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Molecular Pharmacology, Vol 17, 233-238, Copyright © 1980 by the American Society for Pharmacology and Experimental Therapeutics

Spin Trapping of the Primary Radical Involved in the Activation of the Carcinogen N-Hydroxy-2-acetylaminofluorene by Cumene Hydroperoxide-Hematin

GERALD M. ROSEN 1 and ELMER J. RAUCKMAN 1

1 Departments of Pharmacology and Surgery, Duke University Medical Center, Durham, North Carolina 27710

We have verified that the cumene hydroperoxide-hematin system reacts with 5,5-dimethyl-1-pyrroline-1-oxide to form the nitroxide 5,5-dimethyl-pyrrolidone-(2)-oxyl-(1) (DMPOX). We have investigated the mechanism of this reaction and found that it is not a simple oxidation, as has been previously reported, but that DMPOX is formed via the spin trapping of a cumene hydroperoxyl radical followed by an intramolecular carbanion displacement. The activation of the carcinogen, N-hydroxyl-2-acetylaminofluorene, by the cumene hydroperoxide-hematin system is most likely mediated by cumene hydroperoxyl radical.

Submitted on September 24, 1979
Accepted on November 1, 1979




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