the observed K1:1 value. An enthalpic contribution of hydrophilic polymers led to enhance the spontaneity of BNZ-β-CD interaction and a slight increasing in entropy change (ΔS) did possible to stabilize the interaction between BNZ and β-CD.
publishDate 2013
dc.date.none.fl_str_mv 2013-07
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/11336/25189
Melo, Polyanne Nunes de; Barbosa, Euzébio Guimarães; Caland, Lília Basílio de; Carpegianni, Hugo; Garnero, Claudia; et al.; Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution; Elsevier Science; Journal of Molecular Liquids; 186; 7-2013; 147-156
0167-7322
CONICET Digital
CONICET
url http://hdl.handle.net/11336/25189
identifier_str_mv Melo, Polyanne Nunes de; Barbosa, Euzébio Guimarães; Caland, Lília Basílio de; Carpegianni, Hugo; Garnero, Claudia; et al.; Host–guest interactions between benznidazole and beta-cyclodextrin in multicomponent complex systems involving hydrophilic polymers and triethanolamine in aqueous solution; Elsevier Science; Journal of Molecular Liquids; 186; 7-2013; 147-156
0167-7322
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molliq.2013.07.004
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0167732213002250
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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 13.13397

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