Adenovirus mediated overexpression of CYP2E1 increases sensitivity of HepG2 cells to acetaminophen induced cytotoxicity

Molecular and Cellular Biochemistry

Volumn 262, Issue 1-2, 2004, Pages 165-176

  Bai, Jingxiang ^a   Cederbaum, Arthur I ^a  

^a MOUNT SINAI SCHOOL OF MEDICINE   (United States)

Author keywords

Acetaminophen; Adenovirus; Apoptosis; BSO; CYP2E1; HepG2; Toxicity

Indexed keywords

ADENOVIRUS VECTOR; BENZYLOXYCARBONYLVALYLALANYLASPARTYL FLUOROMETHYL KETONE; BETA GALACTOSIDASE; CASPASE; CASPASE INHIBITOR; COMPLEMENTARY DNA; CYTOCHROME P450 2E1; GLUTATHIONE; PARACETAMOL;

ALCOHOL LIVER DISEASE; APOPTOSIS; ARTICLE; CELL DEATH; CELL LEVEL; CELL STRAIN HEPG2; CONTROLLED STUDY; DRUG CYTOTOXICITY; ENZYME INHIBITION; GENE OVEREXPRESSION; GENETIC ENGINEERING; HUMAN; HUMAN CELL; METABOLITE; MITOCHONDRION; NONHUMAN; PROTEIN FUNCTION; VALIDATION PROCESS;

ACETAMINOPHEN; ADENOVIRIDAE; APOPTOSIS; CARCINOMA, HEPATOCELLULAR; CELL LINE, TUMOR; CYTOCHROME P-450 CYP2E1; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SYNERGISM; GENETIC VECTORS; HUMANS; TRANSFECTION;

ADENOVIRIDAE;

EID: 4344640630     PISSN: 03008177     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MCBI.0000038232.61760.9e     Document Type: Article

References (62)

