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Title

Epothilone Analogs with Benzimidazole and Quinoline Side Chains: Chemical Synthesis, Antiproliferative Activity, and Interactions with Tubulin

AuthorsDietrich, Silvia Anthoine; Lindauer, Renate; Stierling, Claire; Gertsch, Jürg; Matesanz, Ruth CSIC ; Notararigo, Sara CSIC; Díaz, José Fernando CSIC ORCID ; Altmann, Karl-Heinz
KeywordsAntitumor agents
epothilone
microtubules
natural products
structure–activity relationships
total synthesis
Issue Date5-Oct-2009
PublisherWiley-VCH
CitationChemistry - A European Journal 15(39):10144-10157(2009)
AbstractA 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
Description14 páginas, 1 figura, 2 tablas, 6 esquemas -- PAGS nros. 10144-10157
Publisher version (URL)http://dx.doi.org/10.1002/chem.200901376
URIhttp://hdl.handle.net/10261/55701
DOI10.1002/chem.200901376
ISSN0947-6539
E-ISSN1521-3765
Appears in Collections:(CIB) Artículos

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