Butane-2,3-dionethiosemicarbazone: An oxime with antioxidant properties

Abstract

Oximes are compounds generally used to reverse the acetylcholinesterase (AChE) inhibition caused by organophosphates (OPs). The aim of this study was to examine the capacity of the butane-2,3-dionethiosemicarbazone oxime to scavenge different forms of reactive species (RS) in vitro, as well as counteract their formation. The potential antioxidant and toxic activity of the oxime was assayed both in vitro and ex vivo. The obtained results indicate a significant hydrogen peroxide (H 2O 2), nitric oxide (NO) and 1,1-diphenyl-2-picrylhydrazyl (DPPH ) radical scavenging activity at 0.275, 0.5 and 5 μM of oxime, respectively ( p ≤ 0.05). The oxime exhibited a powerful inhibitory effect on dihydroxybenzoate formation (25 μM) ( p ≤ 0.05) and also decreased deoxyribose degradation induced by Fe 2+ and via Fenton reaction (0.44 and 0.66 mM, respectively) ( p ≤ 0.05). The oxime showed a significant inhibitory effect on σ-phenantroline reaction with Fe 2+ (0.4 mM) suggesting a possible interaction between the oxime and iron. A significant decrease in the basal and pro-oxidant-induced lipid peroxidation in brain, liver, and kidney of mice was observed both in vitro and ex vivo ( p ≤ 0.05). In addition, in our ex vivo experiments the oxime did not depict any significant changes in thiol levels of liver, kidney and brain as well as did not modify the δ-aminolevulinate dehydratase (δ-ALA-D) activity in these tissues. Taken together our results indicate an in vitro and ex vivo antioxidant activity of the oxime possibly due to its scavenging activity toward different RS and a significant iron interaction.