Copper(II) Furancarboxylate Complexes with 5-Nitro-1,10-Phenanthroline as Promising Biological Agents

• Published in: Russian journal of coordination chemistry 2023-10, Vol.49 (10), p.660-671
• Main Authors: Koshenskova, K. A., Baravikov, D. E., Nelyubina, Yu. V., Primakov, P. V., Shender, V. O., Maljants, I. K., Bekker, O. B., Aliev, T. M., Borodin, E. A., Kotel’nikov, D. D., Leusova, N. Yu, Mantrov, S. N., Kiskin, M. A., Eremenko, I. L., Lutsenko, I. A.
• Format: Article
• Language: English
• Subjects: Amino acids; Aromatic compounds; Binding; Biological activity; Chemistry; Chemistry and Materials Science; Coordination compounds; Coordination numbers; Copper; Copper acetate; Glutamic acid; Histidine; Hydrogen bonds; Inorganic Chemistry; Ions; Nitrogen atoms; Oxygen atoms; Physical Chemistry; Polypeptides; Proteins; X-ray diffraction
• ISSN: 1070-3284; 1608-3318
• DOI: 10.1134/S1070328423600730

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 [Cu 2 (L) 4 (Nphen) 2 ]·X (L = Fur ( I ), Nfur ( II ); X = H 2 O ( 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 {CuN 2 O 3 } 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 Cu 2+ cation and oxygen of the Nphen 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 Cu 2+ 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.