Effects of AF3442 [N-(9-ethyl-9H-carbazol-3-yl)-2-(trifluoromethyl) benzamide], a novel inhibitor of human microsomal prostaglandin E synthase-1, on prostanoid biosynthesis in human monocytes in vitro

Biochemical Pharmacology

Volumn 79, Issue 7, 2010, Pages 974-981

  Bruno, Annalisa ^a   Di Francesco, Luigia ^a   Coletta, Isabella ^b   Mangano, Giorgina ^b   Alisi, Maria Alessandra ^b   Polenzani, Lorenzo ^b   Milanese, Claudio ^b   Anzellotti, Paola ^a   Ricciotti, Emanuela ^a   Dovizio, Melania ^a   Di Francesco, Andrea ^a   Tacconelli, Stefania ^a   Capone, Marta L ^a   Patrignani, Paola ^a  

^a UNIVERSITY OF CHIETI   (Italy)

^b Università Politecnica delle Marche ACRAF Gruppo Angelini   (Italy)

Author keywords

Human whole blood; Inflammation; Monocytes; MPGE synthase 1

Indexed keywords

6 OXOPROSTAGLANDIN F1 ALPHA; AF 3442; DIMETHYL SULFOXIDE; LIPOPOLYSACCHARIDE; N ( 9 ETHYL 9H CARBAZOL 3 YL) 2 (TRIFLUOROMETHYL)BENZAMIDE; PROSTAGLANDIN E SYNTHASE 1; PROSTAGLANDIN E2; PROSTAGLANDIN F2 ALPHA; PROSTAGLANDIN H2; PROSTAGLANDIN INHIBITOR; PROSTAGLANDIN SYNTHASE; PROSTANOID; RECOMBINANT ENZYME; RECOMBINANT PROSTAGLANDIN E SYNTHASE 1; SYNTHETASE; THROMBOXANE B2; UNCLASSIFIED DRUG; BENZAMIDE DERIVATIVE; CARBAZOLE DERIVATIVE; ENZYME INHIBITOR; ISOMERASE; PROSTACYCLIN; PROSTAGLANDIN; PROSTAGLANDIN E SYNTHASE;

ARTICLE; BLOOD; BLOOD SAMPLING; CELL ISOLATION; CELL STIMULATION; CONTROLLED STUDY; DRUG INHIBITION; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MONOCYTE; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROSTAGLANDIN METABOLISM; PROSTAGLANDIN SYNTHESIS; PROTEIN EXPRESSION; BIOSYNTHESIS; DOSE RESPONSE; DRUG ANTAGONISM; ENZYMOLOGY; METABOLISM; MICROSOME; TUMOR CELL LINE;

BENZAMIDES; CARBAZOLES; CELL LINE, TUMOR; DINOPROSTONE; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; EPOPROSTENOL; HUMANS; INTRAMOLECULAR OXIDOREDUCTASES; LIPOPOLYSACCHARIDES; MICROSOMES; MONOCYTES; PROSTAGLANDIN H2; PROSTAGLANDINS;

EID: 77449125422     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2009.11.011     Document Type: Article

References (38)

