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Amidoxime platinum(II) complexes: pH-dependent highly selective generation and cytotoxic activity

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Abstract

The reaction of cis-[PtCl2(Me2[S with combining low line]O)2] with 1 equiv. of each of the amidoximes RC(NH2)[double bond, length as m-dash]NOH in neutral media in MeOH results in the formation of complexes cis-[PtCl2{RC(NH2)[double bond, length as m-dash][N with combining low line]OH}(Me2[S with combining low line]O)] (5 examples; 83–98% isolated yields). In the presence of 2 equiv. of NaOH in MeOH solution, the reaction of cis-[PtCl2(Me2[S with combining low line]O)2] with 1 equiv. of each of the amidoximes RC(NH2)[double bond, length as m-dash]NOH leads to [Pt{RC([N with combining low line]H)[double bond, length as m-dash]N[O with combining low line]}(Me2[S with combining low line]O)2] (7 examples; 74–95% isolated yields). All new complexes were characterized by C, H, and N elemental analyses, HRESI+-MS, IR, 1H, 13C{1H}, and CP-MAS TOSS 13C{1H} NMR spectroscopies, and additionally by single-crystal XRD (for seven species). The cytotoxic potency of six compounds was determined in the human cancer cell lines CH1/PA-1, A549, SK-BR-3, and SW480. Generally, the second class of complexes containing chelating amidoximato ligands shows much higher cytotoxicity than the non-chelate amidoxime analogs, despite the lack of easily exchangeable chlorido ligands. Especially, the complex [Pt(p-CF3C6H4C([N with combining low line]H)[double bond, length as m-dash]N[O with combining low line])(Me2[S with combining low line]O)2] displays a remarkable activity in the inherently cisplatin resistant SW480 cell line (0.51 μM vs. 3.3 μM).

Graphical abstract: Amidoxime platinum(ii) complexes: pH-dependent highly selective generation and cytotoxic activity

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Publication details

The article was received on 24 Mar 2017, accepted on 01 Jun 2017 and first published on 01 Jun 2017


Article type: Paper
DOI: 10.1039/C7NJ00982H
Citation: New J. Chem., 2017, Advance Article
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    Amidoxime platinum(II) complexes: pH-dependent highly selective generation and cytotoxic activity

    D. S. Bolotin, M. Ya. Demakova, A. A. Legin, V. V. Suslonov, A. A. Nazarov, M. A. Jakupec, B. K. Keppler and V. Yu. Kukushkin, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ00982H

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