Interaction of zinc(II) with the non-steroidal anti-inflammatory drug niflumic acid

Abstract

The reaction of ZnCl2 with the non-steroidal anti-inflammatory drug niflumic acid (Hnif) resulted in the formation of complex [Zn(nif-O)2(MeOH)4], 1. When this reaction was performed in the presence of a N,N′-donor heterocyclic ligand such as 2,2′-bipyridine (bipy), 2,2′-bipyridylamine (bipyam), 1,10-phenanthroline (phen) and 2,2′-dipyridylketone oxime (Hpko), the complexes [Zn(nif-O,O′)(bipy)Cl], 2, [Zn(nif-O)(nif-O,O′)2(bipyam)], 3, [Zn(nif-O,O′)2(phen)], 4 and [Zn(nif-O)2(Hpko-N,N′)2], 5 were formed, respectively. The complexes were characterized by physicochemical and spectroscopic techniques and X-ray crystallography (for complexes 1–3). The complexes can scavenge 1,1-diphenyl-picrylhydrazyl, 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) and hydroxyl radicals, may inhibit soybean lipoxygenase and are more active compounds than free Hnif. The interaction of the complexes with serum albumins was monitored by fluorescence emission spectroscopy and the corresponding binding constants were calculated. The affinity of the complexes with calf-thymus DNA was investigated by UV–vis spectroscopy, viscosity measurements and fluorescence emission spectroscopy for the competitive studies of the complexes with ethidium bromide revealing their interaction probably via intercalation.