Microsomal omega-hydroxylated metabolites of N-arachidonoyl dopamine are active at recombinant human TRPV1 receptors

Prostaglandins and Other Lipid Mediators

Volumn 88, Issue 1-2, 2009, Pages 10-17

  Rimmerman, N ^a   Bradshaw, H B ^a   Basnet, A ^a   Tan, B ^a   Widlanski, Theodore S ^a   Walker, J M ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Cannabinoid; Cytochrome P450; Hydroxylated metabolites; Lipid signaling; Liver microsomes; Mass spectrometry; N Arachidonoyl dopamine; TRPV1; Vanilloid

Indexed keywords

ADRENOCHROME; CYTOCHROME P450; LIPID; N ARACHIDONOYLDOPAMINE; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1;

ANIMAL TISSUE; ARTICLE; CALCIUM TRANSPORT; CONTROLLED STUDY; ENZYME ACTIVATION; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPID METABOLISM; LIVER MICROSOME; MASS SPECTROMETRY; NONHUMAN; RAT; SIGNAL TRANSDUCTION;

ANIMALS; ARACHIDONIC ACIDS; CYTOCHROME P-450 ENZYME SYSTEM; DOPAMINE; HUMANS; HYDROXYEICOSATETRAENOIC ACIDS; KINETICS; MASS SPECTROMETRY; MICROSOMES, LIVER; RATS; RECOMBINANT PROTEINS; TRPV CATION CHANNELS;

EID: 57649217870     PISSN: 10988823     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.prostaglandins.2008.08.004     Document Type: Article

References (46)

