Protective role of palmitoylethanolamide in contact allergic dermatitis

Allergy: European Journal of Allergy and Clinical Immunology

Volumn 65, Issue 6, 2010, Pages 698-711

  Petrosino, S ^a,b   Cristino, L ^a   Karsak, M ^c   Gaffal, E ^c   Ueda, N ^d   Tuting T ^c   Bisogno, T ^a   De Filippis, D ^e   D'Amico, A ^e   Saturnino, C ^b   Orlando, P ^a,f   Zimmer, A ^c   Iuvone, T ^a,e   Di Marzo, Vincenzo ^a  

^a CNR   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

^c UNIVERSITY OF BONN   (Germany)

^d KAGAWA UNIVERSITY   (Japan)

^e UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^f INSTITUTE OF PROTEIN BIOCHEMISTRY   (Italy)

Author keywords

Chemokines; Contact allergens; Dermatology; Dermatology contact dermatitis; Pharmacology

Indexed keywords

1 FLUORO 2,4 DINITROBENZENE; ANANDAMIDE; MESSENGER RNA; MONOCYTE CHEMOTACTIC PROTEIN 2; PALMIDROL; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; POLYINOSINIC POLYCYTIDYLIC ACID; VANILLOID RECEPTOR 1; ANTIINFLAMMATORY AGENT; ENDOCANNABINOID; ETHANOLAMINE DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT; PALMITIC ACID DERIVATIVE; PROTECTIVE AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CELL STIMULATION; CONTACT DERMATITIS; CONTROLLED STUDY; DRUG DOSE COMPARISON; EAR; FEMALE; HUMAN; HUMAN TISSUE; IN VITRO STUDY; KERATINOCYTE; LIPID DEGRADATION; LIPOGENESIS; MOUSE; NONHUMAN; NUCLEOTIDE SEQUENCE; OTITIS; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN SECRETION; UPREGULATION; ANIMAL; DERMATITIS, ALLERGIC CONTACT; IMMUNOLOGY; INFLAMMATION; KNOCKOUT MOUSE; METABOLISM; PATHOLOGY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DERMATITIS, ALLERGIC CONTACT; DINITROFLUOROBENZENE; ENDOCANNABINOIDS; ETHANOLAMINES; FEMALE; INFLAMMATION; KERATINOCYTES; MICE; MICE, KNOCKOUT; PALMITIC ACIDS; PROTECTIVE AGENTS;

EID: 77951881966     PISSN: 01054538     EISSN: 13989995     Source Type: Journal    
DOI: 10.1111/j.1398-9995.2009.02254.x     Document Type: Article

References (58)

