Potential urinary and plasma biomarkers of peroxisome proliferation in the rat: identification of N-methylnicotinamide and N-methyl-4-pyridone-3-carboxamide by ¹H nuclear magnetic resonance and high performance liquid chromatography

Reference

• ASHBY, J., BRADY, A., ELCOMBE, C. R, ELLIOTT, B. M., ISHMAEL, J., ODUM, J., TUGWOOD, J. D., KETTLE, S. and PURCHASE, I. F. H. 1994, Mechanistically-based human hazard assessment of peroxisome proliferator-induced hepatocarcinogenesis. Human and Experimental Toxicology, 13 (Supplement 2), S1 —S117.
   Google Scholar
• BEIER, K 1992, Light microscopic morphometric analysis of peroxisomes by automatic image analysis: advantages of immunostaining over the alkaline DAB method. Journal of Histochemistry and Cytochemistry, 40, 115–121.
   PubMed Web of Science ®Google Scholar
• BENTLEY, P., CALDER, I., ELCOMBE, C., GRASSO, P., STRINGER, D. and WIEGAND, H. J. 1993, Hepatic peroxisome proliferation in rodents and its significance for humans. Food and Chemical Toxicology, 31, 857–907.
   PubMed Web of Science ®Google Scholar
• BERNOFSKY, C. 1979, New synthesis of the 4- and 6-pyridones of 1-methylnicotinamide and 1-methylnicotinic acid (trigonelline). Analytical Biochemistry, 96, 189–200.
   PubMed Web of Science ®Google Scholar
• BROWN, R R. 1994, Tryptophan metabolism: a review. In L-Tryptophan: Current Prospects in Medicine and Drug Safety, edited by W. Kochen and H. Steinhart (Berlin: Walter de Gruyter & Co), pp. 17-30. BYBEE, A., STYLES, J. A., BECK, S. L. and BLACKBURN, D. 1990, Mitosis and histopathology in rat liverduring methylclofenapate induced hyperplasia. Cancer Letters, 52, 95–100.
   Google Scholar
• Cuomo, R., PumEo, R., SARNELLI, G., CAPUANO, G. and Burn:LT.0N, G. 1995, Nicotinamide methylation and hepatic energy reserve: a study by liver perfusion in vitro. Journal of Hepatology, 23, 465–470.
   Google Scholar
• DELucA, J. G., DOEBBER, T. W., KELLY, L. J., KEMP, R K., MOLON-NOBLOT, S., SAHOO, S. P., VENTRE, J., Wu, M. S., PETERS, J. M., GONZALEZ, F. J. and MOLLER, D. E. 2000, Evidence for peroxisome proliferator-activated receptor (PPAR)alpha-independent peroxisome proliferation: effects of PPARgammaidelta-specific agonists in PPARalpha-null mice. Molecular Pharmacology, 58, 470 — 476.
   Google Scholar
• DEPREZ, S., SWEATMAN, B. C., CONNOR, S. C., HASELDEN, J. N. and WATERFIELD, C. J. 2003, Optimisation of collection, storage and preparation of rat plasma for 1H NMR spectroscopic analysis in toxicology studies to determine inherent variation in biochemical profiles. Journal of Pharmaceutical and Biomedical Analysis, 30, 1297–1310.
   Web of Science ®Google Scholar
• DuNNETr, C. W. 1955, A multiple comparisons procedure for comparing several treatments with a control. Journal of the American Statistical Association, 50, 1096–1121.
   Web of Science ®Google Scholar
• EGASHIRA, Y, YAMAMIYA, Y. and SANADA, H. 1992, Effects of various dietary fatty acids on a-amino-13-carboxymuconate-c-semialdehyde decarboxylase activity in rat liver. Bioscience, Biotechnology, and Biochemistry, 56, 2015–2019.
   PubMed Web of Science ®Google Scholar
• EGASHIRA, Y, OGAWARA, R., OHTA, T. and SANADA, H. 1994, Suppression of hepatic oc-amino-I3-carboxymuconate-c-semialdehyde decarboxylase (ACMSD) activity by linoleic acid in relation to its induction by glucocorticoids and dietary protein. Bioscience, Biotechnology, and Biochemistry, 58, 339–343.
   PubMed Web of Science ®Google Scholar
• EGASHIRA, Y, KOMINE, T., OHTA, T., SHIBATA, K. and SANADA, H. 1997, Change of tryptophan-niacin metabolism in u-galactosamine-induced liver injury in rat. Journal of Nutritional Science and Vitaminology, 43, 233–239.
   PubMed Web of Science ®Google Scholar
• EGASHIRA, Y., TANABE, A., OHTA, T. and SANADA, H. 1998, Dietary linoleic acid alters alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase (ACMSD), a key enzyme of niacin synthesis from tryptophan, in the process of protein expression in rat liver. Journal of Nutritional Sciences and Vitaminology, 44, 129–136.
