Synthesis, structural characterization, density functional theory calculations and biological evaluation of a new organotin(IV) complex containing N‐isonicotinyl‐N',N″‐diaryl phosphorictriamide as N‐donor ligand

Abstract

A new diorganotin(IV) complex with the formula SnCl2(CH3)2L2 (C1a), L = 4‐NC5H4CONHPO(NCH3CH2C6H5)2, was synthesized and characterized using 1H NMR, 13C NMR, 31P NMR, 119Sn NMR and infrared spectroscopies. The molecular structure of C1a was determined using X‐ray crystallography, revealing that C1a contains hexa‐coordinated Sn(IV) centres with trans‐configuration of donor atoms around them. Each Sn(IV) atom is positioned in the centre of inversion of an octahedron. C1a forms one‐dimensional chains via two equal intermolecular PO…HN hydrogen bonds. These hydrogen bonds produce centrosymmetric rings as a supramolecular hydrogen‐bonded pattern. In order to compare the relative stability of C1a (with N‐ligated configuration) and its possible O‐ligated isomer, C1b, density functional theory calculations were performed, the results showing a preference of C1a over C1b from an energy point of view. Also, natural bond orbital analysis was carried out to obtain detailed information on the electronic features of the optimized structures. The theoretical results show that intermolecular hydrogen bonding in the crystal structure has a significant role in the stabilization of C1a, and Sn(IV) interacts more strongly with the Npy atom than the PO functional group. Furthermore, the free ligand and its complex were tested against three human cancer cell lines, i.e. human cervical carcinoma (HeLa), human prostate cancer (PC‐3) and human breast adenocarcinoma cancer (MCF‐7). C1a displays moderate to good cytotoxicity towards all three cancer cell lines. Moreover, antibacterial tests were carried out using the disc‐diffusion method, in which C1a shows high activity against selected Gram‐negative and Gram‐positive bacteria. Copyright © 2015 John Wiley & Sons, Ltd.

Synthesis, characterization and biological evaluation of a nanorod five‐coordinated Sn(IV) complex. Theoretical studies of (CH3)2Sn(O2PPh2)2

“…For example, some tin(IV) complexes containing semicarbazonates have IC 50 values in the nM range towards A253, A549 and DLD‐1 cell lines, as well as dinuclear organotin(IV) complexes having IC 50 values of 0.1–100 μM for a number of human tumour cell lines . Notably, the IC 50 values of a tin–phosphorictriamide complex against some tumour cell lines (Hela, PC‐3, MCF‐7 in the range 99.8–1150 μM) have been reported in the literature, which are higher than the IC 50 values determined in this study of Sn(IV) complexes for the tested cell lines. It can also be seen from Table that compared with ligand L and bulk complex C 1 , the cytotoxicity of nanoscale complex C 2 against A2780 shows a 1.5‐ and 1.3‐fold increase, which is similar to the results of our previously reported nano‐diorganotin complex .…”

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP2O7 nano‐structure

“…The assay showed that survival values were 90% and 93% for 1a and 1b respectively. According to the literature data, our complexes ( 1a and 1b ) can be considered as potent cytotoxic agents against both cell lines.…”

“…Gholivand et al have reported high cytotoxicity of diorganotin (IV) complexes with N ‐nicotinyl phosphoramide ligands against MCF‐7, MDA‐MB‐468 and T47‐D cells (7.58–13.73 μM) . The antitumor activity of tin(IV) complexes of N ‐isonicotinyl phosphoramides have also exhibited moderate effect on PC‐3 and HeLa, but they are significantly active against MCF‐7 (IC 50 99.8 μM) . We found that tin complex 1a and 1b with Sn‐O = P[−N] segment show higher cytotoxicity in comparison to those of the free ligand, suggesting that the activity of complexes is reasonably dependent on the presence of metal atom.…”

“…Nowadays, phosphoramide complexes have received considerable attention due to their diverse chemical structures and wide applications in biomedical, magnetic, catalysis, and theoretical studies . The coordination chemistry of organotin compounds has become of great interest because of their important applications as anticancer agents, agrochemical fungicides and biocides, as well as catalysts .…”

Theoretical investigation into the coordination of R‐/S‐asymmetric uranyl–salophens containing six‐membered ring lactam with cis−/trans‐cyclohexylamines

“…[29][30][31] Valkonen and others explored the coordination properties of uranyl cations by studying the detailed single-crystal X-ray structure and using crystallography and calculation methods, including molecular dynamics, gas phase Hartree-Fock and DFT calculations. [32][33][34] Bodo et al studied the recognition of anions of uranyl-salophen derivatives by using infrared multiphoton dissociation spectroscopy and ab initio calculations. [35] For supramolecular polymers, the resonance light scattering method was developed based on uranylsalophens containing phosphate groups [36][37][38] and successfully applied to the determination of uranium(VI) in environmental water samples.…”