A novel indazolo-triazolo-benzotriazepine exerts anti-inflammatory effects by inhibition of cyclooxygenase-2 activity and nitric oxide synthase-2 expression

Naunyn-Schmiedeberg's Archives of Pharmacology

Volumn 368, Issue 1, 2003, Pages 26-32

  Fernández, Patricia ^a   Guillén, M Isabel ^a   Ubeda, Amalia ^a   López Cremades, Pablo ^b   Aller, Enrique ^b   Lorenzo, Angeles ^b   Molina, Pedro ^b   Alcaraz, M José ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITY OF MURCIA   (Spain)

Author keywords

Anti inflammatory; Cyclooxygenase 2; Indazolo bis(guanidines); Indazolo triazolo benzotriazepines; Nitric oxide synthase 2

Indexed keywords

6 (4 BROMOPHENYL)AMINO 7 (4 CHLOROPHENYL)INDAZOLO[2',3':1,5] 1,2,4 TRIAZOLO[4,3 A] 1,3,5 BENZOTRIAZEPINE; ACETYLSALICYLIC ACID; CARRAGEENAN; CYCLOOXYGENASE 2; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDAZOLE DERIVATIVE; INDAZOLOBIS(GUANIDINE); INDAZOLOTRIAZOLOBENZOTRIAZEPINE; INDOMETACIN; LIPOPOLYSACCHARIDE; NITRIC OXIDE SYNTHASE; PROSTAGLANDIN E2; UNCLASSIFIED DRUG; ZYMOSAN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA BINDING; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; INFLAMMATION; MACROPHAGE; MOUSE; NONHUMAN; PAW EDEMA; PROTEIN EXPRESSION; STOMACH; SYNTHESIS;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; AZEPINES; BLOOD PLATELETS; BLOTTING, WESTERN; CARRAGEENAN; CELL SURVIVAL; CELLS, CULTURED; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DINOPROSTONE; EDEMA; ELECTROPHORETIC MOBILITY SHIFT ASSAY; FEMALE; HUMANS; INDAZOLES; ISOENZYMES; MACROPHAGES; MEMBRANE PROTEINS; MICE; MICROSOMES; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE TYPE II; NITRITES; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; TRIAZOLES;

EID: 0042660889     PISSN: 00281298     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00210-003-0768-6     Document Type: Article

References (33)

