Halogenated PtIV Complexes from N-Halosuccinimide Oxidation of PtII Antitumor Drugs : Synthesis, Mechanistic Investigation, and Cytotoxicity

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

11 Scopus Citations
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Author(s)

  • Cai Li
  • Zixuan Tong
  • Man-Kit Tse

Related Research Unit(s)

Detail(s)

Original languageEnglish
Pages (from-to)1706-1712
Journal / PublicationEuropean Journal of Inorganic Chemistry
Volume2017
Issue number12
Publication statusPublished - 27 Mar 2017

Abstract

Compared with square-planar PtII drugs, PtIV-based anticancer prodrugs are relatively inert under physiological conditions and can be activated after entering cells. The two axial ligands in PtIV complexes provide an opportunity to further functionalize these prodrugs. In recent years, much effort has been devoted to developing new PtIV-based anticancer prodrugs with higher cytotoxicity but fewer side effects. New synthetic methods, however, are intensely desired for structurally diversified and biologically distinct PtIV complexes. Herein, we utilize N-halosuccinimides as oxidants and carry out the oxidation reaction on PtII drugs including cisplatin, carboplatin, and oxaliplatin to obtain halogenated PtIV complexes. The related mechanism of the reaction of N-bromosuccinimide (NBS) with cisplatin in ethanol is thoroughly investigated. N-chlorosuccinimide is also utilized to obtain the respective dichlorinated PtIV complexes. When N-iodosuccinimide reacts with PtII drugs, new PtIV compounds containing iodide and succinimide ligands in the axial position are formed. Cytotoxicity test shows that some of the complexes are active against cisplatin-resistant human ovarian cancer cells. Our study provides a detailed understanding of the reaction mechanism between NBS and cisplatin and offers a more convenient strategy to obtain dichlorinated and new iodinated PtIV anticancer prodrugs.

Research Area(s)

  • Cancer, Cisplatin, Cytotoxicity, Halogenation, N-Halosuccinimide, Platinum

Citation Format(s)

Halogenated PtIV Complexes from N-Halosuccinimide Oxidation of PtII Antitumor Drugs : Synthesis, Mechanistic Investigation, and Cytotoxicity. / Xu, Zoufeng; Li, Cai; Tong, Zixuan; Ma, Lili; Tse, Man-Kit; Zhu, Guangyu.

In: European Journal of Inorganic Chemistry, Vol. 2017, No. 12, 27.03.2017, p. 1706-1712.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review