Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 29, 1999 - Issue 6
115
Views
25
CrossRef citations to date
0
Altmetric
Research Article

In vitro metabolism of 6-mercaptopurine by human liver cytosol

, &
Pages 615-628 | Published online: 22 Sep 2008

References

  • ABRAHAM, E. T., BENSON, L. M. and JARDINE, I., 1983, Synthesis and pH dependent stability of purine-6-sulfenic acid, a putative reactive metabolite of 6-thiopurine. Journal of Medicinal Chemistry, 26, 1523–1526.
  • ADAMSON, P. C., BALIS, F. M., STEINBERG, S. M. and POPLACK, D. G., 1990, Pharmacokinetics of mercaptopurine in children with acute lymphoblastic leukaemia. New England Journal of Medicine, 323, 1565–1566.
  • BERGAN, S., BENTDAL 0., SODAL, G., BRUN, A., RUGSTAD, H. E. and STOKICE O., 1997, Patterns of azathioprine metabolites in neutrophils, lymphocytes, reticulocytes, and erythrocytes: Relevance to toxicity and monitoring in recipients of renal transplants. Therapeutic Drug Monitoring, 19, 502–509.
  • BERGMANN, F. and UNGAR, H., 1960, The enzymatic oxidation of 6-mercaptopurine to 6-thiouric acid. Biochimica et Biophyska Acta, 33, 3957–3959.
  • BOULlEU, R. and LENOIR, A., 1995, Determination of thiopurine nucleotides in human lung tissue by high-performance liquid chromatography. Journal of Chromatography, Biomedical Applications, 665, 213–216.
  • CARNEY, D. M., ZUKOWSKI, C. F. and OGDEN D. A., 1974, Massive azathioprine overdose. American Journal of Medicine, 56, 133–136.
  • CUFFARI C., SEIDMAN, E. G., LATOUR, S. and THEORET, Y., 1996, Quantitation of 6-thioguanine in peripheral blood leukocyte DNA in Crohn's disease patients on maintenance 6-mercatopurine therapy. Canadian Journal of Physiology and Pharmacology, 74, 580–585.
  • EmoN, G. B., CALLAHAN, S. W. and HITCHINGS, G. H., 1962, Experimental, clinical and metabolic studies of thiopurines. Cancer Chemotherapy Reports, 16, 197–202.
  • ELION, G. B., 1967, Biochemistry and pharmacology of purine analogues. Federation. Proceedings, 26, 898–904.
  • EVANS, W. E., HORNER, M. H., CHU, Y. Q., KALWINSKY, D. and ROBERTS, W. M., 1991, Altered mercaptopurine metabolism, toxic effects, and dosage requirement in a thiopurine methyl-transferase deficient child with acute lymphoblastic leukaemia. Journal of Pediatrics, 119, 985–989.
  • GUERCIOLINI, R., SZUMLANSKI, C. L. and WEINSHILBOUM, R. M., 1991, Human liver xanthine oxidase: nature and extent of individual variation. Clinical Pharmacology and Therapeutics, 50, 663–672.
  • HAYDER, S., LAFOLIE, P., BJORK, 0. and PETERSON, C., 1989,6-Mercaptopurine plasma levels in children with acute lymphoblastic leukaemia: relation to relapse risk and myelotoxicity. Therapeutic Drug Monitoring, 11, 617–622.
  • HEMMENS, V. J. and MOORE, D. E., 1984, Photo-oxidation of 6-mercaptopurine in aqueous solution. Journal of the Chemical Society, Perkin Transactions, 11, 209–211.
  • HENDRICK, D. and MIRKIN, B. L., 1984, Metabolic disposition and toxicity of 6-mercaptopurine after a massive overdose. Lancet, i (8371), 277.
  • HON, Y. Y. and EVANS, W. E., 1998, Making TDM work to optimize cancer chemotherapy: a multidisciplinary team approach. Clinical Chemistry, 44, 388–400.
  • HYSLOP, R. M. and JARDINE, I., 1981, Metabolism of 6-thiopurines I. Irreversible binding of a metabolite of 6-thiopurine to mammalian hepatic protein in vitro. Journal of Pharmacology and Experimental Therapeutics 218,621–628.
  • KEUZENKAMP -JANSEN, C. W., VAN BAAL, J. M., DE ABREU, R. A., DE JONG, J. G. N., ZUIDERENT, R. and TRUBELS, J. M. F., 1996, Detection and identification of 6-methylmercaptopurine, a major metabolite of 6-mercaptopurine, in plasma during intravenous administration. Clinical Chemistry, 42, 380–386.
  • KOREN, G., FERRAZINI, G., SULH, H., LANGEVIN, A. M., KAPELUSHNIK J., KLEIN, J., GlESBRECHT, E. SOLDIN, S. and GREENBERG, M., 1990, Systemic exposure to mercaptopurine as a prognostic factor in acute lymphocytic leukaemia in children. New England Journal of Medicine, 323, 17–21.
  • KRENITSKY, T. A., NEIL, S. M., ELION, G. B. and HITCHINGS, G. H., 1972, A comparison of the specificities of xanthine oxidase and aldehyde oxidase. Archives of Biochemistry and Biophysics, 150, 585–599.
