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Antioxidative vs cytotoxic activities of organotin complexes bearing 2,6‐di‐ tert ‐butylphenol moieties
Author(s) -
Antonenko T.A.,
Shpakovsky D.B.,
Vorobyov M.A.,
Gracheva Yu.A.,
Kharitonashvili E.V.,
Dubova L.G.,
Shevtsova E.F.,
Tafeenko V.A.,
Aslanov L.A.,
Iksanova A.G.,
Shtyrlin Yu.G.,
Milaeva E.R.
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4381
Subject(s) - chemistry , schiff base , octahedron , tin , stereochemistry , medicinal chemistry , crystal structure , octahedral molecular geometry , tetrahedral molecular geometry , chelation , dpph , crystallography , base (topology) , antioxidant , inorganic chemistry , organic chemistry , mathematical analysis , mathematics
Two series of organotin(IV) complexes with Sn–S bonds on the base of 2,6‐di‐ tert ‐butyl‐4‐mercaptophenol ( L 1 SH ) of formulae Me 2 Sn(L 1 S) 2 ( 1 ); Et 2 Sn(L 1 S) 2 ( 2 ); Bu 2 Sn(L 1 S) 2 ( 3 ); Ph 2 Sn(L 1 S) 2 ( 4 ); (L 1 ) 2 Sn(L 1 S) 2 ( 5 ); Me 3 Sn(L 1 S) ( 6 ); Ph 3 Sn(L 1 S) ( 7 ) (L 1 = 3,5‐di‐ tert ‐butyl‐4‐hydroxyphenyl), together with the new ones [Me 3 SnCl(L 2 )] ( 8 ), [Me 2 SnCl 2 (L 2 ) 2 ] ( 9 ) ( L 2 = 2‐(N‐3 ′ ,5 ′ ‐di‐ tert ‐butyl‐4 ′ ‐hydroxyphenyl)‐iminomethylphenol) were used to study their antioxidant and cytotoxic activity. Novel complexes 8 , 9 of Me n SnCl 4 − n ( n = 3, 2) with Schiff base were synthesized and characterized by 1 H, 13 C NMR, IR and elemental analysis. The crystal structures of compounds 8 and 9 were determined by X‐ray diffraction analysis. The distorted tetrahedral geometry around the Sn center in the monocrystals of 8 was revealed, the Schiff base is coordinated to the tin(IV) atom by electrostatic interaction and formation of short contact Sn–O 2.805 Å. In the case of complex 9 the distorted octahedron coordination of Sn atom is formed. The antioxidant activity of compounds as radical scavengers and reducing agents was proved spectrophotometrically in tests with stable radical DPPH, reduction of Cu 2+ (CUPRAC method) and interaction with superoxide radical‐anion. Moreover, compounds have been screened for in vitro cytotoxicity on eight human cancer cell lines. A high activity against all cell lines with IC 50 values 60–160 nM was determined for the triphenyltin complex 7 , while the introduction of Schiff base decreased the cytotoxicity of the complexes. The influence on mitochondrial potential and mitochondrial permeability for the compounds 8 and 9 has been studied. It is shown that studied complexes depolarize the mitochondria but don't influence the calcium‐induced mitochondrial permeability transition.