High-throughput lipidomic analysis of fatty acid derived eicosanoids and N-acylethanolamines

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1811, Issue 11, 2011, Pages 724-736

  Dumlao, Darren S ^a   Buczynski, Matthew W ^a   Norris, Paul C ^a   Harkewicz, Richard ^a   Dennis, Edward A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Eicosanoid; High throughput methodology; LIPID MAPS; Lipidomics; Mass spectrometry; N acylethanolamine

Indexed keywords

CYTOCHROME P450; ETHANOLAMINE DERIVATIVE; ICOSANOID; LIPOXYGENASE; N ACYLETHANOLAMINE; PROSTAGLANDIN SYNTHASE; SATURATED FATTY ACID; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ANIMAL CELL; ANIMAL CELL CULTURE; ANIMAL TISSUE; ARTICLE; CELL STRAIN HEK293; CHEMICAL STRUCTURE; CONNECTIVE TISSUE; EXTRACTION; FATTY ACID ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; LIPIDOMICS; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; DINOPROSTONE; EICOSANOIDS; ETHANOLAMINES; HIGH-THROUGHPUT SCREENING ASSAYS; LIPID METABOLISM; RATS; REFERENCE STANDARDS; SOLUTIONS; TIME FACTORS;

EID: 80255124832     PISSN: 13881981     EISSN: 18792618     Source Type: Journal    
DOI: 10.1016/j.bbalip.2011.06.005     Document Type: Article

References (35)

