HPLC/MS/MS-based approaches for detection and quantification of eicosanoids

Methods in Molecular Biology

Volumn 579, Issue , 2009, Pages 161-183

  Lundström, Susanna L ^a   D’Alexandri, Fabio L ^a,b   Nithipatikom, Kasem ^c   Haeggström, Jesper Z ^a   Wheelock, Åsa M ^a   Wheelock, Craig E ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

Arachidonic acid; BALF; Bronchoalveolar lavage fluid; Eicosanoid; Electrospray; Ion trap; LC MS MS; Mass spectrometry; Oxylipin

Indexed keywords

11,12 EPOXYEICOSATRIENOIC ACID; 12 HYDROXYICOSATETRAENOIC ACID; 14,15 EPOXY 5,8,11 ICOSATRIENOIC ACID; 15 HYDROXYICOSATETRAENOIC ACID; 5 HYDROXYICOSATETRAENOIC ACID; 5 OXOEICOSATETRAENOIC ACID; 6 OXOPROSTAGLANDIN F1 ALPHA; ICOSANOID; LEUKOTRIENE B4; REAGENT; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; BRONCHOALVEOLAR LAVAGE FLUID; FATTY ACID ANALYSIS; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; PH; PRIORITY JOURNAL; PROCESS OPTIMIZATION; QUANTITATIVE ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID PHASE EXTRACTION; CYCLOTRON; FOURIER ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LUNG LAVAGE; METHODOLOGY; TANDEM MASS SPECTROMETRY;

BRONCHOALVEOLAR LAVAGE FLUID; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOTRONS; EICOSANOIDS; FOURIER ANALYSIS; TANDEM MASS SPECTROMETRY;

EID: 74949128457     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-60761-322-0_8     Document Type: Article

References (99)

1. Funk CD. (2001) Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 294, 1871–1875.
2. Conrad DJ. (1999) The arachidonate 12/15 lipoxygenases. A review of tissue expression and biologic function. Clin Rev Allergy Immunol 17, 71–89.
3. Newman JW, Watanabe T, Hammock BD. (2002) The simultaneous quantification of cytochrome P450 dependent linoleate and arachidonate metabolites in urine by HPLCMS/ MS. J Lipid Res 43, 1563–1578.
4. Natarajan R, Reddy MA. (2003) HETEs/ EETs in renal glomerular and epithelial cell functions. Curr Opin Pharmacol 3, 198–203.
5. Schmelzer KR, Inceoglu B, Kubala L, et al. (2006) Enhancement of antinociception by coadministration of nonsteroidal anti-inflammatory drugs and soluble epoxide hydrolase inhibitors. Proc Natl Acad Sci U S A 103, 13646–13651.
6. Samuelsson B, Dahlen SE, Lindgren JA, Rouzer CA, Serhan CN. (1987) Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science 237, 1171–1176.
7. Schmelzer KR, Wheelock AM, Dettmer K, Morin D, Hammock BD. (2006) The role of inflammatory mediators in the synergistic toxicity of ozone and 1-nitronaphthalene in rat airways. Environ Health Perspect 114, 1354–1360.
8. Hoagland KM, Maier KG, Moreno C, Yu M, Roman RJ. (2001) Cytochrome P450 metabolites of arachidonic acid: novel regulators of renal function. Nephrol Dial Transplant 16, 2283–2285.
9. Roman RJ. (2002) P-450 metabolites of arachidonic acid in the control of cardiovascular function. Physiol Rev 82, 131–185.
10. Natarajan R, Nadler JL. (2004) Lipid inflammatory mediators in diabetic vascular disease. Arterioscler Thromb Vasc Biol 24, 1542–1548.
11. Hussey HJ, Tisdale MJ. (1996) Inhibition of tumour growth by lipoxygenase inhibitors. Br J Cancer 74, 683–687.
12. Nie D, Tang K, Szekeres K, Trikha M, Honn KV. (2000) The role of eicosanoids in tumor growth and metastasis. Ernst Schering Res Found Workshop 31, 201–217.
