2. Academic Validation
  3. Design, synthesis, and bioactivity of putative tubulin ligands with adamantane core

Design, synthesis, and bioactivity of putative tubulin ligands with adamantane core

  • Bioorg Med Chem Lett. 2008 Sep 15;18(18):5091-4. doi: 10.1016/j.bmcl.2008.07.116.
Olga N Zefirova 1,  Evgeniya V Nurieva,  Heiko Lemcke,  Andrei A Ivanov,  Dmitrii V Shishov,  Dieter G Weiss,  Sergei A Kuznetsov,  Nikolay S Zefirov
Affiliations

Affiliation

  • 1 Department of Chemistry, M. V. Lomonosov Moscow State University, 119992 Moscow, Russian Federation. [email protected]
PMID: 18715782 DOI: 10.1016/j.bmcl.2008.07.116
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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