Metabolism of 4-hydroxynonenal, a cytotoxic product of lipid peroxidation, in rat precision-cut liver slices

Toxicology Letters

Volumn 114, Issue 1-3, 2000, Pages 203-214

  Laurent, A ^a   Perdu Durand, E ^a   Alary, J ^a   Debrauwer, L ^a   Cravedi, J P ^a  

^a CEMAGREF   (France)

Author keywords

4 Hydroxy 2 nonenal; Biotransformation; Lipid peroxidation; Rat liver slices

Indexed keywords

1,4 DIHYDROXYNON 2 ENE; 1,4 DIHYDROXYNONENE; 4 HYDROXY 9 CARBOXY 2 NONENOIC ACID; 4 HYDROXYNONENAL; 4 HYDROXYNONENOIC ACID; 4,9 DIHYDROXYNONANOIC ACID; ALCOHOL; CYSTEINE; GLUTATHIONE; TRITIUM; TRITIUM OXIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION KINETICS; CONJUGATE; CONJUGATION; CONTROLLED STUDY; CYTOTOXICITY; FATTY ACID OXIDATION; LIPID PEROXIDATION; LIVER SLICE; MALE; METABOLITE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT;

ALDEHYDES; ALKENES; ANIMALS; BIOTRANSFORMATION; CARBON RADIOISOTOPES; CELL SURVIVAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CULTURE TECHNIQUES; CYSTEINE PROTEINASE INHIBITORS; FATTY ACIDS, MONOUNSATURATED; FATTY ACIDS, UNSATURATED; GLUTATHIONE; HYDROXY ACIDS; KINETICS; LIPID PEROXIDATION; LIVER; MALE; MASS SPECTROMETRY; RATS; RATS, WISTAR; TRITIUM;

EID: 0034599916     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-4274(99)00301-X     Document Type: Article

References (40)

