Polyamines are traps for reactive intermediates in furan metabolism

Chemical Research in Toxicology

Volumn 24, Issue 11, 2011, Pages 1924-1936

  Peterson, Lisa A ^a,b   Phillips, Martin B ^a,b   Lu, Ding ^b,c   Sullivan, Mathilde M ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (S GLUTATHIONYL)SUCCINALDEHYDE; ACETYLCYSTEINE DERIVATIVE; ALDEHYDE DERIVATIVE; FURAN; LYSINE; ORNITHINE; POLYAMINE DERIVATIVE; PUTRESCINE; SPERMIDINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CELL LEVEL; CONTROLLED STUDY; CROSS LINKING; IN VIVO STUDY; LIVER CELL; MALE; METABOLISM; NONHUMAN; RAT; URINE LEVEL;

ACETYLCYSTEINE; ALDEHYDES; ANIMALS; BIOTRANSFORMATION; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; ENVIRONMENTAL POLLUTION; FURANS; GLUTAMINE; GLUTATHIONE; HEPATOCYTES; HUMANS; LIVER; LYSINE; MASS SPECTROMETRY; ORNITHINE; OXIDATION-REDUCTION; PUTRESCINE; PYRROLES; RATS; SPERMIDINE;

RATTUS; RODENTIA;

EID: 81755172321     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200273z     Document Type: Article

References (56)

