Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy

Autores
Arrua, Eva Carolina; Ferreira, M.João G.; Salomon, Claudio Javier; Nunes, Teresa G.
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Praziquantel is the drug of choice to treat several parasitic infections including the neglected tropical disease schistosomiasis. Due to its low aqueous solubility, cyclodextrins have been tested as potential host candidates to prepare praziquantel inclusion complexes with improved solubility. For the first time, the interactions of praziquantel with β-cyclodextrin and β-cyclodextrin derivatives (methyl-β-cyclodextrin and hydroxypropyl-β-cyclodextrin) were investigated using high resolution solid-state NMR spectroscopy. The results of this work confirmed that solid-state NMR experiments provided structural characterization, demonstrating the formation of inclusion complexes most probably with PZQ adopting an anti conformation, also the most likely in amorphous raw PZQ. Further information on the interaction of praziquantel with methyl-β-cyclodextrin was obtained from proton rotating-frame relaxation time measurements, sensitive to kilohertz-regime motions but modulated by spin-diffusion. Evidences were presented in all cases for praziquantel complexation through the aromatic ring. In addition, 1:2 drug:carrier molar ratio appears to be the most probable and therefore suitable stoichiometry to improve pharmaceutical formulations of this antischistosomal drug.
Fil: Arrua, Eva Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Ferreira, M.João G.. Universidade de Lisboa; Portugal
Fil: Salomon, Claudio Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Nunes, Teresa G.. Universidade de Lisboa; Portugal
Materia
Inclusion Complex
Praziquantel
Schistosomiasis Disease
Solid-State Nmr
Β-Cyclodextrin Derivatives
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:11336/52569
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/52569
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopyArrua, Eva CarolinaFerreira, M.João G.Salomon, Claudio JavierNunes, Teresa G.Inclusion ComplexPraziquantelSchistosomiasis DiseaseSolid-State NmrΒ-Cyclodextrin Derivativeshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Praziquantel is the drug of choice to treat several parasitic infections including the neglected tropical disease schistosomiasis. Due to its low aqueous solubility, cyclodextrins have been tested as potential host candidates to prepare praziquantel inclusion complexes with improved solubility. For the first time, the interactions of praziquantel with β-cyclodextrin and β-cyclodextrin derivatives (methyl-β-cyclodextrin and hydroxypropyl-β-cyclodextrin) were investigated using high resolution solid-state NMR spectroscopy. The results of this work confirmed that solid-state NMR experiments provided structural characterization, demonstrating the formation of inclusion complexes most probably with PZQ adopting an anti conformation, also the most likely in amorphous raw PZQ. Further information on the interaction of praziquantel with methyl-β-cyclodextrin was obtained from proton rotating-frame relaxation time measurements, sensitive to kilohertz-regime motions but modulated by spin-diffusion. Evidences were presented in all cases for praziquantel complexation through the aromatic ring. In addition, 1:2 drug:carrier molar ratio appears to be the most probable and therefore suitable stoichiometry to improve pharmaceutical formulations of this antischistosomal drug.Fil: Arrua, Eva Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Ferreira, M.João G.. Universidade de Lisboa; PortugalFil: Salomon, Claudio Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Nunes, Teresa G.. Universidade de Lisboa; PortugalElsevier Science2015-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/52569Arrua, Eva Carolina; Ferreira, M.João G.; Salomon, Claudio Javier; Nunes, Teresa G.; Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy; Elsevier Science; International Journal Of Pharmaceutics; 496; 2; 12-2015; 812-8210378-5173CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.ijpharm.2015.11.026info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0378517315303720info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:54:12Zoai:ri.conicet.gov.ar:11336/52569instacron: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:34982025-10-15 14:54:13.208CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy
title Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy
spellingShingle Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy
Arrua, Eva Carolina
Inclusion Complex
Praziquantel
Schistosomiasis Disease
Solid-State Nmr
Β-Cyclodextrin Derivatives
title_short Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy
title_full Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy
title_fullStr Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy
title_full_unstemmed Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy
title_sort Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy
dc.creator.none.fl_str_mv Arrua, Eva Carolina
Ferreira, M.João G.
