Issue 32, 2024

Synergy of experimental and computational chemistry: structure and biological activity of Zn(ii) hydrazone complexes

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 [ZnL2](BF4)2, while complexes 2 [ZnL(NCO)2] and 3 [ZnL(N3)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.

Graphical abstract: Synergy of experimental and computational chemistry: structure and biological activity of Zn(ii) hydrazone complexes

Supplementary files

Article information

Article type
Paper
Submitted
08 mai 2024
Accepted
17 jul 2024
First published
23 jul 2024

Dalton Trans., 2024,53, 13436-13453

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

M. Savić, A. Pevec, N. Stevanović, I. Novaković, I. Z. Matić, N. Petrović, T. Stanojković, K. Milčić, M. Zlatar, I. Turel, B. Čobeljić, M. Milčić and M. Gruden, Dalton Trans., 2024, 53, 13436 DOI: 10.1039/D4DT01353K

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