Evaluation of the anionic effect on the formation of biologically active {CuII-phenx; x = 1, 2, 3} fragments - Synthetic and structural variations, antimycobacterial and antiblastoma effects
Koshenskova K.A. Baravikov D.E. Kayukova L.A. Ergalieva E.M. Nelyubina Y.V. Nikiforova M.E. Dolgushin F.M. Fedin M.V. Bekker O.B. Shender V.O. Malyants I.K. Aliev T.M. Titov K.O. Eremenko I.L. Lutsenko I.A.
15 March 2024Elsevier Ltd
Polyhedron
2024#251
Two cationic and molecular copper(II) complexes - mixed ligand [{Cu(phen)2benz}{Cu(phen)2Cl}]2+·2Cl-·benz-·H3O+·4·.5H2O (1), [Cu(benz)2phen] (2) (benz- = m-Cl-benzoate anion; phen = 1,10-phenantroline) and [Cu(phen)3]2+·2OTf-·2EtOH (3) (OTf = trifluoromethylsulfonate, triflate anion, CF3SO3-) were synthesized using various synthetic approaches and thoroughly characterized by spectroscopic methods and single crystal X-ray diffraction analysis. The structures of the complexes according to X-ray diffraction data are characterized by a diverse geometric environment of the complexing agent - the cationic form of 1 comprises two structurally nonequivalent moieties: the Cu (1) and Cu (2) complex-forming atoms coordinate, in chelate manner, two phen moieties each and the benz- (1)/Cl- (2) anions, respectively, thus forming different-ligand formula units, a trigonal–bipyramidal {Cu(1)N4Cl} and a pseudo octahedral one {Cu(2)N4O2}. The copper(II) ion in the complex 2 coordinates one phen ligand in a bidentate mode and two benz- anions to produce a distorted planar square environment {CuN2O2}. In complex 3, the copper(II) cation is surrounded by three phenanthroline fragments {Cu(phen)3}2+ and non-coordinated OTf- ions. The results of an EPR study 1 show that in the solid phase, intermolecular exchange interactions that cause exchange narrowing of the spectrum are efficient, whereas in solutions, resolved spectra of copper(II) ion with rhombic symmetry of the g-tensor are observed. An in vitro study of the biological properties of 1–3 toward nonpathogenic mycobacterial strain Mycolicibacterium smegmatis showed an increase in biological effectiveness depending on the structure of complexes (MIC, 1 (2 nmol/disk) > 3 (5 nmol/disk) > 2 (12.5 nmol/disk)). Complex 1 was also tested for antitumor activity against an ovarian adenocarcinoma SKOV3 demonstrated high efficiency: the IC50 value is almost 9 times higher than the activity of cisplatin.
10-phenantroline , Antiblastoma activity , copper(II) complexes , Crystal structure , EPR , Non-pathogenic strain
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N. S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninsky Prosp. 31, Moscow, 119991 GSP-1, Russian Federation
JSC «A.B. Bekturov Institute of Chemical Sciences», 106 Shokan Uakikhanov Str., 050010 Almaty, Kazakhstan
A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova Str. 28, Moscow, 119991, Russian Federation
International Tomography Center SB RAS, Institutskaya str. 3a, Novosibirsk, 630090, Russian Federation
N. I. Vavilov Institute of General Genetics, Russian Academy of Sciences, Gubkina, 3, Moscow, 119333, Russian Federation
Federal Research and Clinical Center of Physical-Chemical Medicine of Federal Medical Biological Agency, 1a M. Pirogovscaya, Moscow, 119435, Russian Federation
Moscow Institute of Physics and Technology, 9 Institutskiy per, Dolgoprudny, Moscow, 141701, Russian Federation
N. S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
JSC «A.B. Bekturov Institute of Chemical Sciences»
A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
International Tomography Center SB RAS
N. I. Vavilov Institute of General Genetics
Federal Research and Clinical Center of Physical-Chemical Medicine of Federal Medical Biological Agency
Moscow Institute of Physics and Technology
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