13. Kumlin M. (1996) Analytical methods for the measurement of leukotrienes and other eicosanoids in biological samples from asthmatic subjects. J Chromatogr A 725, 29–40.
14. Powell WS, Funk CD. (1987) Metabolism of arachidonic acid and other polyunsaturated fatty acids by blood vessels. Prog Lipid Res 26, 183–210.
15. Tsukamoto H, Hishinuma T, Mikkaichi T, et al. (2002) Simultaneous quantification of prostaglandins, isoprostane and thromboxane in cell-cultured medium using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 774, 205–214.
16. Tsikas D. (1998) Application of gas chromatography- mass spectrometry and gas chromatography-tandem mass spectrometry to assess in vivo synthesis of prostaglandins, thromboxane, leukotrienes, isoprostanes and related compounds in humans. J Chromatogr B Biomed Sci Appl 717, 201–245.
17. Baranowski R, Pacha K. (2002) Gas chromatographic determination of prostaglandins. Mini Rev Med Chem 2, 135–144.
18. Murphy RC, Barkley RM, Zemski Berry K, et al. (2005) Electrospray ionization and tandem mass spectrometry of eicosanoids. Anal Biochem 346, 1–42.
19. Deems R, Buczynski MW, Bowers-Gentry R, Harkewicz R, Dennis EA. (2007) Detection and quantitation of eicosanoids via high performance liquid chromatography-electrospray ionization-mass spectrometry. Methods Enzymol 432, 59–82.
20. Blewett AJ, Varma D, Gilles T, Libonati JR, Jansen SA. (2008) Development and validation of a high-performance liquid chromatography- electrospray mass spectrometry method for the simultaneous determination of 23 eicosanoids. J Pharm Biomed Anal 46, 653–662.
21. Masoodi M, Nicolaou A. (2006) Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom 20, 3023–3029.
22. Wilson ID, Plumb R, Granger J, Major H, Williams R, Lenz EM. (2005) HPLC-MSbased methods for the study of metabonomics. J Chromatogr B Analyt Technol Biomed Life Sci 817, 67–76.
23. Zhang JH, Pearson T, Matharoo-Ball B, et al. (2007) Quantitative profiling of epoxyeicosatrienoic, hydroxyeicosatetraenoic, and dihydroxyeicosatetraenoic acids in human intrauterine tissues using liquid chromatography/ electrospray ionization tandem mass spectrometry. Anal Biochem 365, 40–51.
24. Han X, Gross RW. (2005) Shotgun lipidomics: electrospray ionization mass spectrometric analysis and quantitation of cellular lipidomes directly from crude extracts of biological samples. Mass Spectrom Rev 24, 367–412.
25. Wheelan P, Murphy RC. (1997) Quantitation of 5-lipoxygenase products by electrospray mass spectrometry: effect of ethanol on zymosan-stimulated production of 5-lipoxygenase products by human neutrophils. Anal Biochem 244, 110–115.
26. Yue H, Jansen SA, Strauss KI, et al. (2007) A liquid chromatography/mass spectrometric method for simultaneous analysis of arachidonic acid and its endogenous eicosanoid metabolites prostaglandins, dihydroxyeicosatrienoic acids, hydroxyeicosatetraenoic acids, and epoxyeicosatrienoic acids in rat brain tissue. J Pharm Biomed Anal 43, 1122–1134.
27. Luria A, Weldon SM, Kabcenell AK, et al. (2007) Compensatory mechanism for homeostatic blood pressure regulation in Ephx2 genedisrupted mice. J Biol Chem 282, 2891–2898.
28. Bylund J, Ericsson J, Oliw EH. (1998) Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography- mass spectrometry with ion trap MS. Anal Biochem 265, 55–68.
