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Synthesis, characterization, and cytotoxicity of Pt(IV) complexes containing 1,10-phenanthroline and 2,2′-bipyridine and diaminocyclohexane ligands

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Abstract

Four platinum(IV) complexes containing intercalating ligands [1,10-phenanthroline (phen) and 2,2′-bipyridine (bpy)] and ancillary ligands [(1S,2S)-diaminocyclohexane (SS-DACH) and (1R,2R)-diaminocyclohexane (RR-DACH)] were synthesized and characterized by 1H nuclear magnetic resonance, electrospray ionization mass spectrometry, X-ray crystal structure analysis, elemental analysis, ultraviolet absorption spectroscopy, circular dichroism spectroscopy, and electrochemical analysis. The reactions between [Pt(phen)(SS-DACH)Cl2]2+ and glutathione and Ac-CPFC-NH2 were investigated by high-performance liquid chromatography. [Pt(phen)(SS-DACH)Cl2]2+ was reduced to its corresponding Pt(II) complex [Pt(phen)(SS-DACH)]2+, while glutathione and Ac-CPFC-NH2 were oxidized to glutathione-disulfide and a peptide containing an intramolecular disulfide bond, respectively. The cytotoxicities of the Pt(IV) complexes against a human non-small cell lung cancer cell line (A549) and the corresponding cisplatin-resistant cell line (A549cisR) were evaluated. These Pt(IV) complexes showed a higher activity toward A549 and A549cisR than did cisplatin. Also, the cytotoxicities of the Pt(IV) complexes were higher for A549cisR than for A549 cells. Moreover, the cytotoxicities of the (SS-DACH)-liganded platinum complexes were higher than those of the (RR-DACH)-liganded platinum complexes in either A549 or A549cisR cells. Phen-liganded platinum complexes were more cytotoxic than the bpy-liganded platinum complexes. The cytotoxicities of these Pt(IV) complexes had no correlation with reduction potentials.

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Acknowledgements

This work was supported financially by grants from the National Natural Science Foundation of China (21406047), the Natural Science Foundation of Hebei Province (B2016201014), and the Natural Science Foundation of Educational Commission of Hebei Province (ZD2016073), which are gratefully acknowledged.

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Authors and Affiliations

  1. College of Chemistry and Environmental Science, Key Laboratory of Analytical Science and Technology of Hebei Province, and MOE Key Laboratory of Medicinal Chemistry and Molecular Diagnostics, Hebei University, Baoding, 071002, Hebei Province, People’s Republic of China

    Xiaowei Zhao, Yamei Zhang, Xiaonan Hou, Shigang Shen & Shuying Huo

  2. Affiliated Hospital of Hebei University, Baoding, 071000, Hebei Province, People’s Republic of China

    Jianhong Shi

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  1. Xiaowei Zhao
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  2. Yamei Zhang
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  3. Xiaonan Hou
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  4. Jianhong Shi
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  5. Shigang Shen
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  6. Shuying Huo
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Correspondence to Jianhong Shi, Shigang Shen or Shuying Huo.

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Zhao, X., Zhang, Y., Hou, X. et al. Synthesis, characterization, and cytotoxicity of Pt(IV) complexes containing 1,10-phenanthroline and 2,2′-bipyridine and diaminocyclohexane ligands. Transit Met Chem 42, 219–228 (2017). https://doi.org/10.1007/s11243-017-0125-0

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  • DOI: https://doi.org/10.1007/s11243-017-0125-0

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