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  • Title: Synthesis and biological evaluation of (-)-16-normethyldictyostatin: a potent analogue of (-)-dictyostatin.
    Author: Shin Y, Fournier JH, Balachandran R, Madiraju C, Raccor BS, Zhu G, Edler MC, Hamel E, Day BW, Curran DP.
    Journal: Org Lett; 2005 Jul 07; 7(14):2873-6. PubMed ID: 15987158.
    Abstract:
    [structure: see text] (-)-16-Normethyldictyostatin has been made by total synthesis and is a potent antitumor agent in cells expressing wild-type tubulin and in one mutant cell line that is resistant to paclitaxel, but it is much less active than dictyostatin in another paclitaxel-resistant cell line where Val is substituted for Phe270. This provides strong evidence that the C16 methyl group of the dictyostatins is oriented toward Phe270 in the paclitaxel-binding site on beta-tubulin.
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