Phenylsulphonyl urenyl chalcone derivatives as dual inhibitors of cyclo-oxygenase-2 and 5-lipoxygenase

Life Sciences

Volumn 78, Issue 25, 2006, Pages 2911-2918

  Araico, A ^a   Terencio, M C ^a   Alcaraz, M J ^a   Dominguez J N ^b   Leon C ^b   Ferrandiz M L ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

Author keywords

5 LO; Chalcone derivatives; COX 2

Indexed keywords

4' N [N'' (4'' METHYLPHENYLSULFONYL)]URENYLCHALCONE; ARACHIDONATE 5 LIPOXYGENASE; CHALCONE DERIVATIVE; CYCLOOXYGENASE 2; ELASTASE; LEUKOTRIENE B4; MYELOPEROXIDASE; NITRIC OXIDE; PROSTAGLANDIN E2; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL LINE; DRUG POTENCY; ENZYME ACTIVITY; ENZYME RELEASE; HUMAN; HUMAN CELL; IC 50; MACROPHAGE; MONOCYTE; MOUSE; NEUTROPHIL; NONHUMAN; PROTEIN SYNTHESIS;

ANIMALS; ARACHIDONATE 5-LIPOXYGENASE; CELL LINE; CHALCONES; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; DINOPROSTONE; HUMANS; LEUKOTRIENE B4; LIPOXYGENASE INHIBITORS; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NEUTROPHILS; NITRIC OXIDE; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 33646192579     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2005.11.017     Document Type: Article

References (50)

