Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/103963
COMPARTIR / EXPORTAR:
logo share SHARE logo core CORE BASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE

Invitar a revisión por pares abierta
Campo DC Valor Lengua/Idioma
dc.contributor.authorElhalem, Eleonora-
dc.contributor.authorRecio, Rocío-
dc.contributor.authorWerner, Sabine-
dc.contributor.authorLieder, Franziska-
dc.contributor.authorCalderón-Montaño, José Manuel-
dc.contributor.authorLópez-Lázaro, Miguel-
dc.contributor.authorFernández Fernández, Inmaculada-
dc.contributor.authorKhiar el Wahabi, Noureddine-
dc.date.accessioned2014-10-29T10:17:59Z-
dc.date.available2014-10-29T10:17:59Z-
dc.date.issued2014-
dc.identifierdoi: 10.1016/j.ejmech.2014.09.052-
dc.identifierissn: 1768-3254-
dc.identifier.citationEuropean Journal of Medicinal Chemistry 87: 552- 563 (2014)-
dc.identifier.urihttp://hdl.handle.net/10261/103963-
dc.description.abstractReported is an enantiodivergent approach for the synthesis of both enantiomers of sulforaphane (SFN) homologues with different chain lengths between the sulfinyl sulfur and the isothiocyanate groups and different substituents on the sulfinyl sulfur. The homologues were designed in order to unravel the effect of all the diversity elements included in sulforaphane's structure. The key step of the approach is the diastereoselective synthesis of both sulfinate ester epimers at sulfur, using as single chiral auxiliary the sugar derived diacetone-d-glucose. The approach allows the first synthesis of both enantiomers of 5-methylsulfinylpentyl isothiocyanate, and the biologically important 6-methylsulfinylhexyl isothiocyanate (6-HITC) found in Japanese horseradish, wasabi (Wasabia japonica). The ability of the synthesized compounds as inductors of phase II detoxifying enzymes has been studied by determining their ability to activate the cytoprotective transcription factor Nrf2. The cytotoxic activity of all the synthesized compounds against human lung adenocarcinoma (A549) and foetal lung fibroblasts (MRC-5) is also reported. Both enantiomers of sulforaphane and six homologues were obtained.The ability of the synthesized compounds to activate the Nrf2 is studied.The cytotoxic activity of the analogues against cancer and healthy cells is reported.-
dc.rightsopenAccess-
dc.subjectCytotoxic activity-
dc.subjectDAG-methodology-
dc.subjectActivation of Nrf2 factor-
dc.subjectEnantiodivergent synthesis-
dc.subjectR and S Sulforaphane and Homologues-
dc.titleSulforaphane homologues: Enantiodivergent synthesis of both enantiomers, activationof the Nrf2 transcription factor and selective cytotoxic activity-
dc.typeartículo-
dc.identifier.doi10.1016/j.ejmech.2014.09.052-
dc.date.updated2014-10-29T10:17:59Z-
dc.description.versionPeer Reviewed-
dc.language.rfc3066eng-
dc.type.coarhttp://purl.org/coar/resource_type/c_6501es_ES
item.openairetypeartículo-
item.cerifentitytypePublications-
item.grantfulltextopen-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.fulltextWith Fulltext-
Aparece en las colecciones: (IIQ) Artículos
Ficheros en este ítem:
Fichero Descripción Tamaño Formato
Revised EJMECH-D-14-01345.pdf959,97 kBAdobe PDFVista previa
Visualizar/Abrir
Show simple item record

CORE Recommender

SCOPUSTM   
Citations

30
checked on 25-mar-2024

WEB OF SCIENCETM
Citations

30
checked on 26-feb-2024

Page view(s)

333
checked on 28-mar-2024

Download(s)

608
checked on 28-mar-2024

Google ScholarTM

Check

Altmetric

Altmetric


NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.