English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/103963
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:
Title

Sulforaphane homologues: Enantiodivergent synthesis of both enantiomers, activationof the Nrf2 transcription factor and selective cytotoxic activity

AuthorsElhalem, Eleonora; Recio, Rocío; Werner, Sabine; Lieder, Franziska; Calderón-Montaño, José Manuel; López-Lázaro, Miguel; Fernández Fernández, Inmaculada; Khiar el Wahabi, Noureddine
KeywordsCytotoxic activity
DAG-methodology
Activation of Nrf2 factor
Enantiodivergent synthesis
R and S Sulforaphane and Homologues
Issue Date2014
CitationEuropean Journal of Medicinal Chemistry 87: 552- 563 (2014)
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.
URIhttp://hdl.handle.net/10261/103963
DOI10.1016/j.ejmech.2014.09.052
Identifiersdoi: 10.1016/j.ejmech.2014.09.052
issn: 1768-3254
Appears in Collections:(IIQ) Artículos
Files in This Item:
File Description SizeFormat 
Revised EJMECH-D-14-01345.pdf959,97 kBAdobe PDFThumbnail
View/Open
Show full item record
Review this work
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.