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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/55701
Title: Epothilone Analogs with Benzimidazole and Quinoline Side Chains: Chemical Synthesis, Antiproliferative Activity, and Interactions with Tubulin
Authors: Dietrich, Silvia Anthoine; Lindauer, Renate; Stierling, Claire; Gertsch, Jürg; Matesanz, Ruth; Notararigo, Sara; Díaz, José Fernando; Altmann, Karl-Heinz
Keywords: Antitumor agents
natural products
structure–activity relationships
total synthesis
Issue Date: 5-Oct-2009
Publisher: Wiley-VCH
Citation: Chemistry - A European Journal 15(39):10144-10157(2009)
Abstract: A series of epothilone B and D analogues bearing isomeric quinoline or functionalized benzimidazole side chains has been prepared by chemical synthesis in a highly convergent manner. All analogues have been found to interact with the tubulin/microtubule system and to inhibit human cancer cell proliferation in vitro, albeit with different potencies (IC(50) values between 1 and 150 nM). The affinity of quinoline-based epothilone B and D analogues for stabilized microtubules clearly depends on the position of the N-atom in the quinoline system, while the induction of tubulin polymerization in vitro appears to be less sensitive to N-positioning. The potent inhibition of human cancer cell growth by epothilone analogues bearing functionalized benzimidazole side chains suggests that these systems might be conjugated with tumor-targeting moieties to form tumor-targeted prodrugs
Description: 14 páginas, 1 figura, 2 tablas, 6 esquemas -- PAGS nros. 10144-10157
Publisher version (URL): http://dx.doi.org/10.1002/chem.200901376
URI: http://hdl.handle.net/10261/55701
ISSN: 0947-6539
DOI: 10.1002/chem.200901376
E-ISSN: 1521-3765
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