Detection of mono- and di-hexoses as metabolites of 4-bromoaniline using HPLC-TOF-MS/MS

Reference

• ABOU-SHAKRA, F. R., SAGE, A. B., CASTRO-PEREZ, J., NICHOLSON, J. K., LINDON, J. C., SCARFE, G. B. and WILSON, I. D., 2002, High-performance liquid chromatography-UV diode array, inductively coupled plasma mass spectrometry (ICPMS) and orthogonal acceleration time-of-flight mass spectrometry (oa-TOFMS) applied to the simultaneous detection and identification of metabolites of 4-bromoaniline in rat urine. Chromatographia, 55S, S9—S13.
   Google Scholar
• ADAMS, P. E., FEIL, V. J. and PAULSON, G. D., 1996, Metabolism of 14C-sulpadimethoxane in swine. Xenobiotica, 26, 921–933.
   PubMed Web of Science ®Google Scholar
• BOBERG, M., ANGERBAUER, R., KANHAI, W. K., KERN, A., RADTKE, M. and STEINKE, W., 1998, Biotransformation of cerivastatin in mice, rats and dogs in vivo. Drug Metabolism and Disposition, 26, 640–652.
   PubMed Web of Science ®Google Scholar
• CHMELA, Z., VESELY, J., LEMR, K., RYPKA, M., HANUS, J., HAVLICEK, L., KRYSTOF, V., MICHNOVA, L., FUKSOVA, K. and LURES, J., 2001, In vivo metabolism of 2,6,9-trisubstituted purine-derived cyclin-dependent kinase inhibitor bohemine in mice: glucosidation as the principal metabolic route. Drug Metabolism and Disposition, 29, 326–334.
   PubMed Web of Science ®Google Scholar
• CUPID, B. C., BEDDELL, C. R., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1996, Quantitative structure—metabolism relationships for substituted benzoates in the rabbit, prediction of urinary excretion of glycine and glucuronide conjugates. Xenobiotica, 26, 157–176.
   PubMed Web of Science ®Google Scholar
• CUPID, B. C., HOLMES, E., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1999, Quantitative structure—metabolism relationships (QSMR) using computational chemistry: pattern recognition analysis and statistical prediction of phase II conjugation reactions of substituted benzoic acids in the rat. Xenobiotica, 29, 22–42.
   Google Scholar
• DAHMS, M., LOTZ, R., LANG, W., RENNER, U., BAYER, E. and SPAHN-LANGGUTH, H., 1997, Elucidation of phase I and phase II metabolic pathways of rhein: species differences and their potential relevance. Drug Metabolism and Disposition, 25, 442–452.
   Google Scholar
• DUGGAN, D. E., BALDWIN, J., ARISON, B. H. and RHODES, R. E., 1974, N-glucoside formation as a detoxification mechanism in mammals. Journal of Pharmacology and Experimental Therapeutics, 190, 563–569.
   PubMed Web of Science ®Google Scholar
• GHAURI, F. Y. K., BLACKLEDGE, C. A., GLEN, R. C., LINDON, J. C., BEDELL, C. R., WILSON, I. D. and NICHOLSON, J. K., 1992, Quantitative structure—metabolism relationships for substituted benzoic acids in the rat: computational chemistry, NMR spectroscopy and pattern recognition studies. Biochemical Pharmacology, 44, 1935–1946.
   Google Scholar
• GIERA, D. D., ABDULLA, R. F., OCCOLOWITZ, J. L., DORMAN, D. E., MERTZ, J. L. and STECK, R. F., 1982, Isolation and identification of a polar sulfamethazine 'metabolite' from swine. Journal of Agricultural and Food Chemistry, 30, 260–266.
   Web of Science ®Google Scholar
• GORROD, J. W. and MANSON, D., 1986, The metabolism of aromatic amines. Xenobiotics, 16, 933–955.
   PubMed Web of Science ®Google Scholar
• KAMIMURA, H., KAWAI, R. and KUDO, H., 1988, Metabolic fate of indeloxazine: hydrochloride a-glucoside formation in rats. Xenobiotica, 18, 141–149.
   PubMed Web of Science ®Google Scholar
• KAMIMURA, H., OGATA, H. and TAKAHARA, H., 1992, oc-Glucoside formation of xenobiotics by rat liver a-glucosidases. Drug Metabolism and Disposition, 20, 309–315.
   PubMedGoogle Scholar
• KIRKMAN, S. K., ZHANG, M. Y., HORWATT, P. M. and SCATINA, J., 1998, Isolation and identification of bromfenac glucoside from rat bile. Drug Metabolism and Disposition, 26, 720–723.
   PubMed Web of Science ®Google Scholar
• MAJOR, H. J., CASTRO-PEREZ, J., NICHOLSON, J. K. and WILSON, I. D., 2003, Characterisation of putative pentose-containing conjugates as minor metabolites of 4-bromoaniline present in the urine of rats following intraperitoneal administration. Rapid Communications in Mass Spectrometry, 17, 76–80.
