Studying fatty aldehyde metabolism in living cells with pyrene-labeled compounds

Journal of Lipid Research

Volumn 53, Issue 7, 2012, Pages 1410-1416

  Keller, Markus A ^a   Watschinger, Katrin ^a   Lange, Karsten ^b   Golderer, Georg ^a   Werner Felmayer, Gabriele ^a   Hermetter, Albin ^c   Wanders, Ronald J A ^d   Werner, Ernst R ^a  

^a INNSBRUCK MEDICAL UNIVERSITY   (Austria)

^b UNIVERSITY OF WUPPERTAL   (Germany)

^c GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^d UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Fatty aldehyde metabolism; Inborn errors of metabolism; Long chain fatty aldehyde dehydrogenase; Oxidized lipids; Sj gren Larsson Syndrome; Skin; Toxicology

Indexed keywords

ALDEHYDE; ALDEHYDE DEHYDROGENASE; ALKYLGLYCEROL; FATTY ACID; FATTY ALCOHOL; GLYCEROL; HEXADECANOL; PYRENE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL LABELING; CELL METABOLISM; CONCENTRATION RESPONSE; CONTROLLED STUDY; CULTURE MEDIUM; CYTOTOXICITY; ENZYME ACTIVITY; ENZYME SPECIFICITY; FEMALE; FIBROBLAST CULTURE; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIPID ANALYSIS; LIPID METABOLISM; LIPID STORAGE; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SJOEGREN LARSSON SYNDROME; TIME;

ALDEHYDE OXIDOREDUCTASES; ALDEHYDES; ANIMALS; CELLS, CULTURED; CHO CELLS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRICETINAE; DOSE-RESPONSE RELATIONSHIP, DRUG; FATTY ACIDS; FIBROBLASTS; HUMANS; PYRENES; SJOGREN-LARSSON SYNDROME; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

EID: 84862321607     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.D025650     Document Type: Article

References (23)

