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Synthesis, DNA binding, and cytotoxicity activity of bis-naphalenyl compounds with different diamine linkers

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Abstract

A series of novel bis-naphalenyl compounds with different diamine linkers were synthesized and characterized by 1H NMR, 13C NMR, and HR-MS. The DNA binding abilities of the compounds were studied by using flourescence titration, DNA thermal denaturation experiments, viscosity titration, and NMR studies. The DNA binding abilities of all the bis-naphalenyl compounds were on the same order of magnitude. Compared with the groove binding mode of the monomer, the bis-naphalenyl compounds exhibited partial intercalating binding mode. The cytotoxicity activities of the compounds were evaluated by MTT assay in vitro. According to the results of MTT assay, bis-naphalenyl compound 3c with hexamethylenediamine linker, and 3d with p-xylylenediamine linker were found to be more toxic against BGC823 cells. The IC50 values of the two compounds were similar to that of the control drug (5-Fluorouracil) on BGC823 cells. Compared with the results on BGC823 cells, better results were found on SW480 cells. Compounds 3c and 3d exhibited smaller IC50 values than that of control drug (5-Fluorouracil). The IC50 values of 3c, 3d, and 5-Fluorouracil were 52.01, 66.09, and 230.11 μM, respectively.

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Acknowledgments

This work was financially supported by the National Science Foundation of China (Nos. 21172182, 21362026).

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Authors and Affiliations

  1. Key Laboratory of Hui Ethnic Medicine Modernization, Ministry of Education; Ningxia Engineering and Technology Research Centre of Hui Medicine Modernization; College of Pharmacy, Ningxia Medical University, Yinchuan, 750004, People’s Republic of China

    Yu Huang, Yu Song, Yan-Ru Fan, Qi-Peng Zhao & Wan-Nian Zhang

  2. College of Public Health, Ningxia Medical University, Ningxia, Yinchuan, 750004, People’s Republic of China

    Min Huang & Da-Nian Tian

  3. Rongchang Campus, Southwest University, Chongqing, 402460, People’s Republic of China

    Xin-Bin Yang

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  1. Yu Huang
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Huang, Y., Song, Y., Huang, M. et al. Synthesis, DNA binding, and cytotoxicity activity of bis-naphalenyl compounds with different diamine linkers. Res Chem Intermed 42, 7329–7344 (2016). https://doi.org/10.1007/s11164-016-2539-2

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