Effects of induction on the metabolism and cytochrome P-450 binding of harman and other β-carbolines

References

• Airaksinen M. M., Mikkonen E. Affinity of β-carbolines on rat brain benzodiazepine and opiate binding sites. Medical Biology 1980; 58: 341–344
   PubMedGoogle Scholar
• Barker S. A., Harrison R. E. W., Monti J. A., Brown G. B., Christian S. T. Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-THβC and 6-methoxy-THβC as in vivo constituents of rat brain and adrenal gland. Biochemical Pharmacology 1981; 30: 9–17
   PubMed Web of Science ®Google Scholar
• Beck O., Bosin T. R., Holmstedt B., Lundman A. A GC-MS study on the occurrence of two tetrahydro-β-carbolines implicated in alcoholism. Progress in Clinical and Biological Research 90, F. Bloom, I. Barchas, M. Sandler, E. Usdin. A. R. Liss, New York 1982; 29–40
   Google Scholar
• Beck O., Holmstedt B. Analysis of 1-methyl-1,2,3,4-tetrahydro-β-carboline in alcoholic beverages. Food and Cosmetics Toxicology 1981; 19: 173–177
   PubMedGoogle Scholar
• Bertoni G., Merlini L., Nasini G., Abenaim U. 1-Methyl-β-carboline-3-carboxylic acid, an unusual metabolite from cows fed with corn silage. Journal of Agricultural and Food Chemistry 1980; 28: 673–675
   PubMedGoogle Scholar
• Bidder T. G., Shoemaker D. W., Boettger H. G., Evans M., Cummins J. T. Harman in human platelets. Life Sciences 1979; 25: 157–164
   PubMed Web of Science ®Google Scholar
• Buckholtz N. S., Boggan W. O. Monoamine oxidase inhibition in brain and liver produced by β-carbolines: structure-activity relationships and substrate specificity. Biochemical Pharmacology 1977; 26: 1991–1996
   PubMed Web of Science ®Google Scholar
• Bulleid N. J., Craft J. A. Effects of metyrapone and norharmane on microsomal monooxygenase and epoxide hydrolase activities. Biochemical Pharmacology 1984; 33: 1451–1457
   PubMedGoogle Scholar
• Castellani A., Setlow R. B. Harman inhibits the removal of pyrimidine dimers from the DNA of human cells. Biochemical and Biophysics Research Communications 1981; 98: 823–828
   PubMedGoogle Scholar
• Coutts R. T., Locock R. A., Slywka G. W. A. Mass spectra of selected beta-carbolines. Organic Mass Spectrometry 1970; 3: 879–889
   Google Scholar
• Fehske K. J., Muller W. E., Platt K. L., Stillbauer A. E. Inhibition of benzodiazepine receptor by several tryptophen and indole derivatives. Biochemical Pharmacology 1981; 30: 3016–3019
   PubMedGoogle Scholar
• Glennon R. A. Serotonin receptor interactions of harmaline and several related β-carbolines. Live Science 1981; 29: 861–865
   Google Scholar
• Greiner B., Fahndrich C., Strauss S., Rommelspacher H. Pharmacokinetics of tetrahydronorharmane (tetrahydro-β-carboline) in rats. Naunyn-Schmied. Arch. Pharmacol 1983; 322: 140–146
   PubMedGoogle Scholar
• Greiner B., Rommelspacher H. Two metabolic pathways of tetrahydronorharman (tetrahydro-β-carboline) in rats. Naunyn-Schmied. Archives of Pharmacology 1984; 325: 349–355
   Google Scholar
• Ho B. T., Taylor D., Walker K. E., McIsaac W. Metabolism of 6-methoxytetrahydro-β-carboline in rats. Xenobiotica 1972; 2: 349–362
   PubMed Web of Science ®Google Scholar
• Holme J. A., Soderlunde E., Aune T. Effects of harman and norharman on the metabolism and genotoxicity of 2-acetylaminofluorene in cultured rat hepatocytes. Cell Biology and Toxicology 1985; 1: 223–240
   PubMedGoogle Scholar
• Jefcoate C. R. E., Gaylor J. L., Calabrese R. L. Ligand interactions with cytochrome P-450. I. Binding of primary amines. Biochemistry 1969; 8: 3455–3463
   PubMed Web of Science ®Google Scholar
• Lau P. P., Luh Y. Effects of the comutagens harman and norharman on the interaction of a tryptophan pyrolysis product, 3-amino-1-methyl-5H-pyrido (4, 3-b) indole with DNA. Biochemical and Biophysical Research Communications 1979; 89: 188–194
   PubMedGoogle Scholar
• Lesca P., Lecointe P., Pelaprat D., Paoletti C., Murray D. Structure-activity relationships in the inhibitory effects of ellipticines on benzo‘a’ pyrene hydroxylase activity and 3-methylcholanthrene mutagenicity. Biochemical Pharmacology 1980; 29: 3231–3237
