The xenobiotic-metabolizing enzymes arylamine N-acetyltransferases in human lens epithelial cells: Inactivation by cellular oxidants and UVB-induced oxidative stress

Molecular Pharmacology

Volumn 67, Issue 4, 2005, Pages 1299-1306

  Dairou, Julien ^a,c   Malecaze, François ^b   Dupret, Jean Marie ^a,c   Rodrigues Lima, Fernando ^a,c  

^a PITIÉ SALPÊTRIÈRE HOSPITAL   (France)

^b CHU PURPAN   (France)

^c UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLAMINE ACETYLTRANSFERASE; ISOENZYME; OXIDIZING AGENT; PEROXYNITRITE;

ACETYLATION; ANIMAL CELL; ARTICLE; CATARACT; CATARACTOGENESIS; CONTROLLED STUDY; DETOXIFICATION; DNA POLYMORPHISM; ENVIRONMENTAL FACTOR; ENZYME ACTIVITY; HOMEOSTASIS; HUMAN; HUMAN CELL; LENS EPITHELIUM; METABOLIC ACTIVATION; NONHUMAN; OXIDATIVE STRESS; PHOTOOXIDATION; PRIORITY JOURNAL; PROTEIN FUNCTION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; ULTRAVIOLET B RADIATION; WESTERN BLOTTING; XENOBIOTIC METABOLISM;

ARYLAMINE N-ACETYLTRANSFERASE; CATARACT; CELL LINE; EPITHELIAL CELLS; HUMANS; HYDROGEN PEROXIDE; ISOENZYMES; LENS, CRYSTALLINE; OXIDANTS; OXIDATION-REDUCTION; OXIDATIVE STRESS; ULTRAVIOLET RAYS;

EID: 15744370426     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.104.009738     Document Type: Article

References (57)

