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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/33583
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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 Técnicas2025-09-03T10:03:46Zoai: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:34982025-09-03 10:03:47.227CONICET 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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1842269819635761152 |
score |
13.13397 |