Radical-radical reactions of superoxide: a potential route to toxicity.
Superoxide reacts with many radicals, such as phenoxyl radicals, at near diffusion-controlled rates. These reactions are usually considered to be repair processes and have received little biological attention. However, addition of superoxide to give hydroperoxides and secondary oxidation products can also occur. The relative contributions of addition and repair vary depending on the properties of the phenol. With tyrosine, addition to give tyrosine hydroperoxide predominates, but in peptides the efficiency of hydroperoxide formation depends on the proximity of free amine groups. Radicals from other phenolic compounds, such as alpha-tocopherol and serotonin, also undergo addition reactions with superoxide. Physiologically, these reactions are likely to be more significant than dimerization when both radicals are generated together. They warrant attention as potential contributors to superoxide toxicity.
Winterbourn
Christine C
CC
Free Radical Research, Department of Pathology, Christchurch School of Medicine and Health Sciences, P.O. Box 4345, Christchurch, New Zealand. christine.winterbourn@chmeds.ac.nz
Kettle
Anthony J
AJ
D000818:Animals; D005609:Free Radicals / Q000737:chemistry* / Q000378:metabolism; D007211:Indoles / Q000737:chemistry / Q000378:metabolism; D008956:Models, Chemical; D009569:Nitric Oxide / Q000378:metabolism; D010455:Peptides / Q000737:chemistry; D010545:Peroxides / Q000737:chemistry / Q000378:metabolism; D010636:Phenols / Q000737:chemistry / Q000378:metabolism; D011506:Proteins / Q000737:chemistry; D013481:Superoxides / Q000737:chemistry* / Q000378:metabolism / Q000633:toxicity; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D014810:Vitamin E / Q000737:chemistry / Q000378:metabolism
D005609:Free Radicals; D007211:Indoles; D010455:Peptides; D010545:Peroxides; D010636:Phenols; D011506:Proteins; C104002:tyrosine peroxide; D013481:Superoxides; D014810:Vitamin E; D009569:Nitric Oxide; C042329:phenoxy radical; D014443:Tyrosine