The Reactive Oxygen Species- and Michael Acceptor-inducible Human Aldo-Keto Reductase AKR1C1 Reduces the α,β-Unsaturated Aldehyde 4-Hydroxy-2-nonenal to 1,4-Dihydroxy-2-nonene

Journal of Biological Chemistry

Volumn 276, Issue 4, 2001, Pages 2890-2897

  Burczynski, Michael E ^a   Sridhar, Gopishetty R ^c   Palackal, Nisha T ^c   Penning, Trevor M ^b  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANTS; AROMATIC HYDROCARBONS; LIPIDS; METABOLITES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; RNA;

PEROXIDATION;

BIOCHEMISTRY;

1,4 DIHYDROXY 2 NONENE; 2 QUINONE; 20ALPHA HYDROXYSTEROID DEHYDROGENASE; 20ALPHA(3ALPHA) HYDROXYSTEROID DEHYDROGENASE; 4 HYDROXYNONENAL; ALDEHYDE DERIVATIVE; ANTIOXIDANT; ETACRYNIC ACID; GLUTATHIONE; HYDROXYSTEROID; ISOENZYME; MESSENGER RNA; NICOTINAMIDE; OXIDOREDUCTASE; PROTEIN AKR1C1; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; RECOMBINANT ENZYME; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG; 1,4-DIHYDROXY-2-NONENE; 3 ALPHA BETA, 20 BETA HYDROXYSTEROID DEHYDROGENASE; 3 ALPHA-BETA, 20 BETA-HYDROXYSTEROID DEHYDROGENASE; 3ALPHA(OR 20BETA) HYDROXYSTEROID DEHYDROGENASE; 4-HYDROXY-2-NONENAL; ALDEHYDE; ALKENE; DEHYDROASCORBIC ACID; GLUTATHIONE DEHYDROGENASE (ASCORBATE); GLUTATHIONE TRANSFERASE; NICOTINAMIDE ADENINE DINUCLEOTIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RECOMBINANT PROTEIN;

ARTICLE; CATALYSIS; CATALYST; CELL STRAIN HEPG2; CYTOSOL; DNA RESPONSIVE ELEMENT; ENZYME INDUCTION; HUMAN; HUMAN CELL; KINETICS; LIPID PEROXIDATION; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATIVE STRESS; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; GENETICS; METABOLISM; OXIDATION REDUCTION REACTION; PHYSIOLOGY;

FELIS CATUS;

20-HYDROXYSTEROID DEHYDROGENASES; ALDEHYDES; ALKENES; DEHYDROASCORBIC ACID; ENZYME INDUCTION; GLUTATHIONE; GLUTATHIONE TRANSFERASE; HUMANS; NAD; NADP; OXIDATION-REDUCTION; OXIDATIVE STRESS; OXIDOREDUCTASES; RECOMBINANT PROTEINS;

EID: 0035951825     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M006655200     Document Type: Article

References (66)

