English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/48179
Title: Synthesis of Antimitotic Thioglycosides: In Vitro and in Vivo Evaluation of Their Anticancer Activity
Authors: García-Álvarez, Isabel; Groult, Hugo; Casas, Josefina; Barreda-Manso, M. Asunción; Yanguas-Casás, Natalia; Nieto-Sampedro, Manuel; Romero-Ramírez, Lorenzo; Fernández-Mayoralas, Alfonso
Issue Date: 2011
Publisher: American Chemical Society
Citation: Journal of Medicinal Chemistry
Abstract: The synthesis and biological activity of oleylN-acetyl-α- and β-d-glucosaminides (1 and 2, respectively) and their thioglycosyl analogues (3 and 4, respectively) are reported. The compounds exhibited antimitotic activity on rat glioma (C6) and human lung carcinoma (A549) cell cultures in the micromolar range. Analysis of cell extracts using ultra performance liquid chromatography–mass spectrometry showed that the synthetic glycosides produce alterations in glycosphingolipid metabolism, with variable effect on the level of glucosylceramide depending on the configuration of the antimitotic used. In vivo experiments in nude mice bearing an implanted C6 glioma showed that the α-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides.
Publisher version (URL): http://dx.doi.org/10.1021/jm200961q
URI: http://hdl.handle.net/10261/48179
ISSN: 0022-2623
DOI: 10.1021/jm200961q
E-ISSN: 1520-4804
Appears in Collections:(IQAC) Artículos
(IC) Artículos
Files in This Item:
There are no files associated with this item.
Show full item record

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