Anti-inflammatory effects of 4-phenyl-3-butenoic acid and 5-(acetylamino)-4-oxo-6-phenyl-2-hexenoic acid methyl ester, potential inhibitors of neuropeptide bioactivation

Journal of Pharmacology and Experimental Therapeutics

Volumn 320, Issue 3, 2007, Pages 1171-1177

  Bauer, John D ^a   Sunman, Jeffrey A ^a   Foster, Michael S ^b   Thompson, Jeremy R ^b   Ogonowski, Alison A ^a   Cutler, Stephen J ^a   May, Sheldon W ^b   Pollock, Stanley H ^a  

^a MERCER UNIVERSITY   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 PHENYL 3 BUTENOIC ACID; 5 ACETYLAMINO 4 OXO 6 PHENYL 2 HEXENOIC ACID; 5 ACETYLAMINO 4 OXO 6 PHENYL 2 HEXENOIC ACID METHYL ESTER; ADJUVANT; ALPHA AMIDATING ENZYME; ANTIINFLAMMATORY AGENT; CARRAGEENAN; NEUROPEPTIDE; OXYGENASE INHIBITOR; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG;

AMIDATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHRONIC INFLAMMATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; ENZYME BLOOD LEVEL; ENZYME INHIBITION; HUMAN; MALE; NONHUMAN; NORMAL HUMAN; PAW EDEMA; POLYARTHRITIS; PRIORITY JOURNAL; RAT;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARTHRITIS, EXPERIMENTAL; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DOSE-RESPONSE RELATIONSHIP, DRUG; EDEMA; ESTERS; FATTY ACIDS, MONOUNSATURATED; HEXANOIC ACIDS; HUMANS; MALE; MOLECULAR STRUCTURE; NEUROPEPTIDES; PHOSPHOLIPASES A; RATS; RATS, SPRAGUE-DAWLEY; SCIATIC NERVE; SUBSTANCE P;

EID: 33847142374     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.106.110940     Document Type: Article

References (37)