1. Trush, M. A., and Kensler, T. W. (1991) Free Radic. Biol. Med. 10, 201-209
2. Ross, R. (1993) Nature 362, 801-809
3. Poulsen, H. E., Prieme, H., and Loft, S. (1998) Eur. J. Cancer Prev. 7, 9-16
4. Sun, A. Y., and Chen, Y. M. (1998) J. Biomed. Sci. 5, 401-414
5. Facchinetti, F., Dawson, V. L., and Dawson, T. M. (1998) Neurobiology 18, 667-682
6. Esterbauer, H., Schaur, R. J., and Zollner, H. (1991) Free Radic. Biol. Med. 11, 81-128
7. Uchida, K., Toyokuni, S., Nishikawa, K., Kawakishi, S., Oda, H., Hiai, H., and Stadtman, E. R. (1994) Biochemistry 33, 12487-12494
8. Yoritaka, A., Hattori, N., Uchida, K., Tanaka, M., Stadtman, E. R., and Mizuno Y. (1996) Proc. Natl. Acad. Sci. U. S. A. 93, 2696-2701
9. Markesbery, W. R., and Carney, J. M. (1999) Brain Pathol. 9, 133-146
10. Yi, P., Zhan, D. J., Samokyszyn, V. M., Doerge, D. R., and Fu, P. P. (1997) Chem. Res. Toxicol. 10, 1259-1265
11. Nair, J., Barbin, A., Velic, I., and Bartsch, H. (1999) Mutat. Res. 424, 59-69
12. Rindgen, D., Nakajima, M., Wehrli, S., Xu, K., and Blair, I. A. (1999) Chem. Res. Toxicol. 12, 1195-1204
13. Lee, S. H., Rindgen, D., Bible, R. H., Hajdu, E., and Blair, I. A. (2000) Chem. Res. Toxicol. 17, 565-574
14. Hartley, D. P., Ruth, J. A., and Petersen, D. R. (1995) Arch. Biochem. Biophys. 316, 197-205
15. Hubatsch, J., Ridderstrom, M., and Mannervik, B. (1998) Biochem. J. 330, 175-179
16. Jez, J. M., Flynn, T. G., and Penning, T. M. (1997) Biochem. Pharmacol. 54, 639-647
17. Vander Jagt, D. L., Kolb, N. S., Vander Jagt, T. J., Chino, J., Martinez, F. J., Hunsaker, L. A., and Royer, R. E. (1995) Biochim. Biophys. Acta 1249, 117-126
18. Srivastava, S., Chandra, A., Bhatnagar A., Srivastava S. K., and Ansari, N. H. (1995) Biochem. Biophys. Res. Commun. 217, 741-746
19. Srivastava, S., Harter, T. M., Chandra, A., Bhatnagar, A., Srivastava, S. K., and Petrash, J. M. (1998) Biochemistry 37, 12909-12917
20. Ciaccio, P. J., Jaiswal, A. K., and Tew, K. D. (1994) J. Biol. Chem. 269, 15558-15562
21. Ciaccio, P. J., Shen, H., Jaiswal, A. K., Lyttle, M. H., and Tew, K. D. (1995) Mol. Pharmacol. 48, 639-647
22. Burczynski, M. E., Lin, H. K., and Penning, T. M. (1999) Cancer Res. 59, 607-614
23. Penning, T. M. (1997) Endocrine Rev. 18, 281-305
24. Lin, H-K., Jez, J. M., Schlegel, B. P., Peehl, D. M., Pachter, J. A., and Penning, T. M. (1997) Mol. Endocrinol. 11, 1971-1984
25. Penning, T. M., Burczynski, M. E., Jez, J. M., Hung, F-C., Lin, H-K., Ma, H., Moore, M., Palackal, N., and Ratnam, K. (2000) Biochem. J. 351, 67-77
26. Smithgall, T. E., Harvey, R. G., and Penning, T. M. (1986) J. Biol. Chem. 261, 6184-6191
27. Smithgall, T. E., Harvey, R. G., and Penning, T. M. (1988) J. Biol. Chem. 263, 1814-1820
28. Burczynski, M. E., Harvey, R. G., and Penning, T. M. (1998) Biochemistry 37, 6781-6790
29. Burczynski, M. E., Palackal, N. T., Harvey, R. G., and Penning, T. M. (1999) Polycyclic Arom. Cmpds. 16, 205-214
30. Del Bello, B., Maellaro, E., Sugherini, L., Santucci, A., Comporti, M., and Casini, A. F. (1994) Biochem. J. 304, 385-390
31. Pawlowski, J. E., and Penning, T. M. (1994) J. Biol. Chem. 269, 13502-13510
32. Palackal, N. T., Burczynski, M. E., Harvey, R. G., and Penning, T. M. (1999) Proc. Am. Assoc. Cancer Res. 40, Abstr. 4883
33. Bates, R. W., Dietz-Martin, D., Kerr, W. J., Knight, J. G., Ley, S. V., and Sakellaridis, A. (1990) Tetrahedron 46, 4063-4082