1. Grabbe S, Schwarz T. Immunoregulatory mechanisms involved in elicitation of allergic contact hypersensitivity. Immunol Today 1998 19 : 37 44. (Pubitemid 28078607)
2. Krasteva M, Kehren J, Ducluzeau MT, Sayag M, Cacciapuoti M, Akiba H et al. Contact dermatitis I pathophysiology of contact sensitivity. Eur J Dermatol 1999 9 : 65 77.
3. Di Marzo V, De Petrocellis L, Sepe N, Buono A. Biosynthesis of anandamide and related acylethanolamides in mouse J774 macrophages and N18 neuroblastoma cells. Biochem J 1996 316 : 977 984. (Pubitemid 26278452)
4. Bisogno T, Maurelli S, Melck D, De Petrocellis L, Di Marzo V. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. J Biol Chem 1997 272 : 3315 3323. (Pubitemid 27066825)
5. Berdyshev EV, Boichot E, Germain N, Allain N, Anger JP, Lagente V. Influence of fatty acid ethanolamides and delta9-tetrahydrocannabinol on cytokine and arachidonate release by mononuclear cells. Eur J Pharmacol 1997 330 : 231 240. (Pubitemid 27296727)
6. Calignano A, La Rana G, Giuffrida A, Piomelli D. Control of pain initiation by endogenous cannabinoids. Nature 1998 394 : 277 281. (Pubitemid 28335039)
7. Jaggar SI, Hasnie FS, Sellaturay S, Rice AS. The anti-hyperalgesic actions of the cannabinoid anandamide and the putative CB2 receptor agonist palmitoylethanolamide in visceral and somatic inflammatory pain. Pain 1998 76 : 189 199. (Pubitemid 28304956)
8. 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)
9. Costa B, Conti S, Giagnoni G, Colleoni M. Therapeutic effect of the endogenous fatty acid amide, palmitoylethanolamide, in rat acute inflammation: inhibition of nitric oxide and cyclo-oxygenase systems. Br J Pharmacol 2002 137 : 413 420. (Pubitemid 35221894)
10. Darmani NA, Izzo AA, Degenhardt B, Valenti M, Scaglione G, Capasso R et al. Involvement of the cannabimimetic compound, N-palmitoyl-ethanolamine, in inflammatory and neuropathic conditions: review of the available pre-clinical data, and first human studies. Neuropharmacology 2005 48 : 1154 1163. (Pubitemid 40725988)
11. Okamoto Y, Morishita J, Tsuboi K, Tonai T, Ueda N. Molecular characterization of a phospholipase D generating anandamide and its congeners. J Biol Chem 2004 279 : 5298 5305. (Pubitemid 38220550)
12. Cravatt BF, Giang DK, Mayfield SP, Boger DL, Lerner RA, Gilula NB. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 1996 384 : 83 87.
13. Bracey MH, Hanson MA, Masuda KR, Stevens RC, Cravatt BF. Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling. Science 2002 298 : 1793 1796.
14. Ueda N, Yamanaka K, Terasawa Y, Yamamoto S. An acid amidase hydrolyzing anandamide as an endogenous ligand for cannabinoid receptors. FEBS Lett 1999 454 : 267 270. (Pubitemid 29304613)
15. Ueda N, Yamanaka K, Yamamoto S. Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance. J Biol Chem 2001 276 : 35552 35557. (Pubitemid 37384354)
16. Aloe L, Leon A, Levi-Montalcini R. A proposed autacoid mechanism controlling mastocyte behaviour. Agents Actions 1993 39 : C145 C147. (Pubitemid 23276753)
17. Facci L, Dal Toso R, Romanello S, Buriani A, Skaper SD, Leon A. Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide. Proc Natl Acad Sci USA 1995 92 : 3376 3380.
18. Mazzari S, Canella R, Petrelli L, Marcolongo G, Leon A. N-(2-hydroxyethyl)hexadecanamide is orally active in reducing edema formation and inflammatory hyperalgesia by down-modulating mast cell activation. Eur J Pharmacol 1996 300 : 227 236. (Pubitemid 26144798)
19. Berdyshev EV, Schmid PC, Dong Z, Schmid HH. Stress-induced generation of N-acylethanolamines in mouse epidermal JB6 P+ cells. Biochem J 2000 346 : 369 374. (Pubitemid 30148122)
20. Conti S, Costa B, Colleoni M, Parolaro D, Giagnoni G. Antiinflammatory action of endocannabinoid palmitoylethanolamide and the synthetic cannabinoid nabilone in a model of acute inflammation in the rat. Br J Pharmacol 2002 135 : 181 187. (Pubitemid 34102111)
21. Farquhar-Smith WP, Rice AS. A novel neuroimmune mechanism in cannabinoid-mediated attenuation of nerve growth factor-induced hyperalgesia. Anesthesiology 2003 99 : 1391 1401.
22. Ben-Shabat S, Fride E, Sheskin T, Tamiri T, Rhee MH, Vogel Z et al. An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. Eur J Pharmacol 1998 353 : 23 31. (Pubitemid 28352285)
