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Transition metal complexes of a multidentate Schiff base ligand containing pyridine: synthesis, characterization, enzyme inhibitions, antioxidant properties, and molecular docking studies

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Abstract

A series of Fe(II), Ni(II), and Pd(II) complexes were prepared with a novel Schiff base ligand containing pyridine moiety. The prepared compounds were characterized using FT-IR, 1H and 13 C NMR, UV–Vis, powder XRD, thermogravimetric analysis, mass spectra, magnetic susceptibility, and elemental analysis. The coordination geometry of Fe(II) and Ni(II) complexes were octahedral, where Fe(II) and Ni(II) metal ions were coordinated by an oxygen atom of the carbonyl group, a nitrogen atom of the azomethine moiety, and a phenolic oxygen atom. The Pd(II) complex had square planar geometry. All of the synthesized compounds were tested for their biochemical properties, including enzyme inhibition and antioxidant activities. According to the in vitro DPPH and FRAP antioxidant methods, the Schiff base ligand and its Fe(II)/Pd(II) complexes showed close antioxidant activities against the standards (BHA, BHT, ascorbic acid, and α-tocopherol). Enzyme inhibitions of the metal complexes were investigated against glutathione S-transferase (GST), acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) enzymes. The best inhibition value (Ki) was observed for the Ni(II) complex against GST (2.63 ± 0.04 µM). Also, the Pd(II) complex showed the best inhibition value (10.17 ± 1.88 µM) against AChE. Molecular docking specified significant interactions at the active pockets of respective target enzymes. The Ni(II) complex exhibited good binding affinity against both BChE (− 9.0 kcal/mol and 9.36 ± 2.03 µM) and GST (− 7.0 kcal/mol and 2.63 ± 0.04 µM) enzymes.

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Authors and Affiliations

  1. Department of Nursing, Faculty of Health, Muş Alparslan University, 49250, Muş, Turkey

    Ercan Bursal

  2. Health Services Vocational School, Igdır University, 76000, Igdır, Turkey

    Fikret Turkan

  3. Department of Food Processing, Vocational School of Technical Sciences, Muş Alparslan University, 49250, Muş, Turkey

    Kenan Buldurun

  4. Department of Chemistry, Faculty of Arts and Sciences, Muş Alparslan University, 49250, Muş, Turkey

    Nevin Turan

  5. Department of Biochemistry, Faculty of Arts and Sciences, Igdır University, 76100, Igdır, Turkey

    Abdulmelik Aras

  6. Department of Chemistry, Faculty of Arts and Sciences, Hitit University, Çorum, Turkey

    Naki Çolak

  7. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, M.S. Ramaiah University of Applied Sciences, Bangalore, India

    Manikanta Murahari

  8. Department of Pharmaceutical Chemistry, SPP School of Pharmacy & Technology Management, SVKM’s NMIMS, Mumbai, 400 056, India

    Mayur C. Yergeri

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  1. Ercan Bursal
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Bursal, E., Turkan, F., Buldurun, K. et al. Transition metal complexes of a multidentate Schiff base ligand containing pyridine: synthesis, characterization, enzyme inhibitions, antioxidant properties, and molecular docking studies. Biometals 34, 393–406 (2021). https://doi.org/10.1007/s10534-021-00287-z

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