One pot synthesis of structurally different mono and dimeric Ni(ii) thiosemicarbazone complexes and N-arylation on a coordinated ligand: a comparative biological study

Abstract

One pot synthesis of three structurally different Ni(II) thiosemicarbazone complexes 1, 2 and 3 were obtained from the reaction between [NiCl(2)(PPh(3))(2)], 1,2-bis(diphenylphosphino)ethane, and [H(2)-(Sal-tsc)]. The obtained products were characterized by various spectral and analytical techniques. From the X-ray crystallographic analysis, an unexpected N-arylation on the coordinated salicylaldehydethiosemicarbazone was found in complex 2. The comparative biological evolutions such as DNA/protein binding, antioxidant, cytotoxicity (MTT, LDH, and NO) and cellular uptake studies have been examined for [Ni(Sal-tsc)(PPh(3))] (1) and [(Ni(Sal-tsc))(2)(μ-dppe)] (3). When comparing the cytotoxicity of the complexes, 1 exhibited higher activity than 2 and 3 and by comparing with standard cis-platin, both of them were found to exhibit better activity under identical conditions.

Spectroscopic, electrochemical and X-ray diffraction studies on nickel(II)-complexes of acetophenone thiosemicarbazones substituted six-carbon groups

“…In all complexes, the Ni-P, Ni-S, Ni-O and Ni-N bond lengths are comparable with those of the reported complexes [16,17,[23][24][25][26][27]. As can be seen from Table 2, the cis and trans angles around the nickel atom in the complexes depart from the ideal values of 90°and 180°, respectively, indicating noticeable angular distortion from a square planar geometry due to the steric bulk of the ligands and the formation of the five-and six-membered chelate rings.…”

“…In electrochemical studies of the complexes having a redox active metal ion, metal-based oxidation and reduction processes are observed in addition to redox processes of ligand [23][24][25][26][27][28]. The ONS chelating ligands and their metal complexes generally give electron transfer reactions at negative potentials (higher than À1.50 V) and at positive potentials (at around 1.50 V) [29][30][31][32][33][34][35][36][37][38].…”

Effects of Terminal Dimethylation and Metal Coordination of Proline-2-formylpyridine Thiosemicarbazone Hybrids on Lipophilicity, Antiproliferative Activity, and hR2 RNR Inhibition

“…38 Some salicylaldehyde TSC based nickel(II) complexes exhibited higher cytotoxicity than cisplatin (cis-diamminedichloridoplatinum(II), CDDP) in human cancer cell lines, while they were relatively nontoxic in normal kidney cells, demonstrating the potential of nickel(II)-TSC complexes for clinical development. 39 Zinc(II) shows low systemic cytotoxicity and forms easily TSC complexes. Moreover, the cytotoxicity of the zinc(II) complex is often enhanced compared to the free ligand.…”

DNA(CT), protein(BSA) binding studies, anti-oxidant and cytotoxicity studies of new binuclear Ni(II) complexes containing 4(N)-substituted thiosemicarbazones

“…Moreover, the characteristic absorption bands corresponding to the presence of diphenylphosphinomethane were also present in the expected region [44,45]. The electronic spectra of nickel(II) complexes displayed two to four bands in the region around 263-418 nm (Fig.…”

“…S1). The band appeared at 263-268 nm has been assigned to intra ligand transition and the bands at 313-371 nm to LMCT ( 3 A 2g → 3 T 2g ) and the shoulder at 418-429 nm to forbidden ( 3 A 2g → 3 T 1g ) transition [42,45]. The 1 H-NMR spectra of the ligands (H 2 L) 1-4 and the corresponding complexes (1-4) recorded in DMSO and CDCl 3 at the field strength of 400…”