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1. Synergy of experimental and computational chemistry: structure and biological activity of Zn(II) hydrazone complexes.

Author

Savić M, Pevec A, Stevanović N, Novaković I, Matić IZ, Petrović N, Stanojković T, Milčić K, Zlatar M, Turel I, Čobeljić B, Milčić M, and Gruden M

Subjects
Humans, Cell Line, Tumor, Molecular Structure, Molecular Docking Simulation, Drug Screening Assays, Antitumor, Gram-Negative Bacteria drug effects, Gram-Positive Bacteria drug effects, Models, Molecular, Fungi drug effects, Structure-Activity Relationship, Hydrazones chemistry, Hydrazones pharmacology, Hydrazones chemical synthesis, Zinc chemistry, Zinc pharmacology, Coordination Complexes pharmacology, Coordination Complexes chemistry, Coordination Complexes chemical synthesis, Density Functional Theory, Anti-Bacterial Agents pharmacology, Anti-Bacterial Agents chemistry, Anti-Bacterial Agents chemical synthesis, Antifungal Agents pharmacology, Antifungal Agents chemistry, Antifungal Agents chemical synthesis, Antineoplastic Agents pharmacology, Antineoplastic Agents chemistry, Antineoplastic Agents chemical synthesis, Microbial Sensitivity Tests
Abstract

In this paper, three different Zn(II) complexes with ( E )-2-(2-(1-(6-bromopyridin-2-yl)ethylidene)hydrazinyl)- N , N , N -trimethyl-2-oxoethan-1-aminium chloride (HLCl) have been synthesized and characterized by single crystal X-ray diffraction, elemental analysis, IR and NMR spectroscopy. All complexes are mononuclear, with the ligand (L) coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Complex 1 forms an octahedral geometry with the composition [ZnL 2 ](BF 4 ) 2 , while complexes 2 [ZnL(NCO) 2 ] and 3 [ZnL(N 3 ) 2 ] form penta-coordinated geometry. Density functional theory (DFT) calculations were performed to enhance our understanding of the structures of the synthesized complexes and the cytotoxic activity of the complexes was tested against five human cancer cell lines (HeLa, A549, MDA-MB-231, K562, LS 174T) and normal human fibroblasts MRC-5. Additionally, antibacterial and antifungal activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two fungal strains, and a yeast strain. It is noteworthy that all three complexes show selective antifungal activity comparable to that of amphotericin B. Molecular docking analysis predicted that geranylgeranyl pyrophosphate synthase, an enzyme essential for sterol biosynthesis, is the most likely target for inhibition by the tested complexes.

Published
2024
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2. Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity.

Author

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 )(CH 3 OH)]BF 4 and [ZnL1(N 3 ) 2 ], respectively, while Mn(II) forms a binuclear [Mn 2 L1 2 (μ- 1,1 -N 3 ) 2 (N 3 ) 2 ]·2CH 3 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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