Obligatory free radical intermediate in the oxidative activation of the carcinogen N-hydroxy-2-acetylaminofluorene |
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Authors: | Robert A. Floyd Lailing M. Soong |
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Affiliation: | Biomembrane Research Laboratory, Oklahoma Medical Research Foundation, Oklahoma City, Okla. 73104 U.S.A. |
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Abstract: | We have demonstrated that the nitroxyl free radical form of the carcinogen N-hydroxy-2-acetylaminofluorene (OH-AAF) is an obligatory intermediate in the cumene hydroperoxide-hematin-induced oxidative activation of this carcinogen into 2-nitrosofluorene and N-acetoxy-2-acetylaminofluorene. Both the rate of N-OH-2-acetylaminofluorene oxidation and the amount of its nitroxyl free radical were experimently observed as a function of reaction time. Rate equations were derived for a model in which the nitroxyl free radical form of OH-AAF was an obligatory intermediate in the reaction. Using this theory it was possible to compute one experimental variable, the rate of OH-AAF oxidation, utilizing the other experimental variable, the amount of nitroxyl free radical present at any time during the reaction. The theory also predicts a linear relationship between the rate of OH-AAF oxidation and the square of the free radical content; and this was found to be true experimentally. The dismutation rate of constant of the nitroxyl free radical of OH-AAF was found to be 2.7 · 105 M?1 · s?1. |
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Keywords: | AAF acetylaminofluorene OH-AAAF OAc-AAF |
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