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Xenobiotica
the fate of foreign compounds in biological systems
Volume 31, 2001 - Issue 5
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Research Article

Identification and reactivity of the major metabolite (ß-1-glucuronide) of the anti-tumour agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA) in humans

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Pages 277-293 | Published online: 22 Sep 2008

References

  • BAGULEY, B. C., ZHUANG, L. and KESTELL, P., 1997, Increased plasma serotonin following treatment with flavone-8-acetic acid, 5,6-dirnethylxanthenone -4-acetic acid, vinblastine, and colchicine: relation to vascular effects. Oncology Research, 9, 55–60.
  • BENET, L. Z., SPAHN-LANGGUTH, H., IwAKAw, S., C., V., MIZUMA, T., MAYER, S., MUTSCHLER, E. and UN, E. T., 1993, Predictability of the covalent binding of acidic drugs in man. Life Science, 53, 141–146.
  • BISCHER, A., ZIAAMIRHOSSEINI, P., IwARI, M., MCDONAGH, A. F. and BENET, L. Z., 1995, Stereoselective binding properties of naproxen glucuronide diastereomers to proteins. Journal of Pharmacokinetics and Biopharmaceutics, 23, 379–395.
  • BURCHELL, B., BRIELEY, C. H., MONAGHAN, G. and CLARKE, D. J., 1998, The structure and function of the UDP-glucuronosyltransferaw gene family. Advances in Pharmacology, 42, 335–338.
  • DING, A., OJINGWA, J. C., MCDONAGH, A. F., BURLINGAME, A. L. and BENET, L. Z., 1993, Evidence for covalent binding of acyl glucuronides to serum albumin via an amine mechanism as revealed by tandem mass spectrometry. Proceedings of the National Academy of Sciences, USA, 90, 3797–3801.
  • DING, A., ZIA-AMIRHOSSEINI, P., MCDONAGH, A. F., BURLINGAME, A. L. and BENET, L. Z., 1995, Reactivity of tolmetin glucuronide with human serum albumin - identification of binding sites and mechanisms of reaction by tandem mass spectrometry. Drug Metabolism and Disposition, 23, 369–376.
  • DOUMAS, B. T. and BIGGS, H. G., 1972, Determination of serum albumin. Standard Methods in Clinical Chemistry, 7, 175–188.
  • DWIVEDI, C., DOWNIE, A. A. and WEBB, T. E., 1987, Net glucuronidation in different rat strains: importance of microsomal beta-glucuronidase. FASEB Journal, 1, 303–307.
  • EBNER, T., HEINZEL, G., PROX, A., BESCHKE, K. and WACHSMUT H., 1999, Disposition and chemical stability of telmisartan 1-0-acylglucuronide. Drug Metabolism and Disposition, 27, 1143-1149. FAED, E. M., 1984, Properties of acyl glucuronide: implications for studies of the pharmacokinetics and metabolism of acidic drugs. Drug Metabolism Review, 15, 1213–1249.
  • FENSELAU, C., 1994, Acyl glucuronide as chemical reactive intermediates. In F. C. Kauffman (ed) Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity (Berlin: Springer-Verlag), pp. 367–389.
  • JAMESON, M. B., THOMSON, P. I., BAGULEY, B. C., EVANS, B. D., HARVEY, V. J., MCCRYSTAL, M. R. and KESTELL, P., 2000, Phase I pharmacokinetic and pharmacodynamic study of 5,6-dirnethylxanthenone-4-acetic acid (DMXAA), a novel antivascular agent. In Proceedings of the Annual Meeting of American Society of Clinical Oncologists, p. 705.
