Characterization of adducts of ethanol metabolites with cytochrome c

Alcoholism: Clinical and Experimental Research

Volumn 23, Issue 1, 1999, Pages 26-37

  Anni, Helen ^a   Israel, Yedy ^a,b  

^a THOMAS JEFFERSON UNIVERSITY   (United States)

^b UNIVERSITY OF CHILE   (Chile)

Author keywords

Acetaldehyde; Cytochrome c; Ethanol adducts; Hydroxyethyl radical; Mass spectroscopy

Indexed keywords

ACETALDEHYDE; ALCOHOL; CYTOCHROME C; CYTOCHROME P450; FREE RADICAL; HYDROGEN PEROXIDE; ISOENZYME; PEPTIDE;

ALCOHOL CONSUMPTION; ALCOHOLISM; ARTICLE; BINDING AFFINITY; ELECTRON TRANSPORT; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MAMMAL CELL; MASS SPECTROMETRY; OXIDATION; OXIDATIVE STRESS; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

MAMMALIA;

EID: 0032938001     PISSN: 01456008     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1530-0277.1999.tb04020.x     Document Type: Article

References (75)

1. Adachi S, Cross AR, Babior BM, Gottlieb RA (1997) Bcl-2 and the outer mitochondrial membrane in the inactivation of cytochrome c during Fas-mediated apoptosis. J Biol Chem 272:21878-21882.
2. Albano E, Tomasi A, Persson JO, Terelius Y, Goria-Gatti L, Ingelman-Sundberg M (1991) Role of ethanol-inducible cytochrome P450 (P450IIE1) in catalysing the free radical activation of aliphatic alcohols. Biochem Pharmacol 41:1895-1902.
3. Albano E, Parola M, Comoglio A, Dianzani MU (1993) Evidence for the covalent binding of hydroxyethyl radicals to rat liver microsomal proteins. Alcohol Alcohol 28:453-459.
4. Albano E, Tomasi A, Ingelman-Sundberg M (1994) Spin trapping of alcohol-derived radicals in microsomes and reconstituted systems by electron spin resonance. Meth Enzymol 233:117-127.
5. Albano E, Clot P, Morimoto M, Tomasi A, Ingelman-Sundberg M, French SW (1996) Role of cytochrome P4502E1-dependent formation of hydroxyethyl free radical in the development of liver damage in rats intragastrically fed with ethanol. Hepatology 23:155-163.
6. Anni H, Dey I, Israel Y (1997) Hydroxyethyl radical-cytochrome c adducts. Alcohol Clin Exp Res 21:282.
7. Austin JE, Fraenkel-Conrat H (1992) Tryptophan analogues form adducts by cooperative reaction with aldehydes and alcohols or with aldehydes alone: Possible role in ethanol toxicity. Proc Natl Acad Sci USA 89: 8439-8442.
8. Barr DP, Gunther MR, Deterding LJ, Tomer KB, Mason RP (1996) ESR spin-trapping of a protein-derived tyrosyl radical from the reaction of cytochrome c with hydrogen peroxide. J Biol Chem 271:15498-15503.
9. Bell LC, Guengerich FP (1997) Oxidation kinetics of ethanol by human cytochrome P450 2E1. Rate-limiting product release accounts for effects of isotopic hydrogen substitution and cytochrome b5 on steady-state kinetics. J Biol Chem 272:29643-29651.
10. Braun KP, Cody RB Jr, Jones DR, Peterson CM (1995) A structural assignment for a stable acetaldehyde-lysine adduct. J Biol Chem 270: 11263-11266.
11. Braun KP, Pavlovich JG, Jones DR, Peterson CM (1997) Stable acetaldehyde adducts: Structural characterization of acetaldehyde adducts of human hemoglobin N-terminal beta-globin chain peptides. Alcohol Clin Exp Res 21:40-43.
12. Bushnell GW, Louie GV, Brayer GD (1990) High-resolution three-dimensional structure of horse heart cytochrome c. J Mol Biol 214:585-595.
13. Cadenas E, Boveris A, Chance B (1980) Chemiluminescence of lipid vesicles supplemented with cytochrome c and hydroperoxide. Biochem J 188:577-583.
14. Cederbaum AI (1991) Microsomal generation of reactive oxygen species and their possible role in alcohol hepatotoxicity. Alcohol Alcohol 1S: 291-296.
