Synthesis, Characterization, and Bioactivity of the Photoisomerizable Tubulin Polymerization Inhibitor azo-Combretastatin A4

Organic Letters
Ashton J EngdahlCraig N Streu

Abstract

Combretastatin A4 is a stilbenoid tubulin binding mitotic inhibitor whose conformation greatly influences its potency, making it an excellent candidate for adaptation as a photoactivatable tool. Herein we report a novel synthesis, the facile isomerization with commercial grade equipment, and biological activity of azo-combretastatin A4 in vitro and in human cancer cells. Photoisomerized azo-combretestatin A4 is at least 200-fold more potent in cellular culture, making it a promising phototherapeutic and biomedical research tool.

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Citations

Jan 4, 2017·Bioorganic & Medicinal Chemistry Letters·M Michael DconaMatthew C T Hartman
Oct 28, 2015·Organic & Biomolecular Chemistry·Jonathon E SheldonMatthew C T Hartman
Aug 20, 2016·Chemical Communications : Chem Comm·Robert J Mart, Rudolf K Allemann
Sep 11, 2018·ChemMedChem·Dorian SchmidtChristian Peifer
Oct 17, 2018·Chembiochem : a European Journal of Chemical Biology·Yuan Qi YeohAndrew D Abell
Jan 19, 2019·Chembiochem : a European Journal of Chemical Biology·Takato MashitaShin Mizukami
Jan 18, 2020·Pharmaceuticals·Eavan C McLoughlin, Niamh M O'Boyle
Jul 5, 2016·Angewandte Chemie·Michael M LerchBen L Feringa

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