User menu

Accès à distance ? S'identifier sur le proxy UCLouvain

'Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism

Primary tabs

Smart, D Jonsson, KO Vandevoorde, Severine [UCL] Lambert, DM. Fowler, CJ.

1 The abilities of a series of saturated N-acyl ethanolamines and related compounds to affect the ability of anandamide (AEA) to produce a Ca2+ influx into human embryonic kidney cells expressing the human vanilloid receptor (hVR1-HEK293 cells) has been investigated. 2 The C3:0, C4:0, C6:0 and C10:0 ethanolamides neither affected basal Ca2+-influx, nor the influx in response to a submaximal concentration of AEA (1 muM). In contrast, the C12:0, C17:0, C18:0 ethanolamides and the monounsaturated compound oleoylethanolamide (C18:1) greatly potentiated the response to AEA. Palmitoylethanolamide (C16:0) produced both a response per se and an augmentation of the response to AEA. 3 Lauroylethanolamide (C12:0) produced a leftward shift in the dose-response curve for AEA. EC50 values for AEA to produce Ca2+ influx into hVR1-HEK293 cells were 1.8, 1.5, 1.1 and 0.22 muM in the presence of 0, 1, 3 and 10 muM lauroylethanolamide, respectively. Lauroylethanolamide did not affect the dose-response curves to capsaicin. 4 Palmitoylethylamide was synthesized and found to be a mixed-type inhibitor (K-i(slope) 4.1 muM, K-i(intercept) 66 muM) of [H-3]-AEA metabolism by rat brain membranes. 5 The -amide, -ethylamide, -isopropylamide, -butylamide, -cyclohexamide and -trifluoromethyl ketone analogues of palmitoylethanolamide had little or no effect on the Ca2+ influx response to 1 muM AEA. 6 There was no obvious relation between the abilities of the compounds to enhance the Ca2+-influx response to 1 muM EA into hVR1-HEK293 cells and to prevent the hydrolysis of AEA by rat brain membranes. 7 It is concluded that although palmitoylethanolamide has entourage-like effects at VR1 receptors expressed on hVR1-HEK293 cells, other N-acyl ethanolamines have even more dramatic potentiating effects. It is possible that they may play an important role under conditions where their synthesis is increased, such as in severe inflammation.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2002
Language Anglais
Journal information "British Journal of Pharmacology" - Vol. 136, no. 3, p. 452-458 (2002)
Peer reviewed yes
Publisher Nature Publishing Group (London)
issn 0007-1188
e-issn 1476-5381
Publication status Publié
Affiliation UCL
Keywords vanilloid receptors ; anandamide ; fatty acid amidohydrolase ; N-acyl ethanolamines
Links
  1. BEN-SHABAT, Eur. J. Pharmacol., 353, 23 (1998)
  2. BERDYSHEV, Biochem. J., 346, 369 (2000)
  3. BOGER, Bioorg. Med. Chem. Lett., 10, 2613 (2000)
  4. CATERINA, Nature, 389, 816 (1997)
  5. CRAIB, Br. J. Pharmacol., 134, 30 (2001)
  6. CRAVATT, Nature, 384, 83 (1996)
  7. PETROCELLIS, J. Biol. Chem., 276, 12856 (2001)
  8. PETROCELLIS, FEBS Letts., 506, 253 (2001)
  9. DEVANE, Science, 258, 1946 (1992)
  10. DEUTSCH, Biochem. Pharmacol., 46, 791 (1993)
  11. DI MARZO, Trends Pharmacol. Sci., 22, 346 (2001)
  12. Eisenthal Robert, Cornish-Bowden Athel, The direct linear plot. A new graphical procedure for estimating enzyme kinetic parameters, 10.1042/bj1390715
  13. EPPS, J. Biol. Chem., 257, 1383 (1982)
  14. EPPS, Biochem. Biophys. Res. Commun., 90, 628 (1979)
  15. FOWLER, J. Pharmacol. Exp. Ther., 283, 729 (1997)
  16. GIANG, Proc. Natl. Acad. Sci. USA, 94, 2238 (1997)
  17. GAULDIE, Br. J. Pharmacol., 132, 617 (2001)
  18. HANSEN, J. Neurochem., 78, 1415 (2001)
  19. JONSSON, Br. J. Pharmacol., 133, 1263 (2001)
  20. JUNG, J. Neurosci., 19, 529 (1999)
  21. KONDO, Arch. Biochem. Biophys., 354, 303 (1998)
  22. Lambert Didier M, DiPaolo Federica G, Sonveaux Pierre, Kanyonyo Martial, Govaerts Sophie J, Hermans Emmanuel, Bueb Jean-Luc, Delzenne Nathalie M, Tschirhart Eric J, Analogues and homologues of N-palmitoylethanolamide, a putative endogenous CB2 cannabinoid, as potential ligands for the cannabinoid receptors, 10.1016/s1388-1981(99)00132-8
  23. LAMBERT, Epilepsia, 42, 321 (2001)
  24. MANG, Br. J. Pharmacol., 134, 161 (2001)
  25. MCLATCHIE, Br. J. Pharmacol., 132, 899 (2001)
  26. OMEIR, Life Sci., 56, 1999 (1995)
  27. RALEVIC, Eur. J. Pharmacol., 424, 211 (2001)
  28. ROSS, Br. J. Pharmacol., 132, 631 (2001)
  29. SCHMID, J. Biol. Chem., 260, 14145 (1985)
  30. SMART, Br. J. Pharmacol., 129, 227 (2000)
  31. SMITH, Br. J. Pharmacol., 134, 655 (2001)
  32. TOGNETTO, J. Neurosci., 21, 1104 (2001)
  33. WELCH, Proc. Natl. Acad. Sci. USA, 97, 13889 (2000)
  34. ZYGMUNT, Nature, 400, 452 (1999)
Bibliographic reference Smart, D ; Jonsson, KO ; Vandevoorde, Severine ; Lambert, DM. ; Fowler, CJ.. 'Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism. In: British Journal of Pharmacology, Vol. 136, no. 3, p. 452-458 (2002)
Permanent URL http://hdl.handle.net/2078.1/41917