23. Lambert DM, Di Marzo V. The palmitoylethanolamide and oleamide enigmas : are these two fatty acid amides cannabimimetic? Curr Med Chem 1999 6 : 757 773. (Pubitemid 29399503)
24. Di Marzo V, Melck D, Orlando P, Bisogno T, Zagoory O, Bifulco M et al. Palmitoylethanolamide inhibits the expression of fatty acid amide hydrolase and enhances the anti-proliferative effect of anandamide in human breast cancer cells. Biochem J 2001 358 : 249 255. (Pubitemid 32778120)
25. De Petrocellis L, Davis JB, Di Marzo V. Palmitoylethanolamide enhances anandamide stimulation of human vanilloid VR1 receptors. FEBS Lett 2001 506 : 253 256. (Pubitemid 32964824)
26. Smart D, Jonsson KO, Vandevoorde S, 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. Br J Pharmacol 2002 136 : 452 458. (Pubitemid 34620526)
27. Ho WS, Barrett DA, Randall MD. 'Entourage' effects of N-palmitoylethanolamide and N-oleoylethanolamide on vasorelaxation to anandamide occur through TRPV1 receptors. Br J Pharmacol 2008 155 : 837 846.
28. Costa B, Comelli F, Bettoni I, Colleoni M, Giagnoni G. The endogenous fatty acid amide, palmitoylethanolamide, has anti-allodynic and anti-hyperalgesic effects in a murine model of neuropathic pain: involvement of CB(1), TRPV1 and PPAR gamma receptors and neurotrophic factors. Pain 2008 139 : 541 550.
29. Szallasi A, Blumberg PM, Annicelli LL, Krause JE, Cortright DN. The cloned rat vanilloid receptor VR1 mediates both R-type binding and C-type calcium response in dorsal root ganglion neurons. Mol Pharmacol 1999 56 : 581 587. (Pubitemid 29406885)
30. Zygmunt PM, Petersson J, Andersson DA, Chuang H, Sørgård M, Di Marzo V et al. Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 1999 400 : 452 457. (Pubitemid 29361798)
31. Smart D, Gunthorpe MJ, Jerman JC, Nasir S, Gray J, Muir AI et al. The endogenous lipid anandamide is a full agonist at the human vanilloid receptor (hVR1). Br J Pharmacol 2000 129 : 227 230. (Pubitemid 30072640)
32. Lo Verme J, Fu J, Astarita G, La Rana G, Russo R, Calignano A et al. The nuclear receptor peroxisome proliferator-activated receptor-alpha mediates the anti-inflammatory actions of palmitoylethanolamide. Mol Pharmacol 2005 67 : 15 19. (Pubitemid 40069962)
33. Lo Verme J, Russo R, La Rana G, Fu J, Farthing J, Mattace-Raso G et al. Rapid broad-spectrum analgesia through activation of peroxisome proliferator-activated receptor-alpha. J Pharmacol Exp Ther 2006 319 : 1051 1061.
34. Lambert DM. Allergic contact dermatitis and the endocannabinoid system: from mechanisms to skin care. Chem MedChem 2007 2 : 1701 1702.
35. Oka S, Wakui J, Ikeda S, Yanagimoto S, Kishimoto S, Gokoh M et al. Involvement of the cannabinoid CB2 receptor and its endogenous ligand 2-arachidonoylglycerol in oxazolone-induced contact dermatitis in mice. J Immunol 2006 177 : 8796 8805. (Pubitemid 44893846)
36. Iwamura H, Suzuki H, Ueda Y, Kaya T, Inaba T. In vitro and in vivo pharmacological characterization of JTE-907, a novel selective ligand for cannabinoid CB2 receptor. J Pharmacol Exp Ther 2001 296 : 420 425. (Pubitemid 32112468)
37. Ueda Y, Miyagawa N, Matsui T, Kaya T, Iwamura H. Involvement of cannabinoid CB(2) receptor-mediated response and efficacy of cannabinoid CB(2) receptor inverse agonist, JTE-907, in cutaneous inflammation in mice. Eur J Pharmacol 2005 520 : 164 171. (Pubitemid 41375825)
38. Karsak M, Gaffal E, Date R, Wang-Eckhardt L, Rehnelt J, Petrosino S et al. Attenuation of allergic contact dermatitis through the endocannabinoid system. Science 2007 316 : 1494 1497. (Pubitemid 46906619)
39. Bánvölgyi A, Pálinkás L, Berki T, Clark N, Grant AD, Helyes Z et al. Evidence for a novel protective role of the vanilloid TRPV1 receptor in a cutaneous contact allergic dermatitis model. J Neuroimmunol 2005 169 : 86 96. (Pubitemid 41527094)
40. Tsuboi K, Zhao LY, Okamoto Y, Araki N, Ueno M, Sakamoto H et al. Predominant expression of lysosomal N-acylethanolamine-hydrolyzing acid amidase in macrophages revealed by immunochemical studies. Biochim Biophys Acta 2007 1771 : 623 632. (Pubitemid 46670796)
41. Bisogno T, Sepe N, Melck D, Maurelli S, De Petrocellis L, Di Marzo V. Biosynthesis, release and degradation of the novel endogenous cannabimimetic metabolite 2-arachidonoylglycerol in mouse neuroblastoma cells. Biochem J 1997 322 : 671 677. (Pubitemid 27116599)
