CC05, a novel anti-inflammatory compound, exerts its effect by inhibition of cyclooxygenase-2 activity

European Journal of Pharmacology

Volumn 520, Issue 1-3, 2005, Pages 172-178

  Yin, Lin Lin ^a   Zhang, Wei Yu ^a   Li, Ming Hui ^a   Shen, Jing Kang ^a   Zhu, Xing Zu ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Air pouch model; Carrageenan induced paw edema; Cyclooxygenase 2; Inflammation; THP 1 cell line

Indexed keywords

4 [5 (3 AMINO 4 METHYLPHENYL) 3 (TRIFLUOROMETHYL) 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; BENZENESULFONAMIDE DERIVATIVE; CARRAGEENAN; CC 05; CYCLOOXYGENASE 2; LIPOPOLYSACCHARIDE; PHORBOL MYRISTATE; UNCLASSIFIED DRUG; ANTIINFLAMMATORY AGENT; BENZENESULFONAMIDE; CELECOXIB; INDOMETACIN; PROSTAGLANDIN E2; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRAZOLE DERIVATIVE; SULFONAMIDE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL DIFFERENTIATION; CONTROLLED STUDY; ENZYME ACTIVITY; GENETIC TRANSCRIPTION; IC 50; MACROPHAGE; MALE; NONHUMAN; PAW EDEMA; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS; RAT; RNA TRANSLATION; RODENT; STOMACH; ANIMAL; ARMYWORM; BACULOVIRUS; CHEMICALLY INDUCED DISORDER; COMPARATIVE STUDY; DOSE RESPONSE; DRUG EFFECT; EDEMA; GENETICS; INFLAMMATION; METABOLISM; SPRAGUE DAWLEY RAT; VIROLOGY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BACULOVIRIDAE; CARRAGEENAN; CYCLOOXYGENASE INHIBITORS; DINOPROSTONE; DOSE-RESPONSE RELATIONSHIP, DRUG; EDEMA; INDOMETHACIN; INFLAMMATION; INHIBITORY CONCENTRATION 50; MALE; PYRAZOLES; RATS; RATS, SPRAGUE-DAWLEY; SPODOPTERA; SULFONAMIDES;

EID: 25444434940     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2005.06.020     Document Type: Article

References (36)

