Quantitative analysis of sphingoid base-1-phosphates as bisacetylated derivatives by liquid chromatography-tandem mass spectrometry.

Sphingosine-1-phosphate (S1P) and dihydrosphingosine-1-phosphate (DHS1P) are important signaling sphingolipids. The presence of nanomolar levels of S1P and DHS1P in tissues, cells, and biological fluids requires a highly sensitive and selective assay method for their reliable detection and quantitation. Preliminary findings employing positive ion electrospray ionization (ESI) liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis indicated significant sample carryover from previous injections of authentic standards of S1P and DHS1P. This article details a negative ion ESI LC-MS/MS technique following modification of the zwitterionic nature of S1P and DHS1P via derivatization. A highly selective and sensitive LC-MS/MS technique capable of reliable detection of less than 50 fmol of the derivatives of S1P and DHS1P without significant sample carryover was developed. Standard curves for S1P and DHS1P are linear over wide ranges (0-300 pmol) of analyte concentrations with correlation coefficients (r2) greater than 0.995. The levels of S1P and DHS1P in human platelet poor plasma were 590.8+/-42.1 and 130.7+/-20.7 pmol/ml, respectively. The levels of S1P and DHS1P in fetal bovine serum were 141.7+/-4.6 and 0.6+/-0.2 pmol/ml, respectively. The addition of sphingosine (1 microM) to human pulmonary artery endothelial cells in culture resulted in a more than 20-fold increase in the cellular level of S1P, whereas the level of DHS1P was unchanged.

[1]  S. Pyne,et al.  Sphingosine 1-phosphate signalling in mammalian cells , 2000 .

[2]  S. Spiegel,et al.  Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate , 1996, Nature.

[3]  S. LeVine,et al.  Sphingolipid profile in the CNS of the twitcher (globoid cell leukodystrophy) mouse: a lipidomics approach. , 2003, Cellular and molecular biology.

[4]  A. Merrill,et al.  Analysis of sphingoid bases and sphingoid base 1-phosphates by high-performance liquid chromatography. , 2000, Methods in enzymology.

[5]  Korey R. Johnson,et al.  The sphingosine kinase 1/sphingosine‐1‐phosphate pathway mediates COX‐2 induction and PGE2 production in response to TNF‐α , 2003 .

[6]  T. Ohmori,et al.  Sphingosine 1-phosphate as a major bioactive lysophospholipid that is released from platelets and interacts with endothelial cells , 2000 .

[7]  Sullards Mc,et al.  Analysis of sphingosine 1-phosphate, ceramides, and other bioactive sphingolipids by high-performance liquid chromatography-tandem mass spectrometry. , 2001 .

[8]  T. Hla,et al.  Sphingosine-1-phosphate signaling in endothelial activation. , 2003, Journal of atherosclerosis and thrombosis.

[9]  T. Ohmori,et al.  Sphingosine 1-phosphate: synthesis and release. , 2001, Prostaglandins & other lipid mediators.

[10]  T. Hla,et al.  Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptors. , 2002, Biochimica et biophysica acta.

[11]  S. Hakomori,et al.  Quantitative measurement of sphingosine 1-phosphate in biological samples by acylation with radioactive acetic anhydride. , 1995, Analytical biochemistry.

[12]  M. C. Sullards,et al.  Metabolomic profiling of sphingolipids in human glioma cell lines by liquid chromatography tandem mass spectrometry. , 2003, Cellular and molecular biology.

[13]  Y. Oda,et al.  Simultaneous quantitative determination method for sphingolipid metabolites by liquid chromatography/ionspray ionization tandem mass spectrometry. , 1997, Analytical biochemistry.

[14]  S. Spiegel,et al.  Sphingosine kinase: a mediator of vital cellular functions. , 2001, Prostaglandins & other lipid mediators.

[15]  S. Spiegel,et al.  Enzymatic measurement of sphingosine 1-phosphate. , 1999, Analytical biochemistry.

[16]  Y. Igarashi,et al.  Sphingosine 1-phosphate, a bioactive sphingolipid abundantly stored in platelets, is a normal constituent of human plasma and serum. , 1997, Journal of biochemistry.

[17]  W. J. Dyer,et al.  A rapid method of total lipid extraction and purification. , 1959, Canadian journal of biochemistry and physiology.

[18]  Yong-Moon Lee,et al.  Simultaneous quantitative analysis of sphingoid base 1-phosphates in biological samples by o-phthalaldehyde precolumn derivatization after dephosphorylation with alkaline phosphatase. , 2002, Analytical biochemistry.

[19]  T. Hla Sphingosine 1-phosphate receptors. , 2001, Prostaglandins & other lipid mediators.

[20]  Sullards Mc Analysis of sphingomyelin, glucosylceramide, ceramide, sphingosine, and sphingosine 1-phosphate by tandem mass spectrometry. , 2000 .

[21]  T. Hla Signaling and biological actions of sphingosine 1-phosphate. , 2003, Pharmacological research.

[22]  M. Schäfer-Korting,et al.  An improved high-performance liquid chromatographic method for the determination of sphingosine-1-phosphate in complex biological materials , 2001, Naunyn-Schmiedeberg's Archives of Pharmacology.

[23]  A. Merrill,et al.  A high-performance liquid chromatographic method to measure sphingosine 1-phosphate and related compounds from sphingosine kinase assays and other biological samples. , 2000, Analytical biochemistry.

[24]  Sarah Spiegel,et al.  Sphingosine-1-phosphate: an enigmatic signalling lipid , 2003, Nature Reviews Molecular Cell Biology.

[25]  E. Kostetsky,et al.  A universal reagent for phospholipid analysis. , 1975, Journal of chromatography.