N-(2-Hydroxyethyl) hexadecanamide is orally active in reducing edema formation and inflammatory hyperalgesia by down-modulating mast cell activation

European Journal of Pharmacology

Volumn 300, Issue 3, 1996, Pages 227-236

  Mazzari, Silvio ^a,b   Canella, Roberto ^b   Petrelli, Lucia ^b   Marcolongo, Gabriele ^b   Leon, Alberta ^b  

^a Ospedale Civile   (Italy)

^b Researchlife ScpA   (Italy)

Author keywords

Autacoid local inflammatory antagonism; Cannabinoid receptor, peripheral; N Acylethanolamide; Neurogenic inflammation; Palmitoylethanolamide; Passive cutaneous anaphylaxis

Indexed keywords

ANTIINFLAMMATORY AGENT; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR; CARRAGEENAN; CROMOGLYCATE DISODIUM; DEXTRAN; ETHANOLAMINE; FORMALDEHYDE; INDOMETACIN; LG 2110 1; N (2 HYDROXYETHYL)HEXADECANAMIDE; PALMITIC ACID; PHOSPHOLIPASE A2; SUBSTANCE P; SUBSTANCE P [6-11]; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG INHIBITION; EDEMA; EXTRAVASATION; FEMALE; HYPERALGESIA; MALE; MAST CELL DEGRANULATION; MOUSE; NEUROGENIC INFLAMMATION; NONHUMAN; ORAL DRUG ADMINISTRATION; PASSIVE SKIN ANAPHYLAXIS; PAW EDEMA; PRIORITY JOURNAL; RAT; TOPICAL DRUG ADMINISTRATION;

ANALYSIS OF VARIANCE; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CARRAGEENAN; CELL DEGRANULATION; DEXTRANS; EAR, EXTERNAL; EDEMA; EVANS BLUE; EXCIPIENTS; EXTRAVASATION OF DIAGNOSTIC AND THERAPEUTIC MATERIALS; FEMALE; FORMALDEHYDE; HYPERALGESIA; MALE; MAST CELLS; MICE; MICE, INBRED BALB C; PALMITIC ACIDS; PASSIVE CUTANEOUS ANAPHYLAXIS; RATS; RATS, WISTAR; SUBSTANCE P;

EID: 0029865544     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/0014-2999(96)00015-5     Document Type: Article

References (61)

