Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy

Autores
Chattah, Ana Karina; Zhang, Rongchun; Mroue, Kamal H.; Pfund, Laura; Longhi, Marcela Raquel; Ramamoorthy, Ayyalusamy; Garnero, Claudia
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Characterization of the molecular structure and physicochemical solid-state properties of the solid forms of pharmaceutical compounds is a key requirement for successful commercialization as potential active ingredients in drug products. These properties can ultimately have a critical effect on the solubility and bioavailability of the final drug product. Here, the desmotropy of Albendazole forms I and II was investigated at the atomic level. Ultrafast magic angle spinning (MAS) solid-state nuclear magnetic resonance (NMR) spectroscopy, together with powder X-ray diffraction, thermal analysis, and Fourier transform infrared spectroscopy, were performed on polycrystalline samples of the two solids in order to fully characterize and distinguish the two forms. High-resolution one-dimensional 1H, 13C, and 15N together with two-dimensional 1H/1H single quantum-single quantum, 1H/1H single quantum-double quantum, and 1H/13C chemical shift correlation solid-state NMR experiments under MAS conditions were extensively used to decipher the intramolecular and intermolecular hydrogen bonding interactions present in both solid forms. These experiments enabled the unequivocal identification of the tautomers of each desmotrope. Our results also revealed that both solid forms may be described as dimeric structures, with different intermolecular hydrogen bonds connecting the tautomers in each dimer.
Fil: Chattah, Ana Karina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Física Enrique Gaviola. Universidad Nacional de Córdoba. Instituto de Física Enrique Gaviola; Argentina. Universidad Nacional de Córdoba. Facultad de Matemática, Astronomía y Física; Argentina
Fil: Zhang, Rongchun. University of Michigan; Estados Unidos
Fil: Mroue, Kamal H.. University of Michigan; Estados Unidos
Fil: Pfund, Laura. University of Michigan; Estados Unidos
Fil: Longhi, Marcela Raquel. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. 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: Ramamoorthy, Ayyalusamy. University of Michigan; Estados Unidos
Fil: Garnero, Claudia. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. 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
Materia
Albendazole
Characterization
Desmotropy
Rfdr
Solid-State Nmr
Tautomerism
Ultrafast Mas
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:11336/51721
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/51721
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Investigating Albendazole Desmotropes by Solid-State NMR SpectroscopyChattah, Ana KarinaZhang, RongchunMroue, Kamal H.Pfund, LauraLonghi, Marcela RaquelRamamoorthy, AyyalusamyGarnero, ClaudiaAlbendazoleCharacterizationDesmotropyRfdrSolid-State NmrTautomerismUltrafast Mashttps://purl.org/becyt/ford/2.10https://purl.org/becyt/ford/2Characterization of the molecular structure and physicochemical solid-state properties of the solid forms of pharmaceutical compounds is a key requirement for successful commercialization as potential active ingredients in drug products. These properties can ultimately have a critical effect on the solubility and bioavailability of the final drug product. Here, the desmotropy of Albendazole forms I and II was investigated at the atomic level. Ultrafast magic angle spinning (MAS) solid-state nuclear magnetic resonance (NMR) spectroscopy, together with powder X-ray diffraction, thermal analysis, and Fourier transform infrared spectroscopy, were performed on polycrystalline samples of the two solids in order to fully characterize and distinguish the two forms. High-resolution one-dimensional 1H, 13C, and 15N together with two-dimensional 1H/1H single quantum-single quantum, 1H/1H single quantum-double quantum, and 1H/13C chemical shift correlation solid-state NMR experiments under MAS conditions were extensively used to decipher the intramolecular and intermolecular hydrogen bonding interactions present in both solid forms. These experiments enabled the unequivocal identification of the tautomers of each desmotrope. Our results also revealed that both solid forms may be described as dimeric structures, with different intermolecular hydrogen bonds connecting the tautomers in each dimer.Fil: Chattah, Ana Karina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Física Enrique Gaviola. Universidad Nacional de Córdoba. Instituto de Física Enrique Gaviola; Argentina. Universidad Nacional de Córdoba. Facultad de Matemática, Astronomía y Física; ArgentinaFil: Zhang, Rongchun. University of Michigan; Estados UnidosFil: Mroue, Kamal H.. University of Michigan; Estados UnidosFil: Pfund, Laura. University of Michigan; Estados UnidosFil: Longhi, Marcela Raquel. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. 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: Ramamoorthy, Ayyalusamy. University of Michigan; Estados UnidosFil: Garnero, Claudia. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. 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; ArgentinaAmerican Chemical Society2015-03info: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/11336/51721Chattah, Ana Karina; Zhang, Rongchun; Mroue, Kamal H.; Pfund, Laura; Longhi, Marcela Raquel; et al.; Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy; American Chemical Society; Molecular Pharmaceutics; 12; 3; 3-2015; 731-7411543-83841543-8392CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/mp500539ginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/mp500539ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:45:27Zoai:ri.conicet.gov.ar:11336/51721instacron: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 09:45:27.848CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy
title Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy
spellingShingle Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy
Chattah, Ana Karina
Albendazole
Characterization
Desmotropy
Rfdr
Solid-State Nmr
Tautomerism
Ultrafast Mas
title_short Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy
title_full Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy
title_fullStr Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy
title_full_unstemmed Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy
title_sort Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy
dc.creator.none.fl_str_mv Chattah, Ana Karina
Zhang, Rongchun
Mroue, Kamal H.
