A re-evaluation of 9-HODE activity at TRPV1 channels in comparison with anandamide: Enantioselectivity and effects at other TRP channels and in sensory neurons

British Journal of Pharmacology

Volumn 167, Issue 8, 2012, Pages 1643-1651

  De Petrocellis, Luciano ^a   Schiano Moriello, Aniello ^b   Imperatore, Roberta ^b   Cristino, Luigia ^a   Starowicz, Katarzyna ^c   Di Marzo, Vincenzo ^a  

^a CNR   (Italy)

^b CNR Consiglio Nazionale delle Ricerche   (Italy)

^c INSTITUTE OF PHARMACOLOGY   (Poland)

Author keywords

endocannabinoids; linoleic acid; lipoxygenases; TRP channels; vanilloid

Indexed keywords

13 HYDROXY OCTADECADIENOIC ACID; 15 HYDROXYANANDAMIDE; 9 HYDROXY OCTADECADIENOIC ACID; ANANDAMIDE; CALCIUM ION; CANNABINOID DERIVATIVE; CAPSAICIN; ESSENTIAL FATTY ACID; TRANSIENT RECEPTOR POTENTIAL CHANNEL; TRANSIENT RECEPTOR POTENTIAL CHANNEL A1; TRANSIENT RECEPTOR POTENTIAL CHANNEL M8; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1; VANILLOID RECEPTOR 2;

ANIMAL CELL; ARTICLE; CALCIUM CELL LEVEL; CELL ASSAY; CELL STRAIN HEK293; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SELECTIVITY; ENANTIOSELECTIVITY; HUMAN; HUMAN CELL; IMAGING; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN INDUCTION; RAT; SENSORY NERVE CELL; SPINAL GANGLION; STABLE EXPRESSION;

ANIMALS; ARACHIDONIC ACIDS; CALCIUM; CELLS, CULTURED; ENDOCANNABINOIDS; GANGLIA, SPINAL; HEK293 CELLS; HUMANS; LINOLEIC ACIDS, CONJUGATED; POLYUNSATURATED ALKAMIDES; RATS; RECOMBINANT PROTEINS; SENSORY RECEPTOR CELLS; STEREOISOMERISM; TRPV CATION CHANNELS;

EID: 84870505112     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2012.02122.x     Document Type: Article

References (54)

