Copper(II) Furancarboxylate Complexes with 5-Nitro-1,10-Phenanthroline as Promising Biological Agents
К. А. Кошенскова, D. E. Baravikov, Yulia V. Nelyubina, Petr V. Primakov, Victoria О. Shender, I. K. Maljants, Olga B. Bekker, Teimur M. Aliev, E.A. Borodin, D. D. Kotel’nikov, N. Yu. Leusova, S. N. Mantrov, Mikhail A. Kiskin, И.Л. Еременко, Irina А. Lutsenko
Abstract
The reaction of copper(II) acetate with 2-furancarboxylic (HFur)/5-nitro-2-furancarboxylic (HNfur) acids and 5-nitro-1,10-phenanthroline (Nphen) in methanol resulted in the formation of the binuclear coordination compounds [Cu2(L)4(Nphen)2]·X (L = Fur (I), Nfur (II); X = H2O (I)), which were structurally studied by direct X-ray diffraction (CCDC no. 2244205 (I) and 2244206 (II)). According to X-ray diffraction data, the coordination environment of the central metal ion in I and II is composed of two nitrogen atoms of Nphen and three oxygen atoms of the acid anions, which thus form the {CuN2O3} tetragonal pyramid in which the copper coordination number is five. Intermolecular hydrogen bonds and stacking interactions between the Nphen aromatic rings provide supramolecular stabilization of I and II. A characteristic feature of supramolecular organization of II is the presence of a coordination bond between the Cu2+ cation and oxygen of the Nphen $${\text{NO}}_{2}^{ - }$$ group of parallel chains. A biological activity assay for complexes I and II concerning the cytotoxic properties against a human ovarian adenocarcinoma cell line (SKOV3) and the mycobacterial strain Mycolicibacterium smegmatis showed an efficient suppression of cell viability. The results of mathematical modeling of the probability of Cu2+ binding to amino acid residues of M. smegmatis proteins suggested the affinity of the Cu(II) ion to a number of amino acids in polypeptide sites. It was shown that metal ion binding in mycobacterial proteins is more characteristic of histidine- and glutamic acid-containing moieties.