   PubMed Web of Science ®Google Scholar
• ELCOMBE, C. R, BELL, D. R, ELIAS, E., HASMALL, S. C. and PLANT, J. P. 1997, Peroxisome proliferators: species differences in response of primary hepatocyte cultures. Annals of the New York Academy of Sciences, 804, 628–635.
   Web of Science ®Google Scholar
• FUKUWATARI, T, MORLKAWA, Y., HAYAKAWA, F., STJGIMOTO, E. and SHIBATA, K 2001, Influence of adenine-induced renal failure on tryptophan-niacin metabolism in rats. Bioscience, Biotechnology, and Biochemistry, 65, 2154–2161.
   Google Scholar
• FUKUWATARL T., Suzuxi, Y, SUGIMOTO, E. and SHIBATA, K. 2002, Elucidation of the toxic mechanism of the plasticizers, phthalic acid esters, putative endocrine disrupters: effects of dietary di(2-ethylhexyl)phthalate on the metabolism of tryptophan to niacin in rats. Bioscience, Biotechnology, and Biochemistry, 66, 705–710.
   PubMed Web of Science ®Google Scholar
• HANEFELD, M., KEMMER, C. and KADNER, E. 1983, Relationship between morphological changes and lipid-lowering action of p -chlorphenoxyisobutyric acid (CPIB) on hepatic mitochondria and peroxisomes in man. Atherosclerosis, 46, 239–246.
   PubMed Web of Science ®Google Scholar
• HENKE, B. R., BLANcHARD, S. G., BRACKEEN, M. F., BROWN, K K, COBB, J. E., COLLINS, J. L., HARRINGTON, W. W. JR, HASHIM, M. A., HULL-RYDE, E. A., KALDOR, I., KLIEWER, S. A., LAKE, D. H., LEESNITZER, L M., LEHMANN, J. M., LENHARD, J. M., ORBAND-MILLER, L. A., MILLER, J. F., MOOK, R A. JR, NOBLE, S. A., OLIVER, W. JR, PARKS, D. J., PLUNKET, K D., SZEWCZYK, J. R. and Wn I SON, T. M. 1998, N-(2-Benzoylpheny1)-E-tyrosine PPARgamma agonists. 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents. Journal of Medicinal Chemistry, 41, 5020–5036.
   Google Scholar
• HOLLINSHEAD, M. and MEIJER, J. 1988, Immunocytochemical analysis of soluble epoxide hydrolase and catalase in mouse and rat hepatocytes demonstrates a peroxisomal localization before and after clofibrate treatment. European Journal of Cell Biology, 46, 394–402.
   PubMed Web of Science ®Google Scholar
• IARC. 1995, Peroxisome Proliferation and its Role in Carcinogenesis IARC Technical Report No 24 (Lyon: International Agency for Research on Cancer).
   Google Scholar
• IKEDA, M., TSUJI, H., NAKAMUR, S., ICHIYAMA, A., NISHIZUKA, Y. and HAYAISHI, O. 1965, Studies on the biosynthesis of nicotinamide adenine dinucleotide (II). Journal of Biological Chemistry, 240, 1395–1401.
   PubMed Web of Science ®Google Scholar
• JANSEN, E. H. J. M., VAN DEN BERG, R H., BOLNK, A. B. T. J., HEGGER, C. and MEULENBELT, J. 1995, A new physiological biomarker for nitrate exposure in humans. Toxicology Letters, 77, 265–269. LAKE, B. G. 1995a, Mechanisms of hepatocarcinogenicity of peroxisome-proliferating drugs and chemicals. Annual Review of Pharmacology and Toxicology, 35, 483–507.
   Google Scholar
• LAKE, B. G. 1995b, Peroxisome proliferation: current mechanisms relating to non-genotoxic carcinogenesis. Toxicology Letters, 82–83, 673–681.
   Google Scholar
• LALWANI, N. D., REDDY, M. K, GHosx, S., BARNARD, S. D., MOLELLO, J. A. and REDDY, J. K. 1985, Induction of fatty acid I3-oxidation and peroxisome proliferation in the liver of Rhesus monkeys by DL-040, a new hypolipidemic agent. Biochemical Pharmacology, 34, 3473–3482.
   PubMed Web of Science ®Google Scholar
• LEE, Y. C., GHOLSON, R. K and RAICA, N. 1969, Isolation and identification of two new nicotinamide metabolites. Journal of Biological Chemistry, 244, 3277–3282.
   PubMed Web of Science ®Google Scholar
• MOODY, D. E., REDDY, J. K, LAKE, B. G., Pops, J. A. and REESE, D. H. 1991, Peroxisome proliferation and non-genotoxic carcinogenesis: commentary on a symposium. Fundamental and Applied Toxicology, 16, 233–248.