  • KESTELL, P., PAXTON, J. M., REWCASTLE, G. W., DUNLOP, I. and BAGULEY, B. C., 1999, Plasma disposition, metabolism and excretion of the experimental antitumour agent 5,6-dirnethylxanthenone-4-acetic acid in the mouse, rat and rabbit. Cancer Chemotherapy and Pharmacology, 43, 323–330.
  • MAYER, S., MUTSCHLER, E., BENET, L. Z. and SPAHNLUGGUT H., 1993, In vitro and in vivo irreversible plasma protein binding of beclobric acid enantiomers. Chirality, 5, 120–125.
  • MCKINNON, G. E. and DICKINSON, R. G., 1989, Covalent binding of diflunisal and probenecid to plasma protein in humans: persistence of the adducts in the circulation. Research Communications in Chemistry, Pathology, and Pharmacology, 66, 339–354.
  • MEFFIN, P. J., Zwm, D. M. and VEENENDAAL, J. R., 1983, A renal mechanism for the clofibric acid-probenecid interaction. Journal of Pharmacology and Experimental Therapeutics, 227, 739–742.
  • MINERS, J. O., VALENTE, L., LILLYWHITE, K. J., MACKENZIE, P. I., BURCHELL, B., BAGULEY, B. C. and KESTELL, P., 1997, Preclinical prediction of factors influencing the elimination of 5,6-dirnethylxanthenone-4-acetic acid, a new anticancer drug. Cancer Research, 57, 284–289.
  • OJINGWA, J., SPAHN-LUGGUTH, H. and BENET, L. Z., 1988, Studies of tolmetin reversible and irreversible binding to proteins via its glucuronide conjugate. Pharmaceutical Research, 5(suppl.), S214.
  • PHILPOTT, M., BAGULEY, B. C. and CHING, L.-M., 1995, Induction of tumour necrosis factor-alpha by single and repeated doses of the antitumour agent 5,6-dimethylxanthenone-4-acetic acid. Cancer Chemotherapy and Pharmacology, 36, 143–148.
  • POHL, L. R., SATOH, H., CHRIST, D. D. and KENNA, J. G., 1988, The immunological and metabolic basis of drug hypersensitivities. Annual Review in Pharmacology, 28, 367–387.
  • PRESLE, N., LAPICQUE, F., FOURNEL-GIGLEUX, S., MAGDALOU, J. and NETTER, P., 1996, Stereoselecive irreversible binding of ketoprofen glucuronides to albumin: characterization of the site and the mechanism. Drug Metabolism and Disposition, 24, 1050–1057.
  • REWCASTLE, G. W., ATWELL, G. J., BAGULEY, B. C., CALVELEY, S. B. and DENNY, W. A., 1989, Potential antitumour agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumour in vivo. Journal Medicinal Chemistry, 32, 793–799.
  • REWCASTLE, G. W., KESTELL, P., BAGULEY, B. C. and DENNY, W. A., 1990, Light-induced breakdown of flavone acetic acid and xanthenone analogues in solution. Journal of the National Cancer Institute, 82, 528–529.
  • SALLUSTIO, B. C., FAIRCHILD, B. A. and PANNALL, P. R., 1997a, Interaction of human serum albumin with the electrophilic metabolite 1-0-gemfibrozil-b-D-glucuronide. Drug Metabolism and Disposition, 25, 55–60.
  • SALLUSTIO, B. C., HARKIN, L. A., MANN, M. C., KRIVICKAS, S. J. and BURCHAM, P. C., 1997b, Genotoxicity of acyl glucuronide metabolites formed from clofibric acid and gemfibrozil: a novel role for phase II-mediated bioactivation in the hepatocarcinogenicity of the parent aglycone. Toxicology and Applied Pharmacology, 147, 459–464.
  • SALLUSTIO, B. C., KNIGHTS, K. M., ROBERTS, B. J. and ZACEST, R., 1991, In vivo covalent binding of clobibric acid to human plasma proteins and rat liver proteins. Biochemical Pharmacology, 42, 1421–1425.
  • SEMMES, R. L. O. and SHEN, D. D., 1990, Nonlinear binding of valproic acid (VPA) and E-D2-valproic acid to rat plasma proteins. Pharmaceutical Research, 7, 461–467.
