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A platinum(IV)-based metallointercalator: synthesis, cytotoxicity, and redox reactions with thiol-containing compounds

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Abstract

A Pt(IV)-based metallointercalator, trans-dichloro(1,10-phenanthroline)(ethylenediamine)platinum(IV) trans-[PtCl2(phen)(en)]Cl2, was synthesized and characterized by 1H NMR, ESI–MS, and elemental analysis. Three human carcinoma cell lines Hela, MCF-7, and A549 were employed for in vitro cytotoxicity evaluations using the standard MTT assay. Based on the measured IC50 values, the cytotoxicity of this metallointercalator is very similar to that of cisplatin. Reduction of trans-[PtCl2(phen)(en)]2+ by l-glutathione and 3,6-dioxa-1,8-octanedithiol was studied by 1H NMR and ESI–MS; the Pt(IV) complex was reduced to its Pt(II) counterpart. The oxidation products of l-glutathione and 3,6-dioxa-1,8-octanedithiol were identified as the glutathione disulfide and the cyclic intramolecular disulfide, respectively. Mechanisms for these reductions are proposed.

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Acknowledgments

Financial support to this work by Grants from the Natural Science Foundation of Hebei Province (B2013201181), National Undergraduate Innovation and Entrepreneurship Training Programs (2014087, 2014091), and Joint Funds of the Ph.D. Programs Foundation of Ministry of Education of China (20131301110003) is acknowledged. We thank Professor Tiesheng Shi for his critically reading and revising the manuscript.

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Authors and Affiliations

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

    Beibei Liang, Shuying Huo, Yanli Ren, Shaojing Sun, Ziqing Cao & Shigang Shen

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  1. Beibei Liang
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  2. Shuying Huo
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  3. Yanli Ren
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Correspondence to Shuying Huo or Shigang Shen.

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Liang, B., Huo, S., Ren, Y. et al. A platinum(IV)-based metallointercalator: synthesis, cytotoxicity, and redox reactions with thiol-containing compounds. Transition Met Chem 40, 31–37 (2015). https://doi.org/10.1007/s11243-014-9886-x

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