1. 1 Mice, Vol. NTP Technical Report No. 402, US Department of Health and Human Services, Public Health Service, National Institutes of Health, Research Triangle Park, NC.
2. International Agency for Research on Cancer (1995) Furan, in Dry Cleaning, Some Chlorinated Solvents and Other Industrial Chemicals, p 393, IARC, Lyon, France.
3. Perez, L. C. and Yaylayan, V. A. (2004) Origin and mechanistic pathways of formation of the parent furan: a food toxicant J. Agric. Food Chem. 52, 6830-6836
4. National Toxicology Program (2005) 11th Report on Carcinogens, US Department of Health and Human Services, Washington DC.
5. Carfagna, M. A., Held, S. D., and Kedderis, G. L. (1993) Furan-induced cytolethality in isolated rat hepatocytes: Correspondence with in vivo dosimetry Toxicol. Appl. Pharmacol. 123, 265-273 (Pubitemid 23359269)
6. Mugford, C. A., Carfagna, M. A., and Kedderis, G. L. (1997) Furan-mediated uncoupling of hepatic oxidative phosphorylation in Fischer-344 rats: an early event in cell death Toxicol. Appl. Pharmacol. 144, 1-11 (Pubitemid 27208332)
7. Chen, L. J., Hecht, S. S., and Peterson, L. A. (1995) Identification of cis -2-butene-1,4-dial as a microsomal metabolite of furan Chem. Res. Toxicol. 8, 903-906
8. Peterson, L. A., Cummings, M. E., Vu, C. C., and Matter, B. A. (2005) Glutathione trapping to measure microsomal oxidation of furan to cis -2-butene-1,4-dial Drug Metab. Dispos. 33, 1453-1458 (Pubitemid 41323992)
9. Peterson, L. A., Cummings, M. E., Chan, J. Y., Vu, C. C., and Matter, B. A. (2006) Identification of a cis -2-butene-1,4-dial-derived glutathione conjugate in the urine of furan-treated rats Chem. Res. Toxicol. 19, 1138-1141 (Pubitemid 44454029)
10. Kellert, M., Wagner, S., Lutz, U., and Lutz, W. K. (2008) Biomarkers of furan exposure by metabolic profiling of rat urine with liquid chromatography-tandem mass spectrometry and principal component analysis Chem. Res. Toxicol. 21, 761-768 (Pubitemid 351498054)
11. Lu, D., Sullivan, M. M., Phillips, M. B., and Peterson, L. A. (2009) Degraded protein adducts of cis -2-butene-1,4-dial are urinary and hepatocyte metabolites of furan Chem. Res. Toxicol. 22, 997-1007
12. Lu, D. and Peterson, L. A. (2010) Identification of furan metabolites derived from cysteine- cis -2-butene-1,4-dial-lysine cross-links Chem. Res. Toxicol. 23, 142-151
13. Igarashi, K. and Kashiwagi, K. (2010) Modulation of cellular function by polyamines Int. J. Biochem. Cell Biol. 42, 39-51
14. Gerner, E. W. and Meyskens, F. L., Jr. (2004) Polyamines and cancer: old molecules, new understanding Nat. Rev. Cancer 4, 781-792 (Pubitemid 39331150)
15. Casero, R. A., Jr. and Marton, L. J. (2007) Targeting polyamine metabolism and function in cancer and other hyperproliferative diseases Nat. Rev. Drug Discov. 6, 373-390 (Pubitemid 46705201)
16. Casero, R. A. and Pegg, A. E. (2009) Polyamine catabolism and disease Biochem. J. 421, 323-338
17. 4]furan J. Labelled Compd. Radiopharm. 48, 117-121 (Pubitemid 40313565)
18. 2-etheno-2′-deoxyguanosine adducts by cis- 2-butene-1,4-dial, a reactive metabolite of furan Chem. Res. Toxicol. 17, 1607-1613 (Pubitemid 39665552)
19. Chen, L. J., Hecht, S. S., and Peterson, L. A. (1997) Characterization of amino acid and glutathione adducts of cis -2-butene-1,4-dial, a reactive metabolite of furan Chem. Res. Toxicol. 10, 866-874 (Pubitemid 27350045)
20. Peterson, L. A., Naruko, K. C., and Predecki, D. (2000) A reactive metabolite of furan, cis -2-butene-1,4-dial, is mutagenic in the Ames assay Chem. Res. Toxicol. 13, 531-534 (Pubitemid 30491112)
21. Berry, M. N. and Friend, D. S. (1969) High-yield preparation of isolated rat liver parenchymal cells: a biochemical and fine structural study J. Cell Biol. 43, 506-520
22. Wilkinson, C. F., Hetnarski, K., Denison, M. S., and Guengerich, F. P. (1983) Selectivity of 1-phenylimidazole as a ligand for cytochrome P-450 and as an inhibitor of microsomal oxidation Biochem. Pharmacol. 32, 997-1003 (Pubitemid 13084007)
23. Sava, I. G., Battaglia, V., Rossi, C. A., Salvi, M., and Toninello, A. (2006) Free radical scavenging action of the natural polyamine spermine in rat liver mitochondria Free Radical Biol. Med. 41, 1272-1281 (Pubitemid 44479828)
24. Tadolini, B. (1988) Polyamine inhibition of lipoperoxidation. The influence of polyamines on iron oxidation in the presence of compounds mimicking phospholipid polar heads Biochem. J. 249, 33-36
25. Lovaas, E. and Carlin, G. (1991) Spermine: an anti-oxidant and anti-inflammatory agent Free Radical Biol. Med. 11, 455-461
26. Ha, H. C., Sirisoma, N. S., Kuppusamy, P., Zweier, J. L., Woster, P. M., and Casero, R. A., Jr. (1998) The natural polyamine spermine functions directly as a free radical scavenger Proc. Natl. Acad. Sci. U.S.A 95, 11140-11145 (Pubitemid 28450095)
27. Rider, J. E., Hacker, A., Mackintosh, C. A., Pegg, A. E., Woster, P. M., and Casero, R. A., Jr. (2007) Spermine and spermidine mediate protection against oxidative damage caused by hydrogen peroxide Amino. Acids 33, 231-240 (Pubitemid 47222959)
28. Belle, N. A., Dalmolin, G. D., Fonini, G., Rubin, M. A., and Rocha, J. B. (2004) Polyamines reduces lipid peroxidation induced by different pro-oxidant agents Brain Res. 1008, 245-251 (Pubitemid 38624055)
29. Norikura, T., Kojima-Yuasa, A., Opare, K. D., and Matsui-Yuasa, I. (2007) Protective effect of gamma-aminobutyric acid (GABA) against cytotoxicity of ethanol in isolated rat hepatocytes involves modulations in cellular polyamine levels Amino Acids 32, 419-423 (Pubitemid 46559574)
