Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes

Autores
Barbosa, Jahamunna A.; Zoppi, Ariana; Quevedo, Mario Alfredo; de Melo, Polyanne; de Medeiros, Arthur S. A; Streck, Leticia; de Oliveira, Alice R.; Fernandes Pedrosa, Matheus F.; Longhi, Marcela Raquel; da Silva Junior, Arnobio A.
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The interaction of methotrexate (MTX) with beta-cyclodextrin (β-CD) in the presence of triethanolamine (TEA) was investigated with the aim to elucidate the mechanism whereby self-assembly cyclodextrin systems work in association with this third component. Solubility diagram studies showed synergic increment of the MTX solubility to be about thirty-fold. Experiments using 2D ROESY and molecular modeling studies revealed the inclusion of aromatic ring III of the drug into β-CD cavity, in which TEA contributes by intensifying MTX interaction with β-CD and stabilizes MTX:β-CD:TEA ternary complex by electrostatic interaction. The maintenance of these interactions in solid phase was also studied in ternary MTX:β-CD:TEA and comparisons were made with freeze dried binary MTX:β-CD and physical mixtures. FTIR studies evidenced that MTX–β-CD interaction remained in solid ternary complexes, which was also supported by thermal (differential scanning calorimetry (DSC), thermogravimetric analysis (TG)/first derivative of TG analysis (DTG) and C,N,H elementary analysis) and structural (X-ray diffraction analysis, (XRD)) studies, mainly regarding the increment of drug stability. The efficient in vitro drug dissolution studies successfully demonstrated the contribution of ternary complexes, which highlights the importance of this possible new raw material for further applications in drug delivery systems
Fil: Barbosa, Jahamunna A.. 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: 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: de Melo, Polyanne. Universidade Federal do Rio Grande do Norte; Brasil
Fil: de Medeiros, Arthur S. A. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Streck, Leticia. Universidade Federal do Rio Grande do Norte; Brasil
Fil: de Oliveira, Alice R.. 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: da Silva Junior, Arnobio A.. Universidade Federal do Rio Grande do Norte; Brasil
Materia
methotrexate
cyclodextrin
inclusion complexes
ternary complexes
drug delivery systems
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:11336/33583
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/33583
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary ComplexesBarbosa, Jahamunna A.Zoppi, ArianaQuevedo, Mario Alfredode Melo, Polyannede Medeiros, Arthur S. AStreck, Leticiade Oliveira, Alice R.Fernandes Pedrosa, Matheus F.Longhi, Marcela Raquelda Silva Junior, Arnobio A.methotrexatecyclodextrininclusion complexesternary complexesdrug delivery systemshttps://purl.org/becyt/ford/2.10https://purl.org/becyt/ford/2The interaction of methotrexate (MTX) with beta-cyclodextrin (β-CD) in the presence of triethanolamine (TEA) was investigated with the aim to elucidate the mechanism whereby self-assembly cyclodextrin systems work in association with this third component. Solubility diagram studies showed synergic increment of the MTX solubility to be about thirty-fold. Experiments using 2D ROESY and molecular modeling studies revealed the inclusion of aromatic ring III of the drug into β-CD cavity, in which TEA contributes by intensifying MTX interaction with β-CD and stabilizes MTX:β-CD:TEA ternary complex by electrostatic interaction. The maintenance of these interactions in solid phase was also studied in ternary MTX:β-CD:TEA and comparisons were made with freeze dried binary MTX:β-CD and physical mixtures. FTIR studies evidenced that MTX–β-CD interaction remained in solid ternary complexes, which was also supported by thermal (differential scanning calorimetry (DSC), thermogravimetric analysis (TG)/first derivative of TG analysis (DTG) and C,N,H elementary analysis) and structural (X-ray diffraction analysis, (XRD)) studies, mainly regarding the increment of drug stability. The efficient in vitro drug dissolution studies successfully demonstrated the contribution of ternary complexes, which highlights the importance of this possible new raw material for further applications in drug delivery systemsFil: Barbosa, Jahamunna A.. 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: 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: de Melo, Polyanne. Universidade Federal do Rio Grande do Norte; BrasilFil: de Medeiros, Arthur S. A. Universidade Federal do Rio Grande do Norte; BrasilFil: Streck, Leticia. Universidade Federal do Rio Grande do Norte; BrasilFil: de Oliveira, Alice R.. 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: da Silva Junior, Arnobio A.. Universidade Federal do Rio Grande do Norte; BrasilMolecular Diversity Preservation International2014-05info: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/11336/33583de Oliveira, Alice R.; Zoppi, Ariana; de Melo, Polyanne; de Medeiros, Arthur S. A; Streck, Leticia; da Silva Junior, Arnobio A.; et al.; Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes; Molecular Diversity Preservation International; International Journal of Molecular Sciences; 15; 9; 5-2014; 17077-170991422-0067CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/ijms150917077info:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1422-0067/15/9/17077info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:21:33Zoai:ri.conicet.gov.ar:11336/33583instacron: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 10:21:33.466CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes
title Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes
spellingShingle Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes
Barbosa, Jahamunna A.
methotrexate
cyclodextrin
inclusion complexes
ternary complexes
drug delivery systems
title_short Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes
title_full Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes
title_fullStr Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes
title_full_unstemmed Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes
title_sort Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes
dc.creator.none.fl_str_mv Barbosa, Jahamunna A.
