Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct.
Destruction of hepatic cytochrome P-450 during catalytic processing of 1-amino-benzotriazole is accompanied by an equal loss of microsomal haem but not by loss of cytochrome b5, or stimulation of lipid peroxidation. An abnormal porphyrin, tentatively identified as an NN-bridged benzyne-protoporphyrin IX adduct, appears to be formed by the addition of catalytically generated benzyne to prosthetic haem.
D000478:Alkylation; D000818:Animals; D065607:Cytochrome P-450 Enzyme Inhibitors; D003580:Cytochromes / Q000378:metabolism; D015786:Cytochromes b5; D006418:Heme / Q000378:metabolism*; D066298:In Vitro Techniques; D046911:Macromolecular Substances; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000201:enzymology; D011524:Protoporphyrins / Q000302:isolation & purification; D051381:Rats; D011919:Rats, Inbred Strains; D013053:Spectrophotometry; D014230:Triazoles / Q000494:pharmacology*
D065607:Cytochrome P-450 Enzyme Inhibitors; D003580:Cytochromes; D046911:Macromolecular Substances; D011524:Protoporphyrins; D014230:Triazoles; C033020:1-aminobenzotriazole; D006418:Heme; D015786:Cytochromes b5; C028025:protoporphyrin IX