30. Yoshida, M., Tomitori, H., Machi, Y., Hagihara, M., Higashi, K., Goda, H., Ohya, T., Niitsu, M., Kashiwagi, K., and Igarashi, K. (2009) Acrolein toxicity: Comparison with reactive oxygen species Biochem. Biophys. Res. Commun. 378, 313-318
31. Pignatti, C., Tantini, B., Stefanelli, C., and Flamigni, F. (2004) Signal transduction pathways linking polyamines to apoptosis Amino Acids 27, 359-365 (Pubitemid 40110081)
32. Pegg, A. E. (2009) Mammalian polyamine metabolism and function IUBMB Life 61, 880-894
33. Toninello, A., Salvi, M., and Mondovi, B. (2004) Interaction of biologically active amines with mitochondria and their role in the mitochondrial-mediated pathway of apoptosis Curr. Med. Chem. 11, 2349-2374 (Pubitemid 39172354)
34. Wu, C., Kennedy, D. O., Yano, Y., Otani, S., and Matsui-Yuasa, I. (1999) Thiols and polyamines in the cytoprotective effect of taurine on carbon tetrachloride-induced hepatotoxicity J. Biochem. Mol. Toxicol. 13, 71-76 (Pubitemid 129705377)
35. Schipper, R. G., Penning, L. C., and Verhofstad, A. A. (2000) Involvement of polyamines in apoptosis. Facts and controversies: effectors or protectors? Semin. Cancer Biol. 10, 55-68 (Pubitemid 30391957)
36. Casero, R. A., Jr. and Woster, P. M. (2009) Recent advances in the development of polyamine analogues as antitumor agents J. Med. Chem. 52, 4551-4573
37. Clements, R. L., Holt, A., Gordon, E. S., Todd, K. G., and Baker, G. B. (2004) Determination of rat hepatic polyamines by electron-capture gas chromatography J. Pharmacol. Toxicol. Methods 50, 35-39 (Pubitemid 38844999)
38. Marce, M., Brown, D. S., Capell, T., Figueras, X., and Tiburcio, A. F. (1995) Rapid high-performance liquid chromatographic method for the quantitation of polyamines as their dansyl derivatives: application to plant and animal tissues J. Chromatogr., B 666, 329-335
39. Statter, M. and Russel, A. (1978) Competitive interrelationships between lysine and arginine in rat liver under normal conditions and in experimental hyperammonemia Life Sci. 22, 2097-2101 (Pubitemid 9009381)
40. Yamashita, K. and Ashida, K. (1969) Lysine metabolism in rats fed lysine-free diet J. Nutr. 99, 267-273
41. Wahllander, A., Soboll, S., Sies, H., Linke, I., and Muller, M. (1979) Hepatic mitochondrial and cytosolic glutathione content and the subcellular distribution of GSH- S -transferases FEBS Lett. 97, 138-140
42. Zhou, S. and Decker, E. A. (1999) Ability of carnosine and other skeletal muscle components to quench unsaturated aldehydic lipid oxidation products J. Agric. Food Chem. 47, 51-55 (Pubitemid 29179622)
43. Smith, M. B. and March, J. (2007) Effects of Structure and Medium on Reactivity, in Marchs Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, pp 395-416, John Wiley & Sons, Hoboken, NJ.
44. Wang, Y. and Casero, R. A., Jr. (2006) Mammalian polyamine catabolism: a therapeutic target, a pathological problem, or both? J. Biochem. 139, 17-25 (Pubitemid 43258842)
45. Hickling, K. C., Hitchcock, J. M., Oreffo, V., Mally, A., Hammond, T. G., Evans, J. G., and Chipman, J. K. (2010) Evidence of oxidative stress and associated DNA damage, increased proliferative drive, and altered gene expression in rat liver produced by the cholangiocarcinogenic agent furan Toxicol. Pathol. 38, 230-243
46. 14C]furan in the male F344 rat J. Toxicol. Environ. Health 34, 245-257
47. Hamberger, C., Kellert, M., Schauer, U. M., Dekant, W., and Mally, A. (2010) Hepatobiliary toxicity of furan: identification of furan metabolites in bile of male f344/n rats Drug Metab. Dispos. 38, 1698-1706
48. Dawson, R. M. C., Elliott, D. C., Elliott, W. H., and Jones, K. M. (1986) Data for Biochemical Research, Clarendon Press, Oxford, U.K.
49. Prior, R. L., Clifford, A. J., and Visek, W. J. (1970) Tissue amino acid concentrations in rats during acute ammonia intoxication Am. J. Physiol. 219, 1680-1683
50. Prior, R. L. and Visek, W. J. (1972) Effects of urea hydrolysis on tissue metabolite concentrations in rats Am. J. Physiol. 223, 1143-1149
51. Cochon, A. C., Gonzalez, N., and San Martin, de Viale LC (2002) Effects of the porphyrinogenic compounds hexachlorobenzene and 3,5-diethoxycarbonyl-1,4- dihydrocollidine on polyamine metabolism Toxicology 176, 209-219 (Pubitemid 34686961)
52. Watanabe, S., Sato, S., Nagase, S., Shimosato, K., and Ohkuma, S. (1999) Effects of methotrexate and cyclophosphamide on polyamine levels in various tissues of rats J. Drug Target 7, 197-205 (Pubitemid 30028963)
53. Andersson, A. C., Henningsson, S., and Rosengren, E. (1979) Formation of cadaverine in the pregnant rat Acta Physiol. Scand. 105, 508-512 (Pubitemid 9165231)
54. Aikens, D., Bunce, S., Onasch, F., Parker, R., Hurwitz, C., and Clemans, S. (1983) The interactions between nucleic acids and polyamines 0.2. Protonation constants and C-13 NMR chemical-shift assignments of spermidine, spermine, and homologs Biophys. Chem. 17, 67-74 (Pubitemid 13133790)
55. Sies, H., Gerstenecker, C., Menzel, H., and Flohe, L. (1972) Oxidation in the NADP system and release of GSSG from hemoglobin-free perfused rat liver during peroxidatic oxidation of glutathione by hydroperoxides FEBS Lett. 27, 171-175
56. Sies, H., Brigelius, R., and Akerboom, T. P. M. (1983) Intrahepatic Glutathione Status, in Functions of Glutathione: Biochemical, Physiological, Toxicological and Clinical Aspects (Larsson, A., Orrenius, S., Holmgren, A., and Mannervik, B., Eds.) pp 51-64, Raven Press, New York.