1. Funk CD. Prostaglandins and leukotrienes: Advances in eicosanoid biology. Science 2001;294:1871-5. (Pubitemid 33101574)
2. 2 biosynthesis. J Biochem Mol Biol 2005;38:633-8. (Pubitemid 43240966)
3. FitzGerald GA, Patrono C. The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med 2001;345:433-42. (Pubitemid 32747607)
4. Patrono C, Patrignani P, García Rodríguez LA. Cyclooxygenase-selective inhibition of prostanoid formation: Transducing biochemical selectivity into clinical read-outs. J Clin Invest 2001;108:7-13. (Pubitemid 32634915)
5. Grosser T, Fries S, FitzGerald GA. Biological basis for the cardiovascular consequences of COX-2 inhibition: Therapeutic challenges and opportunities. J Clin Invest 2006;116:4-15. (Pubitemid 43121782)
6. García Rodríguez LA, Tacconelli S, Patrignani P. Role of dose potency in the prediction of risk of myocardial infarction associated with nonsteroidal antiinflammatory drugs in the general population. J Am Coll Cardiol 2008;52:1628-36.
7. Patrignani P, Capone ML, Tacconelli S. NSAIDs and cardiovascular disease. Heart 2008;94:395-7. (Pubitemid 351441386)
8. Wang M, Zukas AM, Hui Y, Ricciotti E, PuréE, FitzGerald GA. Deletion of microsomal prostaglandin E synthase-1 augments prostacyclin and retards atherogenesis. Proc Natl Acad Sci 2006;103:14507-12. (Pubitemid 44484780)
9. Wang M, Song WL, Cheng Y, Fitzgerald GA. Microsomal prostaglandin E synthase-1 inhibition in cardiovascular inflammatory disease. J Intern Med 2008;263:500-5. (Pubitemid 351533553)
10. 2 production and alters the gastric prostanoid profile. J Biol Chem 2004;279:23229-37. (Pubitemid 38685630)
11. Jakobsson PJ, Thorén S, Morgenstern R, Samuelsson B. Identification of human prostaglandin e synthase: A microsomal, glutathione-dependent, inducible enzyme constituting a potential novel drug target. Proc Natl Acad Sci 1999;96:7220-5. (Pubitemid 29299642)
12. 2 synthase that acts in concert with cyclooxygenase-2. J Biol Chem 2000;275:32783-92.
13. 2. Arthritis Res Ther 2005;7:114-7. (Pubitemid 40775173)
14. Trebino CE, Eskra JD,Wachtmann TS, Perez JR, Carty TJ, Audoly LP. Redirection of eicosanoid metabolism in mPGES-1-deficient marophages. J Biol Chem 2005;280:16579-85. (Pubitemid 41389113)
15. Huntjens DR, Danhof M, Della Pasqua OE. Pharmacokinetic-pharmacodynamic correlations and biomarkers in the development of COX-2 inhibitors. Rheumatology 2005;44:846-59. (Pubitemid 41511177)
16. Patrignani P, Tacconelli S, Capone ML. Risk management profile of etoricoxib: An example of personalized medicine. Ther Clin Risk Manag 2008;4:983-97.
17. Patrignani P, Panara MR, Greco A, Fusco O, Natoli C, Iacobelli S, et al. Biochemical and pharmacological characterization of the cyclooxygenase activity of human blood prostaglandin endoperoxide synthases. J Pharmacol Exp Ther 1994;271:1705-12. (Pubitemid 24382690)
18. Alisi A, Cazzolla N, Furlotti G, Dragone P, Russo V, Mangano G, et al. 3- Aminocarbazole compounds, pharmaceutical composition containing the same and method for the preparation thereof. PCT n WO2007014687 2007.
19. Di Francesco L, Totani L, Dovizio M, Piccoli A, Di Francesco A, Salvatore T, et al. Induction of prostacyclin by steady laminar shear stress suppresses tumor necrosis factor-alpha biosynthesis via heme oxygenase-1 in human endothelial cells. Circ Res 2009;104:506-13.
20. Mancini JA, Blood K, Guay J, Gordon R, Claveau D, Chan CC, et al. Cloning, expression, and up-regulation of inducible rat prostaglandin E synthase during lipopolysaccharide-induced pyresis and adjuvant-induced arthritis. J Biol Chem 2001;276:4469-75.
