1. Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity.
- Author
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Stevanović N, Zlatar M, Novaković I, Pevec A, Radanović D, Matić IZ, Đorđić Crnogorac M, Stanojković T, Vujčić M, Gruden M, Sladić D, Anđelković K, Turel I, and Čobeljić B
- Subjects
- Animals, Anti-Bacterial Agents chemical synthesis, Anti-Bacterial Agents chemistry, Antifungal Agents chemical synthesis, Antifungal Agents chemistry, Antineoplastic Agents chemical synthesis, Antineoplastic Agents chemistry, Antioxidants chemical synthesis, Antioxidants chemistry, Artemia drug effects, Biphenyl Compounds antagonists & inhibitors, Cell Line, Cell Proliferation drug effects, Cell Survival drug effects, Coordination Complexes chemical synthesis, Coordination Complexes chemistry, Copper chemistry, Copper pharmacology, Crystallography, X-Ray, Drug Screening Assays, Antitumor, Fungi drug effects, Gram-Negative Bacteria drug effects, Gram-Positive Bacteria drug effects, Humans, Hydrazones chemistry, Hydrazones pharmacology, Manganese chemistry, Manganese pharmacology, Microbial Sensitivity Tests, Models, Molecular, Molecular Structure, Picrates antagonists & inhibitors, Quaternary Ammonium Compounds chemistry, Quaternary Ammonium Compounds pharmacology, Zinc chemistry, Zinc pharmacology, Anti-Bacterial Agents pharmacology, Antifungal Agents pharmacology, Antineoplastic Agents pharmacology, Antioxidants pharmacology, Coordination Complexes pharmacology, Density Functional Theory
- Abstract
In this paper, Cu(II), Mn(II) and Zn(II) complexes with N , N , N -trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N
3 )(CH3 OH)]BF4 and [ZnL1(N3 )2 ], respectively, while Mn(II) forms a binuclear [Mn2 L12 (μ-1,1 -N3 )2 (N3 )2 ]·2CH3 OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.- Published
- 2021
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