1. C.D. Funk Prostaglandins and leukotrienes: advances in eicosanoid biology Science 294 2001 1871 1875 New York, N.Y (Pubitemid 33101574)
2. M.W. Buczynski, D.S. Dumlao, and E.A. Dennis Thematic review series: proteomics. An integrated omics analysis of eicosanoid biology J. Lipid Res. 50 2009 1015 1038
3. R. Harkewicz E.A. application of mass spectrometry to lipids and membranes Annu. Rev. Biochem. 80 2011 301 325
4. C. Rodriguez-Antona, and M. Ingelman-Sundberg Cytochrome P450 pharmacogenetics and cancer Oncogene 25 2006 1679 1691
5. C.A. Hyde, and S. Missailidis Inhibition of arachidonic acid metabolism and its implication on cell proliferation and tumour-angiogenesis Int. Immunopharmacol. 9 2009 701 715
6. D. Weitz, H. Weintraub, E. Fisher, and A.Z. Schwartzbard Fish oil for the treatment of cardiovascular disease Cardiol. Rev. 18 2010 258 263
7. P.C. Calder, and R.B. Zurier Polyunsaturated fatty acids and rheumatoid arthritis Curr. Opin. Clin. Nutr. Metab. Care 4 2001 115 121 (Pubitemid 34755453)
8. G.S. Harmon, D.S. Dumlao, D.T. Ng, K.E. Barrett, E.A. Dennis, H. Dong, and C.K. Glass Pharmacological correction of a defect in PPAR-gamma signaling ameliorates disease severity in Cftr-deficient mice Nature Medicine 16 2010 313 318
9. S.R. Pierre, M.A. Lemmens, and M.E. Figueiredo-Pereira Subchronic infusion of the product of inflammation prostaglandin J2 models sporadic Parkinson's disease in mice J. Neuroinflammation 6 2009 18
10. A. Sala, G. Folco, and R.C. Murphy Transcellular biosynthesis of eicosanoids Pharmacol Rep 62 2010 503 510
11. D.A. Six, and E.A. Dennis The expanding superfamily of phospholipase A(2) enzymes: classification and characterization Biochim. Biophys. Acta 1488 2000 1 19
12. R.H. Schaloske, and E.A. Dennis The phospholipase A2 superfamily and its group numbering system Biochim. Biophys. Acta 1761 2006 1246 1259 (Pubitemid 44755364)
13. D.K. Nomura, J.L. Blankman, G.M. Simon, K. Fujioka, R.S. Issa, A.M. Ward, B.F. Cravatt, and J.E. Casida Activation of the endocannabinoid system by organophosphorus nerve agents Nat. Chem. Biol. 4 2008 373 378 (Pubitemid 351693991)
14. J.Z. Long, D.K. Nomura, R.E. Vann, D.M. Walentiny, L. Booker, X. Jin, J.J. Burston, L.J. Sim-Selley, A.H. Lichtman, J.L. Wiley, and B.F. Cravatt Dual blockade of FAAH and MAGL identifies behavioral processes regulated by endocannabinoid crosstalk in vivo Proc. Natl. Acad. Sci. U. S. A. 106 2009 20270 20275
15. D.L. Simmons, R.M. Botting, and T. Hla Cyclooxygenase isozymes: the biology of prostaglandin synthesis and inhibition Pharmacol. Rev. 56 2004 387 437 (Pubitemid 39096597)
16. D. Sacerdoti, A. Gatta, and J.C. McGiff Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology Prostaglandins Other Lipid Mediat. 72 2003 51 71 (Pubitemid 39220485)
17. M.W. Buczynski, and L.H. Parsons Quantification of brain endocannabinoid levels: methods, interpretations and pitfalls British Journal of Pharmacology 160 2010 423 442
18. N. Ueda, K. Tsuboi, and T. Uyama Enzymological studies on the biosynthesis of N-acylethanolamines Biochimica et Biophysica Acta 1801 2010 1274 1285
19. M.W. Buczynski, C.I. Svensson, D.S. Dumlao, B.L. Fitzsimmons, J.H. Shim, T.J. Scherbart, F.E. Jacobsen, X.Y. Hua, T.L. Yaksh, and E.A. Dennis Inflammatory hyperalgesia induces essential bioactive lipid production in the spinal cord Journal of Neurochemistry 114 2010 981 993
20. K. Ahn, D.S. Johnson, M. Mileni, D. Beidler, J.Z. Long, M.K. McKinney, E. Weerapana, N. Sadagopan, M. Liimatta, S.E. Smith, S. Lazerwith, C. Stiff, S. Kamtekar, K. Bhattacharya, Y. Zhang, S. Swaney, K. Van Becelaere, R.C. Stevens, and B.F. Cravatt Discovery and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain Chem. Biol. 16 2009 411 420
21. M.J. Karbarz, L. Luo, L. Chang, C.S. Tham, J.A. Palmer, S.J. Wilson, M.L. Wennerholm, S.M. Brown, B.P. Scott, R.L. Apodaca, J.M. Keith, J. Wu, J.G. Breitenbucher, S.R. Chaplan, and M. Webb Biochemical and biological properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a mechanism-based inhibitor of fatty acid amide hydrolase Anesth. Analg. 108 2009 316 329
22. X. Wang, K. Sarris, K. Kage, D. Zhang, S.P. Brown, T. Kolasa, C. Surowy, O.F. El Kouhen, S.W. Muchmore, J.D. Brioni, and A.O. Stewart Synthesis and evaluation of benzothiazole-based analogues as novel, potent, and selective fatty acid amide hydrolase inhibitors J. Med. Chem. 52 2009 170 180
23. D. Piomelli, G. Tarzia, A. Duranti, A. Tontini, M. Mor, T.R. Compton, O. Dasse, E.P. Monaghan, J.A. Parrott, and D. Putman Pharmacological profile of the selective FAAH inhibitor KDS-4103 URB597 CNS Drug Rev. 12 2006 21 38 (Pubitemid 44133578)
24. M. Reinke Monitoring thromboxane in body fluids: a specific ELISA for 11-dehydrothromboxane B2 using a monoclonal antibody Am. J. Physiol. 262 1992 E658 E662
25. F. Shono, K. Yokota, K. Horie, S. Yamamoto, K. Yamashita, K. Watanabe, and H. Miyazaki A heterologous enzyme immunoassay of prostaglandin E2 using a stable enzyme-labeled hapten mimic Anal. Biochem. 168 1988 284 291 (Pubitemid 18039253)
26. R. Baranowski, and K. Pacha Gas chromatographic determination of prostaglandins Mini Rev. Med. Chem. 2 2002 135 144
27. R.C. Murphy, R.M. Barkley, K. Zemski Berry, J. Hankin, K. Harrison, C. Johnson, J. Krank, A. McAnoy, C. Uhlson, and S. Zarini Electrospray ionization and tandem mass spectrometry of eicosanoids Anal. Biochem. 346 2005 1 42 (Pubitemid 41456623)
28. A. Margalit, K.L. Duffin, and P.C. Isakson Rapid quantitation of a large scope of eicosanoids in two models of inflammation: development of an electrospray and tandem mass spectrometry method and application to biological studies Anal. Biochem. 235 1996 73 81 (Pubitemid 26065199)
29. O. Quehenberger, A. Armando, D. Dumlao, D.L. Stephens, and E.A. Dennis Lipidomics analysis of essential fatty acids in macrophages Prostaglandins Leukot. Essent. Fatty Acids 79 2008 123 129
30. R. Deems, M.W. Buczynski, R. Bowers-Gentry, R. Harkewicz, and E.A. Dennis Detection and quantitation of eicosanoids via high performance liquid chromatography-electrospray ionization-mass spectrometry Methods Enzymol. 432 2007 59 82
31. M.W. Buczynski, D.L. Stephens, R.C. Bowers-Gentry, A. Grkovich, R.A. Deems, and E.A. Dennis TLR-4 and sustained calcium agonists synergistically produce eicosanoids independent of protein synthesis in RAW264.7 cells J. Biol. Chem. 282 2007 22834 22847 (Pubitemid 47267374)
32. V.A. Blaho, M.W. Buczynski, C.R. Brown, and E.A. Dennis Lipidomic analysis of dynamic eicosanoid responses during the induction and resolution of Lyme arthritis J. Biol. Chem. 284 2009 21599 21612
33. M.Y. Golovko, and E.J. Murphy An improved LC-MS/MS procedure for brain prostanoid analysis using brain fixation with head-focused microwave irradiation and liquid-liquid extraction J. Lipid Res. 49 2008 893 902
34. W. Jian, R. Edom, N. Weng, P. Zannikos, Z. Zhang, and H. Wang Validation and application of an LC-MS/MS method for quantitation of three fatty acid ethanolamides as biomarkers for fatty acid hydrolase inhibition in human plasma Journal of Chromatography 878 2010 1687 1699
35. L.M. Hall, and R.C. Murphy Electrospray mass spectrometric analysis of 5-hydroperoxy and 5-hydroxyeicosatetraenoic acids generated by lipid peroxidation of red blood cell ghost phospholipids J. Am. Soc. Mass Spectrom. 9 1998 527 532