   PubMed Web of Science ®Google Scholar
• Levitt R. C., Legraverend C., Nebert D. W., Pelkonen O. Effects of harman and norharman on the mutagenicity and binding to DNA of benzo‘a’-pyrene metabolites in vitro and on aryl hydrocarbon hydroxylase induction in cell culture. Biochemical and Biophysicd Research Communications 1977; 79: 1167–1175
   PubMed Web of Science ®Google Scholar
• Mailman R. B., Kulkarni A. P., Baker R. C., Hodgson E. Cytochrome P-450 difference spectia: effect of chemical structure on Type II spectra in mouse hepatic microsomes. Drug Metabolism and Disposition 1974; 2: 301–308
   PubMed Web of Science ®Google Scholar
• Miwa G. T., Lu A. Y. H. The topology of the mammalian cytochrome P-450 active site. Cytochrome P-450, P. R. Oritz de Montellano. Plenum Press, New York 1986; 77–88
   Google Scholar
• Peura P., Kari I., Airaksinen M. M. Identification by selective ion monitoring of 1-methyl-1,2,3,4-tetrahydro-β-carboline in human platelets and plasma after ethanol intake. Biomedical Mass Spectrometry 1980; 7: 553–555
   PubMedGoogle Scholar
• Poindexter E. H., Carpenter R. D. The isolation of harman and norharman from tobacco and cigarette smoke. Phytochemistry 1962; 1: 215–221
   Web of Science ®Google Scholar
• Rommelspacher H., Barbey M., Strauss S., Greiner B., Fahndrich E. Is there a correlation between the concentration of β-carbolines and their pharmacodynamic effect?. Progress in Clinical and Biological Research 90, F. Bloom, J. Barchas, M. Sandler, E. Usdin. A. R. Liss, New York 1982; 41–55
   Google Scholar
• Rommelspacher H., Nanze C., Borbe H. O., Fehske K. J., Muller W. E., Wollert U. Benzodiazepine antagonism by harmane and other β-carbolines in vitro and, in vivo. European Journal of Pharmacology 1981; 70: 409–416
   PubMed Web of Science ®Google Scholar
• Rommelspacher H., Strauss S., Lindemann J. Excretion of tetrahydroharmane and harmane into the urine of man and rat after a load with ethanol. FEBS Letters 1980; 109: 209–212
   PubMed Web of Science ®Google Scholar
• Schenk G. The Book of Poisons. Weidenfeld and Nicolson, London 1956; 124–126
   Google Scholar
• Schenkman J. B., Remmer H., Estabrook R. W. Spectral studies of drug interactions with hepatic microsomal cytochrome. Molecular Pharmacology 1967; 3: 113–123
   PubMed Web of Science ®Google Scholar
• Shoemaker D. W., Cummins J. T., Bidder T. G. β-Carbolines in rat arcuate nucleus. Neuroscience 1978; 3: 233–239
   PubMedGoogle Scholar
• Shoemaker D. W., Cummins J. T., Bidder T. G., Beottger H. G., Evans M. Identification of harman in the rat arcuate nucleus. Naunyn-Schmied. Archives of Pharmacology 1980; 310: 227–230
   Google Scholar
• Sugimura T., Kawachi T., Nagao M., Yahagi T., Seino Y., Okamoto T., Kosugi K., Tsuji K., Wakabayashi K., Iitaka Y., Itai A. Mutagenic principle(s) in tyrptophan and phenylalanine pyrolysis products. Proceedings of Japanese Academy 1977; 53: 58–61
   Google Scholar
• Tweedie D. J. The metabolism of β-carbolines by cytochrome P-450. Effect of induction and influence of substrate structure. PhD Thesis, University of Aberdeen, Scotland 1984
   Google Scholar
• Tweedie D. J., Burke M. D. Differential effects of phenobarbitone and 3-methylcholanthrene induction on the hepatic metabolism of the β-carbolines, harmine and harmol. Biochemical Pharmacology 1983; 32: 653–663
   PubMedGoogle Scholar
• Tweedie D. J., Burke M. D. Metabolism of the β-carbolines, harmine and harmol, by liver microsomes from phenobarbitone or 3-methylcholanthrene treated mice: identification and quantitation of two novel harmine metabolites. Drug Metabolism and Disposition 1987; 15: 74–81
   PubMed Web of Science ®Google Scholar
• Ullrich V., Kremers P. Multiple forms of cytochrome P-450 in the microsomal monooxygenase. Archives of Toxicology 1977; 39: 41–50
   PubMed Web of Science ®Google Scholar
• Yoshida Y., Kumaoka H. Studies on the substrate-induced spectral change of cytochrome P-450 in liver microsomes. Journal of Biochemistry 1975; 78: 455–468
   Google Scholar