  • SMITH, P. C., BENET, L. Z. and MCDONAGH, A. F., 1986, Irreversible binding of zomepirac to plasma protein in vitro and in vivo. Journal of Clinical Investigation, 77, 934–939.
  • SMITH, P. C., BENET, L. Z. and MCDONAGH, A. F., 1990, Covalent binding of zomepirac glucuronide to proteins: evidence for a Schiff base mechanism. Drug Metabolism and Disposition, 18, 639-644. SMITH, P. C., SONG, W. Q. and RODRIGUEZ, R. J., 1992, Covalent binding of etodolac acyl glucuronide to albumin in vitro. Drug Metabolism and Disposition, 20, 962–965.
  • SMITH, P. K., KROHN, R. I., HERMANSON, G. T., MALLIA, A. K., GARTER, F. H., PROVENZANO, M. D., FUJIMOTO, E. K., GOEKE, N. M., OLSON, B. J. and KLENK, D. C., 1985, Measurement of protein using bicinchoninic acid. Annals of Biochemistry, 150, 76–85.
  • SPAHN-LUGGUTH, H. and BENET, L. Z., 1992, Acyl glucronide revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metabolism Review, 24, 5–48.
  • SPERKER, B., BACKMAN, J. T. and KROEMER, H. K., 1997, The role of [3-glucuronidase in drug disposition and drug targeting in humans. Clinical Pharmacokinetics, 33, 18–31.
  • THOMSEN, L. L., CHING, L. M., ZHUANG, L., GAVIN, J. B. and BAGULEY, B. C., 1991, Tumor-dependent increased plasma nitrate concentrations as an indication of the antitumor effect of flavone-8-acetic acid and analogues in mice. Cancer Research, 51, 77–81.
  • VAN BREEMEN, R. B. and FENSEL, A. U., 1985, Acylation of albumin by 1-0-acyl glucuronide. Drug Metabolism and Disposition, 13, 318–320.
  • WEBSTER, L. K., EHAs, A. G., KESTELL, P. and REWCASTLE, G. W., 1995, Metabolism and elimination of 5,6-dimethylxanthenone-4-acetic acid in the isolated perfused rat liver. Drug Metabolism and Disposition, 23, 363–368.
  • WHITING, J. F., NARCISO, J. P., CHAPMAN, V., RANSIL, B. J., SWANK, R. T. and GOLLAN, J. L., 1993, Deconjugation of bilirubin-IXa glucuronides: a physiologic role of hepatic microsomal /3-glucuronidase. Journal of Biological Chemistry, 268, 231 97–23201.
  • WILLIAM, A. M. and DICKSON, R. G., 1994, Modulation of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro. Biochemical Pharmacology, 47, 457–467.
  • YAMAOKA, K., NAKAGAWA, T. and UNO, T., 1978, Application of Akaike's information criterion (AIC) in the evaluation of linear pharmacokinetic equations. Journal of Pharmacokinetics and Biopharmaceutics, 6, 165–167.
  • ZHOU, S. F., PAXTON, J. W., TINGLE, M. D. and KESTELL, P., 2000, Identification of the human liver cytochrome P450 isozyme responsible for the 6-methylhydroxylation of the novel anticancer drug 5,6-dimethylxanthenone-4-acetic acid. Drug Metabolism and Disposition, 28, 1449–1456.
  • ZHOU, S. F., PAXTON, J. W., TINGLE, M. D., McCALL, J. and KESTELL, P., 1999, Determination of two major metabolites of the novel anti-tumour agent 5,6-dimethylxanthenone-4-acetic acid in hepatic microsomal incubations by high-performance liquid chromatography with fluorescence detection. Journal of Chromatography (B), 734, 129–136.
  • ZIA-AMIRHOSSEINI, P., OJINGWA, J. C., SPAHN-LUGGUTH, H., MCDONAGH, A. F. and BENET, L. Z., 1994, Enhanced covalent binding of tolmetin to proteins in humans after multiple dosing. Clinical Pharmacology and Therapeutics, 55, 21–27.

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