42. Marsicano G, Wotjak CT, Azad SC, Bisogno T, Rammes G, Cascio MG et al. The endogenous cannabinoid system controls extinction of aversive memories. Nature 2002 418 : 530 534. (Pubitemid 34851398)
43. Di Marzo V, Goparaju SK, Wang L, Liu J, Batkai S, Jarai Z et al. Leptin-regulated endocannabinoids are involved in maintaining food intake. Nature 2001 410 : 822 825. (Pubitemid 32303781)
44. Stabile M, Angelino T, Caiazzo F, Olivieri P, De Marchi N, De Petrocellis L et al. Fertility in a i(Xq) Klinefelter patient: importance of XIST expression level determined by qRT-PCR in ruling out Klinefelter cryptic mosaicism as cause of oligozoospermia. Mol Hum Reprod 2008 14 : 635 640.
45. Pfaffl MW, Horgan GW, Dempfle L. Relative expression software tool (REST) for group-wise comparison and statistical analysis of relative expression results in real-time PCR. Nucleic Acids Res 2002 30 : e36.
46. Re G, Barbero R, Miolo A, Di Marzo V. Palmitoylethanolamide, endocannabinoids and related cannabimimetic compounds in protection against tissue inflammation and pain: potential use in companion animals. Vet J 2007 173 : 21 30. (Pubitemid 46132135)
47. Ständer S, Moormann C, Schumacher M, Buddenkotte J, Artuc M, Shpacovitch V et al. Expression of vanilloid receptor subtype 1 in cutaneous sensory nerve fibers, mast cells, and epithelial cells of appendage structures. Exp Dermatol 2004 13 : 129 139. (Pubitemid 38380276)
48. Michalik L, Desvergne B, Tan NS, Basu-Modak S, Escher P, Rieusset J et al. Impaired skin wound healing in peroxisome proliferator-activated receptor (PPAR)alpha and PPARbeta mutant mice. Biol Cell 2001 154 : 799 814. (Pubitemid 34292961)
49. Maccarrone M, Di Rienzo M, Battista N, Gasperi V, Guerrieri P, Rossi A et al. The endocannabinoid system in human keratinocytes. Evidence that anandamide inhibits epidermal differentiation through CB1 receptor-dependent inhibition of protein kinase C, activation protein-1, and transglutaminase. J Biol Chem 2003 278 : 33896 33903. (Pubitemid 37553223)
50. Li WH, Lee YM, Kim JY, Kang S, Kim S, Kim KH et al. Transient receptor potential vanilloid-1 mediates heat-shock-induced matrix metalloproteinase-1 expression in human epidermal keratinocytes. J Invest Dermatol 2007 127 : 2328 2335. (Pubitemid 47619755)
51. Lim SW, Hong SP, Jeong SW, Kim B, Bak H, Ryoo HC et al. Simultaneous effect of ursolic acid and oleanolic acid on epidermal permeability barrier function and epidermal keratinocyte differentiation via peroxisome proliferator-activated receptor-alpha. J Dermatol 2007 34 : 625 634. (Pubitemid 47313253)
52. Taub DD, Proost P, Murphy WJ, Anver M, Longo DL, van Damme J et al. Monocyte chemotactic protein-1 (MCP-1), -2, and -3 are chemotactic for human T lymphocytes. J Clin Invest 1995 95 : 370 1376.
53. de Paulis A, Annunziato F, Di Gioia L, Romagnani S, Carfora M, Beltrame C et al. Expression of the chemokine receptor CCR3 on human mast cells. Int Arch Allergy Immunol 2001 124 : 146 150. (Pubitemid 32304787)
54. Movahed P, Jönsson BA, Birnir B, Wingstrand JA, Jørgensen TD, Ermund A et al. Endogenous unsaturated C18 N-acylethanolamines are vanilloid receptor (TRPV1) agonists. J Biol Chem 2005 280 : 38496 38504. (Pubitemid 43853748)
55. Vandevoorde S, Lambert DM, Smart D, Jonsson KO, Fowler CJ. N-Morpholino- and N-diethyl-analogues of palmitoylethanolamide increase the sensitivity of transfected human vanilloid receptors to activation by anandamide without affecting fatty acid amidohydrolase activity. Bioorg Med Chem 2003 11 : 817 825. (Pubitemid 36287041)
56. García Mdel C, Adler-Graschinsky E, Celuch SM. Enhancement of the hypotensive effects of intrathecally injected endocannabinoids by the entourage compound palmitoylethanolamide. Eur J Pharmacol 2009 610 : 75 80.
57. Facer P, Casula MA, Smith GD, Benham CD, Chessell IP, Bountra C et al. Differential expression of the capsaicin receptor TRPV1 and related novel receptors TRPV3, TRPV4 and TRPM8 in normal human tissues and changes in traumatic and diabetic neuropathy. BMC Neurol 2007 7 : 11. (Pubitemid 46979373)
58. Gunthorpe MJ, Szallasi A. Peripheral TRPV1 receptors as targets for drug development: new molecules and mechanisms. Curr Pharm Des 2008 14 : 32 41. (Pubitemid 351266982)