Sphingosine 1-phosphate lyase enzyme assay using a BODIPY-labeled substrate

Biochemical and Biophysical Research Communications

Volumn 380, Issue 2, 2009, Pages 366-370

  Bandhuvula, Padmavathi ^a   Li, Zaiguo ^b   Bittman, Robert ^b   Saba, Julie D ^a  

^a CHILDREN S HOSPITAL OAKLAND RESEARCH INSTITUTE   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Assay; BODIPY; Fluorescent; NBD; Sphingolipid; Sphingosine 1 phosphate; Sphingosine 1 phosphate lyase

Indexed keywords

2,4 DINITROPHENYLHYDRAZINE; LYASE; MEMBRANE RECEPTOR; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE 1 PHOSPHATE LYASE; UNCLASSIFIED DRUG;

ANGIOGENESIS; ANTIBODY LABELING; ARTICLE; CATABOLISM; CELL STRAIN HEK293; CELLULAR STRESS RESPONSE; ENZYME ASSAY; ENZYME LINKED IMMUNOSORBENT ASSAY; ENZYME SUBSTRATE; ENZYME SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LYMPHOCYTE ACTIVATION; PRIORITY JOURNAL; SIGNAL TRANSDUCTION;

ALDEHYDE-LYASES; ANIMALS; BORON COMPOUNDS; CATALYSIS; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCENT DYES; HUMANS; LYSOPHOSPHOLIPIDS; METHODS; MICE; SPHINGOSINE;

EID: 60349119099     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2009.01.106     Document Type: Article

References (32)