1. Akopian AN, (2011). Regulation of nociceptive transmission at the periphery via TRPA1-TRPV1 interactions. Curr Pharm Biotechnol 12: 89-94.
2. Akopian AN, Ruparel NB, Jeske NA, Patwardhan A, Hargreaves KM, (2009). Role of ionotropic cannabinoid receptors in peripheral antinociception and antihyperalgesia. Trends Pharmacol Sci 30: 79-84.
3. Alexander SP, Mathie A, Peters JA, (2011). Guide to Receptors and Channels (GRAC), 5th edition. Br J Pharmacol 164: S1-324.
4. 9-tetrahydrocannabiorcol. Nat Commun 2: 551. doi: 10.1038/ncomms1559.
5. Batetta B, Griinari M, Carta G, Murru E, Ligresti A, Cordeddu L, et al,. (2009). Endocannabinoids may mediate the ability of (n-3) fatty acids to reduce ectopic fat and inflammatory mediators in obese Zucker rats. J Nutr 139: 1495-1501.
6. Bautista DM, Jordt SE, Nikai T, Tsuruda PR, Read AJ, Poblete J, et al,. (2006). TRPA1 mediates the inflammatory actions of environmental irritants and proalgesic agents. Cell 124: 1269-1282.
7. Bergholte JM, Soberman RJ, Hayes R, Murphy RC, Okita RT, (1987). Oxidation of 15-hydroxyeicosatetraenoic acid and other hydroxy fatty acids by lung prostaglandin dehydrogenase. Arch Biochem Biophys 257: 444-450.
8. Brinckmann R, Schnurr K, Heydeck D, Rosenbach T, Kolde G, Kühn H, (1998). Membrane translocation of 15-lipoxygenase in hematopoietic cells is calcium-dependent and activates the oxygenase activity of the enzyme. Blood 91: 64-74.
9. Caterina MJ, Schumacher MA, Tominaga M, Rosen TA, Levine JD, Julius D, (1997). The capsaicin receptor: a heat-activated ion channel in the pain pathway. Nature 389: 816-824.
10. Caterina MJ, Leffler A, Malmberg AB, Martin WJ, Trafton J, Petersen-Zeitz KR, et al,. (2000). Impaired nociception and pain sensation in mice lacking the capsaicin receptor. Science 288: 306-313.
11. Chu CJ, Huang SM, De Petrocellis L, Bisogno T, Ewing SA, Miller JD, et al,. (2003). N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia. J Biol Chem 278: 13633-13639.
12. Cristino L, De Petrocellis L, Pryce G, Baker D, Guglielmotti V, Di Marzo V, (2006). Immunohistochemical localization of cannabinoid type 1 and vanilloid transient receptor potential vanilloid type 1 receptors in the mouse brain. Neuroscience 139: 1405-1415.
13. Cui M, Honore P, Zhong C, Gauvin D, Mikusa J, Hernandez G, et al,. (2006). TRPV1 receptors in the CNS play a key role in broad-spectrum analgesia of TRPV1 antagonists. J Neurosci 26: 9385-9393.
14. Dai Y, Wang S, Tominaga M, Yamamoto S, Fukuoka T, Higashi T, et al,. (2007). Sensitization of TRPA1 by PAR2 contributes to the sensation of inflammatory pain. J Clin Invest 117: 1979-1987.
15. 2+ signalling. Cell Calcium 45: 611-624.
16. De Petrocellis L, Di Marzo V, (2010). Non-CB1, non-CB2 receptors for endocannabinoids, plant cannabinoids, and synthetic cannabimimetics: focus on G-protein-coupled receptors and transient receptor potential channels. J Neuroimmune Pharmacol 5: 103-121.
17. De Petrocellis L, Bisogno T, Maccarrone M, Davis JB, Finazzi-Agro A, Di Marzo V, (2001). The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism. J Biol Chem 276: 12856-12863.
18. De Petrocellis L, Chu CJ, Moriello AS, Kellner JC, Walker JM, Di Marzo V, (2004). Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels. Br J Pharmacol 143: 251-256.
19. De Petrocellis L, Starowicz K, Moriello AS, Vivese M, Orlando P, Di Marzo V, (2007). Regulation of transient receptor potential channels of melastatin type 8 (TRPM8): effect of cAMP, cannabinoid CB(1) receptors and endovanilloids. Exp Cell Res 313: 1911-1920.
20. De Petrocellis L, Deva R, Mainieri F, Schaefer M, Bisogno T, Ciccoli R, et al,. (2009). Chemical synthesis, pharmacological characterization, and possible formation in unicellular fungi of 3-hydroxy-anandamide. J Lipid Res 50: 658-666.
21. De Petrocellis L, Ligresti A, Moriello AS, Allarà M, Bisogno T, Petrosino S, et al,. (2011). Effects of cannabinoids and cannabinoid-enriched Cannabis extracts on TRP channels and endocannabinoid metabolic enzymes. Br J Pharmacol 163: 1479-1494.
22. Di Marzo V, (2008). Endocannabinoids: synthesis and degradation. Rev Physiol Biochem Pharmacol 160: 1-24.
23. Di Marzo V, De Petrocellis L, (2010). Endocannabinoids as regulators of transient receptor potential (TRP) channels: a further opportunity to develop new endocannabinoid-based therapeutic drugs. Curr Med Chem 17: 1430-1449.
24. Di Marzo V, Bisogno T, Melck D, Ross R, Brockie H, Stevenson L, et al,. (1998). Interactions between synthetic vanilloids and the endogenous cannabinoid system. FEBS Lett 436: 449-454.
25. Gavva NR, (2008). Body-temperature maintenance as the predominant function of the vanilloid receptor TRPV1. Trends Pharmacol Sci 29: 550-557.
26. Gavva NR, Bannon AW, Surapaneni S, Hovland DN, Jr, Lehto SG, Gore A, et al,. (2007). The vanilloid receptor TRPV1 is tonically activated in vivo and involved in body temperature regulation. J Neurosci 27: 3366-3374.
27. 2+-indicator dyes. Cell Calcium 27: 97-106.
28. Hara A, Taketomi T, Iwata M, Ando M, Nagata Y, (1988). Differences in neuronal lipid composition between superior cervical ganglia and nodose ganglia of the rat. Biochim Biophys Acta 960: 427-434.
