Inhibitory properties of ibuprofen and its amide analogues towards the hydrolysis and cyclooxygenation of the endocannabinoid anandamide

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 28, Issue 1, 2013, Pages 172-182

  Fowler, Christopher J ^a   Björklund, Emmelie ^a   Lichtman, Aron H ^b   Naidu, Pattipati S ^b   Congiu, Cenzo ^c   Onnis, Valentina ^c  

^a UMEÅ UNIVERSITY   (Sweden)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^c UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Analgesia; Cannabinoid; Cyclooxygenase; Fatty acid amide hydrolase; Ibuprofen

Indexed keywords

2 (4 ISOBUTYLPHENYL) N [2 (3 METHYLPYRIDIN 2YLAMINO) 2 OXOETHYL]PROPANAMIDE; 2 (4 ISOBUTYLPHENYL) N [2 (6 METHYLPYRIDIN 2YLAMINO) 2 OXOETHYL]PROPANAMIDE; 2 (4 ISOBUTYLPHENYL) N [2 OXO 2 (PYRIDIN 2 YLMETHYLAMINO)ETHYL]PROPANAMIDE; 2 (4 ISOBUTYLPHENYL) N [2 OXO 2 (PYRIDIN 3YLMETHYLAMINO)ETHYL]PROPANAMIDE; 2 (4 ISOBUTYLPHENYL) N [3 (3 METHYLPYRIDIN 2 YLAMINO) 3 OXOPROPYL]PROPANAMIDE; 2 [2 (4 ISOBUTYLPHENYL)PROPANOYLAMINO]ACETIC ACID; 3 [2 (4 ISOBUTYLPHENYL)PROPANOYLAMINO]PROPANOIC ACID; 4 ACETAMIDOPHENYL 2 [2 (4 ISOBUTYLPHENYL)PROPANAMIDO]ACETATE; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; ANANDAMIDE; ARACHIDONIC ACID; CANNABINOID RECEPTOR; CYCLOOXYGENASE 2; ENDOCANNABINOID; FLURBIPROFEN; IBUPROFEN; IBUPROFEN DERIVATIVE; RIMONABANT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BRAIN HOMOGENATE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SYNTHESIS; ESTERIFICATION; HYDROLYSIS; IC 50; IN VITRO STUDY; IN VIVO STUDY; NOCICEPTION; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR BLOCKING;

AMIDOHYDROLASES; ANIMALS; ARACHIDONIC ACIDS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DISEASE MODELS, ANIMAL; DRUG DESIGN; ENDOCANNABINOIDS; ENZYME INHIBITORS; HYDROLYSIS; IBUPROFEN; INHIBITORY CONCENTRATION 50; MALE; MICE; MICE, INBRED C57BL; POLYUNSATURATED ALKAMIDES; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; VISCERAL PAIN;

EID: 84874184618     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.643304     Document Type: Article

References (35)

