Copper coordination compounds with (5 Z,5 Z')-2,2'-(alkane-α,ω-diyldiselenyl)-bis-5-(2-pyridylmethylene)-3,5-dihydro-4 H-imidazol-4-ones. Comparison with sulfur analogue

Alexander V Finko; Anatolii I Sokolov; Dmitry A Guk; Victor A Tafeenko; Anna A Moiseeva; Dmitry A Skvortsov; Andrei A Stomakhin; Andrei A Beloglazkin; Roman S Borisov; Vladimir I Pergushov; Mikhail Ya Melnikov; Nikolay V Zyk; Alexander G Majouga; Elena K Beloglazkina

doi:10.1039/d1ra08995a

Copper coordination compounds with (5 Z,5 Z')-2,2'-(alkane-α,ω-diyldiselenyl)-bis-5-(2-pyridylmethylene)-3,5-dihydro-4 H-imidazol-4-ones. Comparison with sulfur analogue

RSC Adv. 2022 Mar 2;12(12):7133-7148. doi: 10.1039/d1ra08995a. eCollection 2022 Mar 1.

Authors

Alexander V Finko^{1

2}, Anatolii I Sokolov¹, Dmitry A Guk¹, Victor A Tafeenko¹, Anna A Moiseeva¹, Dmitry A Skvortsov^{1

3}, Andrei A Stomakhin⁴, Andrei A Beloglazkin^{1

2}, Roman S Borisov², Vladimir I Pergushov¹, Mikhail Ya Melnikov¹, Nikolay V Zyk¹, Alexander G Majouga^{1

5

6}, Elena K Beloglazkina¹

Affiliations

¹ Moscow State University, Department of Chemistry Leninskie Gory, Building 1/3 Moscow 119991 Russia bel@org.chem.msu.ru.
² Topchiev Institute of Petrochemical Synthesis RAS Leninskii pr., 29 Moscow 119991 Russia.
³ Higher School of Economics Myasnitskaya 13 Moscow 101000 Russia.
⁴ Engelhardt Institute of Molecular Biology RAS Vavilova 32 Moscow 119991 Russia.
⁵ National University of Science and Technology Leninskii pr., 4 Moscow 119049 Russia.
⁶ Mendeleev University of Chemical Technology Miusskaya pl. 9 Moscow 125047 Russia.

Abstract

A series of new organic ligands (5Z,5Z')-2,2'-(alkane-α,ω-diyldiselenyl)-bis-5-(2-pyridylmethylene)-3,5-dihydro-4H-imidazol-4-ones (L) consisting of two 5-(2-pyridylmethylene)-3,5-dihydro-4H-imidazol-4-one units linked with polymethylene chains of various lengths (n = 2-10, where n is the number of CH₂ units) have been synthesized. The reactions of these ligands with CuCl₂·2H₂O and CuClO₄·6H₂O gave Cu²⁺ or Cu¹⁺ containing mono- and binuclear complexes with Cu₂LCl _x (x = 2-4) or CuL(ClO₄) _y (y = 1, 2) composition. It was shown that the agents reducing Cu²⁺ to Cu¹⁺ in the course of complex formation can be both a ligand and an organic solvent in which the reaction is carried out. This fundamentally distinguishes the selenium-containing ligands L from their previously described sulfur analogs, which by themselves are not capable of reducing Cu²⁺ during complexation under the same conditions. A higher cytotoxicity and reasonable selectivity to cancer cell lines for synthesized complexes of selenium-containing ligands was shown; unlike sulfur analogs, ligands L themselves demonstrate a high cytotoxicity, comparable in some cases to the toxicity of copper-containing complexes.