Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone

Autores
Medeiros, Arthur S. A. de; Zoppi, Ariana; Barbosa, Euzébio G.; Oliveira, Jonas I. N.; Fernandes Pedrosa, Matheus F.; Longhi, Marcela Raquel; Silva Júnior, Arnóbio A. da
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A second compound is generally associated with oligosaccharides as a strategy to maximize the solubilizing effect for nonpolar compounds. This study elucidated the role and the mechanism whereby liquid compounds interact in these supramolecular aggregates in the solubilization of triamcinolone. Three different oligosaccharides (beta-cyclodextrin, 2-hydroxipropil-beta-cyclodextrin, and randomly methylated beta-cyclodextrin) and two potent co-solvents (triethanolamine and N-methyl pyrrolidone) were carefully evaluated by using three distinct experimental approaches. Incredibly stable complexes were formed with cyclodextrins (CDs). The structure of the complexes was elucidated by magnetic resonance spectra 2D-ROESY. The interactions of the protons of ring “A” of the drug with H3 and H5 protons of the CD cavity observed in the binary complexes remained in both ternary complexes. Unlike the observed ternary associations with triethanolamine, N-methyl pyrrolidone competed with the triamcinolone CD cavity and considerably decreased the stability of the complex and the solubility of the drug. The molecular dynamics (MD) and quantum mechanics:molecular mechanics (QM:MM) calculations supported that triethanolamine stabilized the drug-CD interactions for the conformer identified in the 2D-ROESY experiments, improving the quality and uniformity of the formed complex. The role played by the co-solvent in the ternary complexes depends on its specific ability to interact with the CD cavity in the presence of the drug, which can be predicted in theoretical studies to select the best candidate.
Fil: Medeiros, Arthur S. A. de. Universidade Federal do Rio Grande do Norte; 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: Barbosa, Euzébio G.. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Oliveira, Jonas I. N.. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Fernandes Pedrosa, Matheus F.. Universidade Federal do Rio Grande do Norte; Brasil
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: Silva Júnior, Arnóbio A. da. Universidade Federal do Rio Grande do Norte; Brasil
Materia
CO-SOLVENTS
CYCLODEXTRINS
OLIGOSACCHARIDES
SUPRAMOLECULAR AGGREGATES
TERNARY COMPLEXES
TRIAMCINOLONE
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:11336/62955
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/62955
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinoloneMedeiros, Arthur S. A. deZoppi, ArianaBarbosa, Euzébio G.Oliveira, Jonas I. N.Fernandes Pedrosa, Matheus F.Longhi, Marcela RaquelSilva Júnior, Arnóbio A. daCO-SOLVENTSCYCLODEXTRINSOLIGOSACCHARIDESSUPRAMOLECULAR AGGREGATESTERNARY COMPLEXESTRIAMCINOLONEhttps://purl.org/becyt/ford/2.10https://purl.org/becyt/ford/2A second compound is generally associated with oligosaccharides as a strategy to maximize the solubilizing effect for nonpolar compounds. This study elucidated the role and the mechanism whereby liquid compounds interact in these supramolecular aggregates in the solubilization of triamcinolone. Three different oligosaccharides (beta-cyclodextrin, 2-hydroxipropil-beta-cyclodextrin, and randomly methylated beta-cyclodextrin) and two potent co-solvents (triethanolamine and N-methyl pyrrolidone) were carefully evaluated by using three distinct experimental approaches. Incredibly stable complexes were formed with cyclodextrins (CDs). The structure of the complexes was elucidated by magnetic resonance spectra 2D-ROESY. The interactions of the protons of ring “A” of the drug with H3 and H5 protons of the CD cavity observed in the binary complexes remained in both ternary complexes. Unlike the observed ternary associations with triethanolamine, N-methyl pyrrolidone competed with the triamcinolone CD cavity and considerably decreased the stability of the complex and the solubility of the drug. The molecular dynamics (MD) and quantum mechanics:molecular mechanics (QM:MM) calculations supported that triethanolamine stabilized the drug-CD interactions for the conformer identified in the 2D-ROESY experiments, improving the quality and uniformity of the formed complex. The role played by the co-solvent in the ternary complexes depends on its specific ability to interact with the CD cavity in the presence of the drug, which can be predicted in theoretical studies to select the best candidate.Fil: Medeiros, Arthur S. A. de. Universidade Federal do Rio Grande do Norte; 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: Barbosa, Euzébio G.. Universidade Federal do Rio Grande do Norte; BrasilFil: Oliveira, Jonas I. N.. Universidade Federal do Rio Grande do Norte; BrasilFil: Fernandes Pedrosa, Matheus F.. Universidade Federal do Rio Grande do Norte; BrasilFil: 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: Silva Júnior, Arnóbio A. da. Universidade Federal do Rio Grande do Norte; BrasilElsevier2016-10info: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/11336/62955Medeiros, Arthur S. A. de ; Zoppi, Ariana; Barbosa, Euzébio G.; Oliveira, Jonas I. N.; Fernandes Pedrosa, Matheus F.; et al.; Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone; Elsevier; Carbohydrate Polymers; 151; 10-2016; 1040-10510144-8617CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0144861716307196info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carbpol.2016.06.044info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-26T08:39:49Zoai:ri.conicet.gov.ar:11336/62955instacron: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:34982025-11-26 08:39:49.905CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
title Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
spellingShingle Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
Medeiros, Arthur S. A. de
CO-SOLVENTS
CYCLODEXTRINS
OLIGOSACCHARIDES
SUPRAMOLECULAR AGGREGATES
TERNARY COMPLEXES
TRIAMCINOLONE
title_short Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
title_full Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
title_fullStr Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
title_full_unstemmed Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
title_sort Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
dc.creator.none.fl_str_mv Medeiros, Arthur S. A. de
Zoppi, Ariana
Barbosa, Euzébio G.
