A Simple and Robust UPLC-SRM/MS Method to Quantify Urinary Eicosanoids

Overview

Journal J Lipid Res

Publisher Elsevier

Specialty Biochemistry

Date 2012 Feb 17

PMID 22338011

Citations 25

Authors

Katharina Sterz

Gerhard Scherer

Josef Ecker

Affiliations

Soon will be listed here.

Abstract

Eicosanoids are key mediators and regulators of inflammation and oxidative stress often used as biomarkers for diseases and pathological conditions such as cardiovascular and pulmonary diseases and cancer. Analytically, comprehensive and robust quantification of different eicosanoid species in a multi-method approach is problematic because most of these compounds are relatively unstable and may differ in their chemical properties. Here we describe a novel ultra-performance liquid chromatography-selected reaction monitoring mass spectroscopy (UPLC-SRM/MS) method for simultaneous quantification of key urinary eicosanoids, including the prostaglandins (PG) tetranor PGE-M, 8-iso-, and 2,3-dinor-8-iso-PGF(2α); the thromboxanes (TXs) 11-dehydro- and 2,3-dinor-TXB₂; leukotriene E₄; and 12-hydroxyeicosatetraenoic acid. In contrast to previous methods, which used time-consuming and complex solid phase extraction, we prepared samples with a simple liquid/liquid extraction procedure. Because collision-induced dissociation produced characteristic product ions for all analytes, no derivatization step for SRM/MS analysis was necessary. Analytes were separated with a short UPLC reversed-phase column (1.7 µm particles), allowing shorter run times than conventional HPLC columns. The method was validated and applied to human urine samples showing excellent precision, accuracy, detection limits, and robustness. In summary, the developed method allows robust and sensitive profiling of urinary eicosanoid species, making it a useful and valuable tool for biomarker profiling in clinical/toxicological studies.

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References

Murphy R, Barkley R, Zemski Berry K, Hankin J, Harrison K, Johnson C . Electrospray ionization and tandem mass spectrometry of eicosanoids. Anal Biochem. 2005; 346(1):1-42. DOI: 10.1016/j.ab.2005.04.042. View

U S Department Of Health And Human Services . Opioid abuse in the United States and Department of Health and Human Services actions to address opioid-drug-related overdoses and deaths. J Pain Palliat Care Pharmacother. 2015; 29(2):133-9. DOI: 10.3109/15360288.2015.1037530. View

Martin-Venegas R, Casillas R, Jauregui O, Moreno J . Rapid simultaneous analysis of cyclooxygenase, lipoxygenase and cytochrome P-450 metabolites of arachidonic and linoleic acids using high performance liquid chromatography/mass spectrometry in tandem mode. J Pharm Biomed Anal. 2011; 56(5):976-82. DOI: 10.1016/j.jpba.2011.06.018. View

Zhou Y, Wang Z, Tang M, Yao C, Xu W, Wang L . Nicotine induces cyclooxygenase-2 and prostaglandin E(2) expression in human umbilical vein endothelial cells. Int Immunopharmacol. 2010; 10(4):461-6. DOI: 10.1016/j.intimp.2009.12.019. View

Yue H, Jansen S, Strauss K, Borenstein M, Barbe M, Rossi L . 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.... J Pharm Biomed Anal. 2006; 43(3):1122-34. PMC: 2855500. DOI: 10.1016/j.jpba.2006.10.009. View

Dennis E, Cao J, Hsu Y, Magrioti V, Kokotos G . Phospholipase A2 enzymes: physical structure, biological function, disease implication, chemical inhibition, and therapeutic intervention. Chem Rev. 2011; 111(10):6130-85. PMC: 3196595. DOI: 10.1021/cr200085w. View

Ecker J, Liebisch G, Grandl M, Schmitz G . Lower SCD expression in dendritic cells compared to macrophages leads to membrane lipids with less mono-unsaturated fatty acids. Immunobiology. 2010; 215(9-10):748-55. DOI: 10.1016/j.imbio.2010.05.016. View

FitzGerald G . Mechanisms of platelet activation: thromboxane A2 as an amplifying signal for other agonists. Am J Cardiol. 1991; 68(7):11B-15B. DOI: 10.1016/0002-9149(91)90379-y. View

Pratico D, MY Lee V, Trojanowski J, Rokach J, FitzGerald G . Increased F2-isoprostanes in Alzheimer's disease: evidence for enhanced lipid peroxidation in vivo. FASEB J. 1998; 12(15):1777-83. DOI: 10.1096/fasebj.12.15.1777. View

10.

BLIGH E, Dyer W . A rapid method of total lipid extraction and purification. Can J Biochem Physiol. 1959; 37(8):911-7. DOI: 10.1139/o59-099. View

11.

Kishi N, Mano N, Asakawa N . 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. 2001; 17(6):709-13. DOI: 10.2116/analsci.17.709. View

12.

McAdam B, Byrne D, Morrow J, Oates J . Contribution of cyclooxygenase-2 to elevated biosynthesis of thromboxane A2 and prostacyclin in cigarette smokers. Circulation. 2005; 112(7):1024-9. DOI: 10.1161/CIRCULATIONAHA.105.542696. View

13.

Chiabrando C, Valagussa A, Rivalta C, Durand T, Guy A, Zuccato E . Identification and measurement of endogenous beta-oxidation metabolites of 8-epi-Prostaglandin F2alpha. J Biol Chem. 1999; 274(3):1313-9. DOI: 10.1074/jbc.274.3.1313. View

14.

Lynch C, OKelly R, Stuart B, Treumann A, Conroy R, Regan C . The role of thromboxane A(2) in the pathogenesis of intrauterine growth restriction associated with maternal smoking in pregnancy. Prostaglandins Other Lipid Mediat. 2011; 95(1-4):63-7. DOI: 10.1016/j.prostaglandins.2011.06.007. View

15.

Morrow J . Quantification of isoprostanes as indices of oxidant stress and the risk of atherosclerosis in humans. Arterioscler Thromb Vasc Biol. 2004; 25(2):279-86. DOI: 10.1161/01.ATV.0000152605.64964.c0. View

16.

Suzuki N, Hishinuma T, Saga T, Sato J, Toyota T, Goto J . 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. 2002; 783(2):383-9. DOI: 10.1016/s1570-0232(02)00666-9. View

17.

Dumlao D, Buczynski M, Norris P, Harkewicz R, Dennis E . High-throughput lipidomic analysis of fatty acid derived eicosanoids and N-acylethanolamines. Biochim Biophys Acta. 2011; 1811(11):724-36. PMC: 3205334. DOI: 10.1016/j.bbalip.2011.06.005. View

18.

Stanke-Labesque F, Moliere P, Bessard J, Laville M, Vericel E, Lagarde M . Effect of dietary supplementation with increasing doses of docosahexaenoic acid on neutrophil lipid composition and leukotriene production in human healthy volunteers. Br J Nutr. 2008; 100(4):829-33. DOI: 10.1017/S0007114508923692. View

19.

Ricciotti E, FitzGerald G . Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol. 2011; 31(5):986-1000. PMC: 3081099. DOI: 10.1161/ATVBAHA.110.207449. View

20.

Dahl J, van Breemen R . Rapid quantitative analysis of 8-iso-prostaglandin-F(2alpha) using liquid chromatography-tandem mass spectrometry and comparison with an enzyme immunoassay method. Anal Biochem. 2010; 404(2):211-6. PMC: 2909638. DOI: 10.1016/j.ab.2010.05.023. View