1. Rizzo, W. B., Z. Lin, and G. Carney. 2001. Fatty aldehyde dehydrogenase: genomic structure, expression and mutation analysis in Sjögren-Larsson syndrome. Chem. Biol. Interact. 130-132: 297-307. (Pubitemid 32295824)
2. Rizzo, W. B., and D. Craft. 1991. Sjögren-Larsson syndrome. Deficient activity of the fatty aldehyde dehydrogenase component of fatty alcohol:NAD+ oxidoreductase in cultured fibroblasts. J. Clin. Invest. 88: 1643-1648.
3. Kelson, T. L., J. Secor McVoy, and W. Rizzo. 1997. Human liver fatty aldehyde dehydrogenase: microsomal localization, purification, and biochemical characterization. Biochim. Biophys. Acta. 1335: 99-110. (Pubitemid 27174510)
4. Keller, M. A, K. Watschinger, G. Golderer, M. Maglione, B. Sarg, H. Lindner, G. Werner-Felmayer, A. Terrinoni, R. Wanders, and E. Werner. 2010. Monitoring of fatty aldehyde dehydrogenase by formation of pyrenedecanoic acid from pyrenedecanal. J. Lipid Res. 51: 1554-1559.
5. Ashibe, B., T. Hirai, K. Higashi, K. Sekimizu, and K. Motojima. 2007. Dual subcellular localization in the endoplasmic reticulum and peroxisomes and a vital role in protecting against oxidative stress of fatty aldehyde dehydrogenase are achieved by alternative splicing. J. Biol. Chem. 282: 20763-20773. (Pubitemid 47100018)
6. Rizzo, W. B., and G. Carney. 2005. Sjögren-Larsson syndrome: diversity of mutations and polymorphisms in the fatty aldehyde dehydrogenase gene (ALDH3A2). Hum. Mutat. 26: 1-10. (Pubitemid 40983989)
7. Rizzo, W. B., D. Craft, T. Somer, G. Carney, J. Trafrova, and M. Simon. 2008. Abnormal fatty alcohol metabolism in cultured keratinocytes from patients with Sjögren-Larsson syndrome. J. Lipid Res. 49: 410-419. (Pubitemid 351213626)
8. Sjögren, T., and T. Larsson. 1957. Oligophrenia in combination with congenital ichthyosis and spastic disorders; a clinical and genetic study. Acta Psychiatr. Neurol. Scand., Suppl. 113: 1-112.
9. James, P. F., and R. Zoeller. 1997. Isolation of animal cell mutants defective in long-chain fatty aldehyde dehydrogenase. Sensitivity to fatty aldehydes and Schiff's base modification of phospholipids: implications for Sjogren-Larsson syndrome. J. Biol. Chem. 272: 23532-23539. (Pubitemid 27410921)
10. Demozay, D., S. Rocchi, J. Mas, S. Grillo, L. Pirola, C. Chavey, and E. Van Obberghen. 2004. Fatty aldehyde dehydrogenase: potential role in oxidative stress protection and regulation of its gene expression by insulin. J. Biol. Chem. 279: 6261-6270. (Pubitemid 38258224)
11. Demozay, D., J. Mas, S. Rocchi, and E. Van Obberghen. 2008. FALDH reverses the deleterious action of oxidative stress induced by lipid peroxidation product 4-hydroxynonenal on insulin signaling in 3T3-L1 adipocytes. Diabetes. 57: 1216-1226.
12. Watschinger, K., M. Keller, G. Golderer, M. Hermann, M. Maglione, B. Sarg, H. Lindner, A. Hermetter, G. Werner-Felmayer, R. Konrat, et al. 2010. Identification of the gene encoding alkylglycerol monooxygenase defines a third class of tetrahydrobiopterin-dependent enzymes. Proc. Natl. Acad. Sci. USA. 107: 13672-13677.
13. Willemsen, M. A., J. Rotteveel, J. de Jong, R. Wanders, L. IJlst, G. Hoffmann, and E. Mayatepek. 2001. Defective metabolism of leukotriene B4 in the Sjögren-Larsson syndrome. J. Neurol. Sci. 183: 61-67. (Pubitemid 32141074)
14. Rizzo, W. B, E. Heinz, M. Simon, and D. Craft. 2000. Microsomal fatty aldehyde dehydrogenase catalyzes the oxidation of aliphatic aldehyde derived from ether glycerolipid catabolism: implications for Sjögren-Larsson syndrome. Biochim. Biophys. Acta. 1535: 1-9.
15. Werner, E. R., A. Hermetter, H. Prast, G. Golderer, and G. Werner-Felmayer. 2007. Widespread occurrence of glyceryl ether monooxygenase activity in rat tissues detected by a novel assay. J. Lipid Res. 48: 1422-1427. (Pubitemid 47312046)
16. Fernandes, R. A., K. Pradeep. 2000. A stereoselective synthesis of dihydrosphingosine. Eur. J. Org. Chem. 3447-3449.
17. He, L., H. S. Byun, and R. Bittman. 2000. A stereocontrolled, efficient synthetic route to bioactive sphingolipids: synthesis of phytosphingosine and phytoceramides from unsaturated ester precursors via cyclic sulfate intermediates. J. Org. Chem. 65: 7618-7626.
18. Sanders, R. J., R. Ofman, C. Dekker, S. Kemp, and R. Wanders. 2009. Enzymatic diagnosis of Sjögren-Larsson syndrome using electrospray ionization mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 877: 451-455.
19. Rizzo, W. B., A. Dammann, and D. Craft. 1988. Sjögren-Larsson syndrome. Impaired fatty alcohol oxidation in cultured fibroblasts due to deficient fatty alcohol:nicotinamide adenine dinucleotide oxidoreductase activity. J. Clin. Invest. 81: 738-744. (Pubitemid 18079721)
20. Strunnikova, N., S. Hilmer, J. Flippin, M. Robinson, E. Hoffman, and K. G. Csaky. 2005. Differences in gene expression profiles in dermal fibroblasts from control and patients with age-related macular degeneration elicited by oxidative injury. Free Radic. Biol. Med. 39: 781-796. (Pubitemid 41139892)
21. Marchitti, S. A., C. Brocker, D. Stagos, and V. Vasiliou. 2008. Non-P450 aldehyde oxidizing enzymes: the aldehyde dehydrogenase superfamily. Expert Opin. Drug Metab. Toxicol. 4: 697-720. (Pubitemid 352003194)
22. Estey, T., J. Piatigorsky, N. Lassen, and V. Vasiliou. 2007. ALDH3A1: a corneal crystallin with diverse functions. Exp. Eye Res. 84: 3-12. (Pubitemid 44792047)
23. Somerharju, P. 2002. Pyrene-labeled lipids as tools in membrane biophysics and cell biology. Chem. Phys. Lipids. 116: 57-74. (Pubitemid 34686987)