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Structural Features of 1,3,4-Thiadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin

1
Department of Analytical Chemistry (C1), Faculty of Chemical Engineering and Technology, Cracow University of Technology, 31155 Kraków, Poland
2
Department of Biophysics, University of Life Sciences in Lublin, 20-950 Lublin, Poland
3
Department of General and Coordination Chemistry and Crystallography, Institute of Chemical Sciences, Maria Curie-Sklodowska University in Lublin, 20-031 Lublin, Poland
4
School of Chemical and Pharmaceutical Sciences, Technological University Dublin, Kevin St., D2 Dublin, Ireland
5
Department of Biotechnology and Bioinformatics, Faculty of Chemistry, Rzeszow University of Technology, 35-959 Rzeszów, Poland
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(16), 5735; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21165735
Received: 9 July 2020 / Revised: 3 August 2020 / Accepted: 7 August 2020 / Published: 10 August 2020
(This article belongs to the Section Physical Chemistry and Chemical Physics)
Classical synthetic protocols were applied for the isolation of three novel 1,3,4-thiadiazole derivatives which were then complexed with the biologically important Cu(II) and Zn(II) ions. All free ligands and their corresponding complexes were characterized using a number of spectroscopic techniques including Ultraviolet-visible (UV–vis), Fluorescence, Infrared (FT-IR), tandem liquid chromatography-mass (LC-MS), X-ray diffraction (XRD), and Nuclear Magnetic Resonance (NMR) spectroscopy (1H, 13C, HSQC, HMBC). The results obtained are consistent with the formation of dihydrate complexes, in which the chelation of the metal ion occurs via one of the thiadiazole nitrogen atoms and the deprotonated hydroxyl group of the neighboring resorcynyl moiety. The Zn(II) complexes utilize a 1:1 ligand–metal ratio, while in the Cu(II) complexes the ligand–metal ratio is 2:1. Although the antibacterial testing identified moderate activity of the compounds against the tested bacterial strains and additionally modest antioxidant activity, a strong synergistic antibacterial effect against Staphylococcus aureus, using concomitant treatment of thiadiazole derivatives with the commercial antibiotic kanamycin, was observed. The most active thiadiazole derivative demonstrated a minimal inhibitory concentration (MIC) of 500 μg/mL while it was 125 μg/mL in the presence of kanamycin. Moreover, in the presence of few thiadiazole derivatives the MIC value of kanamycin decreased from 0.39 μg/mL to 0.5 μg/mL. The antioxidant activity (IC50) of the most active thiadiazole derivative was determined as 0.13 mM which was nearly three-fold lower compared to that of TROLOX (0.5 mM). View Full-Text
Keywords: 1,3,4-thiadiazole; thiadiazole ligands; thiadiazole complex; antibacterial; antioxidant; neurodegeneration; synergistic effect; kanamycin 1,3,4-thiadiazole; thiadiazole ligands; thiadiazole complex; antibacterial; antioxidant; neurodegeneration; synergistic effect; kanamycin
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MDPI and ACS Style

Karcz, D.; Matwijczuk, A.; Kamiński, D.; Creaven, B.; Ciszkowicz, E.; Lecka-Szlachta, K.; Starzak, K. Structural Features of 1,3,4-Thiadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin. Int. J. Mol. Sci. 2020, 21, 5735. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21165735

AMA Style

Karcz D, Matwijczuk A, Kamiński D, Creaven B, Ciszkowicz E, Lecka-Szlachta K, Starzak K. Structural Features of 1,3,4-Thiadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin. International Journal of Molecular Sciences. 2020; 21(16):5735. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21165735

Chicago/Turabian Style

Karcz, Dariusz, Arkadiusz Matwijczuk, Daniel Kamiński, Bernadette Creaven, Ewa Ciszkowicz, Katarzyna Lecka-Szlachta, and Karolina Starzak. 2020. "Structural Features of 1,3,4-Thiadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin" International Journal of Molecular Sciences 21, no. 16: 5735. https://0-doi-org.brum.beds.ac.uk/10.3390/ijms21165735

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