   PubMed Web of Science ®Google Scholar
• MUSFELD, C., BIOLLAZ, J., BELAZ, N., KESSELRIG, U. W and DECOSTERD, L. A. 2001, Validation of an HPLC method for the determination of urinary and plasma levels of N-methylnicotinamide, an endogenous marker of renal cationic transport and plasma flow. Journal of Pharmaceutical and Biomedical Analysis, 24, 391–404.
   PubMed Web of Science ®Google Scholar
• NicHotis, A. W, NICHOLSON, J. K, HASEIMEN, J. N. and WATERFIELD, C. J. 2000, A metabonomic approach to the investigation of drug induced phospholipidosis: an NMR spectroscopy and pattern recognition study. Biomarkers, 5, 410–423.
   PubMed Web of Science ®Google Scholar
• NICHOLSON, J. K., HIGHAM, D. P., TIMBRELL, J. A. and SADLER, P. J. 1989, Quantitative high-resolution NMR urinalysis studies on the biochemical effects of cadmium in the rat. Molecular Pharmacology, 36, 398–404.
   PubMed Web of Science ®Google Scholar
• NICHOLSON, J. K, LINDON, J. C. and HOUVIES, E. 1999, `Metabonomics': understanding the metabolic responses of living systems to pathophysiological stimuli via multivariate statistical analysis of biological NMR spectroscopic data. Xenobiotica, 29, 1181–1189.
   PubMed Web of Science ®Google Scholar
• OIKAWA, I. and NOVIKOFF, P. M. 1995, Catalase-negative peroxisomes: transient appearance in rat hepatocytes during liver regeneration after partial hepatectomy. American Journal of Pathology, 146, 673–687.
   PubMed Web of Science ®Google Scholar
• PALM-EY, C. J., LEDwrrii, B. J. and KAPLANSKI, C. 2002, Peroxisome proliferators activate growth regulatory pathways largely via peroxisome proliferator-activated receptor a-independent me-chanisms. Cellular Signalling, 14, 351–358.
   Google Scholar
• Pump°, R., SARNELLI, G., SPINELLA, A., BUDILLON, G. and Cuomo, R 2001, The metabolism of nicotinamide in human liver cirrhosis: a study on N-methylnicotinamide and 2-pyridone-5-carboxamide production. American Journal of Gastroenterology, 96, 1183–1187.
   Google Scholar
• QUALLS, C. W., HOIVLK, D. J., SANTOSTEFANO, M. J., BROWN, H. R., ANDERSON, S. P., OTT, R. J., MIRABILE, R. C., OLIVER, B. R., MUDD, P. N., KIMBROUGH, C. L. and MILLER, R. T. 2003, Fibrates induce peroxisomal and mitochondrial proliferation in cynomolgus monkeys without causing cell cycle alterations or oxidative stress. The Toxicologist, in press.
   Google Scholar
• REDDY, J. K, LALWANI, N. D., QURESHI, S. A., REDDY, M. K. and MOEHLE, C. M. 1984, Induction of hepatic peroxisome proliferation in non-rodent species including primates. American Journal of Pathology, 114, 171–183.
   PubMed Web of Science ®Google Scholar
• ROGLANS, N., BEEIroo, A., RODRIGUEZ, C., CABRERO, A., Novi., F., Ros, E., ZAMBON, D. and LAGUNA, J. C. 2002, Fibrate treatment does not modify the expression of acyl coenzyme A oxidase in human liver. Clinical Pharmacology and Therapeutics, 72, 692–701.
   Google Scholar
• ROMACH, E. H., SHENK, J. L, OTT, R J., Wu I SON, T. M. and MILLER, R. T. 2002, Hepatic effects of PPARS are distinct from PPARa. The Toxicologist, 66, 261.
   Google Scholar
• Ross, C. R, DrEzi-CHomEry, F. and ROCH-RAMEL, F. 1975, Renal excretion of N(1-methylnicotina-mide in the rat. American Journal of Physiology, 228, 1641–1645.
   Google Scholar
• SANINS, S. M., NICHOLSON, J. K., ELCOMBE, C. and TIMBRELL, J. A. 1990, Hepatotoxin-induced hypertaurinuria: a proton NMR study. Archives of Toxicology, 64, 407–411.
   PubMed Web of Science ®Google Scholar
• SHIBATA, K 1989, Fate of excess nicotinamide and nicotinic acid differs in rats. Vitamins, 119, 892-895. SHIBATA, K. and MATSUO, H. 1989a, Inhibition of N-methylnicotinamide oxidase activity by a large nicotinamide injection into rats. Agricultural and Biological Chemistry, 53, 2031–2036.
