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    J Med Chem. 2009 Mar 12;52(5):1284-94.

    10-(2-oxo-2-phenylethylidene)-10H-anthracen-9-ones as highly active antimicrotubule agents: synthesis, antiproliferative activity, and inhibition of tubulin polymerization.

    Prinz H, Schmidt P, Böhm KJ, Baasner S, Müller K, Unger E, Gerlach M, Günther EG.

    Source

    Institute of Pharmaceutical and Medicinal Chemistry, Westphalian Wilhelms-University, Munster, Germany. prinzh@uni-muenster.de

    Abstract

    A series of 10-(2-oxo-2-phenylethylidene)-10H-anthracen-9-ones were synthesized and evaluated for interactions with tubulin and for antiproliferative activity against a panel of human and rodent tumor cell lines. The 4-methoxy analogue 17b was most potent, displaying IC(50) values ranging from 40 to 80 nM, including multidrug resistant phenotypes, and had excellent activity as an inhibitor of tubulin polymerization (IC(50) = 0.52 microM). Concentration-dependent flow cytometric studies showed that KB/HeLa cells treated with 17b were arrested in the G2/M phases of the cell cycle (EC(50) = 90 nM). In competition experiments, 17b strongly displaced [(3)H]-colchicine from its binding site in the tubulin. The results obtained demonstrate that the antiproliferative activity is related to the inhibition of tubulin polymerization.

    PMID:
    19220018
    [PubMed - indexed for MEDLINE]

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