1. Bessems JG, Vermeulen NP: Paracetamol (acetaminophen)-induced toxicity: Molecular and biochemical mechanisms, analogues and protective approaches. Crit Rev Toxicol 31: 55-138, 2001
2. Prescott LF: Paracetamol overdosage. Pharmacological considerations and clinical management. Drugs 25: 290-314, 1983
3. Black M: Acetaminophen hepatotoxicity. Annu Rev Med 35: 577-593, 1984
4. Raucy JL, Lasker JM, Lieber CS, Black M: Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch Biochem Biophys 271: 270-283, 1989
5. Dahlin DC, Nelson SD: Synthesis, decomposition kinetics, and preliminary toxicological studies of pure N-acetyl-p-benzoquinone imine, a proposed toxic metabolite of acetaminophen. J Med Chem 25: 885-886, 1982
6. Moldâeus P: Paracetamol metabolism and toxicity in isolated hepatocytes from rat and mouse. Biochem Pharmacol 27: 2859-2863, 1978
7. Van De Straat R, De Vries J, Kulkens T, Debets AJ, Vermeulen NP: Paracetamol, 3-monoalkyl- and 3,5-dialkyl derivatives. Comparison of their microsomal cytochrome P-450 dependent oxidation and toxicity in freshly isolated hepatocytes. Biochem Pharmacol 35: 3693-3699, 1986
8. Hoffmann KJ, Streeter AJ, Axworthy DB, Baillie TA: Identification of the major covalent adduct formed in vitro and in vivo between acetaminophen and mouse liver proteins. Mol Pharmacol 27: 566-573, 1985
9. Hinson JA, Pumford NR, Roberts DW: Mechanisms of acetaminophen toxicity: Immunochemical detection of drug-protein adducts. Drug Metab Rev 27: 72-92, 1995
10. Birge RB, Bartolone JB, Nishanian EV, Bruno MK, Mangold JB, Cohen SD, Khairallah EA: Dissociation of covalent binding from the oxidative effects of acetaminophen. Studies using dimethylated acetaminophen derivatives. Biochem Pharmacol 37: 3383-3393, 1988
11. Tirmenstein MA, Nelson SD: Acetaminophen-induced oxidation of protein thiols. Contribution of impaired thiol-metabolizing enzymes and the breakdown of adenine nucleotides. J Biol Chem 265: 3059-3065, 1990
12. 2derlund EJ, Holme JA: Genotoxicity of paracetamol in mice and rats. Mutagenesis. 9: 93-100, 1994
13. Thummel KE, Lee CA, Kunze KL, Nelson SD, Slattery JT: Oxidation of acetaminophen to N-acetyl-p-aminobenzoquinone imine by human CYP3A4. Biochem Pharmacol 45: 1563-1569, 1993
14. Prasad JS, Chen NQ, Liu YX, Goon DJ, Holtzman JL: Effects of ethanol and inhibitors on the binding and metabolism of acetaminophen and N-acetyl-p-benzoquinone imine by hepatic microsomes from control and ethanol-treated rats. Biochem Pharmacol 40: 1989-1995, 1990
15. Burk RF, Hill KE, Hunt RW, Jr., Martin AE: Isoniazid potentiation of acetaminophen hepatotoxicity in the rat and 4-methylpyrazole inhibition of it. Res Commun Chem Pathol Pharmacol 69: 115-118, 1990
16. Rex DK, Kumar S: Recognizing acetaminophen hepatotoxicity in chronic alcoholics. Postgrad Med 91: 241-245, 1992
17. Dai Y, Cederbaum AI: Cytotoxicity of acetaminophen in human cytochrome P4502E1-transfected HepG2 cells. J Pharmacol Exp Ther 273: 1497-1505, 1995
18. Holownia A, Mapoles J, Menez JF, Braszko JJ: Acetaminophen metabolism and cytotoxicity in PC12 cells transfected with cytochrome P4502E1. J Mol Med 75: 522-527, 1997
19. Lee SS, Buters JT, Pineau T, Fernandez-Salguero P, Gonzalez FJ: Role of CYP2E1 in the hepatotoxicity of acetaminophen. J Biol Chem 271: 12063-12067, 1996
20. Cederbaum AI, Wu D, Mari M, Bai J: CYP2E1-dependent toxicity and oxidative stress in HepG2 cells. Free Radical Biol Med 31: 1539-1543, 2001
21. Guengerich FP, Kim DH, Iwasaki M: Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol 4: 168-179, 1991
22. Yang CS, Yoo JS, Ishizaki H, Hong JY: Cytochrome P450IIE1: Roles in nitrosamine metabolism and mechanisms of regulation. Drug Meta Rev 22: 147-159, 1990
23. Koop DR: Oxidative and reductive metabolism by cytochrome P450 2E1. FASEB J 6: 724-730, 1992
