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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/98768
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T09:41:07Zoai: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:34982025-09-29 09:41:07.311CONICET 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 |
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1844613299544522752 |
score |
13.070432 |