Synthesis, structural characterization and in vitro inhibitory studies against human breast cancer of the bis-(2,6-di-tert-butylphenol)tin(iv) dichloride and its complexes

Abstract

Four new organotin(IV) complexes of bis-(2,6-di-tert-butylphenol)tin(IV) dichloride [(tert-Bu-)(2)(HO-Ph)](2)SnCl(2) (1) with the heterocyclic thioamides 2-mercapto-pyrimidine (PMTH), 2-mercapto-4-methyl-pyrimidine (MPMTH), 2-mercapto-pyridine (PYTH) and 2-mercapto-benzothiazole (MBZTH), of formulae {[(tert-Bu-)(2)(HO-Ph)](2)Sn(PMT)(2)} (2), {[(tert-Bu-)(2)(HO-Ph)](2)Sn(MPMT)(2)} (3), {[(tert-Bu-)(2)(HO-Ph)](2)SnCl(PYT)} (4) and {[(tert-Bu-)(2)(HO-Ph)](2)SnCl(MBZT)} (5), have been synthesized and characterized by elemental analysis, (1)H-, (13)C-, (119)Sn-NMR, EPR, FT-IR, Raman and Mössbauer spectroscopic techniques. The crystal and molecular structures of compounds 1–5 have been determined by X-ray diffraction. The geometries around the metal center adopted in complexes 1–5 varied between tetrahedral in 1, trigonal bipyramidal in 3, 4, 5 and distorted octahedral in 2. Two carbon atoms from aryl groups and two chlorine atoms form a distorted tetrahedron in the case of 1. Two carbon, two sulfur and two nitrogen atoms from thione ligands form a distorted octahedral geometry around tin(IV) with trans-C(2), cis-N(2), cis-S(2)-configurations in 2. However, in the case of 4 and 5 complexes two carbon, one sulfur, one nitrogen and one chloride atom form a distorted trigonal bipyramidal arrangement. Finally, in the case of 3 the trigonal bipyramidal geometry is achieved by two carbon, two sulfur and one nitrogen atom in a unique coordination mode of thioamides toward the tin(IV) cation. Compounds 1–5 were tested for their in vitro cytotoxicity against the human breast adenocarcinoma (MCF-7) cell line. Compound 3 exhibits strong cytotoxic activity against MCF-7 cells (IC(50) = 0.58 ± 0.1 μM).

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

“…It is also observed that the complexes 1a and 1b showed moderate to high activities against Gram negative and Gram‐positive bacteria, respectively. An investigation of literature reveals that tin exhibits outstanding antibacterial property that would lead to biomedical applications . Besides, nano‐size compound 1b showed more antimicrobial activity than its bulk form 1a .…”

Synthesis, structural characterization, and anticancer activity of a monobenzyltin compound against MCF-7 breast cancer cells

“… 4 – 8 In general, the biochemical activity of organotin compounds is influenced by the structure of the resulting compounds and the nature and number of organic groups bound to the tin center. 9 – 15 In addition, the choice of coordinated ligand is also imperative in the biological effects of organotin compounds, such as solubility and bioavailability. A judicious choice of coordinating ligand not only can minimize the drawbacks, but also can enhance or modulate the activity of organotin compounds, 16 as the ligand plays the key role in transporting and directing the molecule to the target site.…”

Unprecedented isolation of a dinuclear tin (II) complex stabilized by pyridine‐2,6‐dimethanol: structure, DFT and in vitro screening of cytotoxic properties

“…Tin complexes have witnessed vast range of applications in various biological and industrial fields . Such compounds possess fascinating medicinal importance like antiparasite agents, in horticulture as bactericidal, acraricidal and fungicidal medium, anti‐HIV and antitumor agents . The biological activity and specially the anticancer activity of tin compounds is governed by geometrical features, extent of hydrolysis of ligands and coordination number around central tin metal ion .…”