1. Ahmed M, Bjurholm A, Schultzberg M, Theodorsson E, and Kreicbergs A (1995) Increased levels of substance P and calcitonin gene-related peptide in rat adjuvant arthritis: a combined immunohistochemical and radioimmunoassay analysis. Arthritis Rheum 38:699-709.
2. Ambalavanar R, Moritani M, Moutanni A, Gangula P, Yallampalli C, and Dessem D (2006) Deep tissue inflammation upregulates neuropeptides and evokes nociceptive behaviors which are modulated by a neuropeptide antagonist. Pain 120:53-68.
3. Appendino G, De Petrocellis L, Trevisani M, Minassi A, Daddario N, Moriello AS, Gazzieri D, Ligresti A, Campi B, Fontana G, et al. (2005) Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential. J Pharmacol Exp Ther 312:561-570.
4. Binder W, Scott C, and Walker JS (1999) Involvement of substance P in the anti-inflammatory effects of the peripherally selective κ-opiod asimadoline and the NK1 antagonist GR205171. Eur J Neurosci 11:2065-2072.
5. Bozic CR, Lu B, Hopken UE, Gerard C, and Gerard NP (1996) Neurogenic amplification of immune complex inflammation. Science (Wash DC) 273:1722-1725.
6. Bradbury AF, Mistry J, Roos BA, and Smyth DG (1990) 4-Phenyl-3-butenoic acid, an in vivo inhibitor of peptidylglycine hydroxylase (peptide amidating enzyme). Eur J Biochem 189:363-368.
7. Brideau C, Kargman S, Liu S, Dallob AL, Ehrich EW, Rodger IW, and Chan CC (1996) A human whole blood assay for clinical evaluation of biochemical efficacy of cyclooxygenase inhibitors. Inflamm Res 45:68-74.
8. Donaldson LF, McQueen DS, and Seckl JR (1995) Neuropeptide gene expression and capsaicin-sensitive primary afferents: maintenance and spread of adjuvant arthritis in the rat. J Physiol (Lond) 486:473-482.
9. Donnerer J, Amann R, Schuligoi R, and Skofitsch G (1996) Complete recovery by nerve growth factor of neuropeptide content and function in capsaicin-impaired sensory neurons. Brain Res 741:103-108.
10. Donnerer J, Schuligoi R, and Stein C (1992) Increased content and transport of substance P and calcitonin gene-related peptide in sensory nerves innervating inflamed tissue: evidence for a regulatory function of nerve growth factor in vivo. Neuroscience 49:693-698.
11. Feng J, Shi J, Sirimanne SR, Mounier-Lee CE, and May SW (2000) Kinetic and stereochemical studies on novel inactivators of C-terminal amidation. Biochem J 350:521-530.
12. Gilligan JP, Lovato SJ, Erior MD, and Jeng AY (1994) Modulation of carrageenan-induced hind paw edema by substance P. Inflammation 18:285-292.
13. Haines KA, Kolasinski SL, Cronstein BN, Reibman J, Gold LI, and Weissmann G (1993) Chemoattraction of neutrophils by substance P and transforming growth factor-beta 1 is inadequately explained by current models of lipid remodeling. J Immunol 151:1491-1499.
14. Han S, Yoon ET, and Cho W (1998) Bacterial expression and characterization of human secretory class V phospholipase A2. Biochem J 331:353-357.
15. Holzer P and Holzer-Petsche U (1997) Tachykinins in the gut: II. Roles in neural excitation, secretion and inflammation. Pharmacol Ther 73:219-263.
16. Katopodis AG and May SW (1990) Novel substrates and inhibitors of peptidylglycine alpha-amidating monooxygenase. Biochemistry 29:4541-4548.
17. Katopodis AG, Ping D, and May SW (1990) A novel enzyme from bovine neurointermediate pituitary catalyzes dealkylation of α-hydroxyglycine derivatives, thereby functioning sequentially with peptidylglycine α-amidating monooxygenase in peptide amidation. Biochemistry 29:6115-6120.
18. Katopodis AG, Ping D, Smith CE, and May SW (1991) Functional and structural characterization of peptidylamidoglycolate lyase, the enzyme catalyzing the second step in peptide amidation. Biochemistry 30:6189-6194.
19. Krause JE, DiMaggio DA, and McCarson KE (1995) Alterations in neurokinin 1 receptor gene expression in models of pain and inflammation. Can J Physiol Pharmacol 73:854-859.
20. Matucci-Cernic M and Partsch G (1992) The contribution of the peripheral nervous system and the neuropeptide network to the development of synovial inflammation. Clin Exp Rheumatol 10:211-215.
21. Menkes CJ, Renoux M, Laoussadi S, Mauborgne A, Bruxelle J, and Cesselin F (1993) Substance P levels in the synovium and synovial fluid from patients with rheumatoid arthritis and osteoarthritis. J Rheumatol 20:714-717.
22. Moore AB and May SW (1999) Kinetic and inhibition studies on substrate channelling in the bifunctional enzyme catalysing C-terminal amidation. Biochem J 341:33-40.
23. Mounier CE, Shi J, Sirimanne SR, Chen BH, Moore AB, Gill-Woznichak MM, Ping D, and May SW (1997) Pyruvate-extended amino acid derivatives as highly potent inhibitors of carboxy-terminal peptide amidation. J Biol Chem 272:5016-5023.
24. Murakami M and Kudo I (2002) Phospholipase A2. J Biochem (Tokyo) 131:285-292.
25. Ogonowski AA, May SW, Moore AB, Barrett LT, O'Bryant CL, and Pollock SH (1997) Antiinflammatory and analgesic activity of an inhibitor of neuropeptide amidation. J Pharmacol Exp Ther 280:846-853.
26. Pernow B (1983) Substance P. Pharmacol Rev 35:85-141.
27. Ping D, Katopodis AG, and May SW (1992) Tandem stereochemistry of peptidylglycine α-monooxygenase and peptidylaminoglycolate lyase, the two enzymes involved in peptide amidation. J Am Chem Soc 114:3998- 4000.
28. Ping D, Mounier CE, and May SW (1995) Reaction versus subsite stereospecificity of peptidylglycine alpha-monooxygenase and peptidylamidoglycolate lyase, the two enzymes involved in peptide amidation. J Biol Chem 270:29250-29255.
29. Pinheiro RM and Calixto JB (2002) Effect of the selective COX-2 inhibitors, celecoxib and rofecoxib, in rat acute models of inflammation. Inflamm Res 51:603-610.
30. Reddy ST, Winstead MV, Tischfield JA, and Herschman HR (1997) Analysis of the secretory phospholipase A2 that mediates prostaglandin production in mast cells. J Biol Chem 272:13591-13596.
31. Seto S, Tanioka A, Ikeda M, and Izawa S (2005) Design and synthesis of novel 9-substituted-7-aryl-3,4,5,6-tetrahydro-2H-pyrido[4,3-b]- and [2,3-b]-1,5-oxazocin-6-ones as NK(1) antagonists. Bioorg Med Chem Lett 15:1479-1484.
32. Smith GD, Harmar AJ, McQueen DS, and Seckl JR (1992) Increase in substance P and CGRP, but not somatostatin content of innervating dorsal root ganglia in adjuvant monoarthritis in the rat. Neurosci Lett 137:257-260.
33. Szekaneez Z, Halloran MM, Volin MV, Woods JM, Strieter RM, Haines KG 3rd, Kunkel SL, Burdick MD, and Koch AE (2000) Temporal expression of inflammatory cytokines and chemokines in rat adjuvant-induced arthritis. Arthritis Rheum 43:1266-1277.
34. Waksman BH (2002) Immune regulation in adjuvant disease and other arthritis models: relevance to pathogenesis of chronic arthritis. Scand J Immunol 56:12-34.
35. Walker JS (2003) Anti-inflammatory effects of opioids. Adv Exp Med Biol 521:148-160.
36. Walz DT, DiMartino MJ, Kuch JH, and Zuccarello W (1971) Adjuvant-induced arthritis in rats. I. Temporal relationship of physiological, biochemical, and hematological parameters. Proc Soc Exp Biol Med 136:907-910.
37. Yu L, Deems RA, Hajdu J, and Dennis EA (1990) The interaction of phospholipase A2 with phospholipids analogues and inhibitors. J Biol Chem 265:2657-2664.