15. Cederbaum AI, Rubin E (1975) Molecular injury to mitochondria produced by ethanol and acetaldehyde. Fed Proc 34:2045-2051.
16. Channareddy S, Jose SS, Eryomin VA, Rubin E, Taraschi TF, Janes N (1996) Saturable ethanol binding in rat liver microsomes. J Biol Chem 271:17625-17628.
17. Chapman JR (1996) Protein and Peptide Analysis by Mass Spectrometry, vol 61. Humana Press, Inc., Totowa, NJ.
18. Chen HM, Scott BK, Braun KP, Peterson CM (1995) Validated fluorimetric HPLC analysis of acetaldehyde in hemoglobin fractions separated by cation exchange chromatography: Three new peaks associated with acetaldehyde. Alcohol Clin Exp Res 19:939-944.
19. Clot P, Bellomo G, Tabone M, Arico S, Albano E (1995) Detection of antibodies against proteins modified by hydroxyethyl free radicals in patients with alcoholic cirrhosis. Gastroenterology 108:201-207.
20. Clot P, Albano E, Eliasson E, Tabone M, Arico S, Israel Y (1996) Cytochrome P4502E1 hydroxyethyl radical adducts as the major antigen in autoantibody formation among alcoholics. Gastroenterology 111: 206-216.
21. Clot P, Parola M, Bellomo G, Dianzani U, Carini R, Tabone M (1997) Plasma membrane hydroxyethyl radical adducts cause antibody-dependent cytotoxicity in rat hepatocytes exposed to alcohol. Gastroenterology 113:265-276.
22. Deterding LJ, Barr DP, Mason RP, Tomer KB (1998) Characterization of cytochrome c free radical reactions with peptides by mass spectrometry. J Biol Chem 273:12863-12869.
23. Dickerson RE, Takano T, Eisenberg D, Kallai OB, Samson L, Cooper A (1971) Ferricytochrome c. I. General features of the horse and bonito proteins at 2.8 A resolution. J Biol Chem 246:1511-1535.
24. Evans SV, Brayer GD (1990) High-resolution study of the three-dimensional structure of horse heart metmyoglobin. J Mol Biol 213: 885-897.
25. Feng Y, Roder H, Englander SW, Wand AJ, Di Stefano DL (1989) Proton resonance assignments of horse ferricytochrome c. Biochemistry 28: 195-203.
26. Fernandez-Checa JC, Kaplowitz N, Garcia-Ruiz C, Colell A, Miranda M, Mari M (1997) GSH transport in mitochondria: Defense against TNF-induced oxidative stress and alcohol-induced defect. Am J Physiol 273:G7-17.
27. Finkelstein E, Rosen GM, Rauckman EJ (1980) Spin trapping of superoxide and hydroxyl radical: Practical aspects. Arch Biochem Biophys 200:1-16.
28. Fowles LF, Beck E, Worrall S, Shanley BC, de Jersey J (1996) The formation and stability of imidazolidinone adducts from acetaldehyde and model peptides. A kinetic study with implications for protein modification in alcohol abuse. Biochem Pharmacol 51:1259-1267.
29. Giulivi C, Cadenas E (1998) Heme protein radicals: Formation, fate, and biological consequences. Free Radic Biol Med 24:269-279.
30. Gross MD, Gapstur SM, Belcher JD, Scanlan G, Potter JD (1992) The identification and partial characterization of acetaldehyde adducts of hemoglobin occurring in vivo: A possible marker of alcohol consumption. Alcohol Clin Exp Res 16:1093-1103.
31. Hamada D, Hoshino M, Kataoka M, Fink AL, Goto Y (1993) Intermediate conformational states of apocytochrome c. Biochemistry 32:10351-10358.
32. 2-chloride system of phagocytes, covalently modifies epsilon-amino groups of protein lysine residues. J Biol Chem 272:16990-16998.
33. Holstege A, Bedossa P, Poynard T, Kollinger M, Chaput JC, Houglum K (1994) Acetaldehyde-modified epitopes in liver biopsy specimens of alcoholic and nonalcoholic patients: Localization and association with progression of liver fibrosis. Hepatology 19:367-374.
34. Ingelman-Sundberg M, Ronis MJ, Lindros KO, Eliasson E, Zhukov A (1994) Ethanol-inducible cytochrome P4502E1: Regulation, enzymology and molecular biology. Alcohol Alcohol 2S:131-139.