1. Andley UP, Rhim JS, Chylack LT, and Fleming TP (1994) Propagation and immortalization of human lens epithelial cells in culture. Investig Ophthalmol Vis Sci 35:3094-3102.
2. Atmane N, Dairou J, Paul A, Dupret JM, and Rodrigues-Lima F (2003) Redox regulation of the human xenobiotic metabolizing enzyme arylamine N-acetyltransferase 1 (NAT1). Reversible inactivation by hydrogen peroxide. J Biol Chem 278:35086-35092.
3. Butcher NJ, Arulpragasam A, and Minchin RF (2004) Proteasomal degradation of N-acetyltransferase 1 is prevented by acetylation of the active site cysteine: A mechanism for the slow acetylator phenotype and substrate-dependent down-regulation. J Biol Chem 279:22131-22137.
4. Butcher NJ, Ilett KF, and Minchin RF (2000) Substrate-dependent regulation of human arylamine N-acetyltransferase-1 in cultured cells. Mol Pharmacol 57:468-473.
5. Campbell DA, Schoenwald RD, Duffel MW, and Berfknecht CF (1991) Characterization of arylamine acetyltransferase in the rabbit eye. Investig Ophthalmol Vis Sci 32:873-877.
6. Couder BC, de Neuville S, Douin-Echinard V, Serres B, Manenti S, Darbon JM, and Malecaze F (1999) Retrovirus-mediated transfer of a suicide gene into lens epithelial cells in vitro and in an experimental model of posterior capsule opacification. Curr Eye Res 19:472-482.
7. Daiber A, Herold S, Schöneich C, Namgaladze D, Peterson J, and Ullrich V (2000) Nitration and inactivation of cytochrome P450BM3 by peroxynitrite. Eur J Biochem 267:6729-6739.
8. Dairou J, Atmane N, Dupret JM, and Rodrigues-Lima F (2003) Reversible inhibition of the human xenobiotic-metabolizing enzyme arylamine N-acetyltransferase 1 by S-nitrosothiols. Biochem Biophys Res Commun 307:1059-1065.
9. Dairou J, Atmane N, Rodrigues-Lima F, and Dupret JM (2004) Peroxynitrite irreversibly inactivates the human xenobiotic-metabolizing enzyme arylamine N-acetyltransferase 1 (NAT1) in human breast cancer cells. A cellular and mechanistic study. J Biol Chem 279:7708-7714.
10. Davies MJ and Truscott RJ (2001) Photo-oxidation of proteins and its role in cataractogenesis. J Photochem Photobiol B 63:114-125.
11. Deguchi T (1992) Sequences and expression of alleles of polymorphic arylamine N-acetyltransferase of human liver. J Biol Chem 267:18140-18147.
12. Dudek EJ, Shang F, and Taylor A (2001) H(2)O(2)-mediated oxidative stress activates NF-kappa B in lens epithelial cells. Free Radic Biol Med 31:651-658.
13. Dupret JM and Grant DM (1992) Site-directed mutagenesis of recombinant human arylamine N-acetyltransferase expressed in Escherichia coli. Evidence for direct involvement of Cys68 in the catalytic mechanism of polymorphic human NAT2. J Biol Chem 267:7381-7385.
14. Fretland AJ, Leff MA, Doll MA, and Hein DW (2001) Functional characterization of human N-acetyltransferase 2 (NAT2) single nucleotide polymorphisms. Pharmacogenetics 11:207-215.
15. Gaudet SJ, Razavi P, Caiafa GJ, and Chader GJ (1995) Identification of arylamine N-acetyltransferase activity in the bovine lens. Curr Eye Res 14:873-877.
16. Grob S, Knebel A, Tenev T, Neininger A, Gaestel M, Herrlich P, and Bohmer F (1999) Inactivation of protein-tyrosine phosphatases as mechanism of UV-induced signal transduction. J Biol Chem 274:26378-26386.
17. Halliwell B and Gutteridge JMC (1999) Free Radicals in Biology and Medicine. Oxford University Press, Oxford.
18. Hein D, McQueen C, Grant D, Goodfellow G, Kadlubar F, and Weber W (2000) Pharmacogenetics of the arylamine N-acetyltransferases: A symposium in honor of Wendell W. Weber. Drug Metab Dispos 28:1425-1432.
19. Hickman D, Pope J, Patil SD, Fakis G, Smelt V, Stanley LA, Payton M, Unadkat JD, and Sim E (1998) Expression of arylamine N-acetyltransferase in human intestine. Gut 42:402-409.
20. Hosler MR, Wang-Su ST, and Wagner BJ (2003) Targeted disruption of specific steps of the ubiquitin-proteasome pathway by oxidation in lens epithelial cells. Int J Biochem Cell Biol 35:685-697.
21. Ilett KF, Ingram DM, Carpenter DS, Teitel CH, Lang NP, Kadlubar FF, and Minchin RF (1994) Expression of monomorphic and polymorphic N-acetyltransferases in human colon. Biochem Pharmacol 47:914-917.
22. Kawakubo Y, Merk HF, Al Masaoudi T, Sieben S, and Blomeke B (2000) N-Acetylation of paraphenylenediamine in human skin and keratinocytes. J Pharmacol Exp Ther 292:150-155.
23. Matas N, Thygesen P, Stacey M, Risch A, and Sim E (1997) Mapping AAC1, AAC2 and AACP, the genes for arylamine N-acetyltransferases, carcinogen metabolising enzymes on human chromosome 8p22, a region frequently deleted in tumours. Cytogenet Cell Genet 77:290-295.
24. Mattano SS, Land S, King CM, and Weber WW (1989) Purification and biochemical characterization of hepatic arylamine N-acetyltransferase from rapid and slow acetylator mice: identity with arylhydroxamic acid N,O-acyltransferase and N-hydroxyarylamine O-acetyltransferase. Mol Pharmacol 35:599-609.
25. Meisel P, Giebel J, Peters M, Foerster Peters, Cascorbi I, Wulff K, Fanghaenel J, and Kocher T (2002) Expression of N-acetyltransferases in periodontal granulation tissue. J Dent Res 81:349-353.
26. Meyer D, Parkin DP, Seifart HI, Maritz JS, Engelbrecht AH, Werely CJ, and van Helden PD (2003) NAT2 slow acetylator function as a risk indicator for age-related cataract formation. Pharmacogenetics 13:285-289.
27. Mihm M and Bauer J (2002) Peroxynitrite-induced inhibition and nitration of cardiac myofibrillar creatine kinase. Bochimie 84:1013-1019.
28. Mueller S, Pantopoulos K, Hubner C, Stremmel W, and Hentze M (2001) IRP1 activation by extracellular oxidative stress in the perfused rat liver. J Biol Chem 276:23192-23196.