Pfund, Laura
Longhi, Marcela Raquel
Ramamoorthy, Ayyalusamy
Garnero, Claudia
author Chattah, Ana Karina
author_facet Chattah, Ana Karina
Zhang, Rongchun
Mroue, Kamal H.
Pfund, Laura
Longhi, Marcela Raquel
Ramamoorthy, Ayyalusamy
Garnero, Claudia
author_role author
author2 Zhang, Rongchun
Mroue, Kamal H.
Pfund, Laura
Longhi, Marcela Raquel
Ramamoorthy, Ayyalusamy
Garnero, Claudia
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Albendazole
Characterization
Desmotropy
Rfdr
Solid-State Nmr
Tautomerism
Ultrafast Mas
topic Albendazole
Characterization
Desmotropy
Rfdr
Solid-State Nmr
Tautomerism
Ultrafast Mas
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.10
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Characterization of the molecular structure and physicochemical solid-state properties of the solid forms of pharmaceutical compounds is a key requirement for successful commercialization as potential active ingredients in drug products. These properties can ultimately have a critical effect on the solubility and bioavailability of the final drug product. Here, the desmotropy of Albendazole forms I and II was investigated at the atomic level. Ultrafast magic angle spinning (MAS) solid-state nuclear magnetic resonance (NMR) spectroscopy, together with powder X-ray diffraction, thermal analysis, and Fourier transform infrared spectroscopy, were performed on polycrystalline samples of the two solids in order to fully characterize and distinguish the two forms. High-resolution one-dimensional 1H, 13C, and 15N together with two-dimensional 1H/1H single quantum-single quantum, 1H/1H single quantum-double quantum, and 1H/13C chemical shift correlation solid-state NMR experiments under MAS conditions were extensively used to decipher the intramolecular and intermolecular hydrogen bonding interactions present in both solid forms. These experiments enabled the unequivocal identification of the tautomers of each desmotrope. Our results also revealed that both solid forms may be described as dimeric structures, with different intermolecular hydrogen bonds connecting the tautomers in each dimer.
Fil: Chattah, Ana Karina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Física Enrique Gaviola. Universidad Nacional de Córdoba. Instituto de Física Enrique Gaviola; Argentina. Universidad Nacional de Córdoba. Facultad de Matemática, Astronomía y Física; Argentina
Fil: Zhang, Rongchun. University of Michigan; Estados Unidos
Fil: Mroue, Kamal H.. University of Michigan; Estados Unidos
Fil: Pfund, Laura. University of Michigan; Estados Unidos
Fil: Longhi, Marcela Raquel. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. 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: Ramamoorthy, Ayyalusamy. University of Michigan; Estados Unidos
Fil: Garnero, Claudia. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. 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
description Characterization of the molecular structure and physicochemical solid-state properties of the solid forms of pharmaceutical compounds is a key requirement for successful commercialization as potential active ingredients in drug products. These properties can ultimately have a critical effect on the solubility and bioavailability of the final drug product. Here, the desmotropy of Albendazole forms I and II was investigated at the atomic level. Ultrafast magic angle spinning (MAS) solid-state nuclear magnetic resonance (NMR) spectroscopy, together with powder X-ray diffraction, thermal analysis, and Fourier transform infrared spectroscopy, were performed on polycrystalline samples of the two solids in order to fully characterize and distinguish the two forms. High-resolution one-dimensional 1H, 13C, and 15N together with two-dimensional 1H/1H single quantum-single quantum, 1H/1H single quantum-double quantum, and 1H/13C chemical shift correlation solid-state NMR experiments under MAS conditions were extensively used to decipher the intramolecular and intermolecular hydrogen bonding interactions present in both solid forms. These experiments enabled the unequivocal identification of the tautomers of each desmotrope. Our results also revealed that both solid forms may be described as dimeric structures, with different intermolecular hydrogen bonds connecting the tautomers in each dimer.
publishDate 2015
dc.date.none.fl_str_mv 2015-03
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/11336/51721
Chattah, Ana Karina; Zhang, Rongchun; Mroue, Kamal H.; Pfund, Laura; Longhi, Marcela Raquel; et al.; Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy; American Chemical Society; Molecular Pharmaceutics; 12; 3; 3-2015; 731-741
1543-8384
1543-8392
CONICET Digital
CONICET
url http://hdl.handle.net/11336/51721
identifier_str_mv Chattah, Ana Karina; Zhang, Rongchun; Mroue, Kamal H.; Pfund, Laura; Longhi, Marcela Raquel; et al.; Investigating Albendazole Desmotropes by Solid-State NMR Spectroscopy; American Chemical Society; Molecular Pharmaceutics; 12; 3; 3-2015; 731-741
1543-8384
1543-8392
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/mp500539g
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/mp500539g
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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