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Título : Epothilone Analogs with Benzimidazole and Quinoline Side Chains: Chemical Synthesis, Antiproliferative Activity, and Interactions with Tubulin
Autor : Dietrich, Silvia Anthoine, Lindauer, Renate, Stierling, Claire, Gertsch, Jürg, Matesanz, Ruth, Notararigo, Sara, Díaz, José Fernando, Altmann, Karl-Heinz
Palabras clave : Antitumor agents
natural products
structure–activity relationships
total synthesis
Fecha de publicación : 5-Oct-2009
Editor: Wiley-VCH
Resumen: 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
Descripción : 14 páginas, 1 figura, 2 tablas, 6 esquemas -- PAGS nros. 10144-10157
Versión del editor:
ISSN: 0947-6539
DOI: 10.1002/chem.200901376
Citación : Chemistry - A European Journal 15(39):10144-10157(2009)
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