Characterization of the human ω-oxidation pathway for ω-hydroxy-very-long-chain fatty acids

FASEB Journal

Volumn 22, Issue 6, 2008, Pages 2064-2071

  Sanders, Robert Jan ^a   Ofman, Rob ^a   Dacremont, Georges ^b   Wanders, Ronald J A ^a   Kemp, Stephan ^a,c  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b GHENT UNIVERSITY   (Belgium)

^c ACADEMIC MEDICAL CENTER   (Netherlands)

Author keywords

ALDH3A2; Cytochrome P450; Sj gren Larson syndrome; X linked adrenoleukodystrophy

Indexed keywords

ALCOHOL DEHYDROGENASE; ALDEHYDE DEHYDROGENASE; ALDEHYDE DEHYDROGENASE 3A2; CYTOCHROME P450; CYTOCHROME P450 4F2; CYTOCHROME P450 4F3A; CYTOCHROME P450 4F3B; DICARBOXYLIC ACID DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; VERY LONG CHAIN FATTY ACID;

ARTICLE; CONTROLLED STUDY; ENZYME ANALYSIS; ENZYME KINETICS; FATTY ACID OMEGA OXIDATION; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL; SJOEGREN LARSSON SYNDROME;

ADRENOLEUKODYSTROPHY; ALDEHYDE OXIDOREDUCTASES; CYTOCHROME P-450 ENZYME SYSTEM; DICARBOXYLIC ACIDS; FATTY ACIDS; HUMANS; LIPID METABOLISM; METABOLIC NETWORKS AND PATHWAYS; NAD; OXIDATION-REDUCTION;

EID: 44949161094     PISSN: 08926638     EISSN: None     Source Type: Journal    
DOI: 10.1096/fj.07-099150     Document Type: Article

References (40)

