Structural identification of oxidized acyl-phosphatidylcholines that induce platelet activation

Journal of Vascular Research

Volumn 42, Issue 2, 2005, Pages 120-132

  Göpfert, Matthias S ^a   Siedler, Frank ^b   Siess, Wolfgang ^a   Sellmayer, Alois ^a  

^a LUDWIG MAXIMILIANS UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

Author keywords

Lipid oxidation; Low density lipoprotein; Phospholipids; Platelet activating factor; Platelets

Indexed keywords

COPPER CHLORIDE; HYDROGEN PEROXIDE; LOW DENSITY LIPOPROTEIN; LYSOPHOSPHATIDIC ACID; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; THROMBOCYTE ACTIVATING FACTOR; THROMBOXANE A2; 1 STEAROYL 2 (5 OXOVALEROYL) SN GLYCERO 3 PHOSPHOCHOLINE; 1 STEAROYL 2 ARACHIDONYLPHOSPHATIDYLCHOLINE; 1 STEAROYL 2 AZELAOYL SN GLYCERO 3 PHOSPHOCHOLINE; 1 STEAROYL 2 GLUTAROYL SN GLYCERO 3 PHOSPHOCHOLINE; 1-STEAROYL-2-(5-OXOVALEROYL)-SN-GLYCERO-3-PHOSPHOCHOLINE; 1-STEAROYL-2-ARACHIDONYLPHOSPHATIDYLCHOLINE; 1-STEAROYL-2-AZELAOYL-SN-GLYCERO-3-PHOSPHOCHOLINE; 1-STEAROYL-2-GLUTAROYL-SN-GLYCERO-3-PHOSPHOCHOLINE; CALCIUM;

ARTICLE; ATHEROGENESIS; CELL INTERACTION; CONCENTRATION (PARAMETERS); ELECTROSPRAY; ENDOTHELIUM CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MASS SPECTROMETRY; MONOCYTE; OXIDATION; PRIORITY JOURNAL; SEPARATION TECHNIQUE; STRUCTURE ANALYSIS; THROMBOCYTE ACTIVATION; THROMBOGENESIS; THROMBOGENICITY; CELL SHAPE; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; CYTOSOL; DRUG EFFECT; ELECTROSPRAY MASS SPECTROMETRY; ISOLATION AND PURIFICATION; METABOLISM; METHODOLOGY; OSMOLARITY; OXIDATION REDUCTION REACTION; THROMBOCYTE;

BLOOD PLATELETS; CALCIUM; CELL SHAPE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOSOL; HUMANS; MOLECULAR STRUCTURE; OSMOLAR CONCENTRATION; OXIDATION-REDUCTION; PHOSPHATIDYLCHOLINES; PLATELET ACTIVATION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 18044375564     PISSN: 10181172     EISSN: None     Source Type: Journal    
DOI: 10.1159/000083461     Document Type: Article

References (41)