21. 2 synthase (mPGES-1) derived from MK-886. Bioorg Med Chem Lett 2005;15:3352-5. (Pubitemid 40835734)
22. Praticó D, FitzGerald GA. Generation of 8-epiprostaglandin F2alpha by human monocytes. Discriminate production by reactive oxygen species and prostaglandin endoperoxide synthase-2. J Biol Chem 1996;271:8919-24.
23. Patrono C, Ciabattoni G, Pinca E, Pugliese F, Castrucci G, De Salvo A, et al. Low dose aspirin and inhibition of thromboxane B2 production in healthy subjects. Thromb Res 1980;17:317-27. (Pubitemid 10129020)
24. Patrignani P, Sciulli MG, Manarini S, Santini G, Cerletti C, Evangelista V. COX-2 is not involved in thromboxane biosynthesis by activated human platelets. J Physiol Pharmacol 1999;50:661-7. (Pubitemid 30022144)
25. Evangelista V, Manarini S, Di Santo A, Capone ML, Ricciotti E, Di Francesco L, et al. De novo synthesis of cyclooxygenase-1 counteracts the suppression of platelet thromboxane biosynthesis by aspirin. Circ Res 2006;98:593-5.
26. Patrignani P, Filabozzi P, Patrono C. Selective cumulative inhibition of platelet thromboxane production by low-dose aspirin in healthy subjects. J Clin Invest 1982;69:1366-72.
27. Sciulli MG, Seta F, Tacconelli S, Capone ML, Ricciotti E, Pistritto G, et al. Effects of acetaminophen on constitutive and inducible prostanoid biosynthesis in human blood cells. Br J Pharmacol 2003;138:634-41. (Pubitemid 36315311)
28. Egan KM, Wang M, Fries S, Lucitt MB, Zukas AM, PuréE, et al. Cyclooxygenases, thromboxane, and atherosclerosis: Plaque destabilization by cyclooxygenase- 2 inhibition combined with thromboxane receptor antagonism. Circulation 2005;111:334-42. (Pubitemid 40165341)
29. Ueno N, Takegoshi Y, Kamei D, Kudo I, Murakami M. Coupling between cyclooxygenases and terminal prostanoid synthases. Biochem Biophys Res Comm 2005;338:70-6. (Pubitemid 41540538)
30. Nugteren DH, Christ-Hazelhof E. Chemical and enzymatic conversions of prostaglandin endoperoxide PGH2. Adv Prostaglandin Thromboxane Res 1980;6:129-37.
31. Soler M, Camacho M, Escudero JR, Iñiguez MA, Vila L. Human vascular smooth muscle cells but not endothelial cells express prostaglandin E synthase. Circ Res 2000;87:504-7.
32. Ueno N, MurakamiM, Tanioka T, Fujimori K, Tanabe T, Urade Y, et al. Coupling between cyclooxygenase, terminal prostanoid synthase, and phospholipase A2. J Biol Chem 2001;276:34918-27.
33. Capone ML, Tacconelli S, Di Francesco L, Sacchetti A, Sciulli MG, Patrignani P. Pharmacodynamic of cyclooxygenase inhibitors in humans. Prostaglandins Other Lipid Mediat 2007;82:85-94. (Pubitemid 44895440)
34. Skazik C, Heise R, Bostanci ö, Paul N, Denecke B, Joussen S, et al. Differential expression of influx and efflux transport proteins in human antigen presenting cells. Exp Dermatol 2008;17:739-47.
35. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL. Identification and characterization of a prostaglandin transporter. Science 1995;268:866-9.
36. 2 synthases. Clin Immunol 2006;119:229-40. (Pubitemid 44269070)
37. Mosca M, Polentarutti N, Mangano G, Apicella C, Doni A, Mancini F, et al. Regulation of the microsomal prostaglandin E synthase-1 in polarized mononuclear phagocytes and its constitutive expression in neutrophils. J Leukoc Biol 2007;82:320-6. (Pubitemid 47230643)
38. Wang M, Lee E, Song W, Ricciotti E, Rader DJ, Lawson JA, et al. Microsomal prostaglandin E synthase-1 deletion suppresses oxidative stress and angiotensin II-induced abdominal aortic aneurysm formation. Circulation 2008;117:1302-9. (Pubitemid 351365673)