1. Alcaraz M.J., Vicente A., Araico M.A., Terencio M.C., and Ferrándiz M.L. Role of nuclear factor-kappaB in the mechanism of action of an anti-inflammatory chalcone derivative in RAW 264.7 cells. British Journal of Pharmacology 142 (2004) 1191-1199
2. Bennett G., al-Rashed S., Hoult J.R., and Brain S.D. Nerve growth factor induced hyperalgesia in the rat hind paw is dependent on circulating neutrophils. Pain 77 (1998) 315-322
3. Betts W.H. Detecting oxy radicals by chemiluminescence. In: Greenwald R.A. (Ed). Handbook of methods for oxygen radical research (1985), CRC Press, Boca Raton 197-201
4. Bustos G., Ferrándiz M.L., Sanz M.J., Payá M., and Alcaraz M.J. A study of the novel anti-inflammatory agent florifenine. Topical anti-inflammatory activity and influence on arachidonic acid metabolism and neutrophil functions. Naunyn-Schmidedeberg's Archives of Pharmacology 351 (1995) 298-304
5. Celotti F., and Laufer S. Anti-inflammatory drugs: new multitarget compounds to face an old problem. The dual inhibition concept. Pharmacology Research 43 (2001) 429-436
6. Chakraborti A.K., and Thilagavathi R. Computer-aided design of non sulphonil COX-2 inhibitors: an improved comparative molecular field analysis incorporating additional descriptors and comparative molecular similarity indices analysis of 1,3-diarylisoindole derivatives. Bioorganic and Medicinal Chemistry 11 (2003) 3989-3996
7. Charlier C., and Michaux C. Dual inhibition of cyclooxygenase-2 (COX-2) and lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. European Journal of Medicinal Chemistry 38 (2003) 645-659
8. 2+-dependent translocation domain with homology to PKC and GAP. Cell 65 (1990) 1043-1051
9. De León E.J., Alcaraz M.J., Domínguez J.N., Charris J., and Terencio M.C. 1-(2,3,4-trimethoxyphenyl)-3-(3-(2-chloroquinolinyl))-2-propen-1-one, a chalcone derivative with analgesic, anti-inflammatory and immunomodulatory properties. Inflammation Research 52 (2003) 246-257
10. De León E.J., Alcaraz M.J., Domínguez J.N., Charris J., and Terencio M.C. A new chlorolquinolinyl chalcone derivative as inhibitor of inflammatory and immune response in mice and rats. Journal of Pharmacy and Pharmacology 55 (2003) 1313-1321
11. Diamant Z., and Sampson A.P. Anti-inflammatory mechanisms of leukotriene modulators. Clinical and Experimental Allergy 29 (1999) 1449-1453
12. Domínguez J.N., León C., Rodrigues J., Gamboa de Domínguez N., Gut J., and Rosenthal P. Synthesis and evaluation of new antimalarial phenylurenyl chalcones derivatives. Journal of Medicinal Chemistry 48 (2005) 3654-3658
13. 2 with anti-inflammatory activity. Journal of Pharmacology and Experimental Therapeutics 282 (1997) 123-131
14. Fiorucci S., Meli R., Bucci M., and Cirino G. Dual inhibitors of cyclooxygenase and lipoxygenase. A new avenue in anti-inflammatory therapy?. Biochemical Pharmacology 62 (2001) 1433-1438
15. Fosslien E. Adverse effects of non-steroidal anti-inflammatory drugs on the gastrointestinal system. Annals of Clinical and Laboratory Science 28 (1998) 67-81
16. 2 associated with rabbit polymorphonuclear leukocyte granules. Journal of Lipid Research 15 (1974) 380-388
17. Gaddi A., Cicero A.F.G., and Pedro E.J. Clinical perspectives of anti-inflammatory therapy in the elderly: the lipoxygenase (LOX)/cyclooxygenase (COX) inhibition concept. Archives of Gerontology and Geriatric 38 (2004) 201-212
18. Gilroy D.W., Tomlinson A., and Willoughby D.A. Differential effects of inhibitors of cyclooxygenase 1 and cyclooxygenase 2 in acute inflammation. European Journal of Pharmacology 355 (1998) 211-217
19. Gross S.S., and Levi R. Tetrahydrobiopterin synthesis. An absolute requirement for cytokine-induced nitric oxide generation by vascular smooth muscle. Journal of Biology and Chemistry 267 (1992) 25722-25729
20. Haraguchi H., Ishikawa H., Mizutani K., Tamura Y., and Kinoshita T. Antioxidative and Superoxide scavenging activities of retrochalcones in Glycyrrhiza inflata. Bioorganic and Medicinal Chemistry 6 (1998) 339-347
21. Henderson W.R. The role of leukotrienes in inflammation. Annals of Internal Medicine 121 (1994) 684-697
22. Herencia F., Ferrándiz M.L., Ubeda A., Domínguez J.N., Charris J.E., Lobo G.M., and Alcaraz M.J. Synthesis and anti-inflammatory activity of chalcone derivatives. Bioorganic and Medicinal Chemistry Letters 8 (1998) 1169-1174
23. Herencia F., Ferrandiz M.L., Ubeda A., Guillen I., Domínguez J.N., Charris J.E., Lobo G.M., and Alcaraz M.J. Novel anti-inflammatory chalcone derivatives inhibit the induction of nitric oxide synthase and cyclooxygenase-2 in mouse peritoneal macrophages. FEBS Letters 453 (1999) 129-134
24. Herencia F., Ferrandiz M., Ubeda A., Guillen I., Domínguez J.N., Charris J.E., Lobo G.M., and Alcaraz M.J. 4-dimethylamino-3′,4′-dimethoxychalcone down-regulates iNOS expression and exerts anti-inflammatory effects. Free Radical Biology & Medicine 30 (2001) 43-50
25. Hinz B., and Brune K. Pain and osteoarthritis: new drugs and mechanisms. Current Opinion in Rheumatology 16 (2004) 628-633
26. Hsieh H.K., Tsao L.T., Wang J.P., and Lin C.N. Synthesis and anti-inflammatory effect of chalcones. Journal of Pharmacy and Pharmacology 52 (2000) 163-171