   Google Scholar
• MANIS, M. 0. and BRASELTON, W. E., 1986, Metabolism of 4,4'-methylenebis(2-chloroaniline) by canine liver and kidney slices. Drug Metabolism and Disposition, 14, 166–174.
   Google Scholar
• NANO, K., ANDO, H., SUGAWARA, Y., OHASHI, M. and HARIGAYA, S., 1986, Hopantenic acid 13-glucoside as a new urinary metabolite of calcium hopantenate in dogs. Drug Metabolism and Disposition, 14, 740–745.
   PubMedGoogle Scholar
• NICHOLSON, J. K., LINDON, J. C., SCARFE, G., WILSON, I. D., ABOU-SHAKRA, F., CASTRO-PEREZ, J., EATON, A. and PREECE, S., 2000, High-performance liquid chromatography and inductively coupled plasma mass spectrometry (HPLC-ICP-MS) for the analysis of xenobiotic metabolites in rat urine: application to the metabolites of 4-bromoaniline. Analyst, 125, 235–236.
   Google Scholar
• PARKS, 0. W., 1984, Evidence for the transformation of sulfamethazine to its N4-glucopyranosyl derivative in swine liver during frozen storage. Journal of the Association of Official Analytical Chemists, 67, 566–569.
   Google Scholar
• PAULSON, G. D., GRIDDINGS, J. M., LAMOREUX, C. H., MANSAGER, E. R. and STRUBLE, C. B., 1981, The isolation and identification of 14C-sulfamethazine {4-amino-N-(4,6-dimethy1-2-pyrimidinyl) [14C]benzensulfonamidel metabolites in the tissues and excreta of swine. Drug Metabolism and Disposition, 9, 142–146.
   PubMed Web of Science ®Google Scholar
• RADOMSKI, J. L., 1979, The primary aromatic amines: their biological properties and structure—activity relationships. Annual Reviews in Pharmacological Toxicology, 19, 129–157.
   PubMed Web of Science ®Google Scholar
• SAMARA, E., BIALER, M. and HARVEY, D. J., 1990, Identification of glucose conjugates as major urinary metabolites of cannabidiol in the dog. Xenobiotica, 20, 177–183.
   PubMed Web of Science ®Google Scholar
• SCARFE, G. B., WILSON, I. D., WARNE, M. A., HOLMES, E., NICHOLSON, J. K. and LINDON, J. C., 2002a, Structure—metabolism relationships of substituted anilines: prediction of N-acetylation and N-oxanillic acid formation using computational chemistry. Xenobiotica, 32, 267–277.
   PubMedGoogle Scholar
• SCARFE, G. B., NICHOLSON, J. K., LINDON, J. C., WILSON, I. D., TAYLOR, S., CLAYTON, E. and WRIGHT, B., 2002b, Identification of the urinary metabolites of 4-bromoaniline and 4-bromo-[carbony/-13q-acetanilide in the rat. Xenobiotica, 32, 325–337.
   PubMedGoogle Scholar
• SOINE, W. H., SOINE, P. J., OVERTON, B. W. and GARRETTSON, L. K., 1986, Product enatioselectivity in the N-glucosylation of amobarbital. Drug Metabolism and Disposition, 14, 619–621.
   PubMed Web of Science ®Google Scholar
• STOBIECKI, M., 2000, Application of mass spectrometry for identification and structural studies of fiavonoid glycosides. Phytochemisty, 54, 327–256.
   Google Scholar
• TANG, B. K., KAKLow, W. and GREY, A. A., 1979, Metabolic fate of phenobarbital in man. N-glucoside formation. Drug Metabolism and Disposition, 7, 315–318.
   PubMed Web of Science ®Google Scholar
• TANG, B. K., KAKLow, W. and GREY, A. A., 1978, Amobarbital metabolism in man: N-glucoside formation. Research Communications in Chemical Pathology and Pharmacology, 21, 45–53.
   PubMedGoogle Scholar
• TJORNELUND, J., HANSEN, S. H. and CORNETT, C., 1989, New metabolites of the drug 5-aminosalicylic acid, I: N-b-D-glucopyranosy1-5-aminosalicylic acid. Xenobiotica, 19, 891–899.
   PubMed Web of Science ®Google Scholar
• TURCANT, A., CAILLEUX, A., LE BOUIL, A., ALLAIN, P., HARRY, P. and RENAULT, A., 2000, Acute metobromuron poisoning with severe methaemoglobinemia, identification of four metabolites in plasma and urine by LC-DAD, LC-ESI-MS and LC-ESI-MS-MS. Journal of Analytical Toxicology, 24, 157–163.
   PubMedGoogle Scholar