Orphan endogenous lipids and orphan GPCRs: A good match

Prostaglandins and Other Lipid Mediators

Volumn 89, Issue 3-4, 2009, Pages 131-134

  Bradshaw, Heather B ^a,b   Lee, Sung Ha ^a   McHugh, Douglas ^a  

^a INDIANA UNIVERSITY   (United States)

^b Kinsey Institute for Research in Sex Gender and Reproduction   (United States)

Author keywords

Cannabinoids; Farnesyl pyrophosphate; Lipoamino acids; N Acyl amides; N Arachidonoyl glycine; N Palmitoyl glycine

Indexed keywords

AMIDE; FARNESYL DIPHOSPHATE; G PROTEIN COUPLED RECEPTOR; G PROTEIN COUPLED RECEPTOR 18; G PROTEIN COUPLED RECEPTOR 92; GLYCINE DERIVATIVE; LIPID; N ARACHIDONOYLGLYCINE; N PALMITOYL GLYCINE; UNCLASSIFIED DRUG;

BIOLOGICAL ACTIVITY; CHEMICAL STRUCTURE; GENE EXPRESSION; GENOME; REVIEW;

AMIDES; ANIMALS; FATTY ACIDS; GLYCINE; HUMANS; LIPID METABOLISM; LIPIDS; PALMITIC ACIDS; POLYISOPRENYL PHOSPHATES; PROTEIN ISOFORMS; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, LYSOPHOSPHATIDIC ACID; RESEARCH DESIGN; SESQUITERPENES; SIGNAL TRANSDUCTION;

EID: 69549085466     PISSN: 10988823     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.prostaglandins.2009.04.006     Document Type: Review

References (45)