  • LENNARD, L., VAN LOON, J. A. and WEINSHILBOUM, R. M., 1989, Pharmacogenetics of acute azathioprine toxicity: Relationship to thiopurine methyltransferase genetic polymorphism. Clinical Phar-macology and Therapeutics, 46, 149–154.
  • LENNARD, L., LILLEYMAN, J. S., VAN LOON, J. A. and WEINSHILBOUM, R. M., 1990, Genetic variation in response to 6-mercaptopurine for childhood acute lymphoblastic leukaemia. Lancet, 336,225–229.
  • LENNARD, L. and SINGLETON, H., 1992, High-performance liquid chromatography assay of the methyl and nucleotide metabolites of 6-mercaptopurine : quantitation of red blood cell 6-thioguanine nucleotide, 6-thioinisinic acid and 6-methylmercaptopurine. Journal of Chromatography, Biomedical Applications, 583, 83–90.
  • LENNARD, L. and SINGLETON, H., 1994, High-performance liquid chromatographic assay of human red blood cell thiopurine methyltransferase activity. Journal of Chromatography, Biomedical Appli-cations, 661, 25–33.
  • LENNARD, L., LEWIS, I. J., MICHELANGNOLI, M. and LILLEYMAN, J. S., 1997, Thiopurine methyl-transferase deficiency in childhood lymphoblastic leukaemia: 6-mercaptopurine dosage strategies. Medical and Pediatric Oncology, 29, 252–255.
  • LILLEYMAN, J. S. and LENNARD, L., 1994, Mercaptopurine metabolism and risk of relapse in childhood lymphoblastic leukaemia. Lancet, 343, 1188–1190.
  • LILlEMARK, J., PETTERSSON, B. and PETERSON, C., 1992, On the biochemical modulation of 6-mercaptopurine by methotrexate in murine WEHI-3b leukaemia cells in vitro. Leukaemia Research, 16, 275–280.
  • LOWRY, 0. H., ROSEBURGH N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin reagent. Journal of Biological Chemistry, 193, 265–275.
  • McLEDD, H. L., RELLING, M. V., LIU, Q., Put, C. H. and EVANS, W. E., 1995, Polymorphic thiopurine methyltransferase in erythrocytes is indicative of activity in leukemic blasts from children with acute lymphoblastic leukemia. Blood, 7, 1897–1902.
  • NELSON, D. J., BUGGE, C. and KRASNY, H. C., 1977, Oxypurine and 6-thiopurine nucleoside triphosphate formation in human erythrocytes. Advances in Experimental Medicine and Biology, 76A, 121–128.
  • RELLING, M. V., LIN, J.-S., AYERS, G. and EVANS, W. E., 1992, Racial and gender differences in N-acetyltransferase, xanthine oxidase, and CYP1A2 activities. Clinical Pharmacology and Therapeutics, 52, 643–658.
  • RUNDLES, R. W. and ELION, G. B., 1984, Mercaptopurine bioavailability'. New England Journal of Medicine, 310, 929.
  • SKIPPER, H. E., SCHABEL, F. M. and WiLcox, W. S., 1967, Experimental evaluation of potential anticancer drugs. Cancer Chemotherapy Reports, 51, 125–141.
  • STET, E. H., DE ABREU, R. A., BOKICERINK, J. P. M., BLOM, H. J., LAMBOOY, L. H. J., VOGELS -MENTINK T. M., DE GRAAF-HESS, A. C., VAN RAAY-SELTEN, B. and TRIJBELS, F. J. M., 1994, Decrease in S - adenosylmethionine synthesis by 6-mercaptopurine and methylmercaptopurine ribonucleoside in Molt F4 human malignant lymphoblasts. Biochemical Journal, 304, 163–168.
  • SZUMLANSKI, C. L., HONCHEL, R., SCOTT, M. C. and WEINSHILBOUM, R. M., 1992, Human liver thiopurine methyltransferase pharmacogenetics : biochemical properties, liver-erythrocyte cor-relation and presence of isozymes. Pharmacogenetics, 2, 148–159.
  • SZUMLANSKI, C., OTTERNESS, D., HER, C., LEE, D., BRAND1FF KELSELL, D., SPURR, N., LENNARD, WlEBEN, E. and WEINSHILBOUM, R. M., 1996, Thiopurine methyltransferase pharmacogenetics : human gene cloning and characterization of a common genetic polymorphism. DNA and Cell Biology, 15, 17–30.
  • TIDD, D. M. and PATERSON, A. R. P., 1974, A biochemical mechanism for the delayed cytotoxic reactions of 6-mercaptopurine. Cancer Research, 34, 738–746.
  • WEINSHILBOUM, R. M. and SLADEK, S. L., 1980, Mercaptopurine pharmacogenetics : monogenic inheritance of erythrocyte thiopurine methyltransferase activity. American Journal of Human Genetics, 32, 651–662.
  • WEINSHILBOUM, R. M., 1992, Methylation pharmacogenetics : thiopurine methyltransferase as a model system. Xenobiotka, 22, 1055–1071.
  • ZDA:m, S., COLLINS, J. M., RICCARDI, R., O'NEILL, D., NARANG, P. K., CHABNER, B. and POPLACK, D. G., 1983, Variable bioavailability of oral mercaptopurine. Is maintenance chemotherapy in acute lymphoblastic leukaemia being optimally delivered? New England Journal of Medicine, 308, 1005–1009.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.