Tishchenko Ksenia, Beloglazkina Elena, Proskurnin Mikhail, Malinnikov Vladislav, Guk Dmitriy, Muratova Marina, Krasnovskaya Olga, Udina Anna, Skvortsov Dmitry, Shafikov Radik R, Ivanenkov Yan, Aladinskiy Vladimir, Sorokin Ivan, Gromov Oleg, Majouga Alexander, Zyk Nikolay
Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.
Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.
J Inorg Biochem. 2017 Oct;175:190-197. doi: 10.1016/j.jinorgbio.2017.07.015. Epub 2017 Jul 21.
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 H 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)×10M, 2a=(4.9±0.4)×10M, and 3a (5.7±0.5)×10M. 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=(8.0±0.4)×10M, K=(6.5±0.4)×10M. The binding of the complex 2a to BSA was made by the Scatchard method, the value of the constant is K=(1.9±0.2)×10M.
