Several novel copper (II) complexes of reduced Schiff bases containing fluoride substituents were prepared and structurally characterized by single-crystal X-ray diffraction. The complexes exhibited diverse structures, with the central atom in distorted tetrahedral geometry. The biological effects of the products were evaluated, specifically their cytotoxicity, antimicrobial, and antiurease activities, as well as affinity for albumin (BSA) and DNA (ct-DNA). The complexes showed marked cytotoxic activities in the HepG2 hepatocellular carcinoma cell line, considerably higher than the standard cisplatin. The cytotoxicity depended significantly on the substitution pattern. The best activity was observed in the complex with a trifluoromethyl group in position 4 of the benzene ring-the dichloro[(±)-trans-N,N'-bis-(4-trifluoromethylbenzyl)-cyclohexane-1,2-diamine]copper (II) complex, whose activity (IC50 28.7 μM) was higher than that of the free ligand and markedly better than the activity of the standard cisplatin (IC50 336.8 μM). The same complex also showed the highest antimicrobial effect in vitro. The affinity of the complexes towards bovine serum albumin (BSA) and calf thymus DNA (ct-DNA) was established as well, indicating only marginal differences between the complexes. In addition, all complexes were shown to be excellent inhibitors of the enzyme urease, with the IC50 values in the lower micromolar region.

Department Chemical Theory of Drugs Faculty of Pharmacy Comenius University in Bratislava Odbojárov 10 832 32 Bratislava Slovakia

Department of Cell and Molecular Biology of Drugs Faculty of Pharmacy Comenius University in Bratislava Odbojárov 10 832 32 Bratislava Slovakia

Department of Materials Chemistry Institute of Inorganic Chemistry of the CAS Husinec Řež č p 1001 250 68 Řež Czech Republic

NMR Laboratory Faculty of Pharmacy Comenius University in Bratislava Odbojárov 10 832 32 Bratislava Slovakia

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