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J. Biol. Chem., Vol. 263, Issue 34, 17921-17924, Dec, 1988

A novel metal-free low molecular weight superoxide dismutase mimic

A Samuni, CM Krishna, P Riesz, E Finkelstein and A Russo
Division of Cancer Treatment, National Cancer Institute, Bethesda, Maryland 20892.

2-Ethyl-1-hydroxy-2,5,5-trimethyl-3-oxazolidine (OXANOH), the one- electron reduction product of the stable nitroxide radical, 2-ethyl- 2,5,5-trimethyl-3-oxazolidinoxyl (OXANO), is reportedly oxidized by superoxide, and its oxidation has been proposed as a method for assaying superoxide. We find that superoxide can both reduce OXANO and oxidize OXANOH. The respective rate constants, k1 and k2, were determined using two superoxide-generating systems (xanthine oxidase/xanthine as well as ionizing radiation). OXANOH oxidation and OXANO reduction are both inhibitable by superoxide dismutase, pH- dependent (4.5-9.3), and result in a steady state distribution of [OXANO] and [OXANOH], independent of their initial concentrations, i.e. the OXANO/OXANOH couple exhibits a metal-independent superoxide dismutase-like function. Thus it provides a prototype for future development of improved low molecular weight superoxide dismutase mimics which will also function in cellular hydrophobic (aprotic) compartments such as membranes.
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