Dietrich, Silvia Anthoine; Lindauer, Renate; Stierlin, Claire; Gertsch, Jürg; Matesanz, Ruth; Notararigo, Sara; Díaz, José Fernando; Altmann, Karl-Heinz (2009). Epothilone analogues with benzimidazole and quinoline side chains: chemical synthesis, antiproliferative activity, and interactions with tubulin. Chemistry - a European journal, 15(39), pp. 10144-57. Weinheim: Wiley-VCH 10.1002/chem.200901376
Full text not available from this repository. (Request a copy)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.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
04 Faculty of Medicine > Pre-clinic Human Medicine > Institute of Biochemistry and Molecular Medicine |
UniBE Contributor: |
Gertsch, Jürg |
ISSN: |
0947-6539 |
Publisher: |
Wiley-VCH |
Language: |
English |
Submitter: |
Factscience Import |
Date Deposited: |
04 Oct 2013 15:12 |
Last Modified: |
05 Dec 2022 14:22 |
Publisher DOI: |
10.1002/chem.200901376 |
PubMed ID: |
19697384 |
Web of Science ID: |
000270854200025 |
URI: |
https://boris.unibe.ch/id/eprint/31618 (FactScience: 196249) |
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