24. Morimoto M, Zern MA, Hagbjèork AL, Ingelman-Sundberg M, French SW: Fish oil, alcohol, and liver pathology: Role of cytochrome P450 2E1. Proc Soc Exp Biol Med 207: 197-205, 1994
25. Nanji AA, Zhao S, Sadrzadeh SM, Dannenberg AJ, Tahan SR, Waxman DJ: Markedly enhanced cytochrome P450 2E1 induction and lipid peroxidation is associated with severe liver injury in fish oil-ethanol-fed rats. Alcohol Clin Exp Res 18: 1280-1285, 1994
26. Lieber CS: Cytochrome P-4502E1: Its physiological and pathological role. Physiol Rev 77: 517-544, 1997
27. Weltman MD, Farrell GC, Hall P, Ingelman-Sundberg M, Liddle C: Hepatic cytochrome P450 2E1 is increased in patients with nonalcoholic steatohepatitis. Hepatology 27: 128-133, 1998
28. Bert AJ, Haddara W, Prevec L, Graham FL: An efficient and flexible system for construction of adenovirus vectors with insertions or deletions in early regions 1 and 3. Proc Natl Acad Sci USA 91: 8802-8806, 1994
29. Bai J, Cederbaum AI: Catalase protects HepG2 cells from apoptosis induced by DNA-damaging agents by accelerating the degradation of p53. J Biol Chem 278: 4660-4667, 2003
30. Wiger R, Finstad HS, Hongslo JK, Haug K, Holme JA: Paracetamol inhibits cell cycling and induces apoptosis in HL-60 cells. Pharmacol Toxicol 81: 285-293, 1997
31. Ray SD, Mumaw VR, Raje RR, Fariss MW: Protection of acetaminophen-induced hepatocellular apoptosis and necrosis by cholesteryl hemisuccinate pretreatment. J Pharmacol Exp Ther 279: 1470-1483, 1996
32. Lindenthal J, Sinclair JF, Howell S, Cargill I, Sinclair PR, Taylor T: Toxicity of paracetamol in cultured chick hepatocytes treated with methotrexate. Eur J Pharmacol 228: 289-298, 1993
33. Patten CJ, Thomas PE, Guy RL, Lee M, Gonzalez FJ, Guengerich FP, Yang CS: Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. Chem Res Toxicol 6: 511-518, 1993
34. Gu J, Zhang QY, Genter MB, Lipinskas TW, Negishi M, Nebert DW, Ding X: Purification and characterization of heterologously expressed mouse CYP2A5 and CYP2G1: Role in metabolic activation of acetaminophen and 2,6-dichlorobenzonitrile in mouse olfactory mucosal microsomes. J Pharmacol Exp Ther 285: 1287-1295, 1998
35. Genter MB, Liang HC, Gu J, Ding X, Negishi M, McKinnon RA, Nebert DW: Role of CYP2A5 and 2G1 in acetaminophen metabolism and toxicity in the olfactory mucosa of the Cyp1a2(-/-) mouse. Biochem Pharmacol 55: 1819-1826, 1998
36. Kostrubsky VE, Szakacs JG, Jeffery EH, Wood SG, Bement WJ, Wrighton SA, Sinclair PR, Sinclair JF: Role of CYP3A in ethanol-mediated increases in acetaminophen hepatotoxicity. Toxicol Appl Pharmacol 143: 315-323, 1997
37. Kostrubsky VE, Szakacs JG, Jeffery EH, Woods SG, Bement WJ, Wrighton SA, Sinclair PR, Sinclair JF: Protection of ethanol-mediated acetaminophen hepatotoxicity by triacetyloleandomycin, a specific inhibitor of CYP3A. Ann Clin Lab Sci 27: 57-62, 1997
38. Zhang J, Huang W, Chua SS, Wei P, Moore DD: Modulation of acetaminophen-induced hepatotoxicity by the xenobiotic receptor CAR. Science 298: 422-424, 2002
39. Pumford NR, Hinson JA, Potter DW, Rowland KL, Benson RW, Roberts DW: Immunochemical quantitation of 3-(cystein-S-yl)acetaminophen adducts in serum and liver proteins of acetaminophen-treated mice. J Pharmacol Exp Ther 248: 190-196, 1989
40. Roberts DW, Bucci TJ, Benson RW, Warbritton AR, McRae TA, Pumford NR, Hinson JA: Immunohistochemical localization and quantification of the 3-(cystein-S-yl)-acetaminophen protein adduct in acetaminophen hepatotoxicity. Am J Pathol 138: 359-371, 1991
41. Hart SG, Cartun RW, Wyand DS, Khairallah EA, Cohen SD: Immunohistochemical localization of acetaminophen in target tissues of the CD-1 mouse: Correspondence of covalent binding with toxicity. Fundam Appl Toxicol 24: 260-274, 1995
42. Coles B, Wilson I, Wardman P, Hinson JA, Nelson SD, Ketterer B: The spontaneous and enzymatic reaction of N-acetyl-p-benzoquinonimine with glutathione: A stopped-flow kinetic study. Arch Biochem Biophys 264: 253-260, 1988
