67282-43-3Relevant academic research and scientific papers
Synthesis, antiradical activity and in vitro cytotoxicity of novel organotin complexes based on 2,6-di-tert-butyl-4-mercaptophenol
Shpakovsky,Banti,Mukhatova,Gracheva,Osipova,Berberova,Albov,Antonenko,Aslanov,Milaeva,Hadjikakou
, p. 6880 - 6890 (2014)
A series of organotin complexes with Sn-S bonds of formulae Me 2Sn(SR)2 (1); Et2Sn(SR)2 (2); (n-Bu)2Sn(SR)2 (3); Ph2Sn(SR)2 (4); R2Sn(SR)2 (5); Me3SnSR (6); Ph3SnSR (7) (R = 3,5-di-tert-butyl-4-hydroxyphenyl) were synthesized and characterized by elemental analysis, 1H, 13C NMR, and IR. The crystal structures of compounds 1, 4, 5, and 7 were determined by X-ray diffraction analysis. The tetrahedral geometry around the Sn center in the monocrystals of 1, 4, 5, and 7 was confirmed by X-ray crystallography. The high radical scavenging activity of the complexes was confirmed spectrophotometrically in a DPPH-test. The binding affinity of 1-7 and the starting R2SnCl 2 (8) towards tubulin through their interaction with SH groups of proteins was studied. It was found that the hindered organotin complexes could interact with the colchicine site of tubulin, which makes them promising antimitotic drugs. Compounds 1-8 were tested for their in vitro cytotoxicity against human breast (MCF-7) and human cervix (HeLa) adenocarcinoma cells. Complexes 1-8 were also tested against normal human fetal lung fibroblast cells (MRC-5). Complexes 2-4 and 8 exhibit significantly lower cytostatic activity against the normal MRC-5 cell line compared to the tumor cell lines MCF-7 and HeLa used. A high activity against both cell lines 250 nM (MCF-7) and 160 nM (HeLa) was determined for the triphenyltin complex 7 while the introduction of hindered phenol groups decreases the cytotoxicity of the complexes against normal cells. This journal is the Partner Organisations 2014.
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
Shpakovsky,Banti,Beaulieu-Houle,Kourkoumelis,Manoli,Manos,Tasiopoulos,Hadjikakou,Milaeva,Charalabopoulos,Bakas,Butler,Hadjiliadis
, p. 14568 - 14582 (2013/01/16)
Four new organotin(iv) complexes of bis-(2,6-di-tert-butylphenol)tin(iv) dichloride [(tert-Bu-)2(HO-Ph)]2SnCl2 (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)]2Sn(PMT) 2} (2), {[(tert-Bu-)2(HO-Ph)]2Sn(MPMT) 2} (3), {[(tert-Bu-)2(HO-Ph)]2SnCl(PYT)} (4) and {[(tert-Bu-)2(HO-Ph)]2SnCl(MBZT)} (5), have been synthesized and characterized by elemental analysis, 1H-, 13C-, 119Sn-NMR, EPR, FT-IR, Raman and M?ssbauer 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-C2, cis-N2, cis-S2-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 (IC50 = 0.58 ± 0.1 μM).