Zoppi, Ariana
Quevedo, Mario Alfredo
de Melo, Polyanne
de Medeiros, Arthur S. A
Streck, Leticia
de Oliveira, Alice R.
Fernandes Pedrosa, Matheus F.
Longhi, Marcela Raquel
da Silva Junior, Arnobio A.
author Barbosa, Jahamunna A.
author_facet Barbosa, Jahamunna A.
Zoppi, Ariana
Quevedo, Mario Alfredo
de Melo, Polyanne
de Medeiros, Arthur S. A
Streck, Leticia
de Oliveira, Alice R.
Fernandes Pedrosa, Matheus F.
Longhi, Marcela Raquel
da Silva Junior, Arnobio A.
author_role author
author2 Zoppi, Ariana
Quevedo, Mario Alfredo
de Melo, Polyanne
de Medeiros, Arthur S. A
Streck, Leticia
de Oliveira, Alice R.
Fernandes Pedrosa, Matheus F.
Longhi, Marcela Raquel
da Silva Junior, Arnobio A.
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv methotrexate
cyclodextrin
inclusion complexes
ternary complexes
drug delivery systems
topic methotrexate
cyclodextrin
inclusion complexes
ternary complexes
drug delivery systems
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.10
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv The interaction of methotrexate (MTX) with beta-cyclodextrin (β-CD) in the presence of triethanolamine (TEA) was investigated with the aim to elucidate the mechanism whereby self-assembly cyclodextrin systems work in association with this third component. Solubility diagram studies showed synergic increment of the MTX solubility to be about thirty-fold. Experiments using 2D ROESY and molecular modeling studies revealed the inclusion of aromatic ring III of the drug into β-CD cavity, in which TEA contributes by intensifying MTX interaction with β-CD and stabilizes MTX:β-CD:TEA ternary complex by electrostatic interaction. The maintenance of these interactions in solid phase was also studied in ternary MTX:β-CD:TEA and comparisons were made with freeze dried binary MTX:β-CD and physical mixtures. FTIR studies evidenced that MTX–β-CD interaction remained in solid ternary complexes, which was also supported by thermal (differential scanning calorimetry (DSC), thermogravimetric analysis (TG)/first derivative of TG analysis (DTG) and C,N,H elementary analysis) and structural (X-ray diffraction analysis, (XRD)) studies, mainly regarding the increment of drug stability. The efficient in vitro drug dissolution studies successfully demonstrated the contribution of ternary complexes, which highlights the importance of this possible new raw material for further applications in drug delivery systems
Fil: Barbosa, Jahamunna A.. 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: 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: de Melo, Polyanne. Universidade Federal do Rio Grande do Norte; Brasil
Fil: de Medeiros, Arthur S. A. Universidade Federal do Rio Grande do Norte; Brasil
Fil: Streck, Leticia. Universidade Federal do Rio Grande do Norte; Brasil
Fil: de Oliveira, Alice R.. 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: da Silva Junior, Arnobio A.. Universidade Federal do Rio Grande do Norte; Brasil
description The interaction of methotrexate (MTX) with beta-cyclodextrin (β-CD) in the presence of triethanolamine (TEA) was investigated with the aim to elucidate the mechanism whereby self-assembly cyclodextrin systems work in association with this third component. Solubility diagram studies showed synergic increment of the MTX solubility to be about thirty-fold. Experiments using 2D ROESY and molecular modeling studies revealed the inclusion of aromatic ring III of the drug into β-CD cavity, in which TEA contributes by intensifying MTX interaction with β-CD and stabilizes MTX:β-CD:TEA ternary complex by electrostatic interaction. The maintenance of these interactions in solid phase was also studied in ternary MTX:β-CD:TEA and comparisons were made with freeze dried binary MTX:β-CD and physical mixtures. FTIR studies evidenced that MTX–β-CD interaction remained in solid ternary complexes, which was also supported by thermal (differential scanning calorimetry (DSC), thermogravimetric analysis (TG)/first derivative of TG analysis (DTG) and C,N,H elementary analysis) and structural (X-ray diffraction analysis, (XRD)) studies, mainly regarding the increment of drug stability. The efficient in vitro drug dissolution studies successfully demonstrated the contribution of ternary complexes, which highlights the importance of this possible new raw material for further applications in drug delivery systems
publishDate 2014
dc.date.none.fl_str_mv 2014-05
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/11336/33583
de Oliveira, Alice R.; Zoppi, Ariana; de Melo, Polyanne; de Medeiros, Arthur S. A; Streck, Leticia; da Silva Junior, Arnobio A.; et al.; Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes; Molecular Diversity Preservation International; International Journal of Molecular Sciences; 15; 9; 5-2014; 17077-17099
1422-0067
CONICET Digital
CONICET
url http://hdl.handle.net/11336/33583
identifier_str_mv de Oliveira, Alice R.; Zoppi, Ariana; de Melo, Polyanne; de Medeiros, Arthur S. A; Streck, Leticia; da Silva Junior, Arnobio A.; et al.; Triethanolamine Stabilization of Methotrexate-β-Cyclodextrin Interactions in Ternary Complexes; Molecular Diversity Preservation International; International Journal of Molecular Sciences; 15; 9; 5-2014; 17077-17099
1422-0067
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/ijms150917077
info:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1422-0067/15/9/17077
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 Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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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