Tin(IV) Schiff base complexes derived from pyridoxal: Synthesis, spectroscopic properties and cytotoxicity

Abstract

The synthesis of monomeric pentacoordinated diorganotin(IV) complexes derived from pyridoxal hydrochloride and 4-or 5-R-substituted ortho-aminophenols is described. The complexes were characterized using UV-visible, infrared, mass, 1 H NMR, 13 C NMR and 119 Sn NMR spectral techniques. The molecular structure of three complexes was established using X-ray diffraction: 3b and 3d show a distorted trigonal bipyramidal geometry, in which the basal plane is defined by the butyl groups and the iminic nitrogen atom, whereas the oxygen atoms from the aromatic ring occupy axial positions; in contrast, complex 3e exhibits a square pyramidal geometry. The cytotoxic activity of all complexes against human cell lines U-251 (glioblastoma), K-562 (chronic myelogenous leukemia), HCT-15 (human colorectal cancer), MCF-7 (human breast cancer) and SKLU-1 (non-small-cell lung cancer) was evaluated, and the inhibitory percentage values indicated higher activity than the reference standard, cisplatin. Acute toxicity studies were performed in vivo for the prepared complexes to determine the lethal medium dose (LD 50 ) after intraperitoneal administration to mice.

Characterization and thermal studies of nano‐synthesized Mn(II), Co(II), Ni(II) and Cu(II) complexes with adipohydrazone ligand as new promising antimicrobial and antitumor agents

“…Schiff bases are a serious category of compounds reported to own nitrogen carbon double bond which is answerable for various biological activities, including anticancer, antipyretic, antitumor, anti‐inflammatory activities . They possess chelatogenic properties, so form interesting ligands in coordination chemistry . Transition metal complexes of hydrazones have many applications such as antibacterial, antifungal, antiviral, and anticancer agents and they are considered as important model for several biological systems .…”

Tin(IV) compounds of tridentate thiosemicarbazone Schiff bases: Synthesis, characterization, in-silico analysis and in vitro cytotoxicity

“…In the spectra of 1 and 2, the v(OH) was not observed, which suggested that the v(OH) band overlapped with the v(N-H) band due to hydrogen bonding (NH...OH) between the two groups [57,58]. The v (OH) was observed in the calculated spectra because they were generated from the gas phase structures, while experimental spectra were analyzed in the solid state where the compounds are in a more concentrated form, resulting in either intermolecular and/or intramolecular hydrogen bonding similar to that observed in structurally-related Schiff bases [23,59,60].…”

Mechanisms of the Cytotoxic Action of Organotin Compounds

“…Кроме того, комплексы, замещенные в положении 8, были более токсичными, чем в положении 9. Более низкая токсичность наблюдалась также для комплексов, которые содержали нитрогруппу и обладали более высокой цитотоксичностью по отношению к клеточным линиям U-251, HCT-15, MCF-7 и SKLU-1 [14].…”