1. Bezman, L., Moser, A. B., Raymond, G. V., Rinaldo, P., Watkins, P. A., Smith, K. D., Kass, N. E., and Moser, H. W. (2001) Adrenoleukodystrophy: incidence, new mutation rate, and results of extended family screening. Ann. Neurol. 49, 512-517
2. Moser, H. W., Smith, K. D., Watkins, P. A., Powers, J., and Moser, A. B. (2001) X-linked adrenoleukodystrophy. In The Metabolic and Molecular Bases of Inherited Disease (Scriver, C. R., Beaudet, A. L., Sly, W. S., and Valle, D., eds) pp. 3257-3301, McGraw-Hill, New York
3. Mosser, J., Douar, A. M., Sarde, C. O., Kioschis, P., Feil, R., Moser, H., Poustka, A. M., Mandel, J. L., and Aubourg, P. (1993) Putative X-linked adrenoleukodystrophy gene shares unexpected homology with ABC transporters. Nature 361, 726-730
4. Wanders, R. J., and Tager, J. M. (1998) Lipid metabolism in peroxisomes in relation to human disease. Mol. Aspects Med. 19, 69-154
5. Wanders, R. J. (2004) Peroxisomes, lipid metabolism, and peroxisomal disorders. Mol. Genet. Metab. 83, 16-27
6. Wanders, R. J., Visser, W. F., Van Roermund, C. W., Kemp, S., and Waterham, H. R. (2007) The peroxisomal ABC transporter family. Pflügers Arch. 453, 719-734
7. Singh, I., Moser, A. E., Moser, H. W., and Kishimoto, Y. (1984) Adrenoleukodystrophy: impaired oxidation of very long chain fatty acids in white blood cells, cultured skin fibroblasts, and amniocytes. Pediatr. Res. 18, 286-290
8. Moser, H. W., Moser, A. B., Frayer, K. K., Chen, W., Schulman, J. D., O'Neill, B. P., and Kishimoto, Y. (1981) Adrenoleukodystrophy: increased plasma content of saturated very long chain fatty acids. Neurology 31, 1241-1249
9. Fouquet, F., Zhou, J. M., Ralston, E., Murray, K., Troalen, F., Magal, E., Robain, O., Dubois-Dalcq, M., and Aubourg, P. (1997) Expression of the adrenoleukodystrophy protein in the human and mouse central nervous system. Neurobiol. Dis. 3, 271-285
10. Dubois-Dalcq, M., Feigenbaum, V., and Aubourg, P. (1999) The neurobiology of X-linked adrenoleukodystrophy, a demyelinating peroxisomal disorder. Trends Neurosci. 22, 4-12
11. Ho, J. K., Moser, H., Kishimoto, Y., and Hamilton, J. A. (1995) Interactions of a very long chain fatty acid with model membranes and serum albumin: implications for the pathogenesis of adrenoleukodystrophy. J. Clin. Invest. 96, 1455-1463
12. Singh, I., Khan, M., Key, L., and Pai, S. (1998) Lovastatin for X-linked adrenoleukodystrophy. N. Engl. J. Med. 339, 702-703
13. Rizzo, W. B., Leshner, R. T., Odone, A., Dammann, A. L., Craft, D. A., Jensen, M. E., Jennings, S. S., Davis, S., Jaitly, R., and Sgro, J. A. (1989) Dietary erucic acid therapy for X-linked adrenoleukodystrophy. Neurology 39, 1415-1422
14. Kemp, S., Wei, H. M., Lu, J. F., Braiterman, L. T., McGuinness, M. C., Moser, A. B., Watkins, P. A., and Smith, K. D. (1998) Gene redundancy and pharmacological gene therapy: implications for X-linked adrenoleukodystrophy. Nat. Med. 4, 1261-1268
15. + cells. Hum. Gene Ther. 9, 1025-1036
16. Peters, C., Charnas, L. R., Tan, Y., Ziegler, R. S., Shapiro, E. G., DeFor, T., Grewal, S. S., Orchard, P. J., Abel, S. L., Goldman, A. I., Ramsay, N. K., Dusenbery, K. E., Loes, D. J., Lockman, L. A., Kato, S., Aubourg, P. R., Moser, H. W., and Krivit, W. (2004) Cerebral X-linked adrenoleukodystrophy: the international hematopoietic cell transplantation experience from 1982 to 1999. Blood 104, 881-888
17. Sanders, R. J., Ofman, R., Duran, M., Kemp, S., and Wanders, R. J. (2006) ω-Oxidation of very long-chain fatty acids in human liver microsomes: implications for X-linked adrenoleukodystrophy. J. Biol. Chem. 281, 13180-13187
18. Kundu, R. K., Tonsgard, J. H., and Getz, G. S. (1991) Induction of omega-oxidation of monocarboxylic acids in rats by acetylsalicylic acid. J. Clin. Invest. 88, 1865-1872
19. Robbins, K. C. (1968) In vitro enzymic ω oxidation of mediumchain fatty acids in mammalian tissue. Arch. Biochem. Biophys. 123, 531-538
20. Sanders, R. J., Ofman, R., Valianpour, F., Kemp, S., and Wanders, R. J. (2005) Evidence for two enzymatic pathways for ω-oxidation of docosanoic acid in rat liver microsomes. J. Lipid Res. 46, 1001-1008
