NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins

Autores
Recio, Rocío; Elhalem, Eleonora; Benito, Juan Andrés; Fernández, Inmaculada; Khiar, Noureddine
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Sulforaphane (SFN), a phytochemical isolated from broccoli, is an important antitumoral compound with additional beneficial effect on other important diseases. However, the chemical instability of SFN has hampered its clinical use. In order to circumvent this problem, we report the first comparative study on the inclusion complexes of SFN and SFN homologues with different cyclodextrins by NMR spectroscopy. From this study it has been shown that α-CD is the most indicated cyclodextrin for the stabilization of SFN and SFN homologues, and that the highest affinity constant is that of the isothiocyanate obtained from the wasabi. Furthermore, the study of the inclusion complexes of α-CD and the non-natural SFN and analogues with S absolute configuration at sulfur shows for the first time that α-CD is able to discriminate between the two enantiomers, with the natural R enantiomers forming the inclusion complexes with higher affinity.
Fil: Recio, Rocío. Universidad de Sevilla; España
Fil: Elhalem, Eleonora. Universidad de Sevilla; España. Consejo Superior de Investigaciones Científicas; España. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Benito, Juan Andrés. Universidad de Sevilla; España
Fil: Fernández, Inmaculada. Universidad de Sevilla; España
Fil: Khiar, Noureddine. Universidad de Sevilla; España
Materia
AFFINITY CONSTANTS
CHIRAL DISCRIMINATION
CYCLODEXTRINS
SULFORAPHANE
SULFORAPHANE ANALOGUES
SULFORAPHANE STABILTY
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:11336/98768
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/98768
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrinsRecio, RocíoElhalem, EleonoraBenito, Juan AndrésFernández, InmaculadaKhiar, NoureddineAFFINITY CONSTANTSCHIRAL DISCRIMINATIONCYCLODEXTRINSSULFORAPHANESULFORAPHANE ANALOGUESSULFORAPHANE STABILTYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Sulforaphane (SFN), a phytochemical isolated from broccoli, is an important antitumoral compound with additional beneficial effect on other important diseases. However, the chemical instability of SFN has hampered its clinical use. In order to circumvent this problem, we report the first comparative study on the inclusion complexes of SFN and SFN homologues with different cyclodextrins by NMR spectroscopy. From this study it has been shown that α-CD is the most indicated cyclodextrin for the stabilization of SFN and SFN homologues, and that the highest affinity constant is that of the isothiocyanate obtained from the wasabi. Furthermore, the study of the inclusion complexes of α-CD and the non-natural SFN and analogues with S absolute configuration at sulfur shows for the first time that α-CD is able to discriminate between the two enantiomers, with the natural R enantiomers forming the inclusion complexes with higher affinity.Fil: Recio, Rocío. Universidad de Sevilla; EspañaFil: Elhalem, Eleonora. Universidad de Sevilla; España. Consejo Superior de Investigaciones Científicas; España. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Benito, Juan Andrés. Universidad de Sevilla; EspañaFil: Fernández, Inmaculada. Universidad de Sevilla; EspañaFil: Khiar, Noureddine. Universidad de Sevilla; EspañaElsevier2018-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/98768Recio, Rocío; Elhalem, Eleonora; Benito, Juan Andrés; Fernández, Inmaculada; Khiar, Noureddine; NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins; Elsevier; Carbohydrate Polymers; 187; 5-2018; 118-1250144-8617CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0144861717314285info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carbpol.2017.12.022info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:31:00Zoai:ri.conicet.gov.ar:11336/98768instacron: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 14:31:00.322CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
title NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
spellingShingle NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
Recio, Rocío
AFFINITY CONSTANTS
CHIRAL DISCRIMINATION
CYCLODEXTRINS
SULFORAPHANE
SULFORAPHANE ANALOGUES
SULFORAPHANE STABILTY
title_short NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
title_full NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
title_fullStr NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
title_full_unstemmed NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
title_sort NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins
dc.creator.none.fl_str_mv Recio, Rocío
Elhalem, Eleonora
Benito, Juan Andrés
Fernández, Inmaculada
Khiar, Noureddine
author Recio, Rocío
author_facet Recio, Rocío
Elhalem, Eleonora
Benito, Juan Andrés
Fernández, Inmaculada
Khiar, Noureddine
author_role author
author2 Elhalem, Eleonora
Benito, Juan Andrés
Fernández, Inmaculada
Khiar, Noureddine
author2_role author
author
author
author
dc.subject.none.fl_str_mv AFFINITY CONSTANTS
CHIRAL DISCRIMINATION
CYCLODEXTRINS
SULFORAPHANE
SULFORAPHANE ANALOGUES
SULFORAPHANE STABILTY
topic AFFINITY CONSTANTS
CHIRAL DISCRIMINATION
CYCLODEXTRINS
SULFORAPHANE
SULFORAPHANE ANALOGUES
SULFORAPHANE STABILTY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Sulforaphane (SFN), a phytochemical isolated from broccoli, is an important antitumoral compound with additional beneficial effect on other important diseases. However, the chemical instability of SFN has hampered its clinical use. In order to circumvent this problem, we report the first comparative study on the inclusion complexes of SFN and SFN homologues with different cyclodextrins by NMR spectroscopy. From this study it has been shown that α-CD is the most indicated cyclodextrin for the stabilization of SFN and SFN homologues, and that the highest affinity constant is that of the isothiocyanate obtained from the wasabi. Furthermore, the study of the inclusion complexes of α-CD and the non-natural SFN and analogues with S absolute configuration at sulfur shows for the first time that α-CD is able to discriminate between the two enantiomers, with the natural R enantiomers forming the inclusion complexes with higher affinity.
Fil: Recio, Rocío. Universidad de Sevilla; España
Fil: Elhalem, Eleonora. Universidad de Sevilla; España. Consejo Superior de Investigaciones Científicas; España. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Benito, Juan Andrés. Universidad de Sevilla; España
Fil: Fernández, Inmaculada. Universidad de Sevilla; España
Fil: Khiar, Noureddine. Universidad de Sevilla; España
description Sulforaphane (SFN), a phytochemical isolated from broccoli, is an important antitumoral compound with additional beneficial effect on other important diseases. However, the chemical instability of SFN has hampered its clinical use. In order to circumvent this problem, we report the first comparative study on the inclusion complexes of SFN and SFN homologues with different cyclodextrins by NMR spectroscopy. From this study it has been shown that α-CD is the most indicated cyclodextrin for the stabilization of SFN and SFN homologues, and that the highest affinity constant is that of the isothiocyanate obtained from the wasabi. Furthermore, the study of the inclusion complexes of α-CD and the non-natural SFN and analogues with S absolute configuration at sulfur shows for the first time that α-CD is able to discriminate between the two enantiomers, with the natural R enantiomers forming the inclusion complexes with higher affinity.
publishDate 2018
dc.date.none.fl_str_mv 2018-05
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/11336/98768
Recio, Rocío; Elhalem, Eleonora; Benito, Juan Andrés; Fernández, Inmaculada; Khiar, Noureddine; NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins; Elsevier; Carbohydrate Polymers; 187; 5-2018; 118-125
0144-8617
CONICET Digital
CONICET
url http://hdl.handle.net/11336/98768
identifier_str_mv Recio, Rocío; Elhalem, Eleonora; Benito, Juan Andrés; Fernández, Inmaculada; Khiar, Noureddine; NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins; Elsevier; Carbohydrate Polymers; 187; 5-2018; 118-125
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/S0144861717314285
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.carbpol.2017.12.022
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
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
_version_ 1846082790089555968
score 13.22299

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