1. Al-Haboubi, H.A. and I.J. Zeitlin, 1983, Re-appraisal of the role of histamine in carrageenan-induced paw edema, Eur. J. Pharmacol. 88, 169.
2. Aloe, L., A. Leon and R.L. Montalcini, 1993, A proposed autacoid mechanism controlling mastocyte behaviour, Agents Actions 39, C145.
3. Bani-Sacchi, T., M. Barattini, S. Bianchi, P. Blandina, S. Brunelleschi, R. Fantozzi, P.P. Mannaioni and E. Masini, 1986, The release of histamine by parasympathetic stimulation in guinea-pig auricle and rat ileum, J. Physiol. 371, 29.
4. Bronner, C., V. Cothenet, D. Monté, M. Joseph, Y. Landry and A. Capron, 1990, Role of phospholipase A2 and G-protein in the IgE-de-pendent activation of mast cells and macrophages, Agents Actions 30, 95.
5. Carnuccio, R., M. Di Rosa, B. Guerrasio, T. Iuvone and L. Sautebin, 1987, Vasocortin: a novel glucocorticoid-induced anti-inflammatory protein, Br. J. Pharmacol. 90, 443.
6. Cirino, G., S.M. Peers, J.L., Wallace and R.J. Rower, 1989, A study of phospholipase Arinduced edema in rat paw, Eur. J. Pharmacol. 166, 505.
7. Couture, R. and A.C. Cuello, 1984, Studies on the trigeminal antidromic vasodilation and plasma extravasation in the rat, J. Physiol. (London) 346, 273.
8. Cunha, F.Q., S. Poole, B.B. Lorenzetti and S.M. Ferreira, 1992, The pivotal role of tumor necrosis factor a in the development of inflammatory hyperalgesia, Br. J. Pharmacol. 107, 660.
9. Devane, W.A., L. Hanùs, A. Breuer, R.G. Pertwee, L.A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger and R. Mechoulam, 1992, Isolation and structure of a brain constituent that binds to the cannabinoid receptor, Science 258, 1946.
10. Devane, W.A. and J. Axelrod, 1994, Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain mem-branes, Proc. Natl. Acad. Sci. USA 91, 6698.
11. Devillier, P., G. Drapeau, M. Renoux and D. Regoli, 1989, Role of N terminal arginine in the histamine-releasing activity of substance P, bradykinin and related peptides, Eur. J. Pharmacol. 168, 53.
12. Di Rosa, M. and D.A. Willoughby, 1971, Screens for anti-inflammatory drugs, J. Pharm. Pharmacol. 23, 297.
13. Di Rosa, M., J.P. Giroud and D.A. Willoughby, 1971, Studies of the mediators of the acute inflammatory response induced in rats in different sites by carrageenan and turpentine, J. Pathol. 104, 15.
14. Di Rosa, M., A. Calignano, R. Carnuccio, A. lalenti and L. Sautebin, 1985, Multiple control of inflammation by glucocorticoids, Agents Actions 17, 284.
15. Di Marzo, V., A. Fontana, H. Cadas, S. Schinelli, G. Cimino, J.-C. Schwartz and D. Piomelli, 1994, Formation and inactivation of endogenous cannabinoid anandamide in central neurons, Nature 372, 686.
16. Dinarello, C.A., 1991, Inflammatory cytokines: Interleukin-1 and tumor necrosis factor as effector molecules in autoimmune diseases, Curr. Opinion Immunol. 3, 941.
17. Epps, D.E., P.C. Schmid, V. Natarajan and H.H.O. Schmid, 1979, N-Acylethanolamine accumulation in infarcted myocardium, Biochem. Biophys. Res. Commun. 90, 628.
18. Facci, L., R. Dal Toso, S. Romanello, A. Buriani, S.D. Skaper and A. Leon, 1995, Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide, Proc. Natl. Acad. Sci. USA 92, 3376.
19. Felder, C.C., E.M. Briley, J. Axelrod, J.T. Simpson, K. Mackie and W.A. Devane, 1993, Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction, Proc. Natl. Acad. Sci. USA 90, 7656.
20. Ferreira, S.H., B.B. Lorenzetti, A.F. Bristow and S. Poole, 1988, Inter-leukin1 β;as a potent hyperalgesic agent antagonized by a tripeptide analogue, Nature 334, 698.
21. Galli, SJ., 1993, New concepts about the mast cell, New Engl. J. Med. 328, 257.
22. Hansen, H.S., L. Lauritzen, A.M. Strand, B. Moesgaard and A. Frandsen, 1995, Glutamate stimulates the formation of N-acylphosphatidyl-ethanolamine and N-acylethanolamine in cortical neurons in culture, Biochim. Biophys. Acta 1258, 303.
23. Inagaki, N., S. Goto, H. Yamasaki, H. Nagai and A. Koda, 1986, Studies on vascular permeability increasing factor involved in 48 hour homologous PCA in the mouse ear, Int. Arch. Allergy Appl. Immunol. 80, 285.
24. Janiszewski, J., J. Bienenstock and M.G. Blennerhassett, 1990, Activation of rat peritoneal MCs in culture with sympathetic neurons alters neuronal physiology, Brain Behav. Immunol. 4, 139.
25. Jansḱ, N., A. Janskö-Gabor and J. Szolcsakoani, 1967, Direct evidence for neurogenic inflammation and its prevention by denervation and by pretreatment with capsaicin, Br. J. Pharmacol. 31, 138.
26. Johnson, A.R., T.E. Hugli and HJ. Muller-Eberhard, 1975, Release of histamine from mast cells by complement peptides C3a and C5a, Immunology 28, 1067.
27. Khalil, Z. and R.D. Helme, 1989a, Sympathetic neurons modulate plasma extravasation in rat through a non-adrenergic mechanism. Clin. Exp. Neurol. 26, 45.
28. Khalil, Z. and R.D. Helme, 1989b, Sequence of events in substance P-mediated plasma extravasation in rat skin, Brain Res. 500, 256.
29. Khalil, Z. and R.D. Helme, 1990, Serotonin modulates substance P-induced plasma extravasation and vasodilation in rat skin by an action through capsaicin-sensitive primary afferent nerves, Brain Res. 527, 292.