Salomon, Claudio Javier
Nunes, Teresa G.
author Arrua, Eva Carolina
author_facet Arrua, Eva Carolina
Ferreira, M.João G.
Salomon, Claudio Javier
Nunes, Teresa G.
author_role author
author2 Ferreira, M.João G.
Salomon, Claudio Javier
Nunes, Teresa G.
author2_role author
author
author
dc.subject.none.fl_str_mv Inclusion Complex
Praziquantel
Schistosomiasis Disease
Solid-State Nmr
Β-Cyclodextrin Derivatives
topic Inclusion Complex
Praziquantel
Schistosomiasis Disease
Solid-State Nmr
Β-Cyclodextrin Derivatives
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Praziquantel is the drug of choice to treat several parasitic infections including the neglected tropical disease schistosomiasis. Due to its low aqueous solubility, cyclodextrins have been tested as potential host candidates to prepare praziquantel inclusion complexes with improved solubility. For the first time, the interactions of praziquantel with β-cyclodextrin and β-cyclodextrin derivatives (methyl-β-cyclodextrin and hydroxypropyl-β-cyclodextrin) were investigated using high resolution solid-state NMR spectroscopy. The results of this work confirmed that solid-state NMR experiments provided structural characterization, demonstrating the formation of inclusion complexes most probably with PZQ adopting an anti conformation, also the most likely in amorphous raw PZQ. Further information on the interaction of praziquantel with methyl-β-cyclodextrin was obtained from proton rotating-frame relaxation time measurements, sensitive to kilohertz-regime motions but modulated by spin-diffusion. Evidences were presented in all cases for praziquantel complexation through the aromatic ring. In addition, 1:2 drug:carrier molar ratio appears to be the most probable and therefore suitable stoichiometry to improve pharmaceutical formulations of this antischistosomal drug.
Fil: Arrua, Eva Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Ferreira, M.João G.. Universidade de Lisboa; Portugal
Fil: Salomon, Claudio Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Nunes, Teresa G.. Universidade de Lisboa; Portugal
description Praziquantel is the drug of choice to treat several parasitic infections including the neglected tropical disease schistosomiasis. Due to its low aqueous solubility, cyclodextrins have been tested as potential host candidates to prepare praziquantel inclusion complexes with improved solubility. For the first time, the interactions of praziquantel with β-cyclodextrin and β-cyclodextrin derivatives (methyl-β-cyclodextrin and hydroxypropyl-β-cyclodextrin) were investigated using high resolution solid-state NMR spectroscopy. The results of this work confirmed that solid-state NMR experiments provided structural characterization, demonstrating the formation of inclusion complexes most probably with PZQ adopting an anti conformation, also the most likely in amorphous raw PZQ. Further information on the interaction of praziquantel with methyl-β-cyclodextrin was obtained from proton rotating-frame relaxation time measurements, sensitive to kilohertz-regime motions but modulated by spin-diffusion. Evidences were presented in all cases for praziquantel complexation through the aromatic ring. In addition, 1:2 drug:carrier molar ratio appears to be the most probable and therefore suitable stoichiometry to improve pharmaceutical formulations of this antischistosomal drug.
publishDate 2015
dc.date.none.fl_str_mv 2015-12
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/11336/52569
Arrua, Eva Carolina; Ferreira, M.João G.; Salomon, Claudio Javier; Nunes, Teresa G.; Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy; Elsevier Science; International Journal Of Pharmaceutics; 496; 2; 12-2015; 812-821
0378-5173
CONICET Digital
CONICET
url http://hdl.handle.net/11336/52569
identifier_str_mv Arrua, Eva Carolina; Ferreira, M.João G.; Salomon, Claudio Javier; Nunes, Teresa G.; Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by 13C and 15N solid-state NMR spectroscopy; Elsevier Science; International Journal Of Pharmaceutics; 496; 2; 12-2015; 812-821
0378-5173
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.ijpharm.2015.11.026
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0378517315303720
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
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 13.22299

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