Enzyme-induced aziridine formation by rat liver microsomes.
The metabolic reaction of 2-chloroethylaminobenzoquinone derivatives with rat liver microsomes was studied. In buffer solution containing cellular macromolecules such as DNA or protein, 2-chloroethylaminobenzoquinones were usually stable and could be recovered quantitatively after an appropriate period of incubation. However, in microsomal solution, they were gradually converted into aziridinobenzoquinones via elimination of hydrogen chloride by NADPH-dependent enzyme action. Based on the study of the enzymatic cyclization reaction of 4-chlorobutylaminonaphthoquinone, we concluded that the hydroquinone derivative is an important intermediate for aziridine formation.
D000818:Animals; D001388:Aziridines / Q000378:metabolism*; D001389:Azirines / Q000378:metabolism*; D001711:Biotransformation; D007700:Kinetics; D008297:Male; D008862:Microsomes, Liver / Q000201:enzymology*; D009247:NADH, NADPH Oxidoreductases / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D001388:Aziridines; D001389:Azirines; D009247:NADH, NADPH Oxidoreductases