   Web of Science ®Google Scholar
• SHIBATA, K and MATSUO, H. 1989b, Inhibition of N-methylnicotinamide oxidase activity by a large amount of N-methylnicotinamide injected into rats. Agricultural and Biological Chemistry, 53, 2393–2397.
   Web of Science ®Google Scholar
• SHIBATA, K., KAKEHI, H. and MATSUO, H. 1990, Niacin catabolism in rodents. Journal of Nutritional Science and Vitaminology, 36, 87–98.
   PubMed Web of Science ®Google Scholar
• SHIBATA, K, KONDO, T., MARUGAMI, M. and UMEZAWA, C. 1996a, Increased conversion ratio of tryptophan to niacin by the administration of clofibrate, a hypolipidemic drug, to rats. Bioscience, Biotechnology, and Biochemistry, 60, 1455–1459.
   PubMed Web of Science ®Google Scholar
• SHIBATA, K., SHIMADA, H. and TAGUCHI, H. 1996b, Fate of nicotinamide differs due to an intake of nicotinamide. Bioscience, Biotechnology, and Biochemistry, 60, 1204–1206.
   PubMed Web of Science ®Google Scholar
• SHIN, M., Mom, Y, KIMURA, A., FunrA, Y, YOSHIDA, K, SANO, K. and UMEZAWA, C. 1996, NAD + biosynthesis and metabolic fluxes of tryptophan in hepatocytes isolated from rats fed a chlofibrate-containing diet. Biochemical Pharmacology, 52, 247–252.
   PubMed Web of Science ®Google Scholar
• SHIN, M., IWAMOTO, N., YAmAsHrrA, M., SANO, K and UMEZAWA, C. 1998a, Pyridine nucleotide levels in liver of rats fed chlofibrate- or pyrazinamide-containing diets. Biochemical Pharmacology, 55, 367–371.
   Google Scholar
• SHIN, M., AsADA, S., Mizumom, N., SANO, K and UMEZAWA, C. 1998b, Effect of thioridazine or chlorpromazine on increased hepatic NAD + levels in rats fed clofibrate, a hypolipidaemic drug. Journal of Pharmaceutical Pharmacology, 50, 431–436.
   Google Scholar
• SHIN, M., NAKAKrrA, S., HASHIMOTO, C., SANO, K. and UMEZAWA, C. 1998c, NAD + biosynthesis from tryptophan in the presence of nicotinic acid or vice versa by rat hepatocytes - effect of clofibrate-feeding. International Journal for Vitamin and Nutrition Research, 68, 104–108.
   PubMed Web of Science ®Google Scholar
• SHIN, M., OHNISHI, M., IGUCHI, S., SANO, K and UMEZAWA, C. 1999a, Peroxisome-proliferator regulates key enzymes of the tryptophan-NAD + pathway. Toxicology and Applied Pharmacology, 158, 71–80.
   Google Scholar
• SHIN, M., SANO, K and UMEZAWA, C. 1999b, Effects of peroxisome-proliferators on the TRP-NAD pathway. Advances in Experimental Medicine and Biology, 467, 333–340.
   Google Scholar
• TAMULEVICIUS, P. and STREFFER, C. 1984, N-Methylnicotinamide as a possible prognostic indicator of recovery from leukaemia in patients treated with total-body irradiation and bone marrow transplants. Strahlentherapie, 160, 249–254.
   PubMedGoogle Scholar
• TANABE, A., EGASHIRA, Y., FUKUOKA, S., SHIBATA, K. and SANADA, H. 2002, Expression of rat hepatic 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase is affected by a high protein diet and by streptozotocin-induced diabetes. Journal of Nutrition, 132, 1153–1159.
   PubMed Web of Science ®Google Scholar
• TUCKER, M. J. and ORTON, T. C. 1995, Comparative Toxicology of Hypolipidaemic Fibrates (London: Taylor SE Francis).
   Google Scholar
• Wom, S., ANTTI, H., LINDGREN, F. and OHMAN, J. 1998, Orthogonal signal correction of near-infrared spectra. Chemometrics and Intelligent Laboratory Systems, 44, 175–185.
   Web of Science ®Google Scholar
• WOLF, H. 1974, Studies on tryptophan metabolism in man: the effect of hormones and vitamin B6 on urinary excretion of metabolites of the kynurenine pathway. Scandinavian Journal of Clinical and Laboratory Investigation Supplementum, 136, 1–186.
   PubMedGoogle Scholar
• YUYAMA, S. and Suzulu, T. 1985, Isolation and identification of N-methylnicotinic acid (Trigonelline) from rat urine. Journal of Nutritional Science and Vitaminology, 31, 157–167.
   PubMed Web of Science ®Google Scholar