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Synthesis, in vitro Cytotoxicity, and Interaction with DNA of Platinum(II) Complexes with N-Monocycloalkyl Derivatives of 1R,2R-Diaminocyclohexane as Carrier Ligands

Authors

  • Yanyan Sun,

    1. Pharmaceutical Research Center, School of Chemistry and Chemical Engineering
    2. Jiangsu Province High-Tech Key Laboratory for Biomedical Research, Southeast University, Nanjing 211189 (China)
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  • Prof. Shaohua Gou,

    Corresponding author
    1. Pharmaceutical Research Center, School of Chemistry and Chemical Engineering
    2. Jiangsu Province High-Tech Key Laboratory for Biomedical Research, Southeast University, Nanjing 211189 (China)
    • Pharmaceutical Research Center, School of Chemistry and Chemical Engineering
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  • Fei Liu,

    1. Pharmaceutical Research Center, School of Chemistry and Chemical Engineering
    2. Jiangsu Province High-Tech Key Laboratory for Biomedical Research, Southeast University, Nanjing 211189 (China)
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  • Dr. Runting Yin,

    1. Pharmaceutical Research Center, School of Chemistry and Chemical Engineering
    2. Jiangsu Province High-Tech Key Laboratory for Biomedical Research, Southeast University, Nanjing 211189 (China)
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  • Dr. Lei Fang

    1. Pharmaceutical Research Center, School of Chemistry and Chemical Engineering
    2. Jiangsu Province High-Tech Key Laboratory for Biomedical Research, Southeast University, Nanjing 211189 (China)
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Abstract

A series of platinum(II) complexes with N-monocyclopentyl/cyclohexyl derivatives of 1R,2R-diaminocyclohexane as carrier ligands and dicarboxylate anions as leaving groups were synthesized and characterized. All complexes were characterized by elemental analysis, IR, 1H NMR, and 13C NMR spectroscopy, as well as ESIMS. The in vitro antiproliferative activities were tested by MTT assay against four human cancer cell lines; breast carcinoma (MCF-7) and colon cancer (HCT-116) cells were particularly sensitive, especially to complexes 1 f (IC50=9.81 and 1.49 μM) and 2 f (IC50=4.59 and 0.36 μM). Flow cytometry indicated that representative compounds exert cytotoxicity toward MCF-7 and HCT-116 cells through induction of apoptosis and blockage of cell-cycle progression in the S phase, similar to cisplatin. The interaction between the platinum(II) complexes and pET22b plasmid DNA was observed by agarose gel electrophoresis, revealing that complex 2 f has the capacity to distort plasmid DNA in a manner distinct from that of oxaliplatin.

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