Oliveira, Jonas I. N.
Fernandes Pedrosa, Matheus F.
Longhi, Marcela Raquel
Silva Júnior, Arnóbio A. da
author Medeiros, Arthur S. A. de
author_facet Medeiros, Arthur S. A. de
Zoppi, Ariana
Barbosa, Euzébio G.
Oliveira, Jonas I. N.
Fernandes Pedrosa, Matheus F.
Longhi, Marcela Raquel
Silva Júnior, Arnóbio A. da
author_role author
author2 Zoppi, Ariana
Barbosa, Euzébio G.
Oliveira, Jonas I. N.
Fernandes Pedrosa, Matheus F.
Longhi, Marcela Raquel
Silva Júnior, Arnóbio A. da
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv CO-SOLVENTS
CYCLODEXTRINS
OLIGOSACCHARIDES
SUPRAMOLECULAR AGGREGATES
TERNARY COMPLEXES
TRIAMCINOLONE
topic CO-SOLVENTS
CYCLODEXTRINS
OLIGOSACCHARIDES
SUPRAMOLECULAR AGGREGATES
TERNARY COMPLEXES
TRIAMCINOLONE
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.10
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv A second compound is generally associated with oligosaccharides as a strategy to maximize the solubilizing effect for nonpolar compounds. This study elucidated the role and the mechanism whereby liquid compounds interact in these supramolecular aggregates in the solubilization of triamcinolone. Three different oligosaccharides (beta-cyclodextrin, 2-hydroxipropil-beta-cyclodextrin, and randomly methylated beta-cyclodextrin) and two potent co-solvents (triethanolamine and N-methyl pyrrolidone) were carefully evaluated by using three distinct experimental approaches. Incredibly stable complexes were formed with cyclodextrins (CDs). The structure of the complexes was elucidated by magnetic resonance spectra 2D-ROESY. The interactions of the protons of ring “A” of the drug with H3 and H5 protons of the CD cavity observed in the binary complexes remained in both ternary complexes. Unlike the observed ternary associations with triethanolamine, N-methyl pyrrolidone competed with the triamcinolone CD cavity and considerably decreased the stability of the complex and the solubility of the drug. The molecular dynamics (MD) and quantum mechanics:molecular mechanics (QM:MM) calculations supported that triethanolamine stabilized the drug-CD interactions for the conformer identified in the 2D-ROESY experiments, improving the quality and uniformity of the formed complex. The role played by the co-solvent in the ternary complexes depends on its specific ability to interact with the CD cavity in the presence of the drug, which can be predicted in theoretical studies to select the best candidate.
Fil: Medeiros, Arthur S. A. de. Universidade Federal do Rio Grande do Norte; 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: Barbosa, Euzébio G.. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Oliveira, Jonas I. N.. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Fernandes Pedrosa, Matheus F.. Universidade Federal do Rio Grande do Norte; Brasil
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: Silva Júnior, Arnóbio A. da. Universidade Federal do Rio Grande do Norte; Brasil
description A second compound is generally associated with oligosaccharides as a strategy to maximize the solubilizing effect for nonpolar compounds. This study elucidated the role and the mechanism whereby liquid compounds interact in these supramolecular aggregates in the solubilization of triamcinolone. Three different oligosaccharides (beta-cyclodextrin, 2-hydroxipropil-beta-cyclodextrin, and randomly methylated beta-cyclodextrin) and two potent co-solvents (triethanolamine and N-methyl pyrrolidone) were carefully evaluated by using three distinct experimental approaches. Incredibly stable complexes were formed with cyclodextrins (CDs). The structure of the complexes was elucidated by magnetic resonance spectra 2D-ROESY. The interactions of the protons of ring “A” of the drug with H3 and H5 protons of the CD cavity observed in the binary complexes remained in both ternary complexes. Unlike the observed ternary associations with triethanolamine, N-methyl pyrrolidone competed with the triamcinolone CD cavity and considerably decreased the stability of the complex and the solubility of the drug. The molecular dynamics (MD) and quantum mechanics:molecular mechanics (QM:MM) calculations supported that triethanolamine stabilized the drug-CD interactions for the conformer identified in the 2D-ROESY experiments, improving the quality and uniformity of the formed complex. The role played by the co-solvent in the ternary complexes depends on its specific ability to interact with the CD cavity in the presence of the drug, which can be predicted in theoretical studies to select the best candidate.
publishDate 2016
dc.date.none.fl_str_mv 2016-10
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/11336/62955
Medeiros, Arthur S. A. de ; Zoppi, Ariana; Barbosa, Euzébio G.; Oliveira, Jonas I. N.; Fernandes Pedrosa, Matheus F.; et al.; Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone; Elsevier; Carbohydrate Polymers; 151; 10-2016; 1040-1051
0144-8617
CONICET Digital
CONICET
url http://hdl.handle.net/11336/62955
identifier_str_mv Medeiros, Arthur S. A. de ; Zoppi, Ariana; Barbosa, Euzébio G.; Oliveira, Jonas I. N.; Fernandes Pedrosa, Matheus F.; et al.; Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone; Elsevier; Carbohydrate Polymers; 151; 10-2016; 1040-1051
0144-8617
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/S0144861716307196
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carbpol.2016.06.044
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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 13.011256

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