27. Jahng Y., Zhao L., Moon Y., Basnet A., Kim E., Chang H.W., Ju H.K., Jeong T.C., and Lee E. Simple aromatic compounds containing propenone moiety show considerable dual COX/5-LOX inhibitory activities. Bioorganic and Medicinal Chemistry Letters 14 (2004) 2559-2562
28. Jovanovich D.V., Fernandes J.C., Martel-Pelletier J., Jolicoeur F.C., Reboul P., Laufer S., Tries S., and Pelletier J.P. In vivo dual inhibition of cyclooxygenase and lipoxygenase by ML3000 reduces the progression of experimental osteoarthritis. Arthritis and Rheumatism 44 (2001) 2320-2330
29. Laskin D.L., and Pendino K.J. Macrophages and inflammatory mediators in tissue injury. Annual Review of Pharmacology and Toxicology 35 (1995) 655-677
30. Leval X., Julemont F., Delarge J., Pirotte B., and Dogne J.M. New trends in dual 5-LOX/COX inhibition. Current Medicinal Chemistry 9 (2002) 941-962
31. Lewis R.A., Austen K.F., and Soberman R.J. Leukotrienes and other products of the 5-lipoxygenase pathway. Biochemistry and relation to pathobiology in human diseases. New England Journal of Medicine 323 (1990) 645-655
32. MacMicking J., Xie Q., and Nathan C. Nitric oxide and macrophage function. Annual Review of Immunology 15 (1997) 323-350
33. Martell-Pelletier J., Lajeunesse D., Rebaul P., and Pelletier J.P. Therapeutic role of dual inhibitors of 5-LOX and COX, selective and non-selective non-steroidal anti-inflammatory drugs. Annals of Rheumatic Diseases 62 (2003) 501-509
34. Masferrer J.L., Zweifel B.S., Manning P.T., Hauser S.D., Laehy K.M., Smith W.G., Isakson P.C., and Seibert K. Selective inhibition of inducible cyclooxygenase 2 in vivo is anti-inflammatory and nonulcerogenic. Proceedings of the National Academy of Sciences of the United States of America 91 (1994) 3228-3232
35. Misko T.P., Schilling R.J., Salvemini D., Moore W.M., and Currie M.G. A fluorometric assay for the measurement of nitrite in biological samples. Analytical Biochemistry 214 (1993) 11-16
36. Moroney M.A., Alcaraz M.J., Forder R.A., Carey F., and Hoult J.R.S. Selectivity of neutrophils 5-lipoxygenase and cyclooxygenase inhibition by an anti-inflammatory flavonoid glycoside and related aglycone flavonoids. Journal of Pharmacy and Pharmacology 40 (1988) 787-792
37. Molloy E.S., and McCarthy G.M. Eicosanoids, osteoarthritis and crystal deposition diseases. Current Opinion in Rheumatology 17 (2005) 346-350
38. Nickerson-Nutter C.L., and Medvedeff E.D. The effect of leukotriene synthesis inhibitors in models of acute and chronic inflammation. Arthritis and Rheumatism 39 (1996) 515-521
39. Parente L. Pros and cons of selective inhibition of cyclooxygenase-2 versus dual lipoxygenase/cyclooxygenase inhibition: is two better than one?. Journal of Rheumatology 28 (2001) 2375-2382
40. Prasanna S., Manivannan E., and Chaturvedy S.C. QSAR analysis of some fused pyrazoles as selective cyclooxygenase-2 inhibitors: a Hansch approach. Archiv der Pharmazie 337 (2004) 440-444
41. Rainsford K.D. Inhibition by leukotriene inhibitors, and calcium and platelet-activating factor antagonists, of acute gastric and intestinal damage in arthritic rats and in cholinomimetic-treated mice. Journal of Pharmacy and Pharmacology 51 (1999) 331-339
42. Rioja I., Ubeda A., Terencio C., Guillen I., Riguera R., Quintela J., et al. An anti-inflammatory ditriazine inhibiting leukocyte functions and expression of inducible nitric oxide synthase and cyclooxygenase-2. European Journal of Pharmacology 397 (2000) 207-217
43. Rojas J., Payá M., Devesa I., Domínguez J.N., and Ferrándiz M.L. Therapeutic administration of 3,4,5-trimethoxy-4′-fluorochalcone, a selective inhibitor of iNOS expression, attenuates the development of adjuvant-induced arthritis in rats. Naunyn-Schmiedeberg's Archives of Pharmacology 368 (2003) 225-233
44. Rojas J., Paya M., Domínguez J.N., and Ferrandiz M.L. ttCH, a new selective inhibitor of inducible nitric oxide synthase expression with antiarthritic properties. European Journal of Pharmacology 465 (2003) 183-189
45. Skelly M.M., and Hawkey C.J. COX-LOX inhibition: current evidence for an emerging new therapy. International Journal of Clinical Practice 57 (2003) 301-304
46. Smith J.A. Neutrophils, host defense, and inflammation: a double-edged sword. Journal of Leukocyte Biology 56 (1994) 672-686
47. Takeyama K., Agusti C., Ueki I., Lausier J., Cardell L.O., and Nadel J.A. Neutrophil-dependent globe cell degranulation: role of membrane-bound elastase and adhesion molecules. American Journal of Physiology 275 (1998) L294-L302
48. Tateson J.E., Randall R.W., Reynolds C.H., Jackson W.P., Bhattacherjee P., Salmon J.A., and Garland L.G. Selective inhibition of arachidonate 5-lipoxygenase by novel acetohydroxamic acids: biochemical assessment in vitro and ex vivo. British Journal of Pharmacology 94 (1988) 528-539
49. 4 in murine dermatitis models. Biochemical Pharmacology 55 (1998) 297-304
50. Vane J.R., Mitchell J.A., Appleton I., Tomlison A., Bishop-Bailey D., Croxtall J., and Willoughby D.A. Inducible isoforms of cyclooxygenase and nitric-oxide synthase in inflammation. Proceedings of the National Academy of Sciences of the United States of America 91 (1994) 2046-2050