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  • Title: Design, synthesis, and bioactivity of putative tubulin ligands with adamantane core.
    Author: Zefirova ON, Nurieva EV, Lemcke H, Ivanov AA, Shishov DV, Weiss DG, Kuznetsov SA, Zefirov NS.
    Journal: Bioorg Med Chem Lett; 2008 Sep 15; 18(18):5091-4. PubMed ID: 18715782.
    Abstract:
    Several adamantane-based taxol mimetics were synthesized and found to be cytotoxic at micromolar concentrations and to cause tubulin aggregation. The extent of the aggregation is maximal for N-benzoyl-(2R,3S)-phenylisoseryloxyadamantane (5) and is very sensitive to the structural modifications. A hybrid compound (15), combining adamantane-based taxol mimetic with colchicine was synthesized and found to possess both microtubule depolymerizing and microtubule bundling activities in A549 human lung carcinoma cells.
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