Approaches for the analysis of chlorinated lipids

Analytical Biochemistry

Volumn 443, Issue 2, 2013, Pages 148-152

  Wang, Wen Yi ^a   Albert, Carolyn J ^a   Ford, David A ^a  

^a SAINT LOUIS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Chlorinated lipids; Chromatography; Fatty acid; Fatty aldehyde; Mass spectrometry; Monocytes

Indexed keywords

ALDEHYDES; CHROMATOGRAPHY; ELECTROSPRAY IONIZATION; GAS CHROMATOGRAPHY; IONIZATION OF GASES; LIPIDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NEGATIVE IONS;

ANALYTICAL APPROACH; CELLULAR METABOLISM; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; HYPOCHLOROUS ACIDS; INTERNAL STANDARDS; MONOCYTES; NEGATIVE ION CHEMICAL IONIZATION; SEPARATION TECHNIQUES;

FATTY ACIDS;

ALDEHYDE; ALPHA CHLOROFATTY ACID; ALPHA CHLOROFATTY ALCOHOL; ALPHA CHLOROFATTY ALDEHYDE; ANION; CARBOXYLIC ACID; CHLORINATED LIPID; ESTER DERIVATIVE; LIPID; UNCLASSIFIED DRUG;

ARTICLE; CELL METABOLISM; ELECTROSPRAY MASS SPECTROMETRY; GAS CHROMATOGRAPHY; HUMAN; LEUKOCYTE; LEUKOCYTE ACTIVATION; LIPID ANALYSIS; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SEPARATION TECHNIQUE; THIN LAYER CHROMATOGRAPHY;

CHLORINATED LIPIDS; CHROMATOGRAPHY; FATTY ACID; FATTY ALDEHYDE; MASS SPECTROMETRY; MONOCYTES;

ANIMALS; CHROMATOGRAPHY; FATTY ACIDS; HALOGENATION; HUMANS; LIPIDS; MASS SPECTROMETRY;

EID: 84885742059     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2013.09.016     Document Type: Review

References (27)

