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Cytotoxic effects, microbiological analysis and inhibitory properties on carbonic anhydrase isozyme activities of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its Cu(II), Co(II), Zn(II) and Mn(II) complexes

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Abstract

Metal complexes of thiosemicarbazones have been receiving considerable attention in biological applications such as antimicrobial and anticancer therapies. In this work, Co(II), Zn(II) and Mn(II) complexes of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone (HMAT) were synthesized for the first time and characterized by EPR, FT-IR, NMR, UV–Vis spectroscopies, TG/DSC and elemental analysis. X-ray powder diffraction analysis was carried out for Zn(II) complex. HMAT and its Cu(II), Co(II), Zn(II) and Mn(II) complexes were tested as enzyme inhibitory agents. All compounds are effective inhibitor of cytosolic carbonic anhydrase I and II isoforms (hCA I and II) enzymes. IC50 values of HMAT and its Cu(II), Co(II), Zn(II) and Mn(II) complexes were determined as 93.35, 324.46, 25.67, 1.06 and 22.36 μM for CA I isozyme and 99.02, 86.64, 57.76, 10.34 and 36.48 μM for CA II isozyme, respectively. The evaluation of potential cytotoxic effects of the compounds was performed against normal epithelial breast mammary gland CRL-4010, estrogen-positive low metastatic MCF-7 and triple negative highly metastatic MDA-MB-231 breast adenocarcinoma cell lines by MTT assay. The results showed that the tested metal complexes have high cytotoxic effects than their ligand molecule. In particular, the Cu(II) complex displayed preciously high cytotoxic properties different from the others. Given these facts, the Cu(II) complex could be debated as potential chemotherapeutic molecule against drug-resistant breast cancer cells. Minimum inhibitory concentrations of the compounds against the test organisms were also detected for the microbiological analysis.

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Acknowledgements

This study was supported by the Necmettin Erbakan University Scientific Research Foundation (BAP-161715001)

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Authors and Affiliations

  1. Department of Science Education, Education Faculty, Agri Ibrahim Cecen University, Agri, Turkey

    Asuman Ucar

  2. Department of Chemistry Education, Research Laboratory, Ahmet Kelesoglu Education Faculty, Necmettin Erbakan University, Konya, Turkey

    Mukerrem Findik

  3. Department of Nutrition and Dietetics, Health Sciences Faculty, Karabuk University, Karabuk, Turkey

    Muslum Kuzu

  4. Department of Molecular Biology and Genetics, Faculty of Science, Necmettin Erbakan University, Konya, Turkey

    Suray Pehlivanoglu

  5. Physics Department, Science Faculty, Selcuk University, Campus, Konya, Turkey

    Ulku Sayin

  6. Department of Microbiology and Immunology, Faculty of Veterinary Medicine, Selcuk University, Konya, Turkey

    Zafer Sayin

  7. Department of Chemistry Education, Ahmet Kelesoglu Education Faculty, Necmettin Erbakan University, Konya, Turkey

    Emine Guler Akgemci

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  1. Asuman Ucar
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Ucar, A., Findik, M., Kuzu, M. et al. Cytotoxic effects, microbiological analysis and inhibitory properties on carbonic anhydrase isozyme activities of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its Cu(II), Co(II), Zn(II) and Mn(II) complexes. Res Chem Intermed 47, 533–550 (2021). https://doi.org/10.1007/s11164-020-04284-8

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