Antioxidant properties of oxime 3-(phenylhydrazono) butan-2-one

Abstract

Oximes are a class of compounds normally used to reverse the acetylcholinesterase (AChE) inhibition caused by organophosphates (OPs). Conversely, researches focusing on the possible antioxidant properties of these compounds are lacking in the literature. The aim of this study was to investigate the potential antioxidant and toxic properties of 3-(phenylhydrazono) butan-2-one oxime in mice. In vitro, hydrogen peroxide-induced lipid peroxidation was decreased by low concentrations of the oxime (0.1-1.0 microM); (P < 0.05). Similarly, lipoperoxidation induced by malonate and iron (Fe2+) was significantly decreased by the oxime (0.4-1.0 microM) (P < 0.05). Oxime pre-treatment did not modify the basal peroxidation level nor prevented the induced lipid peroxidation determined ex-vivo. The present results suggest that 3-(phenylhydrazono) butan-2-one oxime could be a good antioxidant compound. The absence of toxicity signs after in vivo administration of 3-(phenylhydrazono) butan-2-one oxime to mice may indicate that it could be a safe drug for further studies.

In Vivo Evaluation of Cholinesterase Activity, Oxidative Stress Markers, Cyto‐ and Genotoxicity of K048 Oxime – a Promising Antidote against Organophosphate Poisoning

“…Additionally, Puntel et al . showed that 3‐(phenylhydrazono)‐butan‐2‐one oxime was able to decrease TBARS production in brain homogenates induced by malonate and iron. After these considerations, novel insight into the principles of oxime bioactivity can be given.…”

Phenyl 2‐pyridyl ketoxime induces cellular senescence‐like alterations via nitric oxide production in human diploid fibroblasts

“…Previously, an oxime (3‐(phenylhydrazono) butan‐2‐one oxime) was found to act as a potential antioxidant in vitro and in mice (Puntel et al ., 2008). In vitro, hydrogen peroxide‐induced and malonate‐iron mixture‐induced lipid peroxidations were decreased by low concentrations of this oxime (0.1–1.0 μ m ).…”

Pre‐clinical evidence of safety and protective effect of isatin and oxime derivatives against malathion‐induced toxicity

“…On heating, a dark orange product was formed, which was collected by filtration, washed with water and dried in a vacuum (FP 160-163°C). 28 (3Z)-5-Chloro-3-(hydroxyimino)indolin-2-one oxime (Cℓ-HIN) ( Figure 1B) was synthesized as described by Martins and collaborators, with an equimolar mixture of 5-chloroisatin and hydroxylamine chlorhydrate in ethanol. 29 The reaction medium was acidified with acetic acid and placed under reflux (135°C) for 5 h. After that, the reaction was vacuum-filtered and the compound was isolated as a golden yellow precipitate which, in sequence, was washed with cold distilled water (FP 252-274°C).…”