Evidence that 5-lipoxygenase and acetylated cyclooxygenase 2-derived eicosanoids regulate leukocyte-endothelial adherence in response to aspirin

British Journal of Pharmacology

Volumn 139, Issue 7, 2003, Pages 1351-1359

  Fiorucci, Stefano ^a,e   Distrutti, Eleonora ^a   Mencarelli, Andrea ^a   Morelli, Antonio ^a   Laufor, Stefan A ^b   Cirino, Giuseppe ^c   Wallace, John L ^d  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF TÜBINGEN   (Germany)

^c UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^d UNIVERSITY OF CALGARY   (Canada)

^e POLICLINICO MONTELUCE   (Italy)

Author keywords

5 lipoxigenase; Aspirin; Aspirin triggered lipoxin; Celcoxib; Cyclooxygenase; Leukotriene B4; Lipoxin; Neutrophils endothelium adherence; Rofecoxib

Indexed keywords

2 (2,6 DIHYDROXYHEXYL) 6 (3 HYDROXY 1,5 UNDECADIENYL)PYRIDINE; 2 CYCLOPENTYL 2 [4 (2 QUINOLINYLMETHOXY)PHENYL]ACETIC ACID; 6 [[3 FLUORO 5 (3,4,5,6 TETRAHYDRO 4 METHOXY 2H PYRAN 4 YL)]PHENOXYMETHYL] 1 METHYL 2 QUINOLONE; ACETYLSALICYLIC ACID; ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONATE 5 LIPOXYGENASE ACTIVATING PROTEIN; CELECOXIB; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; ENDOTOXIN; ICOSANOID; LEUKOTRIENE B4; LICOFELONE; LIPOXIN; LIPOXIN A; LIPOXYGENASE INHIBITOR; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN E2; ROFECOXIB; TRIPEPTIDE;

ACETYLATION; ARTICLE; BIOSYNTHESIS; CELL ACTIVATION; CELL ADHESION; COCULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SELECTIVITY; ENDOTHELIUM CELL; ENZYME INHIBITION; HUMAN; HUMAN CELL; LEUKOCYTE; NORMAL HUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ACETIC ACIDS; ACETYLATION; ADHESIVENESS; ANTIGENS, CD11A; ARACHIDONATE 5-LIPOXYGENASE; ASPIRIN; CELLS, CULTURED; CYCLOOXYGENASE 2; DOSE-RESPONSE RELATIONSHIP, DRUG; E-SELECTIN; EICOSANOIDS; ENDOTHELIAL CELLS; ENDOTHELIUM, VASCULAR; FATTY ALCOHOLS; GLYCOLS; HUMANS; ISOENZYMES; LEUKOCYTES; LEUKOTRIENE B4; LIPOPOLYSACCHARIDES; LIPOXINS; LIPOXYGENASE; MEMBRANE PROTEINS; NEUTROPHILS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PROSTAGLANDINS E; PYRANS; PYRROLES; QUINOLINES; QUINOLONES; UMBILICAL CORD; UP-REGULATION;

EID: 0042388365     PISSN: 00071188     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjp.0705356     Document Type: Article

References (34)

