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Search for new antimicrobials: spectroscopic, spectrometric, and in vitro antimicrobial activity investigation of Ga(III) and Fe(III) complexes with aroylhydrazones

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Abstract

The in vitro antimicrobial activity of Fe(III) and Ga(III) complexes with N'-(2,3-dihydroxy-phenylmethylidene)-3-pyridinecarbohydrazide (H2L1), N'-(2,4-dihydroxy-phenyl-methylidene)-3-pyridinecarbohydrazide (H2L2), N'-(2,5-dihydroxy-phenylmethylidene)-3-pyridinecarbohydrazide (H2L3), N'-(2-hydroxy-3-methoxyphenyl-methylidene)-3-pyridine-carbohydrazide (H2L4), N'-(2-hydroxy-4-methoxyphenylmethyl-idene)-3-pyridine-carbohydrazide (H2L5), and N'-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbo-hydrazide (H2L6) toward several Gram-positive strains of Staphylococcus aureus, a Gram-negative strain of Escherichia coli, and a yeast Candida albicans were investigated. Fe(III)-complexes do not possess antimicrobial activity against all tested strains at concentrations up to 10 mg mL–1. Ga(III) complexes with dihydroxy derivatives showed selective activity, while the broadest range of antibacterial and antifungal activities was observed for complex with 2-hydroxy-3-methoxy-derivative, ligand H2L5. In addition, the coordination properties of ligands H2L1–H2L3 in solution were investigated by UV–Vis spectroscopy. The stability constants (logK) for Ga(III)-H2L 1:1 complexes in MeOH/H2O 1/1 at pH 2.52 were determined, and amounted to 5.8, 5.68, and 4.7, respectively. Detailed characterization of complexes was performed by high-resolution mass spectrometry. The fragmentation pathways for dimer [Fe2(L1)2]2+, [Fe(HL)2]+, [Ga(HL2)2]+ and adduct ions are given. The comparison with analogue Ga(III) and Fe(III) complexes with compounds H2L4–H2L6 was made as well.

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Acknowledgements

This work was supported by the Croatian Science Foundation (project IP-2014-09-4841) and project CIuK co-financed by the Croatian Government and the European Union through the European Regional Development Fund-Competitiveness and Cohesion Operational Programme (Grant KK.01.1.1.02.0016.).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000, Zagreb, Croatia

    David Klarić, Marijana Pocrnić & Nives Galić

  2. Department of Microbiology, Faculty of Pharmacy and Biochemistry, University of Zagreb, Schrottova 39, 10000, Zagreb, Croatia

    Dražen Lež, Saša Polović & Ivan Kosalec

  3. Department of General and Inorganic Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, 10000, Zagreb, Croatia

    Saša Polović & Ana Budimir

  4. Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, PO Box 180, 10002, Zagreb, Croatia

    Darko Kontrec

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Klarić, D., Pocrnić, M., Lež, D. et al. Search for new antimicrobials: spectroscopic, spectrometric, and in vitro antimicrobial activity investigation of Ga(III) and Fe(III) complexes with aroylhydrazones. J Biol Inorg Chem 27, 715–729 (2022). https://doi.org/10.1007/s00775-022-01967-y

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