New Palladium(II) and Platinum(II) 5,5-Diethylbarbiturate Complexes with 2-Phenylpyridine, 2,2′-Bipyridine and 2,2′-Dipyridylamine: Synthesis, Structures, DNA Binding, Molecular Docking, Cellular Uptake, Antioxidant Activity and Cytotoxicity

Abstract

Novel palladium(ii) and platinum(ii) complexes of 5,5-diethylbarbiturate (barb) with 2-phenylpyridine (Hppy), 2,2′-bipyridine (bpy) and 2,2′-dipyridylamine (dpya) have been prepared and characterized by elemental analysis, IR, UV-Vis, NMR and ESI-MS. Single-crystal diffraction measurements show that complex 1 consists of binuclear [Pd<inf>2</inf>(μ-barb-κN,O)<inf>2</inf>(ppy-κN,C)<inf>2</inf>] moieties, while complexes 3-5 are mononuclear, [M(barb-κN)<inf>2</inf>(L-κN,N′)] (L = bpy or dpya). 6 has a composition of [Pt(dpya-κN,N′)<inf>2</inf>][Ag(barb-κN)<inf>2</inf>]<inf>2</inf>·4H<inf>2</inf>O and 2 was assumed to have a structure of [Pt(barb-κN)(Hppy-κN)(ppy-κN,C)]·3H<inf>2</inf>O. The complexes were found to exhibit significant DNA binding affinity by a non-covalent binding mode, in accordance with molecular docking studies. In addition, complexes 1 and 2 displayed strong binding with supercoiled pUC19 plasmid DNA. Cellular uptake studies were performed to assess the subcellular localization of the selected complexes. A moderate radical scavenging activity of 1 and 2 was confirmed by DPPH and ABTS tests. Complexes 1, 2, and 5 showed selectivity against HT-29 (colon) cell line. © The Royal Society of Chemistry.2015.