Synthesis, characterization, and insulin-enhancing studies of unsymmetrical tetradentate Schiff-base complexes of oxovanadium(IV)

Abstract

A series of unsymmetrical tetradentate Schiff bases were synthesized by interaction of 2-hydroxy-1-naphthaldehyde, phenylenediamine and salicylaldehyde, or substituted salicylaldehyde in an ethanolic medium. The oxovanadium(IV) complexes and the ligands were synthesized and characterized by elemental analyses, 1H NMR, infrared, electron paramagnetic resonance, electronic spectra, cyclic voltammetry, and room temperature magnetic susceptibility measurements. The elemental analyses for both the ligands and the metal complexes confirmed purity of the compounds as formulated. Electron paramagnetic resonance spectra of the complexes were measured as powder and in toluene/dichloromethane (9 : 1, v/v) solution at room and liquid N2 temperatures. The g values, g o = 1.971, g ⊥ = 1.978, and g = 1.950, are the same for all the complexes examined. The vanadium nuclear hyperfine splitting, A o = 101–99, A ⊥ = 65–64, A ∥ = 179–177, vary slightly with substituents on the salicylaldehyde. Infrared spectra reveal strong V=O stretching bands in the range 970–988 cm−1, typical of monomeric five-coordinate complexes. The room temperature magnetic moments of 1.6–1.8 BM for the complexes confirmed that the complexes are V(IV) complexes, with d1 configuration. Only one quasi-reversible wave is observed for each compound and they all showed redox couples with peak-to-peak separation values (ΔE p) ranging from 78 to 83 mV, indicating a single step one electron transfer process. Insulin-mimetic tests on C2C12 muscle cells using Biovision glucose assay showed that all the complexes significantly stimulated cell glucose utilization with negligible cytotoxicity at 0.05 µg µL−1.