29. Masoodi M, Mir AA, Petasis NA, Serhan CN, Nicolaou A. (2008) Simultaneous lipidomic analysis of three families of bioactive lipid mediators leukotrienes, resolvins, protectins and related hydroxy-fatty acids by liquid chromatography/ electrospray ionisation tandem mass spectrometry. Rapid Commun Mass Spectrom 22, 75–83.
30. Hishinuma T, Suzuki K, Saito M, et al. (2007) Simultaneous quantification of seven prostanoids using liquid chromatography/tandem mass spectrometry: the effects of arachidonic acid on prostanoid production in mouse bone marrow-derived mast cells. Prostaglandins Leukot Essent Fatty Acids 76, 321–329.
31. Oliw E, Wollheim FA. (2000) [New treatment of pain and fever in rheumatoid arthritis and arthrosis. The first cyclooxygenase-2 inhibitors show promising results]. Lakartidningen 97, 2942–2944.
32. Kempen EC, Yang P, Felix E, Madden T, Newman RA. (2001) Simultaneous quantification of arachidonic acid metabolites in cultured tumor cells using high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. Anal Biochem 297, 183–190.
33. Yang P, Chan D, Felix E, et al. (2006) Determination of endogenous tissue inflammation profiles by LC/MS/MS: COX- and LOXderived bioactive lipids. Prostaglandins Leukot Essent Fatty Acids 75, 385–395.
34. Porter NA, Caldwell SE, Mills KA. (1995) Mechanisms of free radical oxidation of unsaturated lipids. Lipids 30, 277–290.
35. Yin H, Porter NA. (2005) New insights regarding the autoxidation of polyunsaturated fatty acids. Antioxid Redox Signal 7, 170–184.
36. Williams MV, Lee SH, Blair IA. (2005) Liquid chromatography/mass spectrometry analysis of bifunctional electrophiles and DNA adducts from vitamin C mediated decomposition of 15-hydroperoxyeicosatetraenoic acid. Rapid Commun Mass Spectrom 19, 849–858.
37. Hammonds TD, Blair IA, Falck JR, Capdevila JH. (1989) Resolution of epoxyeicosatrienoate enantiomers by chiral phase chromatography. Anal Biochem 182, 300–303.
38. Lee SH, Williams MV, DuBois RN, Blair IA. (2003) Targeted lipidomics using electron capture atmospheric pressure chemical ionization mass spectrometry. Rapid Commun Mass Spectrom 17, 2168–2176.
39. Lee SH, Blair IA. (2007) Targeted chiral lipidomics analysis by liquid chromatography electron capture atmospheric pressure chemical ionization mass spectrometry (LC-ECAPCI/ MS). Methods Enzymol 433, 159–174.
40. Lee SH, Williams MV, Blair IA. (2005) Targeted chiral lipidomics analysis. Prostaglandins Other Lipid Mediat 77, 141–157.
41. Suzuki N, Hishinuma T, Saga T, et al. (2003) Determination of urinary 12(S)- hydroxyeicosatetraenoic acid by liquid chromatography- tandem mass spectrometry with column-switching technique: sex difference in healthy volunteers and patients with diabetes mellitus. J Chromatogr B Analyt Technol Biomed Life Sci 783, 383–389.
42. Wei S, Brittin JJ, Falck JR, et al. (2006) Chiral resolution of the epoxyeicosatrienoic acids, arachidonic acid epoxygenase metabolites. Anal Biochem 352, 129–134.
43. Kiss L, Bier J, Roder Y, Weissmann N, Grimminger F, Seeger W. (2008) Direct and simultaneous profiling of epoxyeicosatrienoic acid enantiomers by capillary tandem column chiralphase liquid chromatography with dual online photodiode array and tandem mass spectrometric detection. Anal Bioanal Chem 392, 717–726.
44. Dole M, Mack, L.L., Hines, R.L., Mobley, R.C., Ferguson, L.D. and Alice, M.B.. (1968) Molecular beams of macroions. J Chem Phys 49, 2240–2249.
45. Fenn JB, Mann M, Meng CK, Wong SF, Whitehouse CM. (1989) Electrospray ionization for mass spectrometry of large biomolecules. Science 246, 64–71.
