Redox properties of the nitronyl nitroxide antioxidants studied via their reactions with nitroxyl and ferrocyanide

Free Radical Research
Andrey A Bobko, Valery V Khramtsov

Abstract

Nitronyl nitroxides (NNs) are the paramagnetic probes that are capable of scavenging physiologically relevant reactive oxygen (ROS) and nitrogen (RNS) species, namely superoxide, nitric oxide (NO), and nitroxyl (HNO). NNs are increasingly considered as potent antioxidants and potential therapeutic agents. Understanding redox chemistry of the NNs is important for their use as antioxidants and as paramagnetic probes for discriminative detection of NO and HNO by electron paramagnetic resonance (EPR) spectroscopy. Here we investigated the redox properties of the two most commonly used NNs, including determination of the equilibrium and rate constants of their reduction by HNO and ferrocyanide, and reduction potential of the couple NN/hydroxylamine of nitronyl nitroxide (hNN). The rate constants of the reaction of the NNs with HNO were found to be equal to (1-2) × 10(4) M(-1)s(- 1) being close to the rate constants of scavenging superoxide and NO by NNs. The reduction potential of the NNs and iminonitroxides (INs, product of NNs reaction with NO) were calculated based on their reaction constants with ferrocyanide. The obtained values of the reduction potential for NN/hNN (E'0 ≈ 285 mV) and IN/hIN (E' ≈ 495 mV) are close to the corre...Continue Reading

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Jun 21, 2014·Nitric Oxide : Biology and Chemistry·Andrey A Bobko, Valery V Khramtsov

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Citations

Jan 25, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sibel SuzenLuciano Saso
Jul 31, 2020·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Edinilton Muniz CarvalhoVania Bernardes-Génisson

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