1. Mechoulam R., and Gaoni Y. A total synthesis of dl-delta-1-tetrahydrocannabinol, the active constituent of hashish. J Am Chem Soc 87 (1965) 3273-3275
2. Mechoulam R., and Gaoni Y. Hashish. IV. The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids. Tetrahedron 21 5 (1965) 1223-1229
3. Mackie K. Cannabinoid receptors: where they are and what they do. J Neuroendocrinol 20 Suppl. 1 (2008) 10-14
4. Devane W.A., Hanus L., Breuer A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 5090 (1992) 1946-1949
5. Bradshaw H.B., and Walker J.M. The expanding field of cannabimimetic and related lipid mediators. Br J Pharmacol 144 4 (2005) 459-465
6. Ross R.A. Anandamide and vanilloid TRPV1 receptors. Br J Pharmacol 140 5 (2003) 790-801
7. Felder C.C., Joyce K.E., Briley E.M., et al. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol 48 3 (1995) 443-450
8. Sugiura T., Kondo S., Sukagawa A., et al. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem Biophys Res Commun 215 1 (1995) 89-97
9. Mechoulam R., Ben-Shabat S., Hanus L., et al. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol 50 1 (1995) 83-90
10. Pertwee R.G. The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin. Br J Pharmacol 153 2 (2008) 199-215
11. Di Marzo V. Targeting the endocannabinoid system: to enhance or reduce?. Nat Rev Drug Discov 7 5 (2008) 438-455
12. Guindon J., and Hohmann A.G. Cannabinoid CB2 receptors: a therapeutic target for the treatment of inflammatory and neuropathic pain. Br J Pharmacol 153 2 (2008) 319-334
13. Kunos G., and Osei-Hyiaman D. Endocannabinoids and liver disease. IV. Endocannabinoid involvement in obesity and hepatic steatosis. Am J Physiol Gastrointest Liver Physiol 294 5 (2008) G1101-1104
14. Pattij T., Wiskerke J., and Schoffelmeer A.N. Cannabinoid modulation of executive functions. Eur J Pharmacol 585 2-3 (2008) 458-463
15. Burstein S.M.A., Pearson W., Rooney T., Yagen B., Zipkin R., and Zurier A. Studies with analogs of anandamide and indomethacin. Symposium on Cannabinoids. International Cannabinoid Research Society. Burlington, VT (1997) 31
16. Huang S.M., Bisogno T., Petros T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J Biol Chem 276 46 (2001) 42639-42644
17. 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
18. 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
19. Milman G., Maor Y., Abu-Lafi S., et al. N-Arachidonoyl l-serine, an endocannabinoid-like brain constituent with vasodilatory properties. Proc Natl Acad Sci USA 103 7 (2006) 2428-2433
20. Saghatelian A., McKinney M.K., Bandell M., Patapoutian A., and Cravatt B.F. A FAAH-regulated class of N-acyl taurines that activates TRP ion channels. Biochemistry 45 30 (2006) 9007-9015
21. Rimmerman N., Bradshaw H.B., Hughes H.V., et al. N-Palmitoyl glycine, a novel endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons. Mol Pharmacol 74 1 (2008) 213-224
22. Bradshaw HB, Rimmerman N, Hu S S-J, Burstien S, Walker JM. Novel endogenous N-acyl glycines: identification and characterization. Vitam Horm 81; 2009.
23. Tan B., Bradshaw H.B., Rimmerman N., et al. Targeted lipidomics: discovery of new fatty acyl amides. AAPS J 8 3 (2006) E461-E465
24. Tan B, Yu YW, Monn FM, Hughes HV, O'Dell DK, Walker JM. Targeted lipidomics approach for endogenous N-acyl amino acids in rat brain tissue. J Chromatogr B; 2009.
25. Overton H.A., Babbs A.J., Doel S.M., et al. Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents. Cell Metab 3 3 (2006) 167-175
26. Borrelli F., and Izzo A.A. Role of acylethanolamides in the gastrointestinal tract with special reference to food intake and energy balance. Best Pract Res Clin Endocrinol Metab 23 1 (2009) 33-49
27. Gantz I., Muraoka A., Yang Y.K., et al. Cloning and chromosomal localization of a gene (GPR18) encoding a novel seven transmembrane receptor highly expressed in spleen and testis. Genomics 42 3 (1997) 462-466
28. Kohno M., Hasegawa H., Inoue A., et al. Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18. Biochem Biophys Res Commun 347 3 (2006) 827-832
29. Sheskin T., Hanus L., Slager J., Vogel Z., and Mechoulam R. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 40 5 (1997) 659-667
30. Succar R., Mitchell V.A., and Vaughan C.W. Actions of N-arachidonyl-glycine in a rat inflammatory pain model. Mol Pain 3 (2007) 24
31. Vuong L.A., Mitchell V.A., and Vaughan C.W. Actions of N-arachidonyl-glycine in a rat neuropathic pain model. Neuropharmacology 54 1 (2008) 189-193
32. Burstein S.H., Huang S.M., Petros T.J., Rossetti R.G., Walker J.M., and Zurier R.B. Regulation of anandamide tissue levels by N-arachidonylglycine. Biochem Pharmacol 64 7 (2002) 1147-1150
33. Rosenkilde M.M., Benned-Jensen T., Andersen H., et al. Molecular pharmacological phenotyping of EBI2. An orphan seven-transmembrane receptor with constitutive activity. J Biol Chem 281 19 (2006) 13199-13208
34. Burstein S.H., Rossetti R.G., Yagen B., and Zurier R.B. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat 61 1-2 (2000) 29-41
35. Gustafsson S.B., Lindgren T., Jonsson M., and Jacobsson S.O. Cannabinoid receptor-independent cytotoxic effects of cannabinoids in human colorectal carcinoma cells: synergism with 5-fluorouracil. Cancer Chemother Pharmacol 63 4 (2009) 691-701
36. Wiles A.L., Pearlman R.J., Rosvall M., Aubrey K.R., and Vandenberg R.J. N-Arachidonyl-glycine inhibits the glycine transporter, GLYT2a. J Neurochem 99 3 (2006) 781-786
37. Ikeda Y., Iguchi H., Nakata M., et al. Identification of N-arachidonylglycine, U18666A, and 4-androstene-3,17-dione as novel insulin Secretagogues. Biochem Biophys Res Commun 333 3 (2005) 778-786
38. Rezgaoui M., Susens U., Ignatov A., et al. The neuropeptide head activator is a high-affinity ligand for the orphan G-protein-coupled receptor GPR37. J Cell Sci 119 Pt 3 (2006) 542-549
39. Boels K., Glassmeier G., Herrmann D., et al. The neuropeptide head activator induces activation and translocation of the growth-factor-regulated Ca(2+)-permeable channel GRC. J Cell Sci 114 Pt 20 (2001) 3599-3606
40. Lee C.W., Rivera R., Dubin A.E., and Chun J. LPA(4)/GPR23 is a lysophosphatidic acid (LPA) receptor utilizing G(s)-, G(q)/G(i)-mediated calcium signaling and G(12/13)-mediated Rho activation. J Biol Chem 282 7 (2007) 4310-4317
41. Oh D.Y., Yoon J.M., Moon M.J., et al. Identification of farnesyl pyrophosphate and N-arachidonylglycine as endogenous ligands for GPR92. J Biol Chem 283 30 (2008) 21054-21064
42. Liliom K., Tsukahara T., Tsukahara R., Zelman-Femiak M., Swiezewska E., and Tigyi G. Farnesyl phosphates are endogenous ligands of lysophosphatidic acid receptors: inhibition of LPA GPCR and activation of PPARs. Biochim Biophys Acta 1761 12 (2006) 1506-1514
43. Westfall D., Aboushadi N., Shackelford J.E., and Krisans S.K. Metabolism of farnesol: phosphorylation of farnesol by rat liver microsomal and peroxisomal fractions. Biochem Biophys Res Commun 230 3 (1997) 562-568
44. Sheardown M., Messager S., Mathews E., Dickenson A.H., Aparicio S., and Brice N.L. Knockout of GPR92 reveals key role in neuropathic pain. Soc Neurosci Abstr 64.16 (2004)
45. Lemak M.S., Bravarenko N.I., Bobrov M.Y., et al. Cannabinoid regulation in identified synapse of terrestrial snail. Eur J Neurosci 26 11 (2007) 3207-3214