NDLI: Synthesis, antiradical activity and in vitro cytotoxicity of novel organotin complexes based on 2,6-di-tert-butyl-4-mercaptophenol

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Shpakovsky, D. B. Antonenko, T. A. Milaeva, E. R. Berberova, N. T. Aslanov, L. A. Gracheva, Yu A. Albov, D. V. Mukhatova, E. M. Osipova, V. P. Hadjikakou, S. K. Banti, C. N.
Description	Author Affiliation: Shpakovsky DB ( Moscow State Lomonosov University, Department of Chemistry, Lenin Hill 1-3, Moscow, 119991, Russian Federation. milaeva@org.chem.msu.ru.)
Abstract	A series of organotin complexes with Sn–S bonds of formulae $Me_{2}Sn(SR)_{2}$ (1); $Et_{2}Sn(SR)_{2}$ (2); $(n-Bu)_{2}Sn(SR)_{2}$ (3); $Ph_{2}Sn(SR)_{2}$ (4); $R_{2}Sn(SR)_{2}$ (5); $Me_{3}SnSR$ (6); $Ph_{3}SnSR$ (7) (R = 3,5-di-tert-butyl-4-hydroxyphenyl) were synthesized and characterized by elemental analysis, $^{1}H,$ $^{13}C$ 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 $R_{2}SnCl_{2}$ (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.
ISSN	14779226
Issue Number	18
Volume Number	43
e-ISSN	13645447
Journal	Dalton Trans.
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2014-05-14
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Free Radical Scavengers Chemical Synthesis Free Radicals Antagonists & Inhibitors Organotin Compounds Phenols Sulfhydryl Compounds Toxicity HeLa Cells Humans MCF-7 Cells X-Ray Diffraction Journal Article Research Support, Non-U.S. Gov't Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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