Synthesis, characterization, fluorescence imaging, and cytotoxicity studies of a uracil-based azo derivative and its metal complexes

Abstract

A uracil-based heterocyclic azo derivative was prepared by coupling diazotized 5-aminouracil with 2-naphthol. This ligand, viz., 1-(2,4-dioxopyrimidine-5-yl)-azo-naphth-2-ol (HNAP), was used as a precursor for the synthesis of a series of complexes with manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) ions. Various physicochemical measurements UV–Visible, Infrared (IR), 1H NMR, 13C Nuclear Magnetic Resonance (NMR), and electron spin resonance (ESR) spectral studies were employed to characterize the ligand and the metal complexes. The ligand showed good selectivity toward Mn2+ over the other metal ions with a detection limit of 1.36 μM. This probe was used for the confocal fluorescence imaging of Mn2+ ions in Michigan Cancer Foundation-7 (MCF-7) cells. The ligand and the metal complexes were tested for their cytotoxicity on the MCF-7 cell line. It was observed that complexation of HNAP with the metal ions exhibited a promising cytotoxicity.