1. Alary J., Bravais F., Cravedi J.P., Debrauwer L., Rao D., Bories G. Mercapturic acid conjugates as urinary end metabolites of lipid peroxidation product 4-hydroxynonenal in the rat. Chem. Res. Toxicol. 8:1995;34-39.
2. Alary J., Debrauwer L., Fernandez Y., Paris A., Cravedi J.P., Dolo L., Rao D., Bories G. Identification of novel urinary metabolites of the lipid peroxidation product 4-hydroxy-2-nonenal in rats. Chem. Res. Toxicol. 11:1998;1368-1376.
3. Ball S.E., Thiel V.E., Tio C.O., Lim H.K., Kao J., Sisenwine S.F., Scatina J. [14C]7-Ethoxycoumarin metabolism by precision-cut rat hepatic slices. Drug Metab. Dispos. 24:1996;383-389.
4. Ballatori N., Jacob R., Boyer J.L. Intrabiliary glutathione hydrolysis - a source of glutamate in bile. J. Biol. Chem. 261:1986;7860-7865.
5. Bjorge S.M., Baillie T.A. Inhibition of medium-chain fatty acid β-oxidation by valproic acid and its unsaturated metabolite, 2-n-propyl-4-pentenoic acid. Biophys. Res. Commun. 132:1985;245-252.
6. Boleda M.D., Saubi N., Farrés J., Parés X. Physiological substrates for rat alcohol deshydrogenase classe: aldehydes of lipid peroxidation, ω-hydroxyfatty acids, and retinoids. Arch. Biochem. Biophys. 1:1993;85-90.
7. 3H]-2(E)-nonen-1-al-diethylacetal. J. Label. Compd. Radiopharm. 36:1994;471-477.
8. Chung F.L., Chen H.J.C., Guttenplan J.B., Nishikawa A., Hard G.C. 2,3-Epoxy-4-hydroxynonanal as potential tumor initiating agent of lipid peroxidation. Carcinogenesis. 14:1993;2073-2077.
9. Davies W.E., Hajra A.K., Parmar S.S., Radin N.S., Mead J.F. Decarboxylation of 2-keto fatty acids by brain. J. Lipid Res. 7:1966;270-276.
10. Dogterom P. Development of a simple incubation system for metabolism studies with precision-cut liver slices. Drug Metab. Dispos. 21:1993;699-704.
11. Ekins S. Past, present and future applications of precision-cut liver slices for in vitro xenobiotic metabolism. Drug Metab. Rev. 28:1996;591-623.
12. Ekins S., Murray G.I., Burke M.D., Williams J.A., Marchant N.C., Hawksworth G.M. Quantitative differences in phase I and II metabolism between rat precision-cut liver slices and isolated hepatocytes. Drug Metab. Dispos. 23:1995;1274-1279.
13. Esterbauer H. Aldehydic products of lipid peroxidation. Mc Brien D.C.H., Slater T.F. Free Radicals, Lipid Peroxidation and Cancer. 1982;101-128 Academic Press, London.
14. Esterbauer H., Weger W. Über die wirkungen von aldehyden auf gesunde und maligne zellen, 3. Mitt.: Synthese von homologen 4-hydroxy-2-alkenalen, II. Monatsh. Chem. 98:1967;363-373.
15. Esterbauer H., Ertl A., Scholz N. The reaction of cysteine with α-β-unsaturated aldehydes. Tetrahedron. 32:1976;285-289.
16. Esterbauer H., Zollner H., Lang J. Metabolism of the lipid peroxidation product 4-hydroxynonenal by isolated hepatocytes and by cytosolic fractions. Biochem. J. 228:1985;363-373.
17. Esterbauer H., Zollner H., Schaur R.J. Hydroxyalkenals: cytotoxic products of lipid peroxidation. ISI Atlas Sci. 1:1988;311-317.
18. Esterbauer H., Schaur R.J., Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic. Biol. Med. 11:1991;81-128.
19. Fujita M., Sano M., Yoshino K., Tomita I. Effects of aldehyde dehydrogenase and glutathione on the degradation of (E)-4-hydroxy-2-nonenal and N-hexanal in rat liver. Biochem. Mol. Biol. Int. 32:1994;429-434.
20. Guéraud F., Alary J., Costet P., Debrauwer L., Dolo L., Pineau T., Paris A. In vivo involvement of cytochrome P-450 4A family in the oxidative metabolism of lipid peroxidation product trans-4-hydroxy-2-nonenal, using PPARα-deficient mice. J. Lipid Res. 40:1999;152-159.
21. Hartley D.P., Ruth J.A., Petersen D.R. The hepatocellular metabolism of 4-hydroxynonenal by alcohol dehydrogenase, aldehyde dehydrogenase, and glutathione S-transferase. Arch. Biochem. Biophys. 316:1995;197-205.
22. Hinchman C.A., Matsumoto H., Simmons T.W., Ballatori N. Intrahepatic conversion of a glutathione conjugate to its mercapturic acid. Metabolism of 1-chloro-2,4-dinitrobenzene in isolated perfused rat and guinea pig livers. J. Biol. Chem. 266:1991;22179-22185.
23. Jensson H., Guthenberg C., Alin P., Mannervik B. Rat glutathione transferase 8-8, an enzyme efficiently detoxifying 4-hydroxyalk-2-enals. FEBS Lett. 203:1986;207-209.
24. Koster J.F., Slee R.G., Montfoort A., Lang J., Esterbauer H. Comparison of the inactivation of microsomal glucose-6-phosphatase by in situ lipid peroxidation-derived 4-hydroxynonenal and exogenous 4-hydroxynonenal. Free Rad. Res. Commun. 1:1986;273-287.
25. Krumdieck C.L., Dos Santos J.E., Ho K.J. A new instrument for the rapid preparation of tissue slices. Anal. Biochem. 104:1980;118-123.
26. Lamé M.W., Segall H.J. In vitro effects of trans-4-hydroxy-2-alkenals on mouse liver cytochrome P-450. Chem. Biol. Int. 62:1987;59-74.
27. Lindgreen B.O., Nilsson T. Preparation of carboxylic acids from aldehydes (including hydroxylated benzaldehydes) by oxidation with chlorite. J. Org. Chem. 43:1973;2480-2482.
28. Loft S., Poulsen H.E. Metabolism of metronidazole and antipyrine in isolated rat hepatocytes. Biochem. Pharmacol. 38:1989;1125-1136.
29. Mitchell D.Y., Petersen D.R. The oxidation of α-β unsaturated aldehydic products of lipid peroxidation by rat liver aldehyde deshydrogenases. Toxicol. Appl. Pharmacol. 87:1987;403-410.
30. Pande S.V., Siddiqui A.W., Gattereau A. Inhibition of long-chain fatty acids activation by α-bromopalmitate and phytanate. Biochem. Biophys. Acta. 248:1971;156-166.
31. Parrish A.R., Gandolfi A.J., Brendel K. Precision-cut tissue slices: applications in pharmacology and toxicology. Life Sci. 57:1995;1887-1901.
32. Poli G., Dianzani M.U., Chesseman K.H., Slater T.F., Lang J., Esterbauer H. Separation and characterization of the aldehydic products of lipid peroxidation stimulated by carbon tetrachloride or ADP-iron in isolated rat hepatocytes and rat liver microsomal suspensions. Biochem. J. 227:1985;629-638.
33. Siems W.G., Zollner H., Grune T., Esterbauer H. Qualitative and quantitative determination of metabolites of the lipid peroxidation product 4-hydroxynonenal from hepatocytes, enterocytes and tumor cells. Fresenius J. Anal. Chem. 343:1992;75-76.
34. Siems W.G., Grune T., Zollner H., Esterbauer H. Formation and metabolism of the lipid peroxidation product 4-hydroxynonenal in liver and small intestine. Poli G., Albano E., Dianzani M.U. Basic Science to Medicine. Free Radicals. 1993;89-101 Birkhauser, Basel, Switzerland.
35. Siems W.G., Zollner H., Grune T., Esterbauer H. Metabolic fate of 4-hydroxynonenal in hepatocytes: 1,4-dihydroxynonene is not the main product. J. Lipid Res. 38:1997;612-622.
36. Srivastava S., Chandra A., Bhatnagar A., Srivastra K.S., Ansari N.H. Lipid peroxidation product, 4-hydroxynonenal and its conjugate with GSH are excellent substrates of bovine lens aldose reductase. Biochem. Biophys. Res. Commun. 217:1995;741-746.
37. Uchida K., Stadtman E.R. Selective cleavage of thioether linkage in proteins modified with 4-hydroxynonenal. Proc. Natl. Acad. Sci. USA. 89:1992;5611-5615.
38. Yoshino K., Sano M., Fujita M., Tomita I. Formation of aliphatic aldehydes in rat plasma and liver due to vitamin E deficiency. Chem. Pharm. Bull. 34:1986;5184-5187.
39. Witz G. Biological interactions of alpha, beta-unsaturated aldehydes. Free Rad. Biol. Med. 7:1989;333-349.
40. Zalko D., Perdu-Durand E., Debrauwer L., Bec-Ferte M.P., Tulliez J. Comparative metabolism of clenbuterol by rat and bovine liver microsomes and slices. Drug Metab. Dispos. 26:1998;28-35.