Synthesis, Theoretical Calculation, and Biological Studies of Mono- and Diphenyltin(IV) Complexes of N-Methyl-N-hydroxyethyldithiocarbamate

Abstract

In this study, chlorophenyltin(IV) [(C6H5)(Cl)Sn(L)2] and diphenyltin(IV) [(C6H5)2Sn(L)2] of N-methyl-N-hydroxyethyldithiocarbamate were prepared and characterized using various spectroscopic methods (FTIR, 1H, 13C, and 119Sn NMR) and elemental analysis. The FTIR and NMR spectral data, used to establish the structure of the compounds, showed the formation of the complexes via coordination to the two sulfur atoms from the dithiocarbamate ligand and the respective phenyltin(IV) derivatives. This coordination mode was further explored by DFT calculations, which showed that the bonding around the Sn center in [(C6H5)2Sn(L)2] was more asymmetric compared to the bonding around [(C6H5)(Cl)Sn(L)2]. However, the Sn–S bonds in [(C6H5)(Cl)Sn(L)2] were found to be more covalent than those in [(C6H5)2Sn(L)2]. Furthermore, the charge density of the frontier orbitals showed that the Sn atom in the complexes is relatively electrophilic and the Sn atom in [(C6H5)2Sn(L)2] has a lower atomic dipole moment than that of [(C6H5)(Cl)Sn(L)2]. The cytotoxicity and anti-inflammatory study revealed that [(C6H5)2Sn(L)2], with the higher number of phenyl substituents, has a higher potency than [(C6H5)(Cl)Sn(L)2]. The bio-efficacy study of these complexes as cytotoxic and anti-inflammatory agents showed that the complexes possessed moderate to high activity in comparison to the camptothecin and diclofenac in each case. Nevertheless, the diphenyltin(IV) derivative [(C6H5)2Sn(L)2] was found to possess a better activity than its counterpart due to the number of phenyl rings attached to the Sn center.

Kei-apple-mediated NiO nanoparticles and biological studies: anti-inflammatory and cytotoxicity study against HeLa and HEK 293 cell lines

“…This data thus show that the NiO nanoparticles compare favourably with diclofenac and possess the potential to inhibit inflammations. And as expected, most cytotoxic compounds are expected to exhibit some level of anti-inflammatory properties which this finding adequately corroborates [36,37]. No known reports exist for the anti-inflammatory studies of NiO nanoparticles using the Bovine serum albumin denaturation assay approach as of the time of this report.…”

Synthesis, DFT Calculations, DNA Interaction, and Antimicrobial Studies of Some Mixed Ligand Complexes of Oxalic Acid and Schiff Base Trimethoprim with Various Metal Ions

“…The chemical shift at 59.9 ppm is due to the carbon atom of the CH 2 group. The reported values of the carbon atom of the CH 2 group of the mono-and diphenyl tin(IV) complexes were 59.9-60.46 ppm [28]. The chemical shift of the carbon atoms of the aromatic ring appeared in the range of 105.6-135.8 ppm [26].…”

“…Table 2 displays the selective vibrational frequencies of infrared spectra of the synthesized complexes and ligands. The assignments for the observed infrared bands were made primarily based on the vibration modes as calculated (theoretically) and on the literature data [27][28][29][30][31][32]. The infrared spectrum of the free ligand L 1 exhibits a sharp band at 1658 cm −1 , which is assigned to ν(−C=N−).…”

Organotin (IV) Dithiocarbamate Compounds as Anticancer Agents: A Review of Syntheses and Cytotoxicity Studies

“…Previous research has shown that compounds containing phenyl groups have the highest cytotoxicity activity compared to the other series of complexes being studied, with the lowest IC 50 value of 0.01 µM [37,48,53,109]. Adeyemi et al [150] revealed that compounds containing more phenyl substituents possess a higher lipophilicity and thus exhibit a greater cytotoxic effect. This can be attributed to the reduction in the polarity surrounding the Sn metal center, which is ascribed to the decreased atomic dipole moment observed in the central Sn atom of the diphenyltin complex.…”

“…Organotin (IV) compounds with trialkyl and triaryl substituents are more toxic than those with dialkyl and aryl substitutions [35,37,44,55,56,77,79,84,149]. Di-substituted alkyl or aryl Sn(IV) groups showed a better cytotoxic effect compared to mono-substituted derivatives [48,79,107,141,150]. However, monosubstituted alkyl or aryl tin complexes may have good activity, especially butyl and phenyl derivatives [48], possibly because these complexes have exceptional cytotoxic capabilities.…”