Modification of carbonic anhydrase II with acetaldehyde, the first metabolite of ethanol, leads to decreased enzyme activity

BMC Biochemistry

Volumn 9, Issue 1, 2008, Pages

  Bootorabi, Fatemeh ^a,b   Jänis, Janne ^c   Valjakka, Jarkko ^a   Isoniemi, Sari ^c   Vainiotalo, Pirjo ^c   Vullo, Daniela ^d   Supuran, Claudiu T ^d   Waheed, Abdul ^e   Sly, William S ^e   Niemelä, Onni ^b   Parkkila, Seppo ^a,b  

^a TAMPERE UNIVERSITY HOSPITAL   (Finland)

^b TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

^c UNIVERSITY OF EASTERN FINLAND   (Finland)

^d UNIVERSITY OF FLORENCE   (Italy)

^e SAINT LOUIS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; CARBONATE DEHYDRATASE II; ALCOHOL;

ARTICLE; CHEMICAL REACTION; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME MODIFICATION; MASS SPECTROMETRY; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN EXPRESSION; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; ISOELECTRIC FOCUSING; KINETICS; METABOLISM;

ACETALDEHYDE; CARBONIC ANHYDRASE II; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ETHANOL; HUMANS; ISOELECTRIC FOCUSING; KINETICS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 58149100771     PISSN: None     EISSN: 14712091     Source Type: Journal    
DOI: 10.1186/1471-2091-9-32     Document Type: Article

References (66)