46. Taylor G. (1964) Disintegration of water drops in an electric field. Proc R Soc London, A 280, 383–397.
47. Cech NB, Enke CG. (2001) Practical implications of some recent studies in electrospray ionization fundamentals. Mass Spectrom Rev 20, 362–387.
48. Kingsley PJ, Rouzer CA, Saleh S, Marnett LJ. (2005) Simultaneous analysis of prostaglandin glyceryl esters and prostaglandins by electrospray tandem mass spectrometry. Anal Biochem 343, 203–211.
49. Cui L, Isbell MA, Chawengsub Y, Falck JR, Campbell WB, Nithipatikom K. (2008) Structural characterization of monohydroxyeicosatetraenoic acids and dihydroxy- and trihydroxyeicosatrienoic acids by ESI-FTICR. J Am Soc Mass Spectrom 19, 569–585.
50. Horning EC, Horning MG, Carroll DI, Dzidic I, Stillwell RN. (1973) New picogram detection system based on a mass spectrometer with an external ionization source at atmospheric pressure. Anal Chem 45, 936–943.
51. Caroll DI, Dzidic I, Stillwell RN, Haegele KD, Horning EC. (1975) Atmospheric pressure ionization mass spectrometry: Corona discharge ion source for use in liquid chromatograph- mass spectrometer-computer analytical system. Anal Chem 47, 2369–2373.
52. Montuschi P, Martello S, Felli M, Mondino C, Chiarotti M. (2004) Ion trap liquid chromatography/ tandem mass spectrometry analysis of leukotriene B4 in exhaled breath condensate. Rapid Commun Mass Spectrom 18, 2723–2729.
53. Koga D, Santa T, Fukushima T, Homma H, Imai K. (1997) Liquid chromatographicatmospheric pressure chemical ionization mass spectrometric determination of anandamide and its analogs in rat brain and peripheral tissues. J Chromatogr B Biomed Sci Appl 690, 7–13.
54. Rosenberg E. (2003) The potential of organic (electrospray- and atmospheric pressure chemical ionisation) mass spectrometric techniques coupled to liquid-phase separation for speciation analysis. J Chromatogr A 1000, 841–889.
55. Cai SS, Syage JA. (2006) Comparison of atmospheric pressure photoionization, atmospheric pressure chemical ionization, and electrospray ionization mass spectrometry for analysis of lipids. Anal Chem 78, 1191–1199.
56. Locke DC, Dhingra BS, Baker AD. (1982) Liquid-phase photoionization detector for liquid chromatography. Anal Chem 54, 447–450.
57. Robb DB, Covey TR, Bruins AP. (2000) Atmospheric pressure photoionization: an ionization method for liquid chromatography- mass spectrometry. Anal Chem 72, 3653–3659.
58. Cai SS, Syage JA. (2006) Atmospheric pressure photoionization mass spectrometry for analysis of fatty acid and acylglycerol lipids. J Chromatogr A 1110, 15–26.
59. Short LC, Cai SS, Syage JA. (2007) APPIMS: effects of mobile phases and VUV lamps on the detection of PAH compounds. J Am Soc Mass Spectrom 18, 589–599.
60. Ferguson RE, MCCulloh KE, Rosenstock HM. (1965) Observation of the products of ionic collision processes and ion decomposition in a linear, pulsed time-of-flight mass spectrometer. J Chem Phys 42, 100.
61. Paul W, Steinwedel HS. (1960) US Patent, 2939952.
62. Kita Y, Takahashi T, Uozumi N, Shimizu T. (2005) A multiplex quantitation method for eicosanoids and platelet-activating factor using column-switching reversed-phase liquid chromatography-tandem mass spectrometry. Anal Biochem 342, 134–143.