1. Abouzid KA, el-Abhar HS (2003) Synthesis and antiinflammatory activity of novel indazolones. Arch Pharm Res 26:1-8
2. Atkinson RN, King SB (1999) Guanidine-substituted imidazoles as inhibitors of nitric oxide synthase. Bioorg Med Chem Lett 9: 2953-2958
3. Balsinde J, Balboa MA, Dennis EA (1998) Functional coupling between secretory phospholipase A2 and cyclooxygenase-2 and its regulation by cytosolic group IV phospholipase A2. Proc Natl Acad Sci USA 95:7951-7956
4. Brahn E, Banquerigo ML, Firestein GS, Boyle DL, Salzman AL, Szabo C (1998) Collagen induced arthritis: reversal by mercaptoethylguanidine, a novel antiinflammatory agent with a combined mechanism of action. J Rheumatol 25:1785-1793
5. 2 synthase inhibitor and receptor antagonist in vitro. Br J Pharmacol 110:1600-1606
6. Bustos G, Ferrándiz ML, Sanz MJ, Payá M, Alcaraz MJ (1995) A study of the novel anti-inflammatory agent florifenine. Topical anti-inflammatory activity and influence on arachidonic acid metabolism and neutrophil functions. Naunyn-Schmiedebergs Arch Pharmacol 351:298-304
7. Chandrasekharan NV, Dai H, Roos KL, Evanson NK, Tomsik J, Elton TS, Simmons DL (2002) COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci USA 99:13926-13931
8. 2 from the human monocytic cell line U937. Proc Natl Acad Sci USA 87:7708-7712
9. Demiryurek AT, Cakici I, Kanzik I (1998) Peroxynitrite: a putative cytotoxin. Pharmacol Toxicol 82:113-117
10. Edwards JCW, Sedgwick AD, Willoughby DA (1981) The formation of a structure with the features of synovial lining by subcutaneous injection of air: an in vivo tissue culture system. J Pathol 134:147-156
11. 2 associated with rabbit polymorphonuclear leukocyte granules. J Lipid Res 15:380-388
12. Gross SS, Levi R (1992) Tetrahydrobiopterin synthesis. An absolute requirement for cytokine-induced nitric oxide generation by vascular smooth muscle. J Biol Chem 267:25722-25729
13. Handy RL, Moore PK (1998) A comparison of the effects of L-NAME, 7-NI and L-NIL on carrageenan-induced hindpaw oedema and NOS activity. Br J Pharmacol 123:1119-1126
14. Karin M (1999) The beginning of the end: IkappaB kinase (IKK) and NF-kappaB activation. J Biol Chem 274:27339-27342
15. Knowles RG, Moncada S (1994) Nitric oxide synthases in mammals. Biochem J 298:249-258
16. Kutchera W, Jones DA, Matsunami N, Groden J, McIntyre TM, Zimmerman GA, White RL, Prescott SM (1996) Prostaglandin H synthase 2 is expressed abnormally in human colon cancer: evidence for a transcriptional effect. Proc Natl Acad Sci USA 93:4816-4820
17. Lopez-Cremades P, Molina P, Aller E, Lorenzo A (2000) Solid-phase synthesis of bis(guanidines) based on an Aza Witting/carbodiimide-mediated annulation process. Synlett 10:1411-1414
18. MacMicking J, Xie QW, Nathan C (1997) Nitric oxide and macrophage function. Annu Rev Immunol 15:323-350
19. McGeer PL, McGeer EG (1999) Inflammation of the brain in Alzheimer's disease: implications for therapy. J Leukoc Biol 65: 409-415
20. Misko TP, Schilling RJ, Salvemini D, Moore WM, Currie MG (1993) A fluorometric assay for the measurement of nitrite in biological samples. Anal Biochem 214:11-16
21. Moroney MA, Alcaraz MJ, Forder RA, Carey F, Hoult JRS (1988) Selectivity of neutrophil 5-lipoxygenase and cyclo-oxygenase inhibition by an anti-inflammatory flavonoid glycoside and related aglycone flavonoids. J Pharm Pharmacol 40:787-792
22. Mosti L, Menozzi G, Fossa P, Schenone P, Lampa E, Parrillo C, D'Amisco M, Rossi F (1992) 4-substituted 1-methyl-1H-indazoles with analgesic, antiinflammatory and antipyretic activities. Farmaco 47:567-584
23. Patrono C (1994) Aspirin as an antiplatelet drug. N Engl J Med 330:1287-1294
24. Posadas I, Terencio MC, Guillén I, Ferrándiz ML, Coloma J, Payá M, Alcaraz MJ (2000) Co-regulation between cyclo-oxygenase-2 and inducible nitric oxide synthase expression in the time-course of murine inflammation. Naunyn-Schmiedebergs Arch Pharmacol 361:98-106
25. Riendeau D, Percival MD, Boyce S, Brideau C, Charleson S, Cromlish W, Ethier D, Evans J, Falgueyret J-P, Ford-Hutchinson AW, Gordon R, Greig G, Gresser M, Guay J, Kargman S, Léger S, Mancini JA, O'Neill G, Ouellet M, Rodger IW, Thérien M, Wang Z, Webb JK, Wong E, Xu L, Young RN, Zamboni R, Prasit P, Chan C-C (1997) Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. Br J Pharmacol 121:105-117
26. Rioja I, Ubeda A, Terencio MC, Guillen I, Riguera R, Quintela JM, Peinador C, Gonzalez LM, Alcaraz MJ (2000) An anti-inflammatory ditriazine inhibiting leukocyte functions and expression of inducible nitric oxide synthase and cyclo-oxygenase-2. Eur J Pharmacol 397:207-217
27. Rioja I, Terencio MC, Ubeda A, Riguera R, Quintela JM, Alcaraz MJ (2002) A new ditriazine inhibitor of NF-kappaB modulates chronic inflammation and angiogenesis. Naunyn-Schmiedebergs Arch Pharmacol 365:357-364
28. Schumann P, Collot V, Hommet Y, Gsell W, Dauphin F, Sopkova J, MacKenzie ET, Duval D, Boulouard M, Rault S (2001) Inhibition of neuronal nitric oxide synthase by 7-methoxyindazole and related substituted indazoles. Bioorg Med Chem Lett 11: 1153-1156
29. Sugishita E, Amagaya S, Ogihara Y (1981) Anti-inflammatory testing methods: comparative evaluation of mice and rats. J Pharmacobiodyn 4:565-575
30. Vane JR, Botting RM (1998) Mechanism of action of nonsteroidal anti-inflammatory drugs. Am J Med 104:2S-8S
31. Warner TD, Giuliano F, Vojnovic I, Bukasa A, Mitchell JA, Vane JR (1999) Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci USA 96:7563-7568
32. Wrzeciono U, Linkowska E, Majewska K, Gzella A, Stochla K (1993) [Synthesis and anti-inflammatory activity of some indazole derivatives. 36. Azoles]. Pharmazie 48:582-584
33. Xie QW, Kashiwabara Y, Nathan C (1994) Role of transcription factor NF-kappa B/Rel in induction of nitric oxide synthase. J Biol Chem 269:4705-4708