1. Medical disorders of alcoholism. CS Lieber, N Engl J Med 1995 333 16 1058 1065 7675050
2. Covalent protein adducts in the liver as a result of ethanol metabolism and lipid peroxidation. O Niemela S Parkkila S Yla-Herttuala C Halsted JL Witztum A Lanca Y Israel, Lab Invest 1994 70 4 537 546 8176892
3. Recent advances in alcohol-induced adduct formation. TL Freeman DJ Tuma GM Thiele LW Klassen S Worrall O Niemela S Parkkila PW Emery VR Preedy, Alcohol Clin Exp Res 2005 29 7 1310 1316 16088993
4. Immune responses to acetaldehyde-protein adducts: role in alcoholic liver disease. DJ Tuma LW Klassen, Gastroenterology 1992 103 6 1969 1973 1451988
5. Acetaldehyde adducts with hemoglobin. VJ Stevens WJ Fantl CB Newman RV Sims A Cerami CM Peterson, J Clin Invest 1981 67 2 361 369 7462422
6. Aldehyde-protein adducts in the liver as a result of ethanol-induced oxidative stress. O Niemela, Front Biosci 1999 4 D506 513 10352137
7. Monoclonal and polyclonal antibodies against acetaldehyde-containing epitopes in acetaldehyde-protein adducts. Y Israel E Hurwitz O Niemela R Arnon, Proc Natl Acad Sci USA 1986 83 20 7923 7927 2429322
8. The functional implications of acetaldehyde binding to cell constituents. MF Sorrell DJ Tuma, Ann N Y Acad Sci 1987 492 50 62 3474933
9. Acetaldehyde/protein interactions: are they involved in the pathogenesis of alcoholic liver disease? S Worrall J de Jersey R Nicholls P Wilce, Dig Dis 1993 11 4-5 265 277 8222307
10. Modification of proteins and other biological molecules by acetaldehyde: adduct structure and functional significance. R Nicholls J de Jersey S Worrall P Wilce, Int J Biochem 1992 24 12 1899 1906 1473602
11. Covalent binding of acetaldehyde selectively inhibits the catalytic activity of lysine-dependent enzymes. TJ Mauch TM Donohue Jr RK Zetterman MF Sorrell DJ Tuma, Hepatology 1986 6 2 263 269 2937708
12. The binding of acetaldehyde to the active site of ribonuclease: alterations in catalytic activity and effects of phosphate. TJ Mauch DJ Tuma MF Sorrell, Alcohol Alcohol 1987 22 2 103 112 3651178
13. Autoimmune responses against oxidant stress and acetaldehyde-derived epitopes in human alcohol consumers. K Viitala K Makkonen Y Israel T Lehtimaki O Jaakkola T Koivula JE Blake O Niemela, Alcohol Clin Exp Res 2000 24 7 1103 1109 10924016
14. Alcoholic macrocytosis - is there a role for acetaldehyde and adducts? O Niemela S Parkkila, Addict Biol 2004 9 1 3 10 15203433
15. Serum IgA, IgG, and IgM antibodies directed against acetaldehyde-derived epitopes: relationship to liver disease severity and alcohol consumption. K Viitala Y Israel JE Blake O Niemela, Hepatology 1997 25 6 1418 1424 9185762
16. The formation and stability of imidazolidinone adducts from acetaldehyde and model peptides. A kinetic study with implications for protein modification in alcohol abuse. LF Fowles E Beck S Worrall BC Shanley J de Jersey, Biochem Pharmacol 1996 51 10 1259 1267 8787540
17. Distribution of ethanol-induced protein adducts in vivo: relationship to tissue injury. O Niemela, Free Radic Biol Med 2001 31 12 1533 1538 11744326
18. The chemistry of acetaldehyde-protein adducts. DJ Tuma T Hoffman MF Sorrell, Alcohol Alcohol Suppl 1991 1 271 276 1845549
19. Acetaldehyde adducts with proteins: binding of [14C]acetaldehyde to serum albumin. TM Donohue Jr DJ Tuma MF Sorrell, Arch Biochem Biophys 1983 220 1 239 246 6830235
20. Reaction of acetaldehyde with hemoglobin. RC San George HD Hoberman, J Biol Chem 1986 261 15 6811 6821 3700416
21. The interaction of acetaldehyde with tubulin. DJ Tuma RB Jennett MF Sorrell, Ann N Y Acad Sci 1987 492 277 286 3474930
22. Covalent binding of acetaldehyde to tubulin: evidence for preferential binding to the alpha-chain. RB Jennett MF Sorrell EL Johnson DJ Tuma, Arch Biochem Biophys 1987 256 1 10 18 3606116
23. Increased covalent binding of acetaldehyde to calmodulin in the presence of calcium. RB Jennett A Saffari-Fard MF Sorrell SL Smith DJ Tuma, Life Sci 1989 45 16 1461 1466 2509834