63. Paul W. (1990) Electromagnetic traps for charged and neutral particles (nobel lecture). Angew Chem 29, 739–748.
64. Stafford GC Jr., Kelley PE, Syka JEP, Reynolds WE, Todd JFJ. (1984) Recent Improvements in Analytical Application of Advanced Ion-Trap Technology. Int J Mass Spectrom Ion Processes 60, 85–98.
65. Louris J, Brodbelt-Lustig J, Cooks R, Glish G, Van Berkel G, McLuckey S. (1990) Ion isolation and sequential stages of mass spectrometry in a quadrupole ion trap mass spectrometer. Int J Mass Spectrom Ion Processes 96, 117–137.
66. Liminga M, Oliw E. (2000) Qualitative and quantitative analysis of lipoxygenase products in bovine corneal epithelium by liquid chromatography- mass spectrometry with an ion trap. Lipids 35, 225–232.
67. Kiss L, Roder Y, Bier J, Weissmann N, Seeger W, Grimminger F. (2008) Direct eicosanoid profiling of the hypoxic lung by comprehensive analysis via capillary liquid chromatography with dual online photodiode-array and tandem mass-spectrometric detection. Anal Bioanal Chem 390, 697–714.
68. Hevko JM, Murphy RC. (2001) Electrospray ionization and tandem mass spectrometry of cysteinyl eicosanoids: leukotriene C4 and FOG 7. J Am Soc Mass Spectrom 12, 763–771.
69. Hong S, Lu Y, Yang R, Gotlinger KH, Petasis NA, Serhan CN. (2007) Resolvin D1, protectin D1, and related docosahexaenoic acidderived products: Analysis via electrospray/ low energy tandem mass spectrometry based on spectra and fragmentation mechanisms. J Am Soc Mass Spectrom 18, 128–144.
70. Thomson JJ. (1897) Cathode rays. Philos Mag 44, 29.
71. Stephens WE. (1946) Pulsed mass spectrometer with time dispersion. Phys Rev 69, 691.
72. Shui G, Bendt AK, Pethe K, Dick T, Wenk MR. (2007) Sensitive profiling of chemically diverse bioactive lipids. J Lipid Res 48, 1976–1984.
73. Dickinson JS, Murphy RC. (2002) Mass spectrometric analysis of leukotriene A4 and other chemically reactive metabolites of arachidonic acid. J Am Soc Mass Spectrom 13, 1227–1234.
74. Harks EG, Peters PH, van Dongen JL, van Zoelen EJ, Theuvenet AP. (2005) Autocrine production of prostaglandin F2alpha enhances phenotypic transformation of normal rat kidney fibroblasts. Am J Physiol Cell Physiol 289, C130–137.
75. Laude DA. Electrospray Ionization/Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. In: Cole RB, ed. Elctrospray Ionization Mass Spectrometry: Fundamentals, Instrumentation, and Applications. New York: Wiley, 1997:291–320.
76. Page JS, Masselon CD, Smith RD. (2004) FTICR mass spectrometry for qualitative and quantitative bioanalyses. Curr Opin Biotechnol 15, 3–11.
77. Wu Q, Van Orden S, Cheng X, Bakhtiar R, Smith RD. (1995) Characterization of cytochrome c variants with high-resolution FTICR mass spectrometry: correlation of fragmentation and structure. Anal Chem 67, 2498–2509.
78. Flora JW, Hannis JC, Muddiman DC. (2001) High-mass accuracy of product ions produced by SORI-CID using a dual electrospray ionization source coupled with FTICR mass spectrometry. Anal Chem 73, 1247–1251.
79. Hofstadler SA, Sannes-Lowery KA, Griffey RH. (1999) Infrared multiphoton dissociation in an external ion reservoir. Anal Chem 71, 2067–2070.
80. Stensballe A, Jensen ON, Olsen JV, Haselmann KF, Zubarev RA. (2000) Electron capture dissociation of singly and multiply phosphorylated peptides. Rapid Commun Mass Spectrom 14, 1793–1800.
