Synthesis and Biological Evaluation of a-Tubulin-Binding Pironetin Analogues with Enhanced Lipophilicity
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Títol
Synthesis and Biological Evaluation of a-Tubulin-Binding Pironetin Analogues with Enhanced LipophilicityAutoria
Data de publicació
2013Editor
Wiley-VCH VerlagISSN
1434-193X; ESSN: 1099-0690Cita bibliogràfica
European Journal of Organic Chemistry Volume 2013, Issue 6, pages 1116–1123, February 2013Tipus de document
info:eu-repo/semantics/articleVersió de l'editorial
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201283/abstractParaules clau / Matèries
Resum
The preparation of four new lipophilic analogues of the natural pyrone pironetin is described. The nine-carbon side chain of the latter has been replaced in one analogue by a 4-phenylbutyl chain and in the other three ... [+]
The preparation of four new lipophilic analogues of the natural pyrone pironetin is described. The nine-carbon side chain of the latter has been replaced in one analogue by a 4-phenylbutyl chain and in the other three analogues by long aliphatic chains of thirteen and sixteen carbons, all of them bearing two stereogenic centers.
Their cytotoxic activity and their interactions with tubulin have been investigated. It has been found that all four are cytotoxic towards two either sensitive or resistant tumoral cell lines with similar IC50 values in each case, thus indicating that, like the parent natural compound, they also display a covalent mechanism of action. However, one of them operates in all likelihood through a mechanism very similar to pironetin whereas the other three seem to be cytotoxic via a different mechanism. [-]
Publicat a
European Journal of Organic Chemistry, 2013, vol. 2013, no 6Drets d'accés
Copyright © 1999-2014 John Wiley & Sons, Inc. All Rights Reserved. This is the
pre-peer reviewed version of the following article: European Journal of Organic Chemistry
Volume 2013, Issue 6, pages 1116–1123, February 2013, which has
been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201283/abstract
http://rightsstatements.org/vocab/InC/1.0/
info:eu-repo/semantics/openAccess
http://rightsstatements.org/vocab/InC/1.0/
info:eu-repo/semantics/openAccess
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