1. Bezuglov V.V., Bobrov M., and Archakov A.V. Bioactive amides of fatty acids. Biochemistry 63 1 (1998) 22-30
2. Bezuglov V., Bobrov M., Gretskaya N., et al. Synthesis and biological evaluation of novel amides of polyunsaturated fatty acids with dopamine. Bioorg Med Chem Lett 11 4 (2001) 447-449
3. Bisogno T., Melck D., De Petrocellis L., et al. Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase. Biochem Biophys Res Commun 248 3 (1998) 515-522
4. Bisogno T., Melck D., Bobrov M., et al. N-Acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem J 351 Pt 3 (2000) 817-824
5. Huang S.M., Bisogno T., Trevisani M., et al. An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors. Proc Natl Acad Sci USA 99 12 (2002) 8400-8405
6. Chu C.J., Huang S.M., De Petrocellis L., et al. N-Oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia. J Biol Chem 278 16 (2003) 13633-13639
7. De Petrocellis L., Chu C.J., Moriello A.S., Kellner J.C., Walker J.M., and Di Marzo V. Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels. Br J Pharmacol 143 2 (2004) 251-256
8. Bradshaw H.B., Rimmerman N., Krey J.F., and Walker J.M. Sex and hormonal cycle differences in rat brain levels of pain-related cannabimimetic lipid mediators. Am J Physiol 291 2 (2006) R349-R358
9. Binzen U., Greffrath W., Hennessy S., Bausen M., Saaler-Reinhardt S., and Treede R.D. Co-expression of the voltage-gated potassium channel Kv1.4 with transient receptor potential channels (TRPV1 and TRPV2) and the cannabinoid receptor CB1 in rat dorsal root ganglion neurons. Neuroscience 142 2 (2006) 527-539
10. Sagar D.R., Smith P.A., Millns P.J., Smart D., Kendall D.A., and Chapman V. TRPV1 and CB(1) receptor-mediated effects of the endovanilloid/endocannabinoid N-arachidonoyl-dopamine on primary afferent fibre and spinal cord neuronal responses in the rat. Eur J Neurosci 20 1 (2004) 175-184
11. Bradshaw H.B., and Walker J.M. The expanding field of cannabimimetic and related lipid mediators. Br J Pharmacol 144 4 (2005) 459-465
12. Huang S.M., and Walker J.M. Enhancement of spontaneous and heat-evoked activity in spinal nociceptive neurons by the endovanilloid/endocannabinoid N-arachidonoyldopamine (NADA). J Neurophysiol 95 2 (2006) 1207-1212
13. Butelman E.R., Ball J.W., Harris T.J., and Kreek M.J. Topical capsaicin-induced allodynia in unanesthetized primates: pharmacological modulation. J Pharmacol Exp Ther 306 3 (2003) 1106-1114
14. Sharkey K.A., Cristino L., Oland L.D., et al. Arvanil, anandamide and N-arachidonoyl-dopamine (NADA) inhibit emesis through cannabinoid CB1 and vanilloid TRPV1 receptors in the ferret. Eur J Neurosci 25 9 (2007) 2773-2782
15. Harrison S., De Petrocellis L., Trevisani M., et al. Capsaicin-like effects of N-arachidonoyl-dopamine in the isolated guinea pig bronchi and urinary bladder. Eur J Pharmacol 475 1-3 (2003) 107-114
16. 2+ levels and transmitter release in the hippocampus. Br J Pharmacol 151 4 (2007) 551-563
17. McHugh D., Tanner C., Mechoulam R., Pertwee R.G., and Ross R.A. Inhibition of human neutrophil chemotaxis by endogenous cannabinoids and phytocannabinoids: evidence for a site distinct from CB1 and CB2. Mol Pharmacol 73 2 (2008) 441-450
18. Sancho R., Macho A., de La Vega L., et al. Immunosuppressive activity of endovanilloids: N-arachidonoyl-dopamine inhibits activation of the NF-kappa B, NFAT, and activator protein 1 signaling pathways. J Immunol 172 4 (2004) 2341-2351
19. Goswami C., Schmidt H., and Hucho F. TRPV1 at nerve endings regulates growth cone morphology and movement through cytoskeleton reorganization. FEBS J 274 3 (2007) 760-772
20. Kingsley P.J., and Marnett L.J. LC-MS-MS analysis of neutral eicosanoids. Methods Enzymol 433 (2007) 91-112
21. Yu M., Ives D., and Ramesha C.S. Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 272 34 (1997) 21181-21186
22. Kozak K.R., Crews B.C., Morrow J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J Biol Chem 277 47 (2002) 44877-44885
23. Prusakiewicz J.J., Kingsley P.J., Kozak K.R., and Marnett L.J. Selective oxygenation of N-arachidonylglycine by cyclooxygenase-2. Biochem Biophys Res Commun 296 3 (2002) 612-617
24. Watanabe K., Yamaori S., Funahashi T., Kimura T., and Yamamoto I. Cytochrome P450 enzymes involved in the metabolism of tetrahydrocannabinols and cannabinol by human hepatic microsomes. Life Sci 80 15 (2007) 1415-1419
25. Hu S.S., Bradshaw H.B., Chen J.S., Tan B., and Walker J.M. Prostaglandin E(2) glycerol ester, an endogenous COX-2 metabolite of 2-arachidonoylglycerol, induces hyperalgesia and modulates NF kappaB activity. Br J Pharmacol 153 7 (2008) 1538-1549
26. Gopal V.R., Jagadeesh S.G., Reddy Y.K., Bandyopadhyay A., Capdevila J.H., and Falck J.R. A practical, stereospecific route to 18-, 19-, and 20-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acids (18-, 19-, and 20-HETEs). Tetrahedron Lett 45 (2004) 2563
27. Ryan W.J., Banner W.K., Wiley J.L., Martin B.R., and Razdan R.K. Potent anandamide analogs: the effect of changing the length and branching of the end pentyl chain. J Med Chem 40 22 (1997) 3617-3625
28. Manna S., Falck J.R., Chacos N., and Capdevila J. Synthesis of arachidonic acid metabolites produced by purified kidney cortex microsomal cytochrome P-450. Tetrahedron Lett 24 (1983) 33
29. Corey E.J., Iguchi S., Albright J.O., and De B. Studies on the conformational mobility of arachidonic acid. Facile macrolactonization of 20-hydroxyarachidonic acid. Tetrahedron Lett 24 (1983) 37
30. Spiteller D., and Boland W. N-(15,16-Dihydroxylinoleoyl)-glutamine and N-(15, 16-epoxylinoleoyl)-glutamine isolated from oral secretions of lepidopteran larvae. Tetrahedron 59 (2003) 135
31. Corey E.J., and Venkateswarlu A. Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. J Am Chem Soc 94 (1972) 6190
32. Chuang S.S., Helvig C., Taimi M., et al. CYP2U1, a novel human thymus- and brain-specific cytochrome P450, catalyzes omega- and (omega-1)-hydroxylation of fatty acids. J Biol Chem 279 8 (2004) 6305-6314
33. Bolcato C.A., Frye R.F., Zemaitis M.A., and Poloyac S.M. Determination of 20-hydroxyeicosatetraenoic acid in microsomal incubates using high-performance liquid chromatography-mass spectrometry (HPLC-MS). J Chromatogr 794 2 (2003) 363-372
34. Capdevila J.H., Falck J.R., and Harris R.C. Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase. J Lipid Res 41 2 (2000) 163-181
35. Powell P.K., Wolf I., Jin R., and Lasker J.M. Metabolism of arachidonic acid to 20-hydroxy-5,8,11, 14-eicosatetraenoic acid by P450 enzymes in human liver: involvement of CYP4F2 and CYP4A11. J Pharmacol Exp Ther 285 3 (1998) 1327-1336
36. 2+-induced relaxation of rat mesenteric arteries. Am J Physiol Heart Circ Physiol (2008)
37. Bornheim L.M., Kim K.Y., Chen B., and Correia M.A. Microsomal cytochrome P450-mediated liver and brain anandamide metabolism. Biochem Pharmacol 50 5 (1995) 677-686
38. Snider N.T., Kornilov A.M., Kent U.M., and Hollenberg P.F. Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther 321 2 (2007) 590-597
39. Szallasi A., Blumberg P.M., and Resiniferatoxin. A phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper. Neuroscience 30 2 (1989) 515-520
40. Walpole C.S., Bevan S., Bovermann G., et al. The discovery of capsazepine, the first competitive antagonist of the sensory neuron excitants capsaicin and resiniferatoxin. J Med Chem 37 13 (1994) 1942-1954
41. De Petrocellis L., and Di Marzo V. Lipids as regulators of the activity of transient receptor potential type V1 (TRPV1) channels. Life Sci 77 14 (2005) 1651-1666
42. O'Dell D.K., Rimmerman N., Pickens S.R., and Walker J.M. Fatty acyl amides of endogenous tetrahydroisoquinolines are active at the recombinant human TRPV1 receptor. Bioorg Med Chem 15 18 (2007) 6164-6169
43. Caterina M.J., Rosen T.A., Tominaga M., Brake A.J., and Julius D. A capsaicin-receptor homologue with a high threshold for noxious heat. Nature 398 6726 (1999) 436-441
44. Hwang S.W., Cho H., Kwak J., et al. Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances. Proc Natl Acad Sci USA 97 11 (2000) 6155-6160
45. Bianchi B.R., Lee C.H., Jarvis M.F., et al. Modulation of human TRPV1 receptor activity by extracellular protons and host cell expression system. Eur J Pharmacol 537 1-3 (2006) 20-30
46. Qu W., Bradbury J.A., Tsao C.C., et al. Cytochrome P450 CYP2J9, a new mouse arachidonic acid omega-1 hydroxylase predominantly expressed in brain. J Biol Chem 276 27 (2001) 25467-25479