29. Huang SM, Bisogno T, Trevisani M, Al-Hayani A, De Petrocellis L, Fezza F, et al,. (2002). An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors. Proc Natl Acad Sci U S A 99: 8400-8405.
30. Hwang SW, Cho H, Kwak J, Lee SY, Kang CJ, Jung J, et al,. (2000). Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances. Proc Natl Acad Sci U S A 97: 6155-6160.
31. Jung J, Hwang SW, Kwak J, Lee SY, Kang CJ, Kim WB, et al,. (1999). Capsaicin binds to the intracellular domain of the capsaicin-activated ion channel. J Neurosci 1999: 529-538.
32. Kanai Y, Hara T, Imai A, Sakakibara A, (2007). Differential involvement of TRPV1 receptors at the central and peripheral nerves in CFA-induced mechanical and thermal hyperalgesia. J Pharm Pharmacol 59: 733-738.
33. Kosugi M, Nakatsuka T, Fujita T, Kuroda Y, Kumamoto E, (2007). Activation of TRPA1 channel facilitates excitatory synaptic transmission in substantia gelatinosa neurons of the adult rat spinal cord. J Neurosci 27: 4443-4451.
34. Latorre R, Brauchi S, Orta G, Zaelzer C, Vargas G, (2007). ThermoTRP channels as modular proteins with allosteric gating. Cell Calcium 42: 427-438.
35. McMahon SB, Wood JN, (2006). Increasingly irritable and close to tears: TRPA1 in inflammatory pain. Cell 124: 1123-1125.
36. Mezey E, Tõth ZE, Cortright DN, Arzubi MK, Krause JE, Elde R, et al,. (2000). Distribution of mRNA for vanilloid receptor subtype 1 (VR1), and VR1-like immunoreactivity, in the central nervous system of the rat and human. Proc Natl Acad Sci USA 97: 3655-3660.
37. Mohapatra DP, Nau C, (2005). Regulation of Ca2+-dependent desensitization in the vanilloid receptor TRPV1 by calcineurin and cAMP-dependent protein kinase. J Biol Chem 280: 13424-13432.
38. Moran MM, McAlexander MA, Bírõ T, Szallasi A, (2011). Transient receptor potential channels as therapeutic targets. Nat Rev Drug Discov 10: 601-620.
39. Movahed P, Jönsson BA, Birnir B, Wingstrand JA, JÃrgensen TD, Ermund A, et al,. (2005). Endogenous unsaturated C18 N-acylethanolamines are vanilloid receptor (TRPV1) agonists. J Biol Chem 280: 38496-38504.
40. Nieto-Posadas A, Picazo-Juárez G, Llorente I, Jara-Oseguera A, Morales-Lázaro S, Escalante-Alcalde D, et al,. (2011). Lysophosphatidic acid directly activates TRPV1 through a C-terminal binding site. Nat Chem Biol 8: 78-85.
41. Park C-K, Xu Z-Z, Liu T, Lü N, Serhan CN, Ji R-R, (2011). Resolvin D2 is a potent endogenous inhibitor for transient receptor potential subtype V1/A1, inflammatory pain, and spinal cord synaptic plasticity in mice: distinct roles of resolvin D1, D2, and E1. J Neurosci 31: 18433-18438.
42. Patapoutian A, Tate S, Woolf CJ, (2009). Transient receptor potential channels: targeting pain at the source. Nat Rev Drug Discov 8: 55-68.
43. Patwardhan AM, Scotland PE, Akopian AN, Hargreaves KM, (2009). Activation of TRPV1 in the spinal cord by oxidized linoleic acid metabolites contributes to inflammatory hyperalgesia. Proc Natl Acad Sci U S A 106: 18820-18824.
44. Patwardhan AM, Akopian AN, Ruparel NB, Diogenes A, Weintraub ST, Uhlson C, et al,. (2010). Heat generates oxidized linoleic acid metabolites that activate TRPV1 and produce pain in rodents. J Clin Invest 120: 1617-1626.
45. Pitcher MH, Price TJ, Entrena JM, Cervero F, (2007). Spinal NKCC1 blockade inhibits TRPV1-dependent referred allodynia. Mol Pain 3: 17. doi: 10.1186/1744-8069-3-17.
46. Qin N, Neeper MP, Liu Y, Hutchinson TL, Lubin ML, Flores CM, (2008). TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons. J Neurosci 28: 6231-6238.
47. Starowicz K, Makuch W, Osikowicz M, Piscitelli F, Petrosino S, Di Marzo V, et al,. (2012). Spinal anandamide produces analgesia in neuropathic rats: possible CB(1)- and TRPV1-mediated mechanisms. Neuropharmacology 62: 1746-1755.
48. van der Stelt M, van Kuik JA, Bari M, van Zadelhoff G, Leeflang BR, Veldink GA, et al,. (2002). Oxygenated metabolites of anandamide and 2-arachidonoylglycerol: conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase. J Med Chem 45: 3709-3720.
49. Tang L, Chen Y, Chen Z, Blumberg PM, Kozikowski AP, Wang ZJ, (2007). Antinociceptive pharmacology of N-(4-chlorobenzyl)-N'-(4-hydroxy-3-iodo-5- methoxybenzyl) thiourea, a high-affinity competitive antagonist of the transient receptor potential vanilloid 1 receptor. J Pharmacol Exp Ther 321: 791-798.
50. Touska F, Marsakova L, Teisinger J, Vlachova V, (2011). A 'cute' desensitization of TRPV1. Curr Pharm Biotechnol 12: 122-129.
51. Wahl P, Foged C, Tullin S, Thomsen C, (2001). Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist. Mol Pharmacol 59: 9-15.
52. Wei C, Zhu P, Shah SJ, Blair IA, (2009). 15-oxo-Eicosatetraenoic acid, a metabolite of macrophage 15-hydroxyprostaglandin dehydrogenase that inhibits endothelial cell proliferation. Mol Pharmacol 76: 516-525.
53. Wen H, Ostman J, Bubb KJ, Panayiotou C, Priestley JV, Baker MD, et al,. (2012). 20-hydroxyeicosatetraenoic acid (20-HETE) is a novel activator of TRPV1. J Biol Chem 287: 13868-13876.
54. Zygmunt PM, Petersson J, Andersson DA, Chuang H, SÃrgÃrd M, Di Marzo V, et al,. (1999). Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 400: 452-457.