35. Israel Y, Hurwitz E, Niemela O, Arnon R (1986) Monoclonal and polyclonal antibodies against acetaldehyde-containing epitopes in acetaldehyde-protein adducts. Proc Natl Acad Sci USA 83:7923-7927.
36. Jennett RB, Saffari-Fard A, Sorrell MF, Smith SL, Tuma DJ (1989) Increased covalent binding of acetaldehyde to calmodulin in the presence of calcium. Life Sci 45:1461-1466.
37. Kantrow SP, Piantadosi CA (1997) Release of cytochrome c from liver mitochondria during permeability transition. Biochem Biophys Res Comm 232:669-671.
38. Kluck RM, Bossy-Wetzel E, Green DR, Newmeyer DD (1997a) The release of cytochrome c from mitochondria: A primary site for Bcl-2 regulation of apoptosis. Science 275:1132-1136.
39. Kluck RM, Martin SJ, Hoffman BM, Zhou JS, Green DR, Newmeyer DD (1997b) Cytochrome c activation of CPP32-like proteolysis plays acritical role in a Xenopus cell-free apoptosis system. EMBO J 16:4639-4649.
40. Koppenol WH, Margoliash E (1982) The asymmetric distribution of charges on the surface of horse cytochrome c. Functional implications. J Biol Chem 257:4426-4437.
41. Krippner A, Matsuno-Yagi A, Gottlieb RA, Babior BM (1996) Loss of function of cytochrome c in Jurkat cells undergoing fas-mediated apoptosis. J Biol Chem 271:21629-21636.
42. Kukielka E, Dicker E, Cederbaum AI (1994) Increased production of reactive oxygen species by rat liver mitochondria after chronic ethanol treatment. Arch Biochem Biophys 309:377-386.
43. Kunitoh S, Imaoka S, Hiroi T, Yabusaki Y, Monna T, Funae Y (1997) Acetaldehyde as well as ethanol is metabolized by human CYP2E1. J Pharmacol Exp Ther 280:527-532.
44. Li P, Nijhawan D, Budihardjo I, Srinivasula SM, Ahmad M, Alnemri ES (1997) Cytochrome c and dATP-dependent formation of Apaf-1/caspase-9 complex initiates an apoptotic protease cascade. Cell 91:479-489.
45. Lin RC, Smith JB, Radtke DB, Lumeng L (1995) Structural analysis of peptide-acetaldehyde adducts by mass spectrometry and production of antibodies directed against nonreduced protein-acetaldehyde adducts. Alcohol Clin Exp Res 19:314-319.
46. Liu X, Kim CN, Yang J, Jemmerson R, Wang X (1996) Induction of apoptotic program in cell-free extracts: Requirement for dATP and cytochrome c. Cell 86:147-157.
47. Mauch TJ, Tuma DJ, Sorrell MF (1987) The binding of acetaldehyde to the active site of ribonuclease: Alterations in catalytic activity and effects of phosphate. Alcohol Alcohol 22:103-112.
48. Moncada C, Torres V, Varghese G, Albano E, Israel Y (1994) Ethanol-derived immunoreactive species formed by free radical mechanisms. Mol Pharmacol 46:786-791.
49. Nicholls R, de Jersey J, Worrall S, Wilce P (1992) Modification of proteins and other biological molecules by acetaldehyde: Adduct structure and functional significance. Int J Biochem 24:1899-1906.
50. Niemela O, Israel Y (1992) Hemoglobin-acetaldehyde adducts in human alcohol abusers. Lab Invest 67:246-252.
51. Niemela O, Israel Y, Mizoi Y, Fukunaga T, Eriksson CJ (1990) Hemoglobin-acetaldehyde adducts in human volunteers following acute ethanol ingestion. Alcohol Clin Exp Res 14:838-841.
52. Niemela O, Parkkila S, Yla-Herttuala S, Halsted C, Witztum JL, Lanca A (1994) Covalent protein adducts in the liver as a result of ethanol metabolism and lipid peroxidation. Lab Invest 70:537-546.
53. Nguyen LB, Peterson CM (1986) Differential modification of hemoglobin chains by acetaldehyde. Proc Soc Exp Biol Med 181:151-156.
54. Ortiz de Montellano PR (1990) Free radical modification of prosthetic heme groups. Pharmacol Ther 48:95-120.