43. Henderson CJ, Wolf CR, Kitteringham N, Powell H, Otto D, Park BK: Increased resistance to acetaminophen hepatotoxicity in mice lacking glutathione S-transferase Pi. Proc Natl Acad Sci 97: 12741-12745, 2000
44. Jones AL: Mechanism of action and value of N-acetylcysteine in the treatment of early and late acetaminophen poisoning: A critical review. J Toxicol Clin Toxicol 36: 277-285, 1998
45. Larrauri A, Fabra R, Gâomez-Lechâon MJ, Trullenque R, Castell JV: Toxicity of paracetamol in human hepatocytes. Comparison of the protective effects of sulfhydryl compounds acting as glutathione precursors. Mol Toxicol 1: 301-311, 1987
46. Wendel A, Feuerstein S: Drug-induced lipid peroxidation in mice-I. Modulation by monooxygenase activity, glutathione and selenium status. Biochem Pharmacol 30: 2513-2520, 1981
47. Younes M, Cornelius S, Siegers CP: Ferrous ion supported in vivo lipid peroxidation induced by paracetamol - Its relation to hepatotoxicity. Res Commun Chem Pathol Pharmacol 51: 89-99, 1986
48. Younes M, Siegers CP: The role of iron in the paracetamol- and CC14-induced lipid peroxidation and hepatotoxicity. Chem Biol Interact 55: 327-334, 1985
49. Devalia JL, Ogilvie RC, McLean AE: Dissociation of cell death from covalent binding of paracetamol by flavones in a hepatocyte system. Biochem Pharmacol 31: 3745-3749, 1982
50. Tee LG, Boobis AR, Davies DS: N-acetylcysteine for paracetamol over-dose. Lancet 1: 331-332, 1986
51. Bajt ML, Knight TR, Farhood A, Jaeschke H: Scavenging peroxynitrite with glutathione promotes regeneration and enhances survival during acetaminophen-induced liver injury in mice. J Pharmacol Exp Ther 307: 67-73, 2003
52. Jaeschke H, Knight TR, Bajt ML: The role of oxidant stress and reactive nitrogen species in acetaminophen hepatotoxicity. Toxicol Lett 144: 279-288, 2003
53. Bae MA, Pie JE, Song BJ: Acetaminophen induces apoptosis of C6 glioma cells by activating the cJun NH(2)-termmal protein kinase-related cell death pathway. Mol Pharmacol 60: 847-856, 2001
54. Boulares AH, Zoltoski AJ, Stoica BA, Cuvillier O, Smulson ME: Acetaminophen induces a caspase-dependent and Bcl-XL sensitive apoptosis in human hepatoma cells and lymphocytes. Pharmacol Toxicol 90: 38-50, 2002
55. Lawson JA, Fisher MA, Simmons CA, Farhood A, Jaeschke H: Inhibition of Fas receptor (CD95)-induced hepatic caspase activation and apoptosis by acetaminophen in mice. Toxicol Appl Pharmacol 156: 179-186, 1999
56. Knight TR, Jaeschke H: Acetaminophen-induced inhibition of Fas receptor-mediated liver cell apoptosis: mitochondrial dysfunction versus glutathione depletion. Toxicol Appl Pharmacol 181: 133-141, 2002
57. Shen W, Kamendulis LM, Ray SD, Corcoran GB: Acetaminophen-induced cytotoxicity in cultured mouse hepatocytes: Correlation of nuclear Ca2+ accumulation and early DNA fragmentation with cell death. Toxicol Appl Pharmacol 111: 242-254, 1991
58. Ray SD, Kamendulis LM, Gurule MW, Yorkin RD, Corcoran GB: Ca2+ antagonists inhibit DNA fragmentation and toxic cell death induced by acetaminophen. FASEB J 7: 453-463, 1993
59. Salas VM, Corcoran GB: Calcium-dependent DNA damage and adenosine 3′,5′-cyclic monophosphate-independent glycogen phosphorylase activation in an in vitro model of acetaminophen-induced liver injury. Hepatology 25: 1432-1438, 1997
60. Lemasters JJ, Qian T, Elmore SP, Trost LC, Nishimura Y, Herman B, Bradham CA: Confocal microscopy of the mitochondrial permeability transition in necrotic cell killing, apoptosis and autophagy. BioFactors 8: 283-285, 1998
61. Gores GJ, Miyoshi H, Botla R, Aguilar HI, Bronk SF: Induction of the mitochondrial permeability transition as a mechanism of liver injury during cholestasis: A potential role for mitochondrial proteases. Biochim Biophys Acta 1366: 167-175, 1998
62. Burcham PC, Harman AW: Acetaminophen toxicity results in site-specific mitochondrial damage in isolated mouse hepatocytes. J Biol Chem 266: 5049-5054, 1991