Anticancer activity and DNA binding property of the trimers of triphenylethylene-coumarin hybrids

Novel trimers of triphenylethylene-coumarin hybrid containing two amino side chains (5a-d and 6a-d) were designed and synthesized by the condensation of 1,3,5-benzenetricarboxylic acid with "the varied amino monomeric hybrids catalyzed by HATU and DIPEA at room temperature. The extended trimeric compound 6a (R = piperidinyl) exhibited significant anti-proliferative activity against three cancer cells at IC50 of near 10 mu mol/L.UV-vis, fluorescence (lifetime) and thermal denaturation exhibited that 6a had significant interaction with Ct-DNA by the intercalative mode of binding. The order of their anti proliferative activities was 6(a, d) > 5(a, d) and (5-6)a > (5-6)d, respectively, in accordance with that of their DNA binding properties, which suggested that the prolonged linker (six carbons) and piperidinyl group on the side chains are beneficial to DNA binding and the anti-tumor activity. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.