29. Paron I, D'Elia A, D'Ambrosio C, Scaloni D'Ambrosio, D'Aurizio F, Prescott A, Damante G, and Tell G (2004) A proteomic approach to identify early molecular targets of oxidative stress in human epithelial lens cells. Biochem J 378:929-937.
30. Pompeo F, Brooke E, Akane K, Mushtaq A, and Sim E (2002) the pharmacogenetics of NAT: structural aspects. Pharmacogenomics 3:19-30.
31. Raghavachari N, Qiao F, and Lou MF (1999) Does glutathione-S-transferase dethiolate lens protein-thiol mixed disulfides? A comparative study with thioltransferase. Exp Eye Res 68:715-724.
32. Ravid T, Sweeney C, Gee P, Carraway K 3rd, and Goldkorn T (2002) Epidermal growth factor receptor activation under oxidative stress fails to promote c-Cbl mediated down-regulation. J Biol Chem 277:31214-31219.
33. Reddy GB, Reddy PY, and Suryanarayana P (2001) alphaA- and alphaB-Crystallins protect glucose-6-phosphate dehydrogenase against UVB irradiation-induced inactivation. Biochem Biophys Res Commun 282:712-716.
34. Rodrigues-Lima F, Cooper R, Goudeau B, Atmane N, Chamagne A, Butler-Browne G, Sim E, Vicart P, and Dupret J (2003) Skeletal muscles express the xenobiotic-metabolizing enzyme arylamine N-acetyltransferase. J Histochem Cytochem 51: 789-796.
35. Rodrigues-Lima F, Deloménie C, Goodfellow GH, Grant DM, and Dupret JM (2001) Homology modelling and structural analysis of human arylamine N-acetyltransferase NAT1: evidence for the conservation of a cysteine protease catalytic domain and an active-site loop. Biochem J 356:327-334.
36. Rodrigues-Lima F and Dupret JM (2002) 3D model of human arylamine N-acetyltransferase 2: structural basis of the slow acetylator phenotype of the R64Q variant and analysis of the active site loop. Biochem Biophys Res Commun 291: 116-123.
37. Rodrigues-Lima F and Dupret JM (2004) Regulation of the activity of the human drug metabolizing enzyme arylamine N-acetyltransferase 1: role of genetic and non genetic factors. Curr Pharm Des 10:2519-2524.
38. Rogers CS, Chan LM, Sims YS, Byrd KD, Hinton DL, and Twining SS (2004) The effects of sub-solar levels of UV-A and UV-B on rabbit corneal and lens epithelial cells. Exp Eye Res 78:1007-1014.
39. Sadrieh N, Davis CD, and Snyderwine EG (1996) N-Acetyltransferase expression and metabolic activation of the food-derived heterocyclic amines in the human mammary gland. Cancer Res 56:2683-2687.
40. Sandy J, Mushtaq A, Kawamura A, Sinclair J, Noble M, and Sim E (2002) The structure of arylamine N-acetyltransferase from Mycobacterium smegmatis-an enzyme which inactivates the anti-tubercular drug, isoniazid. J Mol Biol 318: 1071-1083.
41. Shin DM, Jeon JH, Kim CW, Cho SY, Kwon JC, Lee HJ, Choi KH, Park SC, and Kim IG (2004) Cell type-specific activation of intracellular transglutaminase 2 by oxidative stress or ultraviolet irradiation: implications of transglutaminase 2 in age-related cataractogenesis. J Biol Chem 279:15032-15039.
42. Sim E, Payton M, Noble M, and Minchin R (2000) An update on genetic, structural and functional studies of arylamine N-acetyltransferases in eucaryotes and procaryotes. Hum Mol Genet 8:2435-2441.
43. Sinclair JC, Delgoda R, Noble ME, Jarmin S, Goh NK, and Sim E (1998) Purification, characterization and crystallization of an N-hydroxyarylamine O-acetyltransferase from Salmonella typhimurium. Protein Expr Purif 12:371-380.
44. Sinclair JC, Sandy J, Delgoda R, Sim E, and Noble ME (2000) Structure of arylamine N-acetyltransferase reveals a catalytic triad. Nat Struct Biol 7:560-564.
45. Singh RJ, Hogg N, Joseph J, Konorev E, and Kalyanaraman B (1999) The peroxynitrite generator, SIN-1, becomes a nitric oxide donor in the presence of electron acceptors. Arch Biochem Biophys 361:331-339.
46. Solberg Y, Rosner M, and Belkin M (1998) The association between cigarette smoking and ocular disease. Surv Ophtalmol 42:535-547.
47. Spector A (1991) The Lens and Oxidative Stress, Academic Press, London.
48. Stachowiak O, Dolder M, Wallimann T, and Richter C (1998) Mitochondrial creatine kinase is a prime target of peroxynitrite-induced modification and inactivation. J Biol Chem 273:16694-16699.
49. Stanley LA, Coroneos E, Cuff R, Hickman D, Ward A, and Sim E (1996) Immunochemical detection of arylamine N-acetyltransferase in normal and neoplastic bladder. J Histochem Cytochem 44:1059-1067.
50. Thiagarajan G, Lakshmanan J, Chalasani M, and Balasubramanian D (2004) Peroxynitrite reaction with eye lens proteins: alpha-crystallin retains its activity despite modification. Investig Ophthalmol Vis Sci 45:2115-2121.
51. To TQ and Towsend JC (2000) Ocular toxicity of systemic medications: a case series. J Am Optom Assoc 71:29-39.
52. Truscott RJ (2003) Human cataract: the mechanism responsible; light and butterfly eyes. Int J Biochem Cell Biol 35:1500-1504.
53. Tumminia SJ, Rao PV, Zigler JS, and Russell P (1993) Xenobiotic induction of quinone oxidoreductase activity in lens epithelial cells. Biochim Biophys Acta 1203:251-259.
54. Van Den Brule J, Degueldre F, and Galand A (1998) Drug-induced cataract. Rev Med Liege 53:766-769.
55. von Kobbe C, May A, Grandori C, and Bohr VA (2004) Werner syndrome cells escape hydrogen peroxide-induced cell proliferation arrest. FASEB J 18:1970-1972.
56. Westwood IM, Holton SJ, Rodrigues-Lima F, Dupret JM, Bhakta S, Noble ME, and Sim E (2005) Expression, purification, characterization and structure of Pseudomonas aeruginosa arylamine N-acetyltransferase. Biochem J 385:605-612.
57. Windmill KF, Gaedigk A, Hall PM, Samaratunga H, Grant DM, and McManus ME (2000) Localization of N-acetyltransferases NAT1 and NAT2 in human tissues. Toxicol Sci 54:19-29.