55. Osawa Y, Korzekwa K (1991) Oxidative modification by low levels of HOOH can transform myoglobin to an oxidase. Proc Natl Acad Sci USA 88:7081-7085.
56. 2: Toxicological implications. Free Radic Biol Med 21:35-41.
57. Paradis V, Scoazec JY, Kollinger M, Holstege A, Moreau A, Feldmann G (1996) Cellular and subcellular localization of acetaldehyde-protein adducts in liver biopsies from alcoholic patients. J Histochem Cytochem 44:1051-1057.
58. Peterson CM, Nguyen LB (1985) Clinical implications of acetaldehyde adducts with hemoglobin. Progr Clin Biol Res 183:19-30.
59. Rao DN, Yang MX, Lasker JM, Cederbaum AI (1996) 1-Hydroxyethyl radical formation during NADPH- and NADH-dependent oxidation of ethanol by human liver microsomes. Mol Pharmacol 49:814-821.
60. Rashba-Step J, Cederbaum AI (1994) Generation of reactive oxygen intermediates by human liver microsomes in the presence of NADPH or NADH. Mol Pharmacol 45:150-157.
61. Reinke LA, Moore DR, Hague CM, McCay PB (1994) Metabolism of ethanol to 1-hydroxyethyl radicals in rat liver microsomes: Comparative studies with three spin trapping agents. Free Radic Res 21:213-222.
62. Reinke LA, Rau JM, McCay PB (1994) Characteristics of an oxidant formed during iron (II) autoxidation. Free Radic Biol Med 16:485-492.
63. Roberfroid M, Calderon PB (1995) Targets for Radicals and Reactive Oxygen Species In: Proteins, Free Radicals and Oxidation Phenomena in Biological Systems, Marcel Dekker, Inc., pp 113-121, New York.
64. Sillanaukee P, Hurme L, Tuominen J, Ranta E, Nikkari S, Seppa K (1996) Structural characterisation of acetaldehyde adducts formed by a synthetic peptide mimicking the N-terminus of the hemoglobin beta-chain under reducing and nonreducing conditions. Eur J Biochem 240:30-36.
65. Stevens VJ, Fantl WJ, Newman CB, Sims RV, Cerami A, Peterson CM (1981) Acetaldehyde adducts with hemoglobin. J Clin Invest 67:361-369.
66. Svegliati-Baroni G, Baraona E, Rosman AS, Lieber CS (1994) Collagen-acetaldehyde adducts in alcoholic and nonalcoholic liver diseases. Hepatology 20:111-118.
67. Taiwo FA, Symons MC (1993) Interaction of ethanol with haemoglobin: Implications for alcohol abuse. Free Radic Res Comm 19:121-124.
68. Terelius Y, Norsten-Hoog C, Cronholm T, Ingelman-Sundberg M (1991) Acetaldehyde as a substrate for ethanol-inducible cytochrome P450 (CYP2E1). Biochem Biophys Res Comm 179:689-694.
69. Thiele GM, Wegter KM, Sorrell MF, Tuma DJ, McDonald TL, Klassen LW (1994) Specificity of N-ethyl lysine of a monoclonal antibody to acetaldehyde-modified proteins prepared under reducing conditions. Biochem Pharmacol 48:183-189.
70. Tuma DJ, Newman MR, Donohue TM Jr, Sorrell MF (1987) Covalent binding of acetaldehyde to proteins: Participation of lysine residues. Alcohol Clin Exp Res 11:579-584.
71. Tuma DJ, Smith SL, Sorrell MF (1991) Acetaldehyde and microtubules. Ann NY Acad Sci 625:786-792.
72. 1H-NMR study of inter-segmental hydrogen bonds in sperm whale and horse apomyoglobins. Eur J Biochem 243:292-298.
73. Yamazaki H, Nakano M, Gillam EM, Bell LC, Guengerich FP, Shimada T (1996) Requirements for cytochrome b5 in the oxidation of 7-ethoxycoumarin, chlorzoxazone, aniline, and N-nitrosodimethylamine by recombinant cytochrome P450 2E1 and by human liver microsomes. Biochem Pharmacol 52:301-309.
74. Yang J, Liu X, Bhalla K, Kim CN, Ibrado AM, Cai J (1997) Prevention of apoptosis by Bcl-2: Release of cytochrome c from mitochondria blocked. Science 275:1129-1132.
75. Zhu Y, Fillenwarth MJ, Crabb D, Lumeng L, Lin RC (1996) Identification of the 37-kd rat liver protein that forms an acetaldehyde adduct in vivo as delta 4-3-ketosteroid 5 beta-reductase. Hepatology 23:115-122.