1. Vane J. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nature New Biol 1971;231:232-235
2. Naidu PS, Booker L, Cravatt BF, Lichtman AH. Synergy between enzyme inhibitors of fatty acid amide hydrolase and cyclooxygenase in visceral nociception. J Pharmacol Exp Ther 2009;329:48-56
3. Morphy R, Rankovic Z. Designed multiple ligands. An emerging drug discovery paradigm. J Med Chem 2005;48:6523-6543 (Pubitemid 41504710)
4. Fowler CJ, Tiger G, Stenström A. Ibuprofen inhibits rat brain deamidation of anandamide at pharmacologically relevant concentrations. Mode of inhibition and structure-activity relationship. J Pharmacol Exp Ther 1997;283:729-734 (Pubitemid 27514633)
5. Fowler CJ, Holt S, Tiger G. Acidic nonsteroidal anti-inflammatory drugs inhibit rat brain fatty acid amide hydrolase in a pH-dependent manner. J Enzyme Inhib Med Chem 2003;18:55-58 (Pubitemid 36221714)
6. Holt S, Paylor B, Boldrup L, Alajakku K, Vandevoorde S, Sundström A et al. Inhibition of fatty acid amide hydrolase, a key endocannabinoid metabolizing enzyme, by analogues of ibuprofen and indomethacin. Eur J Pharmacol 2007;565:26-36 (Pubitemid 46782775)
7. Cocco MT, Congiu C, Onnis V, Morelli M, Cauli O. Synthesis of ibuprofen heterocyclic amides and investigation of their analgesic and toxicological properties. Eur J Med Chem 2003;38:513-518 (Pubitemid 36588917)
8. Boldrup L, Wilson SJ, Barbier AJ, Fowler CJ. A simple stopped assay for fatty acid amide hydrolase avoiding the use of a chloroform extraction phase. J Biochem Biophys Methods 2004;60:171-177 (Pubitemid 38953060)
9. Meade EA, Smith WL, DeWitt DL. Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J Biol Chem 1993;268:6610-6614 (Pubitemid 23099364)
10. Onnis V, Congiu C, Björklund E, Hempel F, Söderström E, Fowler CJ. Synthesis and evaluation of paracetamol esters as novel fatty acid amide hydrolase inhibitors. J Med Chem 2010;53:2286-2298
11. Jain NK, Kulkarni SK, Singh A. Modulation of NSAID-induced antinociceptive and anti-inflammatory effects by α2-adrenoceptor agonists with gastroprotective effects. Life Sci 2002;70:2857-2869 (Pubitemid 34442518)
12. Prusakiewicz JJ, Duggan KC, Rouzer CA, Marnett LJ. Differential sensitivity and mechanism of inhibition of COX-2 oxygenation of arachidonic acid and 2-arachidonoylglycerol by ibuprofen and mefenamic acid. Biochemistry 2009;48:7353-7355
13. Fowler CJ, Naidu PS, Lichtman A, Onnis V. The case for the development of novel analgesic agents targeting both fatty acid amide hydrolase and either cyclooxygenase or TRPV1. Br J Pharmacol 2009;156:412-419
14. Lichtman AH, Shelton CC, Advani T, Cravatt BF. Mice lacking fatty acid amide hydrolase exhibit a cannabinoid receptor-mediated phenotypic hypoalgesia. Pain 2004;109:319-327 (Pubitemid 38638709)
15. Naidu PS, Kinsey SG, Guo TL, Cravatt BF, Lichtman AH. Regulation of inflammatory pain by inhibition of fatty acid amide hydrolase. J Pharmacol Exp Ther 2010;334:182-190
16. De Wael F, Muccioli GG, Lambert DM, Sergent T, Schneider YJ, Rees JF et al. Chemistry around imidazopyrazine and ibuprofen: Discovery of novel fatty acid amide hydrolase (FAAH) inhibitors. Eur J Med Chem 2010;45:3564-3574
17. Goparaju SK, Ueda N, Yamaguchi H, Yamamoto S. Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand. FEBS Lett 1998;422:69-73 (Pubitemid 28052868)
18. Yu M, Ives D, Ramesha CS. Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 1997;272:21181-21186 (Pubitemid 27373979)
19. Duggan KC, Hermanson DJ, Musee J, Prusakiewicz JJ, Scheib JL, Carter BD et al. (R)-Profens are substrate-selective inhibitors of endocannabinoid oxygenation by COX-2. Nat Chem Biol 2011;7:803-809
20. Yuan C, Rieke CJ, Rimon G, Wingerd BA, Smith WL. Partnering between monomers of cyclooxygenase-2 homodimers. Proc Natl Acad Sci USA 2006;103:6142-6147
21. Kozak KR, Prusakiewicz JJ, Rowlinson SW, Prudhomme DR, Marnett LJ. Amino acid determinants in cyclooxygenase-2 oxygenation of the endocannabinoid anandamide. Biochemistry 2003;42:9041-9049 (Pubitemid 36935412)
22. Vecchio AJ, Malkowski MG. The structural basis of endocannabinoid oxygenation by cyclooxygenase-2. J Biol Chem 2011;286:20736-20745
23. Holt S, Fowler CJ. Anandamide metabolism by fatty acid amide hydrolase in intact C6 glioma cells. Increased sensitivity to inhibition by ibuprofen and flurbiprofen upon reduction of extrabut not intracellular pH. Naunyn Schmiedebergs Arch Pharmacol 2003;367:237-244 (Pubitemid 36408005)
24. Bishay P, Schmidt H, Marian C, Häussler A, Wijnvoord N, Ziebell S et al. R-flurbiprofen reduces neuropathic pain in rodents by restoring endogenous cannabinoids. PLoS ONE 2010; 5:e10628
25. Gühring H, Hamza M, Sergejeva M, Ates M, Kotalla CE, Ledent C et al. A role for endocannabinoids in indomethacin-induced spinal antinociception. Eur J Pharmacol 2002;454:153-163 (Pubitemid 35287474)
26. Ates M, Hamza M, Seidel K, Kotalla CE, Ledent C, Gühring H. Intrathecally applied flurbiprofen produces an endocannabinoiddependent antinociception in the rat formalin test. Eur J Neurosci 2003;17:597-604 (Pubitemid 36255896)
27. Telleria-Diaz A, Schmidt M, Kreusch S, Neubert AK, Schache F, Vazquez E et al. Spinal anti-nociceptive effects of cyclooxygenase inhibition during inflammation: Involvement of prostaglandins and endocannabinoids. Pain 2010;148:26-35
28. Staniaszek LE, Norris LM, Kendall DA, Barrett DA, Chapman V. Effects of COX-2 inhibition on spinal nociception: The role of endocannabinoids. Br J Pharmacol 2010;160:669-676
29. Guindon J, De Léan A, Beaulieu P. Local interactions between anandamide, an endocannabinoid, and ibuprofen, a nonsteroidal anti-inflammatory drug, in acute and inflammatory pain. Pain 2006;121:85-93 (Pubitemid 43261635)
30. Calignano A, La Rana G, Piomelli D. Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide. Eur J Pharmacol 2001;419:191-198 (Pubitemid 32568218)
31. Lo Verme J, Fu J, Astarita G, La Rana G, Russo R, Calignano A et al. The nuclear receptor peroxisome proliferator-activated receptor-α mediates the anti-inflammatory actions of palmitoylethanolamide. Mol Pharmacol 2005;67:15-19 (Pubitemid 40069962)
32. Högestätt E, Jönsson B, Ermund A, Andersson D, Björk H, Alexander J, et al. Conversion of acetaminophen to the bioactive N-acylphenolamine AM404 via fatty acid amide hydrolasedependent arachidonic acid conjugation in the nervous system. J BiolChem. 2005;280:31405-31412 (Pubitemid 41291881)
33. Mallet C, Daulhac L, Bonnefont J, Ledent C, Etienne M, Chapuy E et al. Endocannabinoid and serotonergic systems are needed for acetaminophen-induced analgesia. Pain 2008;139:190-200
34. Haller VL, Cichewicz DL, Welch SP. Non-cannabinoid CB1, non-cannabinoid CB2 anti-nociceptive effects of several novel compounds in the PPQ stretch test in mice. Eur J Pharmacol 2006;546:60-68 (Pubitemid 44348895)
35. Clapper JR, Moreno-Sanz G, Russo R, Guijarro A, Vacondio F, Duranti A et al. Anandamide suppresses pain initiation through a peripheral endocannabinoid mechanism. Nat Neurosci 2010;13:1265-1270