1. S.J. Weiss, R. Klein, A. Slivka, and M. Wei Chlorination of taurine by human neutrophils: evidence for hypochlorous acid generation J. Clin. Invest. 70 1982 598 607 (Pubitemid 12054584)
2. S.J. Klebanoff Oxygen metabolism and the toxic properties of phagocytes Ann. Intern. Med. 93 1980 480 489 (Pubitemid 10055919)
3. D.A. Ford Lipid oxidation by hypochlorous acid: chlorinated lipids in atherosclerosis and myocardial ischemia Clin. Lipidol. 5 2010 835 852
4. C. Spickett Chlorinated lipids and fatty acids: an emerging role in pathology Pharmacol. Ther. 115 2007 400 409 (Pubitemid 47362376)
5. O. Skaff, D.I. Pattison, and M.J. Davies The vinyl ether linkages of plasmalogens are favored targets for myeloperoxidase-derived oxidants: a kinetic study Biochemistry 47 2008 8237 8245
6. A.A. Farooqui, and L.A. Horrocks Plasmalogen-selective phospholipase A2 and its involvement in Alzheimer's disease Biochem. Soc. Trans. 26 1998 243 246 (Pubitemid 128723606)
7. R.W. Gross High plasmalogen and arachidonic acid content of canine myocardial sarcolemma: a fast atom bombardment mass spectroscopic and gas chromatography-mass spectroscopic characterization Biochemistry 23 1984 158 165 (Pubitemid 14181546)
8. E.J. Murphy, L. Joseph, R. Stephens, and L.A. Horrocks Phospholipid composition of cultured human endothelial cells Lipids 27 1992 150 153
9. J.E. Vance Lipoproteins secreted by cultured rat hepatocytes contain the antioxidant 1-alk-1-enyl-2-acylglycerophosphoethanolamine Biochim. Biophys. Acta 1045 1990 128 134 (Pubitemid 20218821)
10. R.A. Zoeller, T.J. Grazia, P. LaCamera, J. Park, D.P. Gaposchkin, and H.W. Farber Increasing plasmalogen levels protect human endothelial cells during hypoxia Am. J. Physiol. Heart Circ. Physiol. 283 2002 H671 H679
11. D.S. Anbukumar, L.P. Shornick, C.J. Albert, M.M. Steward, R.A. Zoeller, W.L. Neumann, and D.A. Ford Chlorinated lipid species in activated human neutrophils: lipid metabolites of 2-chlorohexadecanal J. Lipid Res. 51 2010 1085 1092
12. V.V. Brahmbhatt, C.J. Albert, D.S. Anbukumar, B.A. Cunningham, W.L. Neumann, and D.A. Ford Oxidation of ω-chlorinated fatty acids: Identification of α-chlorinated dicarboxylic acids J. Biol. Chem. 285 2010 41255 41269
13. A.K. Thukkani, C.J. Albert, K.R. Wildsmith, M.C. Messner, B.D. Martinson, F.F. Hsu, and D.A. Ford Myeloperoxidase-derived reactive chlorinating species from human monocytes target plasmalogens in low density lipoprotein J. Biol. Chem. 278 2003 36365 36372 (Pubitemid 37139964)
14. A.K. Thukkani, F.F. Hsu, J.R. Crowley, R.B. Wysolmerski, C.J. Albert, and D.A. Ford Reactive chlorinating species produced during neutrophil activation target tissue plasmalogens: production of the chemoattractant, 2-chlorohexadecanal J. Biol. Chem. 277 2002 3842 3849 (Pubitemid 34968634)
15. A.K. Thukkani, B.D. Martinson, C.J. Albert, G.A. Vogler, and D.A. Ford Neutrophil-mediated accumulation of 2-ClHDA during myocardial infarction: 2-ClHDA-mediated myocardial injury Am. J. Physiol. Heart Circ. Physiol. 288 2005 H2955 H2964
16. A.K. Thukkani, J. McHowat, F.F. Hsu, M.L. Brennan, S.L. Hazen, and D.A. Ford Identification of α-chloro fatty aldehydes and unsaturated lysophosphatidylcholine molecular species in human atherosclerotic lesions Circulation 108 2003 3128 3133 (Pubitemid 38031803)
17. A. Ullen, G. Fauler, H. Kofeler, S. Waltl, C. Nusshold, E. Bernhart, H. Reicher, H.J. Leis, A. Wintersperger, E. Malle, and W. Sattler Mouse brain plasmalogens are targets for hypochlorous acid-mediated modification in vitro and in vivo Free Radical Biol. Med. 49 2010 1655 1665
18. G. Marsche, R. Heller, G. Fauler, A. Kovacevic, A. Nuszkowski, W. Graier, W. Sattler, and E. Malle 2-Chlorohexadecanal derived from hypochlorite-modified high-density lipoprotein-associated plasmalogen is a natural inhibitor of endothelial nitric oxide biosynthesis Arterioscler. Thromb. Vasc. Biol. 24 2004 2302 2306 (Pubitemid 39658033)
19. A. Ullen, G. Fauler, E. Bernhart, C. Nusshold, H. Reicher, H.J. Leis, E. Malle, and W. Sattler Phloretin ameliorates 2-chlorohexadecanal-mediated brain microvascular endothelial cell dysfunction in vitro Free Radical Biol. Med. 53 2012 1770 1781
20. M.C. Messner, C.J. Albert, and D.A. Ford 2-Chlorohexadecanal and 2-chlorohexadecanoic acid induce COX-2 expression in human coronary artery endothelial cells Lipids 43 2008 581 588
21. H. Van Denbergen, D. Daloze, and J.C. Braekman Synthesis of analogues of 2-iodohexadecanal, a regulator of iodine metabolism in the thyroid gland J. Braz. Chem. Soc. 10 1999 1 12
22. K.R. Wildsmith, C.J. Albert, D.S. Anbukumar, and D.A. Ford Metabolism of myeloperoxidase-derived 2-chlorohexadecanal J. Biol. Chem. 281 2006 16849 16860
23. E.G. Bligh, and W.J. Dyer A rapid method of total lipid extraction and purification Can. J. Biochem. Physiol. 37 1959 911 917
24. J.G. Bollinger, G. Rohan, M. Sadilek, M.H. Gelb, Liquid chromatography/electrospray mass spectrometric detection of fatty acid by charge reversal derivatization with more than 4 orders of magnitude improvement in sensitivity, J. Lipid Res. http://www.jlr.org/content/early/2013/08/14/jlr. D040782.long.
25. C.J. Albert, J.R. Crowley, F.F. Hsu, A.K. Thukkani, and D.A. Ford Reactive chlorinating species produced by myeloperoxidase target the vinyl ether bond of plasmalogens: Identification of 2-chlorohexadecanal J. Biol. Chem. 276 2001 23733 23741
26. C.J. Albert, J.R. Crowley, F.F. Hsu, A.K. Thukkani, and D.A. Ford Reactive brominating species produced by myeloperoxidase target the vinyl ether bond of plasmalogens: disparate utilization of sodium halides in the production of α-halo fatty aldehydes J. Biol. Chem. 277 2002 4694 4703 (Pubitemid 34968500)
27. C.J. Albert, A.K. Thukkani, R.M. Heuertz, A. Slungaard, S.L. Hazen, and D.A. Ford Eosinophil peroxidase-derived reactive brominating species target the vinyl ether bond of plasmalogens generating a novel chemoattractant, α-bromo fatty aldehyde J. Biol. Chem. 278 2003 8942 8950 (Pubitemid 36800371)