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© 1983 Oxford University Press

other

A free radical mediated cooxidation of tetramethylhydrazine by prostaglandin hydroperoxidase

B. Kalyanaraman 1 2, Kandiah Sivarajah 3, Thomas E. Eling 3 and Ronald P. Mason 2

2Laboratory of Environmental Biophysics, National Institute of Environmental Health Sciences, Research Triangle Park NC 27709, USA
3Laboratory of Pulmonary Function and Toxicology, National Institute of Environmental Health Sciences, Research Triangle Park NC 27709, USA

1Present address: National Biomedical ESR Center, The Medical College of Wisconsin, Inc., P.O. Box 26509, Milwaukee, WI 53226, USA.

Prostaglandin endoperoxide synthase catalyzed the oxidation of tetramethylhydrazine to the tetramethylhydrazine radical cation, as detected by electron spin resonance spectroscopy. Oxidation of tetramethylhydrazine by prostaglandin endoperoxide synthase also resulted in the N-demethylation of tetramethylhydrazine leading to the formation of formaldehyde. Both the radical and formaldehyde formation were dependent on arachidonic acid, inhibited by indomethacin, and supported by 15-hydroperoxyarachidonic acid, indicating that the metabolism was peroxidative. We propose that tetramethylhydrazine undergoes two sequential one-electron oxidations yielding an iminium cation, which is then hydrolyzed to yield formaldehyde. Metabolism of hydrazines by prostaglandin endoperoxide synthase may be of importance in tissues containing low mixed-function oxidase activity.


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