34. Leatherbarrow, R. J. (1987) ENZFITTER: A Non-Linear Regression Data Analysis Program for the IBM PC (and True Compatibles), Biosoft, Cambridge, UK
35. Suzuki-Yamamoto, T., Nishizawa, M., Fukui, M., Okuda-Ashitaka, E., and Nakajima, T. (1999) FEBS Lett. 462, 335-340
36. O'Connor, C., Ireland, L. S., Harrison, D. J., and Hayes, J. D. (1999) Biochem. J. 343, 487-504
37. Jez, J. M., and Penning, T. M. (1998) Biochemistry 37, 9695-9703
38. Nguyen, T., and Pickett, C. B. (1992) J. Biol. Chem. 267, 13535-13539
39. Pinkus, R., Weiner, L. M., and Daniel, V. (1995) Biochemistry 34, 81-88
40. Shi, M. M., Kugelman, A., Iwamoto, T., Tian, L., and Forman, H. J. (1994) J. Biol. Chem. 269, 26512-26517
41. Mulcahy, R. T., Wartman, M. A., Bailey, H. H., and Gipp, J. J. (1997) J. Biol. Chem. 272, 7445-7454
42. Dalton, T., Palmiter, R. D., and Andrews, G. K. (1994) Nucleic Acids Res. 22, 5016-5023
43. Klaassen, C. D., and Liu, J. (1998) Environ. Health Perspect. 106, 297-300
44. Favreau, L. V., and Pickett, C. B. (1991) J. Biol. Chem. 266, 4556-4561
45. Li, Y., and Jaiswal, A. K. (1993) J. Biol. Chem. 268, 21454-21459
46. Burczynski, J. M., Hayes, J. R., Longhurst, P. A., and Colby, H. D. (1999) Free Radic. Biol. Med. 26, 987-991
47. Wells, W. W., and Xu, D. P (1994) J. Bioenerg. Biomembr. 26, 369-377
48. Winkler, B. S., Orselli, S. M., and Rex, T. S. (1994) Free Radic. Biol. Med. 17, 333-349
49. Stolz, A., Hammond, L., Lou, H., Takikawa, H., Ronk, M., and Shively, J. E. (1993) J. Biol. Chem. 268, 10448-10457
50. Matsuura, K., Deyashiki, Y., Sato, K., Ishida, N., Miwa, G., and Hara, A. (1997) Biochem. J. 323, 61-64
51. Leonarduzzi, G., Parola, M., Muzio, G., Garramone, A., Maggiora, M., Robino, G., Poli, G., Dianzani, M. U., and Canuto, R. A. (1995) Biochem. Biophys. Res. Commun. 214, 669-675
52. Parola, M., Leonarduzzi, G., Robino, G., Albano, E., Poli, G., and Dianzani, M. U (1996) Free Radic. Biol. Med. 20, 351-359
53. Jez, J. M., Bennett, M. J., Schlegel, B. P., Lewis, M., and Penning, T. M. (1997) Biochem. J. 326, 625-636
54. Sellin, S., Holmquist, B., Mannervik, B., and Vallee, B. L. (1991) Biochemistry 30, 2514-2518
55. Allali-Hassani, A., Peralba, J. M., Martras, S., Farres, J., and Pares, X. (1998) FEBS Lett. 426, 362-366
56. Awasthi, Y. C., Zimniak, P., Singhal, S. S., and Awasthi, S. (1995) Biochem. Arch. 11, 47-54
57. Esterbauer, H., Zollner, H., and Lang, J. (1985) Biochem. J. 228, 363-373
58. Grune, T., Siems, W., Kowalewski, J., Zollner, H., and Esterbauer, H. (1991) Biochem. Int. 25, 963-971
59. Grune, T., Siems, W. G., and Petras, T. (1997) J. Lipid Res. 38, 1660-1665
60. Siems, W. G., Zollner, H., Gruyne, T., and Esterbauer, H. (1997) J. Lipid Res. 38, 612-622
61. Srivastava, S., Chandra, A., Wang, L., Seifert Jr., W. E., Dague, B. B., Ansari, N. H., Srivastava, S. K., and Bhatnagar, A. (1998) J. Biol. Chem. 273, 10893-10900
62. Fukuda, A., Nakamura, Y., Ohigashi, H., Osawa, T., and Uchida, K. (1997) Biochem. Biophys. Res. Commun. 236, 505-509
63. Spycher, S. E., Tabataba-Vakili, S., O'Donnell, V. B., Palomba, L., and Azzi, A. (1997) FASEB J. 11, 181-188
64. Suc, I., Meilhac, O., Lajoie-Mazenc, I., Vandaele, J., Jurgens, G., Salvayre, R., and Negre-Salvayre, A. (1998) FASEB J. 12, 665-671
65. Peterson, G. (1995) J. Nutr. 125, (suppl.) 784-789
66. Spitz, D. R., Kinter, M. T., and Roberts, R. J. (1995) J. Cell. Physiol. 165, 600-609