1. M. Barrios-Rodiles, K. Keller, A. Belley, and K. Chadee Nonsteroidal anti-inflammatory drugs inhibit cyclooxygenase-2 enzyme activity but not mRNA expression in human macrophages Biochem. Biophys. Res. Commun. 225 1996 896 900
2. S. Bouee, A. Charlemagne, F. Fagnani, P. Le Jeunne, C. Sermet, F. Naudin, and P.J. Lancry Changes in osteoarthritis management by general practitioners in the COX-2 inhibitor era-concomitant gastroprotective therapy Jt. Bone Spine 71 2004 214 220
3. D.L. DeWitt, and W.L. Smith Primary structure of prostaglandin G/H synthase from sheep vesicular gland determined from the complementary DNA sequence Proc. Natl. Acad. Sci. U. S. A. 85 1988 1412 1416
4. S.C. Dreskin, G.W. Thomas, S.N. Dale, and L.E. Heasley Isoforms of Jun kinase are differentially expressed and activated in human monocyte/macrophage (THP-1) cells J. Immunol. 166 2001 5646 5653
5. J.N. Francischi, C.T. Chaves, A.C. Moura, A.S. Lima, O.A. Rocha, D.L. Ferreira-Alves, and Y.S. Bakhle Selective inhibitors of cyclo-oxygenase-2 (COX-2) induce hypoalgesia in a rat paw model of inflammation Br. J. Pharmacol. 137 2002 837 844
6. N. Futaki, I. Arai, Y. Hamasaka, S. Takahashi, S. Higuchi, and S. Otomo Selective inhibition of NS-398 on prostanoid production in inflamed tissue in rat carrageenan-air-pouch inflammation J. Pharm. Pharmacol. 45 1993 753 755
7. Y. Guan, M. Chang, W. Cho, Y. Zhang, R. Redha, L. Davis, S. Chang, R.N. Dubois, C.M. Hao, and M.D. Breyer Cloning, expression, and regulation of rabbit cyclooxygenase-2 in renal medullary interstitial cells Am. J. Physiol., Renal Fluid Electrolyte Physiol. 273 1997 18 26
8. R.C. Harris, J.A. McKanna, Y. Akai, H.R. Jacobson, R.N. Dubois, and M.D. Breyer Cyclooxygenase-2 is associated with the macula densa of rat kidney and increases with salt restriction J. Clin. Invest. 94 1994 2504 2510
9. H. Hashimoto, K. Imamura, J. Haruta, and K. Wakitani 4-(4-cycloalkyl/ aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors: enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522(1) J. Med. Chem. 45 2002 1511 1517
10. C.J. Hawkey COX-2 inhibitors Lancet 353 1999 307 314
11. C.A. Heid, J. Stevens, K.J. Livak, and P.M. Williams Real time quantitative PCR Genome Res. 6 1996 986 994
12. H.R. Herschman Prostaglandin synthase 2 Biochim. Biophys. Acta 1299 1996 125 140
13. T. Hla, and T. Maciag Cyclooxyenase gene expression is down-regulated by heparin-binding (acidic fibroblast) growth factor-1 in human endothelial cells J. Biol. Chem. 266 1991 24059 24063
14. T. Hla, and K. Neilson Human cyclooxygeanse-2 cDNA Proc. Natl. Acad. Sci. U. S. A. 89 1992 7384 7388
15. Institute of Laboratory Animal Research, Commission on Life Sciences, National Research Council Guide for the care and use of laboratory animals 1996 National Academy Press Washington, D.C.
16. W.E. Kaufmann, P.F. Worley, J. Pegg, M. Bremer, and P. Isakson COX-2, a synaptically induced enzyme, is expressed by excitatory neurons at postsynaptic sites in rat cerebral cortex Proc. Natl. Acad. Sci. U. S. A. 93 1996 2317 2321
17. K.N. Khan, S.K. Paulson, K.M. Verburg, J.B. Lefkowith, and T.J. Maziasz Pharmacology of cyclooxygenase-2 inhibition in the kidney Kidney Int. 61 2002 1210 1219
18. D.A. Kujubu, B.S. Fletcher, B.C. Varnum, R.W. Lim, and H.R. Herschman TIS10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue J. Biol. Chem. 266 1991 12866 12872
19. J.L. Masferrer, B.S. Zweifel, P.T. Manning, S.D. Hauser, K.M. Leahy, W.G. Smith, P.C. Isakson, and K. Seibert Selective inhibition of inducible cyclooxygenase-2 in vivo is anti-inflammatory and nonulcerogenic Proc. Natl. Acad. Sci. U. S. A. 91 1994 3228 3232
20. J.A. Mitchell, and T.D. Warner Cyclo-oxygenase-2: pharmacology, physiology, biochemistry and relevance to NSAID therapy Br. J. Pharmacol. 128 1999 1121 1132
21. M.A. Moroney, M.J. Alcaraz, R.A. Forder, F. Carey, and J.R. Hoult Selectivity of neutrophil 5-lipoxygenase and cyclo-oxygenase inhibition by an anti-inflammatory flavonoid glycoside and related aglycone flavonoids J. Pharm. Pharmacol. 40 1988 787 792
22. T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, and P.C. Isakson Synthesis and biological evaluation of the 1, 5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, celecoxib) J. Med. Chem. 40 1997 1347 1365
23. P. Prasit, Z. Wang, C. Brideau, C.C. Chan, S. Charleson, W. Cromlish, D. Ethier, J.F. Evans, A.W. Ford-Hutchinson, J.Y. Gauthier, R. Gordon, J. Guay, M. Gresser, S. Kargman, B. Kennedy, Y. Leblanc, S. Léger, J. Mancini, G.P. O'Neill, M. Ouellet, M.D. Percival, H. Perrier, D. Riendeau, I. Rodger, P. Tagari, M. Thérien, P. Vickers, E. Wong, L.J. Xu, R.N. Young, and R. Zamboni The discovery of rofecoxib, [MK 966, VIOXX®, 4-(4′- methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2 inhibitor Bioorg. Med. Chem. Lett. 9 1999 1773 1778
24. H. Schwende, E. Fitzke, P. Ambs, and P. Dieter Differences in the state of differentiation of THP-1 cells induced by phorbol ester and 1,25-dihydroxyvitamin D3 J. Leukoc. Biol. 59 1996 555 561
25. A.D. Sedgwick, and P. Lees Studies of eicosanoid production in the air pouch model of synovial inflammation Agents Actions 18 1986 429 438
26. A.D. Sedgwick, Y.M. Sin, J.C. Edwards, and D.A. Willoughby Increased inflammatory reactivity in newly formed lining tissue J. Pathol. 141 1983 483 495
27. W.L. Smith, and G.P. Wilkin Immunochemistry of prostaglandin endoperoxide-forming cyclooxygenases: the detection of the cyclooxygenases in rat, rabbit and guinea pig kidneys by immnofluorescence Prostaglandins 13 1977 873 892
28. A.H. Swiergiel, and A.J. Dunn Distinct roles for cyclooxygenases 1 and 2 in interleukin-1-induced behavioral changes J. Pharmacol. Exp. Ther. 302 2002 1031 1036
29. J.R. Vane The fight against rheumatism: from willow bark to COX-1 sparing drugs J. Physiol. Pharmacol. 51 2000 573 586
30. J.R. Vane, and R.M. Botting Mechanism of action of anti-inflammatory drugs Int. J. Tissue React. 20 1998 3 15
31. Z. Warzecha, A. Dembinski, P. Ceranowicz, S. Konturek, R. Tomaszewska, J. Stachura, T. Nakamura, and P.C. Konturek Inhibition of cyclooxygenase-2 reduces the protective effect of hepatocyte growth factor in experimental pancreatitis Eur. J. Pharmacol. 486 2004 107 119
32. B.J. Whittle, G.A. Higgs, K.E. Eakins, S. Moncada, and J.R. Vane Selective inhibition of prostaglandin production in inflammatory exudates and gastric mucosa Nature 284 1980 271 273
33. C.A. Winter, E.A. Risley, and G.W. Nuss Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs Proc. Soc. Exp. Biol. Med. 111 1962 544 547
34. J.M. Wright The double-edged sword of COX-2 selective NSAIDs CMAJ 167 2002 1131 1137
35. W.L. Xie, J.G. Chipman, D.L. Robertson, R.L. Erikson, and D.L. Simmons Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing Proc. Natl. Acad. Sci. U. S. A. 88 1991 2692 2696
36. W.Y. Zhang, X.N. Yang, D.Z. Jin, and X.Z. Zhu Expression and enzyme activity determination of human cyclooxygenase-1 and-2 in a baculovirus-insect cell system Acta. Pharmacol. Sin. 25 2004 1000 1006