24. Covalent interactions of acetaldehyde with the actin/microfilament system. DS Xu RB Jennett SL Smith MF Sorrell DJ Tuma, Alcohol Alcohol 1989 24 4 281 289 2789522
25. Covalent binding of acetaldehyde to proteins: participation of lysine residues. DJ Tuma MR Newman TM Donohue Jr MF Sorrell, Alcohol Clin Exp Res 1987 11 6 579 584 3124658
26. Preferential covalent binding of acetaldehyde to the alpha-chain of purified rat liver tubulin. RB Jennett MF Sorrell A Saffari-Fard JL Ockner DJ Tuma, Hepatology 1989 9 1 57 62 2908869
27. Detection of reduced acetaldehyde protein adducts using a unique monoclonal antibody. LW Klassen DJ Tuma MF Sorrell TL McDonald JM DeVasure GM Thiele, Alcohol Clin Exp Res 1994 18 1 164 171 8198215
28. A structural assignment for a stable acetaldehyde-lysine adduct. KP Braun RB Cody Jr DR Jones CM Peterson, J Biol Chem 1995 270 19 11263 11266 7744761
29. Stable acetaldehyde adducts: structural characterization of acetaldehyde adducts of human hemoglobin N-terminal beta-globin chain peptides. KP Braun JG Pavlovich DR Jones CM Peterson, Alcohol Clin Exp Res 1997 21 1 40 43 9046371
30. Production of antibodies that recognize the heterogeneity of immunoreactive sites in human hemoglobin chemically modified by acetaldehyde. RC Lin S Shahidi L Lumeng, Alcohol Clin Exp Res 1993 17 4 882 886 8214430
31. Reaction of acetaldehyde with human erythrocyte membrane proteins. KC Gaines JM Salhany DJ Tuma MF Sorrell, FEBS Lett 1977 75 1 115 119 852571
32. Clinical implications of acetaldehyde adducts with hemoglobin. CM Peterson LB Nguyen, Prog Clin Biol Res 1985 183 19 30 3901019
33. Hemoglobin-acetaldehyde adducts in human alcohol abusers. O Niemela Y Israel, Lab Invest 1992 67 2 246 252 1380106
34. Hemoglobin-acetaldehyde adducts in human volunteers following acute ethanol ingestion. O Niemela Y Israel Y Mizoi T Fukunaga CJ Eriksson, Alcohol Clin Exp Res 1990 14 6 838 841 2088118
35. Acetaldehyde binding increases the catabolism of rat serum low-density lipoproteins. MJ Savolainen E Baraona CS Lieber, Life Sci 1987 40 9 841 846 3821381
36. Cytotoxic protein molecules generated as a consequence of ethanol metabolism in vitro and in vivo. SN Wickramasinghe B Gardner G Barden, Lancet 1986 2 8511 823 826 2876277
37. Formation of acetaldehyde adducts with ethanol-inducible P450IIE1 in vivo. UJ Behrens M Hoerner JM Lasker CS Lieber, Biochem Biophys Res Commun 1988 154 2 584 590 3401224
38. Covalent binding of acetaldehyde to type III collagen. A Jukkola O Niemela, Biochem Biophys Res Commun 1989 159 1 163 169 2493786
39. Identification of the 37-kd rat liver protein that forms an acetaldehyde adduct in vivo as delta 4-3-ketosteroid 5 beta-reductase. Y Zhu MJ Fillenwarth D Crabb L Lumeng RC Lin, Hepatology 1996 23 1 115 122 8550030
40. An overview of the distribution and function of carbonic anhydrase in mammals. S Parkkila, Exs 2000 90 79 93 11268539
41. Characterization of CA XIII, a novel member of the carbonic anhydrase isozyme family. J Lehtonen B Shen M Vihinen A Casini A Scozzafava CT Supuran AK Parkkila J Saarnio AJ Kivela A Waheed, J Biol Chem 2004 279 4 2719 2727 14600151
42. Partial rescue of human carbonic anhydrase II frameshift mutation by ribosomal frameshift. PY Hu A Waheed WS Sly, Proc Natl Acad Sci USA 1995 92 6 2136 2140 7892236
43. Immunohistochemical localization of carbonic anhydrase isoenzymes VI, II, and I in human parotid and submandibular glands. S Parkkila K Kaunisto L Rajaniemi T Kumpulainen K Jokinen H Rajaniemi, J Histochem Cytochem 1990 38 7 941 947 2113069
44. A simplified micromethod for the determination of carbonic anhydrase and its inhibitors. TH Maren, J Pharmacol Exp Ther 1960 130 26 29 14421008
45. Carbonic anhydrase II deficiency: diagnosis and carrier detection using differential enzyme inhibition and inactivation. V Sundaram P Rumbolo J Grubb P Strisciuglio WS Sly, Am J Hum Genet 1986 38 2 125 136 3080873
46. Distribution of the carbonic anhydrase isoenzymes I, II, and VI in the human alimentary tract. S Parkkila AK Parkkila T Juvonen H Rajaniemi, Gut 1994 35 5 646 650 8200558
