Photoresponsive azo-combretastatin A-4 analogues.
Basic Information
ID: ALA4130572
Journal: Eur J Med Chem
Title: Photoresponsive azo-combretastatin A-4 analogues.
Authors: Rastogi SK, Zhao Z, Barrett SL, Shelton SD, Zafferani M, Anderson HE, Blumenthal MO, Jones LR, Wang L, Li X, Streu CN, Du L, Brittain WJ.
Abstract: Colchicine analogues in which an azo group is incorporated into a molecule containing the key pharmacophore of colchicine, have found particular utility as switchable tubulin binding chemotherapeutics. Combretastatin is a related compound containing a stilbene fragment that shows different bioactivity for the cis and trans isomers. We have performed cell assays on 17 new compounds structurally related to a previously reported azo-analogue of combretastatin. One of these compounds showed enhanced potency against HeLa (IC50 = 0.11 μM) and H157 cells (IC50 = 0.20 μM) for cell studies under 400 nm irradiation and the highest photoactivity (IC50 with irradiation/IC50 in dark = 550). We have performed docking and physicochemical studies of this new compound (7). Kinetic studies in water reveal a longer half-life for the cis isomer of 7 which may be one factor responsible for the better IC50 values in cell assays and the improved photoresponsive behavior.
CiteXplore: 29172077
DOI: 10.1016/j.ejmech.2017.11.012
Patent ID: ┄