30. Khalil, Z., P.V. Andrews and R.D. Helme, 1988, VIP modulates substance P-induced plasma extravasation in vivo, Eur. J. Pharmacol. 151, 281.
31. 9-tetrahydrocannabinol in the rat, Eur. J. Pharmacol. 24, 1.
32. Leon, A., A. Buriani, R. Dal Toso, M. Fabris, R. Romanello, L. Aloe and R. Levi-Montalcini, 1994a, Mast cells synthesize, store, and release nerve growth factor, Proc. Natl. Acad. Sci. USA, 91, 3739.
33. Leon, A., R. Canella and S. Mazzari, 1994b, N-(2-Hydroxy-ethyl)hexadecanamide improves neurological deficits accompanying experimental allergic encephalomyelitis in B10/PL mice, Soc. Neurosci. Abstr. 20, 952.
34. Levine, J.D., H.L. Fields and A.I. Basbaum, 1993, Peptides and the primary afferent nociceptor, J. Neurosci. 13, 2273.
35. Lewin G.R. and L.M. Mendell, 1993, Nerve growth factor and nociception, Trend Neurosci. 16, 353.
36. Lowman, M.A., C.R. Benyon and M.K. Church, 1988, Characterization of neuropeptide-induced histamine release from dispersed skin mast cells, Br. J. Pharmacol. 95, 121.
37. Mazzari, S., R. Canella and A. Leon, 1995, N(2-Hydroxyl)ethyOhexadecanamide reduces mechanical hyperalgesia following sciatic nerve constriction injury, Soc. Neurosci. Abstr. 2, 652.
38. 2, J. Immunol. 151, 5675.
39. Nakae, A. and K. Kunihiro, 1987, Separation of homologous fatty acid alkanolamides by high-performance liquid chromatography, J. Chromatogr. 156, 167.
40. Nakamura-Craig, M. and T.W. Smith, 1989, Substance P and inflammatory hyperalgesia, Pain 38, 91.
41. Natarajan, V., P.V. Reddy, P.C. Schmid and H.H.O. Schmid, 1982, N-Acylation of ethanolamine phospholipids in canine myocardium, Biochim. Biophys. Acta 712, 342.
42. Nishida, S. and S. Tomizawa, 1980, Effect of compound 48/80 on dextran-induced paw edema and histamine content of inflammatory exudate, Biochem. Pharmacol. 29, 1073.
43. Nishida, S., K. Kagaka and S. Tomizawa, 1978, Correlation between histamine content in exudate and degree of edema produced by dextran, Biochem. Pharmacol. 27, 242.
44. Olsson, Y., 1968, Mast cells in the nervous system, Int. Rev. Cytol. 24, 27.
45. Payan, D.G., S.D. Levine and E.J. Goetzl, 1984, Modulation of immunity and hypersensitivity by sensory peptides, J. Immunol. 132, 104.
46. Perlik, F. and K. Mašek, 1973, The effect of N-(2-hydroxyethyl)palmitamide on inflammatory processes in animal and man, in: Future Trends in Inflammation, eds. G.P. Velo, D.A. Willoughby and J.P. Giroud (Piccin Medical Books, Padua) p. 301.
47. Perlik, F., J. Elis and H. Raskova, 1971, Anti-inflammatory properties of N-(2-hydroxyethyl)palmitamide, Acta Physiol. Acad. Scient. Hung. 39, 395.
48. Ramos, B.F., Y. Zhang, V. Angkachatchai and B.A. Jackschik, 1992, Mast cell mediators regulate vascular permeability changes in Arthus reaction, J. Pharmacol. Exp. Ther. 262, 559.
49. Randall, L.O. and J.J. Selitto, 1957, A method for measurement of analgesic activity on inflamed tissue, Arch. Int. Pharmacodyn. 111, 409.
50. Roe, E.T., T.D. Moles and D. Swern, 1952, Fatty acid amides. V. Preparation of N-(2-acetoxyethyl)-amides of aliphatic acids, J. Am. Chem. Soc. 74, 3442.
51. Rosland, J.H., A. Tjølsen, B. Maemble and K. Hole, 1990, The formalin test in mice: effect of formalin concentration, Pain 42, 235.
52. Sana, A. and J.M. Lundberg, 1983, Evans blue fluorescence: quantitative and morphological evaluation of vascular permeability in animal tissues, J. Neurosci. Meth. 8, 41.
53. Schmid, H.H.O., P.C. Schmid and V. Natarajan, 1990, N-Acylated glycerophospholipids and their derivatives, Prog. Lipid Res. 29, 1.
54. Schmid, P.C., M.L. Zuzarte-Augustin and H.H.O. Schmid, 1985, Properties of rat liver N-acylethanolamine amidohydrolase, J. Biol. Chem. 260, 14145.
55. Stead, R.H. and J. Bienenstock, 1990, Cellular interactions between the immune and peripheral nervous system. A role for mast cells? in: Cell to Cell Interaction, eds. M.M. Burger, B. Sordat and R.M. Zinkernagel (Karger, Basel) p. 170.
56. Tallarida, R.J. and R.B. Murray, 1987, Manual of Pharmacologic Calculations with Computer Programs (Springer Verlag, New York).
57. Tomoe, S., I. Iwamoto, M. Tomioka and S. Yoshida, 1992, Comparison of substance P-induced and compound 48/80 induced neutrophil infiltration in mouse skin, Int. Arch. Allergy Immunol. 97, 237.
58. Wershil, B.K., G.T. Furuta, J.A. Lavigne, A.R. Choudhury, Z.-S. Wang and S.J. Galli, 1995, Dexamethasone or cyclosporin A suppress mast cell-leukocyte cascades. Multiple mechanisms of inhibition of IgE-and mast cell-dependent cutaneous inflammation in the mouse, J. Immunol. 154, 1391.
59. Winter, C.A., A.E. Risley and G.W. Nuss, 1963, Anti-inflammatory and antipyretic activities ot indomethacin, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-indole-3-acetic acid, J. Pharmacol. Exp. Ther. 141, 369.
60. Yano, H., B.K. Wershill, N. Arizono and S.J. Galli, 1989, Substance P-induced augmentation of cutaneous vascular permeability and granulocyte infiltration in mice is mast cell dependent, J. Clin. Invest. 84, 1276.
61. Zhang, Y., B.F. Ramos and B.A. Jackschik, 1991, Augmentation of reverse Arthus reaction by mast cells in mice, J. Clin. Invest. 88, 841.