47. A systematic quantification of carbonic anhydrase transcripts in the mouse digestive system. PW Pan A Rodriguez S Parkkila, BMC Mol Biol 2007 8 22 17362527
48. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. CT Supuran, Nat Rev Drug Discov 2008 7 2 168 181 18167490
49. Crystal structure of human carbonic anhydrase C. A Liljas KK Kannan PC Bergsten I Waara K Fridborg B Strandberg U Carlbom L Jarup S Lovgren M Petef, Nat New Biol 1972 235 57 131 137 4621826
50. Structure of native and apo carbonic anhydrase II and structure of some of its anion-ligand complexes. K Hakansson M Carlsson LA Svensson A Liljas, J Mol Biol 1992 227 4 1192 1204 1433293
51. The refined atomic structure of carbonic anhydrase II at 1.05 A resolution: implications of chemical rescue of proton transfer. D Duda L Govindasamy M Agbandje-McKenna C Tu DN Silverman R McKenna, Acta Crystallogr D Biol Crystallogr 2003 59 Pt 1 93 104 12499545
52. Carbonic anhydrase inhibitors: binding of an antiglaucoma glycosyl-sulfanilamide derivative to human isoform II and its consequences for the drug design of enzyme inhibitors incorporating sugar moieties. A Di Fiore A Scozzafava JY Winum JL Montero C Pedone CT Supuran G De Simone, Bioorg Med Chem Lett 2007 17 6 1726 1731 17251017
53. Atomic crystal and molecular dynamics simulation structures of human carbonic anhydrase II: insights into the proton transfer mechanism. SZ Fisher CM Maupin M Budayova-Spano L Govindasamy C Tu M Agbandje-McKenna DN Silverman GA Voth R McKenna, Biochemistry 2007 46 11 2930 2937 17319692
54. Expression of testosterone-dependent enzyme, carbonic anhydrase III, and oxidative stress in experimental alcoholic liver disease. S Parkkila CH Halsted JA Villanueva HK Vaananen O Niemela, Dig Dis Sci 1999 44 11 2205 2213 10573363
55. Human mitochondrial carbonic anhydrase: cDNA cloning, expression, subcellular localization, and mapping to chromosome 16. Y Nagao JS Platero A Waheed WS Sly, Proc Natl Acad Sci USA 1993 90 16 7623 7627 8356065
56. The plasma membrane carbonic anhydrase in murine hepatocytes identified as isozyme XIV. S Parkkila AJ Kivela K Kaunisto AK Parkkila J Hakkola H Rajaniemi A Waheed WS Sly, BMC Gastroenterol 2002 2 13 12033992
57. Determination of hepatic acetaldehyde and its biphasic relationship to the ethanol concentration in rats. CJ Eriksson, Adv Exp Med Biol 1980 132 459 467 7424725
58. Impaired acetaldehyde metabolism in patients with non-alcoholic liver disorders. K Matthewson H Al Mardini K Bartlett CO Record, Gut 1986 27 7 756 764 3732886
59. Elevated blood acetaldehyde in alcoholics with accelerated ethanol elimination. KO Lindros A Stowell P Pikkarainen M Salaspuro, Pharmacol Biochem Behav 1980 13 Suppl 1 119 124 7243824
60. Human blood acetaldehyde (update 1992). CJ Eriksson T Fukunaga, Alcohol Alcohol Suppl 1993 2 9 25 7748353
61. Measurement of acetaldehyde: what levels occur naturally and in response to alcohol? CJ Eriksson, Novartis Found Symp 2007 285 247 255 discussion 256-260. 17590999
62. Red blood cells: a new major modality for acetaldehyde transport from liver to other tissues. E Baraona C Di Padova J Tabasco CS Lieber, Life Sci 1987 40 3 253 258 3796223
63. Method of acetaldehyde measurement with minimal artifactual formation in red blood cells and plasma of actively drinking subjects with alcoholism. R Hernandez-Munoz XL Ma E Baraona CS Lieber, J Lab Clin Med 1992 120 1 35 41 1613325
64. Generation of aldehyde-derived protein modifications in ethanol-exposed heart. O Niemela S Parkkila S Worrall PW Emery VR Preedy, Alcohol Clin Exp Res 2003 27 12 1987 1992 14691387
65. Generation of protein adducts with malondialdehyde and acetaldehyde in muscles with predominantly type I or type II fibers in rats exposed to ethanol and the acetaldehyde dehydrogenase inhibitor cyanamide. O Niemela S Parkkila M Koll VR Preedy, Am J Clin Nutr 2002 76 3 668 674 12198016
66. Evidence of acetaldehyde-protein adduct formation in rat brain after lifelong consumption of ethanol. J Rintala P Jaatinen S Parkkila M Sarviharju K Kiianmaa A Hervonen O Niemela, Alcohol Alcohol 2000 35 5 458 463 11022020