1. Fyrst H., and Saba J.D. Sphingosine-1-phosphate lyase in development and disease: sphingolipid metabolism takes flight. Biochim. Biophys. Acta 1781 (2008) 448-458
2. Spiegel S., and Milstien S. Functions of the multifaceted family of sphingosine kinases and some close relatives. J. Biol. Chem. 282 (2007) 2125-2129
3. Hla T. Signaling and biological actions of sphingosine-1-phosphate. Pharmacol. Res. 47 (2003) 401-407
4. Rivera J., Proia R.L., and Olivera A. The alliance of sphingosine-1-phosphate and its receptors in immunity. Nat. Rev. Immunol. 8 (2008) 753-763
5. Matloubian M., Lo C.G., Cinamon G., Lesneski M.J., Xu Y., Brinkmann V., Allende M.L., Proia R.L., and Cyster J.G. Lymphocyte egress from thymus and peripheral lymphoid organs is dependent on S1P receptor 1. Nature 427 (2004) 355-360
6. Venkataraman K., Lee Y.M., Michaud J., Thangada S., Ai Y., Bonkovsky H.L., Parikh N.S., Habrukowich C., and Hla T. Vascular endothelium as a contributor of plasma sphingosine-1-phosphate. Circ. Res.102 (2008) 669-676
7. Schwab S., Pereira J., Matloubian M., Xu Y., Huang Y., and Cyster J. Lymphocyte sequestration through S1P lyase inhibition an disruption of S1P gradients. Science 309 (2005) 1735-1739
8. Billich A., and Baumruker T. Sphingolipid metabolizing enzymes as novel therapeutic targets. Subcell Biochem. 49 (2008) 487-522
9. Oskouian B., and Saba J.D. Death and taxis: what non-mammalian models tell us about sphingosine-1-phosphate. Semin. Cell Dev. Biol. 15 (2004) 529-540
10. Tsegaye Y., Richardson C.G., Bravo J.E., Mulcahy B.J., Lynch D.V., Markham J.E., Jaworski J.G., Chen M., Cahoon E.B., and Dunn T.M. Arabidopsis mutants lacking long chain base phosphate lyase are fumonisin-sensitive and accumulate trihydroxy-18:1 long chain base phosphate. J. Biol. Chem. 282 (2007) 28195-28206
11. Zhang K., Pompey J.M., Hsu F.F., Key P., Bandhuvula P., Saba J.D., Turk J., and Beverley S.M. Redirection of sphingolipid metabolism towards de novo synthesis of ethanolamine in Leishmania. EMBO J. 26 (2007) 1094-1104
12. Van Veldhoven P.P. Sphingosine-1-phosphate lyase. In: Merrill Jr. A.H., and Hannun Y.A. (Eds). Sphingolipid Metabolism and Cell Signaling Part A (2000), Academic Press, New York 244-254
13. Bandhuvula P., Fyrst H., and Saba J. A rapid fluorescent assay for sphingosine-1-phosphate lyase enzyme activity. J. Lipid Res. 48 (2007) 2769-2778
14. Mazeres S., Schram V., Tocanne J.F., and Lopez A. 7-Nitrobenz-2-oxa-1,3-diazole-4-yl-labeled phospholipids in lipid membranes: differences in fluorescence behavior. Biophys. J. 71 (1996) 327-335
15. Loudet A., and Burgess K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chem. Rev. 107 (2007) 4891-4932
16. Sudhakar N., Kumar A., Prabhakar A., Jagadeesh B., and Rao B. The first synthesis of the anhydrophytosphingosine pachastrissamine (jaspine B) from Garner's aldehyde. Tetrahedron Lett. 46 (2005) 325-327
17. Yamamoto T., Hasegawa H., Hakogi T., and Katsumura S. Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis. Org. Lett. 8 (2006) 5569-5572
18. Peters C., Billich A., Ghobrial M., Högenauer K., Ullrich T., and Nussbaumer P. Synthesis of borondipyrromethene (BODIPY)-labeled sphingosine derivatives by cross-metathesis reaction. J. Org. Chem. 72 (2007) 1842-1845
19. Spyridopoulos I., Mayer P., Shook K.S., Axel D.I., Viebahn R., and Karsch K.R. Loss of cyclin A and G1-cell cycle arrest are a prerequisite of ceramide-induced toxicity in human arterial endothelial cells. Cardiovasc. Res. 50 (2001) 97-107
20. Skipski V., Peterson R., and Barclay M. Quantitative analysis of phospholipids by thin-layer chromatography. Biochem. J. 90 (1964) 374-378
21. Bradford M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
22. Stoffel W., Bauer E., and Stahl J. The metabolism of sphingosine bases in Tetrahymena pyriformis. Sphingosine kinase and sphingosine-1-phosphate lyase. Hoppe Seylers Z. Physiol. Chem. 355 (1974) 61-74
23. Oskouian B., Sooriyakumaran P., Borowsky A., Crans A., DIllard-Telm L., Tam Y., Bandhuvula P., and Saba J. Sphingosine-1-phosphate lyase potentiates apoptosis via p53- and p38-dependent pathways and is downregulated in colon cancer. Proc. Natl. Acad. Sci. USA 103 (2006) 17384-17389
24. Schmahl J., Raymond C.S., and Soriano P. PDGF signaling specificity is mediated through multiple immediate early genes. Nat. Genet. 39 (2007) 52-60
25. Li Z., and Bittman R. Synthesis and spectral properties of cholesterol- and FTY720-containing boron dipyrromethene dyes. J. Org. Chem. 72 (2007) 8376-8382
26. Li Z., Mintzer E., and Bittman R. First synthesis of free cholesterol-BODIPY conjugates. J. Org. Chem. 71 (2006) 1718-1721
27. Marks D.L., Bittman R., and Pagano R.E. Use of Bodipy-labeled sphingolipid and cholesterol analogs to examine membrane microdomains in cells. Histochem. Cell Biol. 130 (2008) 819-832
28. Wood T.E., and Thompson A. Advances in the chemistry of dipyrrins and their complexes. Chem. Rev. 107 (2007) 1831-1861
29. Holtta-Vuori M., Uronen R.L., Repakova J., Salonen E., Vattulainen I., Panula P., Li Z., Bittman R., and Ikonen E. BODIPY-cholesterol: a new tool to visualize sterol trafficking in living cells and organisms. Traffic 9 (2008) 1839-1849
30. Kemken D., Mier K., Katus H.A., Richardt G., and Kurz T. A HPLC-fluorescence detection method for determination of cardiac phospholipase D activity in vitro. Anal. Biochem. 286 (2000) 277-281
31. Darroch P.I., Dagan A., Granot T., He X., Gatt S., and Schuchman E.H. A lipid analogue that inhibits sphingomyelin hydrolysis and synthesis, increases ceramide, and leads to cell death. J. Lipid Res. 46 (2005) 2315-2324
32. Burgdorf C., Prey A., Richardt G., and Kurz T. A HPLC-fluorescence detection method for determination of phosphatidic acid phosphohydrolase activity: application in human myocardium. Anal. Biochem. 374 (2008) 291-297