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Synthesis, characterization and anti-cancer properties of water-soluble bis(PYE) pro-ligands and derived palladium(ii) complexes

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Abstract

The two cationic palladium(II) complexes, [Pd(Len)2][OTf]2 (4) and [Pd(Lphen)2][OTf]2 (5), were synthesized by treatment of bis(benzonitrile)dichloropalladium(II) with [H2Len][OTf]2 (2) or [H2Lphen][OTf]2 (3), respectively, in the presence of a weak base. The pro-ligands 2 and 3 were synthesized by melt reactions between N-methyl-4-chloropyridinium triflate (1) and the amines ethylenediamine or phenylenediamine, respectively. The water-soluble compounds 2–5 were fully characterized, including by single-crystal X-ray crystal structure determinations for 2–4. UV-Vis and fluorescence spectroscopy were used to study the binding interactions of 2–5 with CT-DNA. The spectroscopic data suggested the presence of intercalative and groove binding modes and this was supported by molecular docking studies. The in vitro cytotoxicity studies (IC50 values) showed that the human breast cancer cell lines MCF-7 and T47D were more sensitive towards 3, 4 and 5 than cisplatin. The cytotoxicity of the new compounds decreased in the order 5 > 4 > 3 > 2. Furthermore, the annexin V-FITC staining method strongly suggested the presence of phosphatidylserine (PS) on the outer membrane of the treated cells, which is a hallmark of apoptosis.

Graphical abstract: Synthesis, characterization and anti-cancer properties of water-soluble bis(PYE) pro-ligands and derived palladium(ii) complexes

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Publication details

The article was received on 09 May 2019, accepted on 28 Jul 2019 and first published on 01 Aug 2019


Article type: Paper
DOI: 10.1039/C9DT01923E
Dalton Trans., 2019, Advance Article

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    Synthesis, characterization and anti-cancer properties of water-soluble bis(PYE) pro-ligands and derived palladium(II) complexes

    M. N. Zafar, S. Masood, G. Chaudhry, T. S. T. Muhammad, A. F. Dalebrook, M. F. Nazar, F. P. Malik, E. U. Mughal and L. J. Wright, Dalton Trans., 2019, Advance Article , DOI: 10.1039/C9DT01923E

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