21. Wakabayashi, K., and Shimazono, N. (1963) Studies on ω-oxidation of fatty acids in vitro. I. Overall reaction and intermediate. Biochim. Biophys. Acta 70, 132-142
22. Ferdinandusse, S., Denis, S., Van Roermund, C. W., Wanders, R. J., and Dacremont, G. (2004) Identification of the peroxisomal β-oxidation enzymes involved in the degradation of longchain dicarboxylic acids. J. Lipid Res. 45, 1104-1111
23. Rocchiccioli, F., Aubourg, P., and Bougneres, P. F. (1986) Medium- and long-chain dicarboxylic aciduria in patients with Zellweger syndrome and neonatal adrenoleukodystrophy. Pediatr. Res. 20, 62-66
24. Valianpour, F., Selhorst, J. J., van Lint, L. E., van Gennip, A. H., Wanders, R. J., and Kemp, S. (2003) Analysis of very long-chain fatty acids using electrospray ionization mass spectrometry. Mol. Genet. Metab. 79, 189-196
25. Willemsen, M. A., IJlst, L., Steijlen, P. M., Rotteveel, J. J., de Jong, J. G., van Domburg, P. H., Mayatepek, E., Gabreels, F. J., and Wanders, R. J. (2001) Clinical, biochemical and molecular genetic characteristics of 19 patients with the Sjögren-Larsson syndrome. Brain 124, 1426-1437
26. Jansen, G. A., Verhoeven, N. M., Denis, S., Romeijn, G., Jakobs, C., ten Brink, H. J., and Wanders, R. J. (1999) Phytanic acid α-oxidation: identification of 2-hydroxyphytanoyl-CoA lyase in rat liver and its localisation in peroxisomes. Biochim. Biophys. Acta 1440, 176-182
27. Wolvetang, E. J., Wanders, R. J., Schutgens, R. B., Berden, J. A., and Tager, J. M. (1990) Properties of the ATPase activity associated with peroxisome-enriched fractions from rat liver: comparison with mitochondrial F1F0-ATPase. Biochim. Biophys. Acta 1035, 6-11
28. Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gartner, F. H., Provenzano, M. D., Fujimoto, E. K., Goeke, N. M., Olson, B. J., and Klenk, D. C. (1985) Measurement of protein using bicinchoninic acid. Anal. Biochem. 150, 76-85
29. Nguyen, X., Wang, M. H., Reddy, K. M., Falck, J. R., and Schwartzman, M. L. (1999) Kinetic profile of the rat CYP4A isoforms: arachidonic acid metabolism and isoform-specific inhibitors. Am. J. Physiol. 276, R1691-R1700
30. Xu, F., Falck, J. R., Ortiz de Montellano, P. R., and Kroetz, D. L. (2004) Catalytic activity and isoform-specific inhibition of rat cytochrome p450 4F enzymes. J. Pharmacol. Exp. Ther. 308, 887-895
31. Vasiliou, V., and Nebert, D. W. (2005) Analysis and update of the human aldehyde dehydrogenase (ALDH) gene family. Hum. Genomics 2, 138-143
32. De Laurenzi, V., Rogers, G. R., Hamrock, D. J., Marekov, L. N., Steinert, P. M., Compton, J. G., Markova, N., and Rizzo, W. B. (1996) Sjögren-Larsson syndrome is caused by mutations in the fatty aldehyde dehydrogenase gene. Nat. Genet. 12, 52-57
33. Hsu, L. C., Chang, W. C., and Yoshida, A. (1994) Cloning of a cDNA encoding human ALDH7, a new member of the aldehyde dehydrogenase family. Gene 151, 285-289
34. Hsu, L. C., Chang, W. C., Lin, S. W., and Yoshida, A. (1995) Cloning and characterization of genes encoding four additional human aldehyde dehydrogenase isozymes. Adv. Exp. Med. Biol. 372, 159-168
35. Kelson, T. L., Secor, M., Jr., and Rizzo, W. B. (1997) Human liver fatty aldehyde dehydrogenase: microsomal localization, purification, and biochemical characterization. Biochim. Biophys. Acta 1335, 99-110
36. + oxidoreductase from rat liver. J. Biol. Chem. 254, 2892-2896
37. Lindahl, R. (1979) Subcellular distribution and properties of aldehyde dehydrogenase from 2-acetylaminofluorene-induced rat hepatomas. Biochem. J. 183, 55-64
38. Zorzano, A., and Herrera, E. (1990) Differences in kinetic characteristics and in sensitivity to inhibitors between human and rat liver alcohol dehydrogenase and aldehyde dehydrogenase. Gen. Pharmacol. 21, 697-702
39. + oxidoreductase in cultured fibroblasts. J. Clin. Invest. 88, 1643-1648
40. Hsu, M. H., Savas, U., Griffin, K. J., and Johnson, E. F. (2006) Regulation of human cytochrome P450 4F2 expression by sterol regulatory element-binding protein and lovastatin. J. Biol. Chem. 282, 5225-5236