title: Effects of cholesterol side chain cleavage inhibitors on 11 beta-hydroxylation: linkage of mitochondrial oxygenase systems.
abstract: Potent inhibitors of cholesterol side chain cleavage were tested for inhibition of 11 beta-hydroxylation of 11-deoxycortisol by bovine adrenal cortex mitochondria. Compounds which inhibited 11 beta-hydroxylation were metyrapone, 4-phenylimidazole, 1-benzylimidazole, 17 beta-ureido - 1, 4- androstadien-3-one. SU-8000, 4-methylaminoglutethimide, and 20 alpha-hydroxycholestrol. Compounds which did not inhibit 11 beta-hydroxylation at concentrations of 0.5 mM were d-aminoglutethimide tartrate, 1-aminoglutethimide tartrate, N-methylaminoglutethimide, 16 alpha-methylpregnenolone, 16 beta-methylpregnenolone, 20-tolylpregnenediol, 16 alpha-chloropregnenolone-3-acetate, 16 alpha-benzyloxpregnenolone-3-acetate and cyanoketone. The results obtained indicate that aminoglutethimide and its congeners, the 16-halogenated and 16-benzoylated derivatives of pregnenolone and cyanoketone are specific inhibitors of cholesterol side chain cleavage enzyme. The two mitochondrial steroid oxyganase systems are linked through their competition for a single electron source.
mesh_terms: D000302:Adrenal Cortex / Q000201:enzymology*; D000616:Aminoglutethimide / Q000031:analogs & derivatives*; D000737:Androstenols / Q000494:pharmacology*; D000818:Animals; D002417:Cattle; D002786:Cholesterol Side-Chain Cleavage Enzyme / Q000037:antagonists & inhibitors*; D003350:Cortodoxone / Q000378:metabolism; D003489:Cyanoketone / Q000031:analogs & derivatives / Q000494:pharmacology*; D006854:Hydrocortisone / Q000096:biosynthesis; D008928:Mitochondria / Q000201:enzymology*; D010088:Oxidoreductases / Q000037:antagonists & inhibitors*; D011284:Pregnenolone / Q000031:analogs & derivatives*; D013252:Steroid 11-beta-Hydroxylase / Q000037:antagonists & inhibitors*; D013250:Steroid Hydroxylases / Q000037:antagonists & inhibitors*
chemical_list: D000737:Androstenols; D000616:Aminoglutethimide; D003489:Cyanoketone; D011284:Pregnenolone; D010088:Oxidoreductases; D013250:Steroid Hydroxylases; D013252:Steroid 11-beta-Hydroxylase; D002786:Cholesterol Side-Chain Cleavage Enzyme; D003350:Cortodoxone; D006854:Hydrocortisone