Synthesis, characterization, DFT calculations and biological activity of derivatives of 3-acetylpyridine and the zinc(II) complex with the condensation product of 3-acetylpyridine and semicarbazide

•Tetrahedral complex of Zn(II) with 3-acetylpyridine semicarbazone.•DFT calculations on stabilities of various structures.•Moderate antibacterial, antifungal and cytotoxic activities.•Induction of ROS in tumor cell lines by a complex with a non-redox active metal.•Effect on cell cycle progresion in tumor cell lines and induction of autophagy.

A Schiff base of 3-acetylpyridine with semicarbazide as well as the corresponding tetrahedral Zn(II) complex were synthesized and characterized by X-ray crystal structure analysis and spectroscopic methods. It is interesting to note that the ligand coordinated as a monodentate although there are several donor atoms in it. Computational studies showed that such structure is more stable than the hypothetical structure with one ligand bound as a bidentate. The complex exibited moderate antibacterial, antifungal and cytotoxic activities while the ligand was mostly inactive. The complex strongly induced formation of reactive oxygen species in tumor cell lines. It also influenced cell cycle progression in tumor cell lines, and induced autophagy. The latter effect is, at least in part, a protective one.

Graphical abstractSynthesis of tetrahedral Zn(II) complex with 3-acetylpyridine semicarbazone. The complex exibited moderate antibacterial, antifungal and cytotoxic activities, induced formation of ROS and autophagy and influenced cell cycle progression.Figure optionsDownload full-size imageDownload as PowerPoint slide