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

Savić, Milica (author), Pevec, Andrej (author), Stevanović, Nevena Lj. (author), Novaković, Irena (author), Matić, Ivana Z. (author), Petrović, Nina (author), Stanojković, Tatjana (author), Milčić, Karla (author), Zlatar, Matija (author), Turel, Iztok (author), Čobeljić, Božidar R. (author), Milčić, Miloš (author), Gruden-Pavlović, Maja (author)

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.

• Language: English
• Keywords: zinc, zinc(II) complexes, hydrazone
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2024
• Number of pages: Str. 13436-13453
• Numbering: Vol. 53, iss. 32
• PID: 20.500.12556/RUL-161554
• UDC: 546.47
• ISSN on article: 1477-9234
• DOI: 10.1039/D4DT01353K
• COBISS.SI-ID: 205685763
• Publication date in RUL: 12.09.2024

Record is a part of a journal

• Title: Dalton transactions
• Shortened title: Dalton trans
• Publisher: Royal Society of Chemistry
• ISSN: 1477-9234
• COBISS.SI-ID: 519833113

Licences

• License: CC BY-NC-ND 4.0, Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
• Link: http://creativecommons.org/licenses/by-nc-nd/4.0/
• Description: The most restrictive Creative Commons license. This only allows people to download and share the work for no commercial gain and for no other purposes.

Secondary language

• Language: Slovenian
• Keywords: cink, cinkovi(II) kompleksi, hidrazon