1. Berliner JA, Heinecke JW: The role of oxidized lipoproteins in atherogenesis. Free Radic Biol Med 1996;20:707-727.
2. 2. Arterioscler Thromb Vasc Biol 1995;15:1131-1138.
3. 2+ influx in human platelets. J Biol Chem 2000;275:19159-19166.
4. Volf I, Bielek E, Moeslinger T, Koller F, Koller E: Modification of protein moiety of human low density lipoprotein by hypochlorite generates strong platelet agonist. Arterioscler Thromb Vasc Biol 2000;20:2011-2018.
5. Fernandez-Ortiz A, Badimon JJ, Fuster V, Meyer B, Mailhac A, Weng D, Shah PK, Badimon L: Characterization of the relative thrombogenicity of atherosclerotic plaque components: Implications for consequences of plaque rupture. J Am Coll Cardiol 1994;23:1562-1569.
6. Sevanian A, Bittolo-Bom G, Cazzolato G, Hodis H, Hwang J, Zamburlini A, Maiorino M, Ursini F: LDL is a lipid hydroperoxide-enriched circulating lipoprotein. J Lipid Res 1997;38:419-428.
7. Holvoet P, Vanhaecke J, Janssens S, Van de Werf F, Collen D: Oxidized LDL and malondialdehyde-modified LDL in patients with acute coronary syndromes and stable coronary artery disease. Circulation 1998;98:1487-1494.
8. Trip MD, Cats VM, van Capelle FJ, Vreeken J: Platelet hyperreactivity and prognosis in survivors of myocardial infarction. N Engl J Med 1990;322:1549-1554.
9. Esterbauer H, Ramos P: Chemistry and pathophysiology of oxidation of LDL. Rev Physiol Biochem Pharmacol 1996;127:31-64.
10. Watson AD, Navab M, Hama SY, Sevanian A, Prescott SM, Stafforini DM, McIntyre TM, Du BN, Fogelman AM, Berliner JA: Effect of platelet activating factor-acetylhydrolase on the formation and action of minimally oxidized low density lipoprotein. J Clin Invest 1995;95:774-782.
11. Berliner JA, Territo MC, Sevanian A, Ramin S, Kim JA, Bamshad B, Esterson M, Fogelman AM: Minimally modified low density lipoprotein stimulates monocyte endothelial interactions. J Clin Invest 1990;85:1260-1266.
12. McIntyre TM, Zimmerman GA, Prescott SM: Biologically active oxidized phospholipids. J Biol Chem 1999;274:25189-25192.
13. Berliner JA, Subbanagounder G, Leitinger N, Watson AD, Vora D: Evidence for a role of phospholipid oxidation products in atherogenesis. Trends Cardiovasc Med 2001;11:142-147.
14. Siess W, Zangl KJ, Essler M, Bauer M, Brandl R, Corrinth C, Bittman R, Tigyi G, Aepfelbacher M: Lysophosphatidic acid mediates the rapid activation of platelets and endothelial cells by mildly oxidized low density lipoprotein and accumulates in human atherosclerotic lesions. Proc Natl Acad Sci USA 1999;96:6931-6936.
15. Kamido H, Eguchi H, Ikeda H, Imaizumi T, Yamana K, Hartvigsen K, Ravandi A, Kuksis A: Core aldehydes of alkyl glycerophosphocholines in atheroma induce platelet aggregation and inhibit endothelium-dependent arterial relaxation. J Lipid Res 2002;43:158-166.
16. Tanaka T, Iimori M, Tsukatani H, Tokumura A: Platelet-activating effects of platelet-activating factor-like phospholipids formed by oxidation of phosphatidylcholines containing an sn-2-polyunsaturated fatty acyl group. Biochim Biophys Acta 1994;1210:202-208.
17. Marathe GK, Davies SS, Harrison KA, Silva AR, Murphy RC, Castro-Faria-Neto H, Prescott SM, Zimmerman GA, McIntyre TM: Inflammatory platelet-activating factor-like phospholipids in oxidized low density lipoproteins are fragmented alkyl phosphatidylcholines. J Biol Chem 1999;274:28395-28404.
18. Davies SS, Pontsler AV, Marathe GK, Harrison KA, Murphy RC, Hinshaw JC, Prestwich GD, Hilaire AS, Prescott SM, Zimmerman GA, McIntyre TM: Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor gamma ligands and agonists. J Biol Chem 2001;276:16015-16023.
19. Watson AD, Leitinger N, Navab M, Faull KF, Horkko S, Witztum JL, Palinski W, Schwenke D, Salomon RG, Sha W, Subanagounder G, Fogelman AM, Berliner JA: Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo. J Biol Chem 1997;272:13597-13607.
20. Watson AD, Subbanagounder G, Welsbie DS, Faull KF, Navab M, Jung ME, Fogelman AM, Berliner JA: Structural identification of a novel pro-inflammatory epoxyisoprostane phospholipid in mildly oxidized low density lipoprotein. J Biol Chem 1999;274:24787-24798.
