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Bis‐aroylhydrazone based on 2,2′‐bis substituted diphenylamine for synthesis of new binuclear organotin (IV) complexes: Spectroscopic characterization, crystal structures, in vitro DNA‐binding, plasmid DNA cleavage, PCR and cytotoxicity against MCF7 cell line
Author(s) -
Yousefi Maryam,
Sedaghat Tahereh,
Simpson Jim,
Shafiei Mohammad
Publication year - 2019
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.5137
Subject(s) - chemistry , diphenylamine , stereochemistry , tautomer , hydrazone , dna , molecule , ligand (biochemistry) , proton nmr , nuclear magnetic resonance spectroscopy , crystallography , medicinal chemistry , organic chemistry , biochemistry , receptor
New dinuclear organotin (IV) complexes, Me 4 Sn 2 L, Ph 4 Sn 2 L and Bu 4 Sn 2 L, have been synthesized from reaction of R 2 SnCl 2 (R = Me, Ph and Bu) with a 2,2′‐bis‐substituted diphenylamine arοylidene hydrazone, H 4 L. The synthesized compounds were investigated by elemental analysis and infrared, 1 H‐NMR and 119 Sn‐NMR spectroscopy. The structures of H 4 L, Me 4 Sn 2 L and Bu 4 Sn 2 L were also confirmed by X‐ray crystallography. H 4 L molecules adopt ( E )‐configuration and keto‐tautomeric form in the solid state. In all complexes, the bis‐hydrazone acts as a tetra‐anionic ligand with two contiguous ONO tridentate domains that coordinate the two R 2 Sn moieties in the enolate form. The coordination environments of both tin centers are five‐coordinate. DNA‐binding studies were performed by UV–Vis spectroscopy, and the results indicate that the synthesized compounds significantly interact with calf thymus‐DNA in the intercalative mode. The results of polymerase chain reaction assay show that all the compounds affect on amplification of DNA, and complexes are more effective than ligands. The in vitro cytotoxicity against the human breast cancer line (MCF7) was determined using the MTT assay, and H 4 L and the dibutytin complex showed higher activity.

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