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

Bioorganic & Medicinal Chemistry Letters
Olga N ZefirovaNikolay S Zefirov

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.

References

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Citations

Apr 2, 2013·Angiogenesis·E M ProkopiouJ J Walsh
Jul 12, 2013·Chembiochem : a European Journal of Chemical Biology·Olga N ZefirovaSergei A Kuznetsov
Jul 24, 2014·Accounts of Chemical Research·David G I Kingston, James P Snyder

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