21. Leitinger N, Tyner TR, Oslund L, Rizza C, Subbanagounder G, Lee H, Shih PT, Mackman N, Tigyi G, Territo MC, Berliner JA, Vora DK: Structurally similar oxidized phospholipids differentially regulate endothelial binding of monocytes and neutrophils. Proc Natl Acad Sci USA 1999;96:12010-12015.
22. (++)/NFAT. Blood 2002;99:199-206.
23. Subbanagounder G, Leitinger N, Schwenke DC, Wong JW, Lee H, Rizza C, Watson AD, Faull KF, Fogelman AM, Berliner JA: Determinants of bioactivity of oxidized phospholipids. Specific oxidized fatty acyl groups at the sn-2 position. Arterioscler Thromb Vasc Biol 2000;20:2248-2254.
24. Bochkov VN, Kadl A, Huber J, Gruber F, Binder BR, Leitinger N: Protective role of phospholipid oxidation products in endotoxin-induced tissue damage. Nature 2002;419:77-81.
25. Harrison KA, Murphy RC: Isoleukotrienes are biologically active free radical products of lipid peroxidation. J Biol Chem 1995;270:17273-17278.
26. (2+)- independent mechanism. J Biol Chem 1995;270:1057-1061.
27. Rasmussen UB, Gachet C, Schlesinger Y, Hanau D, Ohlmann P, von Obberghen-Schilling E, Pouysségur J, Cazenave JP, Pavirani A: A peptide ligand of the human thrombin receptor antagonizes alpha-thrombin and partially activates platelets. J Biol Chem 1993;268:14322-14328.
28. Casals-Stenzal J, Muacevic G, Weber K: Pharmacological actions of WEB 2086, a new specific antagonist of platelet activating factor. J Pharmacol Exp Ther 1987;241:974-981.
29. Bittman R, Swords B, Liliom K, Tigyi G: Inhibitors of lipid phosphatidate receptors: N-Palmitoyl-serine and N-palmitoyl-tyrosine phosphoric acids. J Lipid Res 1996;37:391-398.
30. Kattelman EJ, Venton DL, LeBreton GC: Characterization of U46619 binding in unactivated, intact human platelets and determination of binding site affinities of four TXA2/PGH2 receptor antagonists (13-APA, BM 13.177, ONO 3708 and SQ 29,548). Thromb Res 1986;41:471-481.
31. Kayganich-Harrison KA, Murphy RC: Characterization of chain-shortened oxidized glycerophosphocholine lipids using fast atom bombardment and tandem mass spectrometry. Anal Biochem 1994;221:16-24.
32. Murphy RC: Mass spectrometry of lipids; in Murphy RC (ed): Handbook of Lipid Research. New York, Plenum Press, 1993, vol 7, pp 57-92.
33. Kern H, Volk T, Knauer-Schiefer S, Mieth T, Rüstow B, Kox WJ, Schlame M: Stimulation of monocytes and platelets by short-chain phosphatidylcholines with and without terminal carboxyl group. Biochim Biophys Acta 1998;1394:33-42.
34. Itabe H, Kushi Y, Handa S, Inoue K: Identification of 2-azelaoylphosphatidylcholine as one of the cytotoxic products generated during oxyhemoglobin-induced peroxidation of phosphatidylcholine. Biochim Biophys Acta 1988;962:8-15.
35. O'Flaherty JT, Salzer WL, Cousart S, McCall CE, Piantadosi C, Surles JR, Hammett MJ, Wykle RL: Platelet-activating factor and analogues: Comparative study with human neutrophils and rabbit platelets. Res Commun Chem Pathol Pharmacol 1983;39:291-309.
36. O'Flaherty JT, Tessner T, Greene T, Redman JR, Wykle RL: Comparison of 1-O-alkyl-, 1-O-alk-1′-enyl- and 1-O-acyl-2-acetyl-sn-glycero-3- phosphoethanolamines and -3-phosphocholines as agonists of the platelet-activating factor family. Biochim Biophys Acta 1994;1210:209-216.
37. Goetzl EJ, An S: Diversity of cellular receptors and functions for the lysophospholipid growth factors lysophosphatidic acid and sphingosine 1-phosphate. FASEB J 1998;12:1589-1598
38. 2α. J Pharmacol Exp Ther 1997;281:957-964.
39. Kitagawa S, Endo J, Kametani F: Activation of bovine platelets induced by long-chain unsaturated fatty acids at just below their lytic concentrations, and its mechanism. Biochim Biophys Acta 1984;802:17-23.
40. Kamido H, Kuksis A, Marai L, Myher JJ: Lipid ester-bound aldehydes among copper-catalyzed peroxidation products of human plasma lipoproteins. J Lipid Res 1995;36:1876-1886.
41. Frey B, Haupt R, Alms S, Holzmann G, König T, Kern H, Kox W, Rüstow B, Schlame M: Increase in fragmented phosphatidylcholine in blood plasma by oxidative stress. J Lipid Res 2000;41:1145-1153.