81. Flora JW, Muddiman DC. (2004) Determination of the relative energies of activation for the dissociation of aromatic versus aliphatic phosphopeptides by ESI-FTICR-MS and IRMPD. J Am Soc Mass Spectrom 15, 121–127.
82. Pfister SL, Spitzbarth N, Nithipatikom K, Edgemond WS, Falck JR, Campbell WB. (1998) Identification of the 11,14,15- and 11,12, 15-trihydroxyeicosatrienoic acids as endothelium-derived relaxing factors of rabbit aorta. J Biol Chem 273, 30879–30887.
83. Pfister SL, Spitzbarth N, Zeldin DC, Lafite P, Mansuy D, Campbell WB. (2003) Rabbit aorta converts 15-HPETE to trihydroxyeicosatrienoic acids: potential role of cytochrome P450. Arch Biochem Biophys 420, 142–152.
84. Falck JR, Barma DK, Mohapatra S, et al. (2004) Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa- 5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator. Bioorg Med Chem Lett 14, 4987–4990.
85. Kerwin JL, Torvik JJ. (1996) Identification of monohydroxy fatty acids by electrospray mass spectrometry and tandem mass spectrometry. Anal Biochem 237, 56–64.
86. Nakamura T, Bratton DL, Murphy RC. (1997) Analysis of epoxyeicosatrienoic and monohydroxyeicosatetraenoic acids esterified to phospholipids in human red blood cells by electrospray tandem mass spectrometry. J Mass Spectrom 32, 888–896.
87. Nakamura T, Henson PM, Murphy RC. (1998) Occurrence of oxidized metabolites of arachidonic acid esterified to phospholipids in murine lung tissue. Anal Biochem 262, 23–32.
88. Wheelan P, Zirrolli JA, Murphy RC. (1993) Low-energy fast atom bombardment tandem mass spectrometry of monohydroxy substituted unsaturated fatty acids. Biol Mass Spectrom 22, 465–473.
89. Harkewicz R, Fahy E, Andreyev A, Dennis EA. (2007) Arachidonate-derived dihomoprostaglandin production observed in endotoxin- stimulated macrophage-like cells. J Biol Chem 282, 2899–2910.
90. Hall LM, Murphy RC. (1998) 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, 527–532.
91. Currie LA. (1995) Nomenclature in evaluation of analytical methods including detection and quantification capabilities. Pure and Appl Chem 67, 1699–1723.
92. Revised Assessment of Detection and Quantitation Approaches; 2004. Report No.: EPA- 821-B-04–005.
93. Assigning Values to Nondetected/Nonquantified Pesticide Residues in Human Health Dietary Exposure Assessments; 2000. Report No.: OPP-00570A
94. Song WL, Lawson JA, Wang M, Zou H, FitzGerald GA. (2007) Noninvasive assessment of the role of cyclooxygenases in cardiovascular health: a detailed HPLC/MS/MS method. Methods Enzymol 433, 51–72.
95. Kishi N, Mano N, Asakawa N. (2001) Direct injection method for quantitation of endogenous leukotriene E4 in human urine by liquid chromatography/electrospray ionization tandem mass spectrometry with a column-switching technique. Anal Sci 17, 709–713.
96. Saunders RD, Horrocks LA. (1984) Simultaneous extraction and preparation for highperformance liquid chromatography of prostaglandins and phospholipids. Anal Biochem 143, 71–75.
97. Folch J, Lees M, Sloane Stanley GH. (1957) A simple method for the isolation and purification of total lipides from animal tissues. J Biol Chem 226, 497–509.
98. Smith KR, Pinkerton KE, Watanabe T, Pedersen TL, Ma SJ, Hammock BD. (2005) Attenuation of tobacco smoke-induced lung inflammation by treatment with a soluble epoxide hydrolase inhibitor. Proc Natl Acad Sci U S A 102, 2186–2191.
99. Yang J, Schmelzer K, Georgi K, Hammock B. (2009) Quantitative profiling method for oxylipin metabolome by liquid chromatography electrospray ionization tandem mass spectrometry. Anal Chem submitted.