1. ALPIN, A.E., HOWE, S., ALAHARI, S.K. & JULIANO, R.L. (1998). Signal transduction and signal modulation by cell adhesion receptors: the role of integrins, cadherins, immunoglobulin-cell adhesion molecules, and selectins. Pharmacol. Rev., 50, 197-263.
2. BOUTAUD, O., ARONOFF, D.M., RICHARDSON, J.H., MARNETT, L.J. & OATES, J.A. (2002). Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H(2) synthases. Proc. Natl. Acad. Sci. U.S.A., 99, 7130-7135.
3. CARLOS, T & HARLAN, J. (1994). Leukocyte-endothelial adhesion molecules. Blood., 84, 2068-2101.
4. CHANDRASEKHARAN, N.V., DAI, H., ROOS, K.L., EVANSON, N.K., TOMSIK, J., ELTON, T.S. & SIMMONS, D.L. (2002). COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc. Natl. Acad. Sci. U.S.A., 99, 13926-13931.
5. 4 ELISA. J. Pharmacol. Exp. Ther., 287, 779-790.
6. CLÀRIA, J. & SERHAN, C.N. (1995). Aspirintriggers previously unrecognized bioactive eicosanoids by human endothelial cell-leukocyte interactions. Proc. Natl. Acad. Sci. U.S.A., 92, 9475-9479.
7. FILEP, J.G., ZOUKI, C., PETASIS, N.A., HACHICHA, M. & SERHAN, C.N. (1999). Anti-inflammatory actions of lipoxin A(4) stable analogs are demonstrable in human whole blood: modulation of leukocyte adhesion molecules and inhibition of neutrophil-endothelial interactions. Blood, 94, 4132-4142.
8. FIORE, S. & SERHAN, C.N. (1995). Lipoxin A4 receptor activation is distinct from that of the formyl peptide receptor in myeloid cells: inhibition of CD11/18 expression by lipoxin A4-lipoxin A4 receptor interaction. Biochemistry, 34, 16678-16686.
9. FIORUCCI, S., MENDES DE LIMA, O., MENCARELLI, A., PALAZZETTI, B., DISTRUTTI, E., MCKNIGHT, W., DICAY, M., MA, L., ROMANO, M., MORELLI, A. & WALLACE, J.L. (2002). COX-2 derived Lipoxin A4 increases gastric resistance to aspirin-induced damage. Gastroenterology, 123, 1598-1606.
10. FITZGERALD, G.A. & PATRONO, C. (2001). The coxibs, selective inhibitors of cyclooxygenase-2. N. Engl. J. Med., 345, 433-442.
11. FUNK, C.D. (2001). Prostaglandins and leukotrienes: advances in eicosanoid biology. Science, 294, 1871-1875.
12. GEWIRTZ, A.T., MCCORMICK, B., NEISH, A.S., PETASIS, N.A., GRONERT, K., SERHAN, C.N. & MADARA, J.L. (1998). Pathogen-induced chemokine secretion from model intestinal epithelium is inhibited by lipoxin A4 analogs. J. Clin. Invest., 101, 1860-1869.
13. GRONERT, K., MARTINSSON-NISKANEN, T., RAVASI, S., CHIANG, N. & SERHAN, C.N. (2001). Selectivity of recombinant human leukotriene D(4), leukotriene B(4), and lipoxin A(4) receptors with aspirin-triggered 15-epi-LXA(4) and regulation of vascular and inflammatory responses. Am. J. Pathol., 158, 3-9.
14. JORDAN, J.E., ZHAO, Z.Q. & VINTEN-JOHANSEN, J. (1999). The role of neutrophils in myocardial ischemia-reperfusion injury. Cardiovasc. Res., 43, 860-878.
15. LAUFER, S.A., AUGUSTIN, J., DANNHARDT, G. & KIEFER, W. (1994). 6,7-Diaryldihydropyrrolizin-5-yl)acetic acids, a novel class of potent dual inhibitors of both cyclooxygenase and 5-lipoxygenase. J. Med. Chem., 37, 1894-1897.
16. LECOMTE, M., LANEUVILLE, O.Ji.C., DEWITT, D.L. & SMITH, W.L. (1994). Acetylation of human prostaglandin endoperoxide synthase-2 (cyclooxygenase-2) by aspirin. J. Biol. Chem., 269, 13207-13215.
17. MANCINI, J.A., VICKERS, P.J., O'NEILL, G.P., BOILY, C., FALGUEYRET, J.P. & RIENDEAU, D. (1997). Altered sensitivity of aspirin-acetylated prostaglandin G/H synthase-2 to inhibition by nonsteroidal anti-inflammatory drugs. Mol. Pharmacol., 51, 52-60.
