3 years ago

New copper(II) thiohydantoin complexes: Synthesis, characterization, and assessment of their interaction with bovine serum albumin and DNA

New copper(II) thiohydantoin complexes: Synthesis, characterization, and assessment of their interaction with bovine serum albumin and DNA
New copper(II) complexes of 2-alkylthio-5-arylmethylene-4H-imidazolin-4-ones: (5Z)-2-(methylsulfanyl)-3-(prop-2-en-1-yl)-5-(pyridin-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one) (1a), (5Z,5′Z)-2,2′-(ethan-1,2-diyldisulfanyldiyl)bis(5-(2-pyridilmethylen)-3-allyl-3,5-dihydo-4Н-imidazole-4-one) (2a) and (5Z,5′Z)-3,3′-hexan-1,6-diylbis[5-(2-pyridilmethylen)-2-methylthiotetrahydro-4Н-imidazole-4-one)] (3a) were synthesized as possible anticancer drugs. Their structures were characterized by 1H NMR spectroscopy, elemental analysis, and X-ray crystallography. The composition of the complexes were found for 1a (Cu:L= 1:1), 2a (Cu:L= 2:1), and 3a (Cu:L= 2:1). The chelation constants were found by competitive complexation with ethylenediamine tetraacetate: 1a (6.7±0.6)×1015 M1, 2a =(4.9±0.4)×1019 M2, and 3a (5.7±0.5)×1019 M2. Supramolecular binding with calf thymus DNA by competitive ethidium bromide quenching was made for complex 2a as the most promising anticancer model, the Stern–Volmer constants were found to be K SV =(8.0±0.4)×106 M1, K q =(6.5±0.4)×105 M1. The binding of the complex 2a to BSA was made by the Scatchard method, the value of the constant is K b =(1.9±0.2)×106 M1.

Publisher URL: www.sciencedirect.com/science

DOI: S0162013417300570

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