Redox-active metal complexes with 2,2′-dipicolylamine containing ferrocenyl moiety: Synthesis, electrochemical behavior and biological activity

Abstract

The novel metal complexes of general formula MCl2·L (M = Cu, Fe, Co, Mn, Zn) based on the di-(2-picolyl)amine ligand L with the redox-active ferrocenyl fragment were synthesized and characterized by elemental analysis, IR, 1H, 13C NMR, UV–vis spectroscopy and MALDI-TOF mass spectrometry. The molecular structure of [ZnCl2L] was established by X-ray crystallography. The redox properties of complexes were studied using cyclic voltammetry (CV) method and feasible schemes of electrochemical transformations were proposed. The antioxidant activity of compounds was tested by various methods. The lipoxygenase (LOX) inhibition activity of the studied compounds was evaluated. The in vitro biological experiments were performed using rat brain homogenates. The results demonstrate that ditopic compounds containing ferrocene and redox active dipicolylamine fragments act as polyfunctional antioxidants. These results let us to conclude that combining in one molecule several redox-active metal centers is a promising way of metallodrug design in modern medicinal chemistry.