The hydroxylamine OXANOH and its reaction product, the nitroxide OXANO., act as complementary inhibitors of lipid peroxidation.
The effects of the nitroxide 2-ethyl-2,5,5-trimethyl-3-oxazolidinoxyl (OXANO.) and the corresponding hydroxylamine 2-ethyl-1-hydroxy-2,5,5-trimethyl-3-oxazolidine (OXANOH) on in vitro lipid peroxidation in rat liver microsomes and reconstituted lipid vesicles were investigated, and compared with those of some commonly used spin trapping agents. OXANO. and OXANOH (10-100 microM) inhibited iron-dependent lipid peroxidation, as did the spin trapping agents (10-100 mM). OXANO. mainly inhibited the rate of peroxidation, but caused only a small delay in the time of onset. OXANOH exerted its effect by delaying the onset of peroxidation in an antioxidant fashion, and also by inhibiting the rate. Higher concentrations of both substances were required to inhibit t-butylhydroperoxide-dependent lipid peroxidation. OXANO. was found to oxidize the ferrous-ADP complex required for initiation of peroxidation, and this is probably the basis of the inhibitory effect of this compound. Since the reaction of OXANO. tends to produce OXANOH and vice versa, either one could inhibit all reactions of lipid peroxidation.
Nilsson
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Department of Biochemistry and Biophysics, Chalmers University of Technology, Göteborg, Sweden.
Carlin
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Bylund-Fellenius
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D000244:Adenosine Diphosphate / Q000031:analogs & derivatives; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D004578:Electron Spin Resonance Spectroscopy; D005609:Free Radicals; D066298:In Vitro Techniques; D007502:Iron Chelating Agents; D007700:Kinetics; D015227:Lipid Peroxidation / Q000187:drug effects*; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism*; D009589:Nitrogen Oxides / Q000494:pharmacology; D010080:Oxazoles / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010101:Oxygen Consumption; D051381:Rats; D011919:Rats, Inbred Strains
D005609:Free Radicals; D007502:Iron Chelating Agents; D009589:Nitrogen Oxides; D010080:Oxazoles; C029936:adenosine diphosphate-ferric chelate; D000244:Adenosine Diphosphate; C034590:2-ethyl-2,5,5-trimethyl-3-oxazolidinoxyl; C034589:2-ethyl-1-hydroxy-2,5,5-trimethyl-3-oxazolidine; C039900:nitroxyl