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Anticancer activity and DNA binding property of the dimers of triphenylethylene–coumarin hybrid with two amino side chains

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Abstract

Novel dimers of triphenylethylene–coumarin hybrid containing two amino side chains were designed and synthesized by the condensation of three dicarboxylic acids with the amino monomeric hybrids catalyzed by HATU and DIPEA at room temperature. All the dimeric compounds exhibited significant anti-proliferative activity against four cancer cells at IC50 of near 10 μM, and higher than their corresponding monomeric compounds except compound 9b. Among them, compounds 9a (R = NEt2) linked by sebacamide and 8b (R = piperidinyl) linked by adipamide were the best ones, respectively. UV–Vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that the monomeric compounds 6b and the dimers 7b, 8b, and 9b had significant interactions with Ct-DNA by the intercalative mode of binding. The order of their anti-proliferative activities was 8b > 7b> 6b > 9b, in accordance with that of their DNA binding properties.

Graphical abstract

Novel dimers of triphenylethylene–coumarin hybrid containing two amino side chains were designed and synthesized. All the dimeric compounds exhibited significant anti-proliferative activity against cancer cells. Both the length of the linker and the basic amino group had certain effects on their anti-proliferative activity.

Anticancer activity and DNA binding property of the dimers of triphenylethylene–coumarin hybrid with two amino side chains

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Acknowledgments

The financial supports were from the 973 Program (2010CB534913) and the National Natural Science Foundation of China (NSFC) (20902016).

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Authors and Affiliations

  1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China

    Mo Zhu, Likai Zhou, Yuchao Yao, Shuai Li, Mengjiao Lv, Kerang Wang, Xiaoliu Li & Hua Chen

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  1. Mo Zhu
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  2. Likai Zhou
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  3. Yuchao Yao
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Correspondence to Hua Chen.

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Zhu, M., Zhou, L., Yao, Y. et al. Anticancer activity and DNA binding property of the dimers of triphenylethylene–coumarin hybrid with two amino side chains. Med Chem Res 24, 2314–2324 (2015). https://doi.org/10.1007/s00044-014-1296-2

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