18. MULLER-PEDDINGHAUS, R., KOHLSDORFER, C., THEISEN-POPP, P., FRUCHTMANN, R., PERZBORN, E., BECKERMANN, B., BUHNER, K., AHR, H.J. & MOHRS, K.H. (1993). BAY X1005, a new inhibitor of leukotriene synthesis: in vivo inflammation pharmacology and pharmacokinetics. J. Pharmacol. Exp. Ther., 267, 51-57.
19. NICOLL-GRIFFITH, D.A., YERGEY, J.A., TRIMBLE, L.A., SILVA, J.M., LI, C., CHAURET, N., GAUTHIER, J.Y., GRIMM, E., LEGER, S., ROY, P., THERIEN, M., WANG, Z., PRASIT, P., ZAMBONI, R., YOUNG, R.N., BRIDEAU, C., CHAN, C.C., MANCINI, J. & RIENDEAU, D. (2000). Synthesis, characterization, and activity of metabolites derived from the cyclooxygenase-2 inhibitor rofecoxib (MK-0966, Vioxx). Bioorg. Med. Chem. Lett., 2000, 10 2683-2686.
20. PATRONO, C. (1994). Aspirin as an antiplatelet drug. N. Engl. J. Med., 330, 1287-1294.
21. PIERCE, J.W., READ, M.A., DING, H., LUSCINSKAS, F.W. & COLLINS, T. (1996). Salicylates inhibit IkB-a phosphorylation, endothelial-leukocyte adhesion molecule expression, and neutrophil transmigration. J. Immunol., 156, 3961-3969.
22. PERRETTI, M., GETTING, S.J., SOLITO, E., MURPHY, P.M. & GAO, J.L. (2001). Involvement of the receptor for formylated peptides in the in vivo anti-migratory actions of annexin 1 and its mimetics. Am. J. Pathol., 158, 1969-1973.
23. PILLINGER, M.H., CAPODICI, C., ROSENTHAL, P., KHETERPAL, N., HANFT, S., PHILIPS, M.R. & WEISSMANN, G. (1998). Modes of action of aspirin-like drugs: salicylates inhibit erk activation and integrin-dependent neutrophil adhesion. Proc. Natl. Acad. Sci. U.S.A., 95, 14540-14545.
24. 4. FASEB J. published online October 4.
25. ROMANO, M. & SERHAN, C.N. (1992). Lipoxin generation by permeabilized human platelets. Biochemistry, 31, 8269-8277.
26. SAMUELSSON, B., DAHLÈN, S.-E., LINDGREN, J.-Å., ROUZER, C.A. & SERHAN, C.N. (1987). Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science, 237, 1171-1176.
27. SCALIA, R., GEFEN, J., PETASIS, N.A., SERHAN, C.N. & LEFER, A.M. (1997). Lipoxin A4 stable analogs inhibit leukocyte rolling and adherence in the rat mesenteric microvasculature: role of P-selectin. Proc. Natl. Acad. Sci. U.S.A., 94, 9967-9972.
28. SERHAN, C. (2002). Lipoxins and aspirin-triggered 15-epi-lipoxin biosynthesis: an update and role on anti-inflammation and pro-resolution. Prostaglandins Other Lipid Mediators, 68-69, 433-455.
29. SERHAN, C.N. & OLIW, E. (2001). Unorthodox routes to prostanoid formation: new twists in cyclooxygenase-initiated pathways. J. Clin. Invest., 107, 1481-1489.
30. SILVERSTEIN, F.E., FAICH, G., GOLDSTEIN, J.L., SIMON, L.S., PINCUS, T., WHELTON, A., MAKUCH, R., EISEN, G., AGRAWAL, N.M., STENSON, W.F., BURR, A.M., ZHAO, W.W., KENT, J.D., LEFKOWITH, J.B., VERBURG, K.M. & GEIS, G.S. (2000). Gastrointestinal toxicity with celecoxib vs nonsteroidal anti-inflammatory drugs for osteoarthritis and rheumatoid arthritis: the CLASS study: a randomized controlled trial. Celecoxib Long-term Arthritis Safety Study. JAMA., 284, 1247-1255.
31. SMITH, W.G., SHAFFER, A.F., CURRIE, J.L., THOMPSON, J.M., KIM, S., RAO, T. & ISAKSON, P.C. (1995). Characterization of 5-lipoxygenase inhibitors in biochemical and functional in vivo assays. J. Pharmacol. Exp. Ther., 275, 1332-1338.
32. 4 stable analogues. J. Clin. Invest., 101, 819-826.
33. 4 stable analogues are potent inhibitors of acute inflammation: evidence for anti-inflammatory receptors. J. Exp. Med., 185, 1693-1704.
34. YOKOMIZO, T., MASUDA, K., KATO, K., TODA, A., IZUMI, T. & SHIMIZU, T. (2000). Leukotriene B4 receptor. Cloning and intracellular signaling. Am. J. Respir. Crit. Care Med., 161, S51-S55.