Synthesis and characterization of a fluorescent substrate for the N- arachidonoylethanolamine (anandamide) transmembrane carrier

Journal of Pharmacology and Experimental Therapeutics

Volumn 293, Issue 1, 2000, Pages 289-295

  Muthian, Shanmugam ^a   Nithipatikom, Kasem ^a   Campbell, William B ^a   Hillard, Cecilia J ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANANDAMIDE; CANNABINOID RECEPTOR; DRUG ANALOG; MEMBRANE PROTEIN; SKM 4451; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CELL LEVEL; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; DRUG UPTAKE; GLIOMA CELL; NONHUMAN; PRIORITY JOURNAL; RAT;

AMIDOHYDROLASES; ANIMALS; ARACHIDONIC ACIDS; BRAIN NEOPLASMS; CANNABINOIDS; CARRIER PROTEINS; CELL MEMBRANE; CEREBELLUM; CYCLOHEXANOLS; ESTERASES; FLUORESCENT DYES; GLIOMA; HUMANS; LACTONES; MICROSCOPY, FLUORESCENCE; POLYUNSATURATED ALKAMIDES; RATS; RATS, SPRAGUE-DAWLEY; TUMOR CELLS, CULTURED;

EID: 0034087481     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Beltramo M, Stella N, Calignano A, Lin SY, Makriyannis A and Piomelli D (1997) Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science (Wash DC) 277:1094-1097.
2. Calignano A, La Rana G, Giuffrida A and Piomelli D (1998) Control of pain initiation by endogenous cannabinoids. Nature (Lond) 394:277-281.
3. Cravatt BF, Giang DK, Mayfield SP, Boger DL, Lerner RA and Gilula NB (1996) Molecular characterization of an enzyme that degrades neuromodulatory fatty acid amides. Nature (Lond) 384:83-87.
4. Desarnaud F, Cadas H and Piomelli D (1995) Anandamide amidohydrolase activity in rat brain microsomes. J Biol Chem 270:6030-6035.
5. Deutsch DG and Chin SA (1993) Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem Pharmacol 47:711-715.
6. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A and Mechoulam R (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science (Wash DC) 258:1946-1949.
7. DiMarzo V, Fontana A, Cadas H, Schinelli S, Cimino G, Schwartz JC and Piomelli D (1994) Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature (Lond) 372:686-691.
8. Edgemond WS, Greenberg MJ, McGinley PJ, Muthian S, Campbell WB and Hillard CJ (1998) Synthesis and characterization of diazomethylarachidonylketone: An irreversible inhibitor of N-arachidonylethanolamine amidohydrolase. J Pharmacol Exp Ther 286:184-190.
9. Felder CC, Briley EM, Axelrod J, Simpson JT, Mackie K and Devane WA (1993) Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90:7656-7660.
10. Fricker G, Gutmann H, Droulle A, Drewe J and Miller DS (1999) Epithelial transport of anthelmintic ivermectin in a novel model of isolated proximal kidney tubules. Pharm Res 16:1570-1575.
11. Fride E and Mechoulam R (1993) Pharmacological activity of the cannabinoid receptor agonist, anandamide, a brain constituent. Eur J Pharmacol 231:313-314.
12. Gualix J, Pintor J and Miras-Portugal MT (1999) Characterization of nucleotide transport into rat brain synaptic vesicles. J Neurochem 73:1098-1104.
13. Hamilton JA (1998) Fatty acid transport: Difficult or easy? J Lipid Res 39:467-481.
14. Hillard CJ, Edgemond WS and Campbell WB (1995a) Characterization of ligand binding to the cannabinoid receptor of rat brain membranes using a novel method: Application to anandamide. J Neurochem 64:677-683.
15. Hillard CJ, Edgemond WS, Jarrahian A and Campbell WB (1997) Accumulation of N-arachidonylethanolamine (anandamide) into cerebellar granule cells occurs via facilitated diffusion. J Neurochem 69:631-638.
16. Hillard CJ, Wilkison DM, Edgemond WS and Campbell WB (1995b) Characterization of the kinetics and distribution of N-arachidonylethanolamine (anandamide) hydrolysis by rat brain. Biochim Biophys Acta 1257:249-256.
17. Jones KH and Senft JA (1985) An improved method to determine cell viability by simultaneous staining with fluorescein diacetate-propidium iodide. J Histochem Cytochem 33:77-79.
18. Jung M, Calassi R, Rinaldi-Carmona M, Chardenot P, Le Fur G, Soubrie P and Oury-Donat F (1997) Characterization of CB1 receptors on rat neuronal cell cultures: Binding and functional studies using the selective receptor antagonist SR 141716A. J Neurochem 68:402-409.
19. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW and Schuster VL (1995) Identification and characterization of a prostaglandin transporter. Science (Wash DC) 268:866-869.
20. Maccarone M, Van der Stelt M, Rossi A, Veldink GA, Vliegenthart JF and Agro AF (1998) Anandamide hydrolysis by human cells in culture and brain. J Biol Chem 273:32332-32339.
21. Mackie K, Devane WA and Hille B (1993) Anandamide, an endogenous cannabinoid, inhibits calcium currents as a partial agonist in N18 neuroblastoma cells. Mol Pharmacol 44:498-503.
22. Muthian SKG, Jarrahian A, Manna S, Greenberg MJ, Nithipatikom K, Campbell WB and Hillard CJ (1998) Structure-activity relationships for substrates and inhibitors of the neuronal anandamide uptake carrier. 1998 Symposium on the Cannabinoids; 1998 Jul 23-25; La Grande Motte, France.
23. Piomelli D, Beltramo M, Glasnapp S, Lin SY, Goutopoulos A, Xie X-Q and Makriyannis A (1999) Structural determinants for recognition and translocation by the anandamide transporter. Proc Natl Acad Sci USA 96:5802-5807.
24. Rinaldi-Carmona M, Barth F, Heaulme M, Alonso R, Shire D, Congy C, Soubrie P, Breliere JC and Le Fur G (1995) Biochemical and pharmacological characterisation of SR141716A, the first potent and selective brain cannabinoid receptor antagonist. Life Sci 56:23-24.
25. Rinaldi-Carmona M, Barth F, Heaulme M, Shire D, Calandra B, Congy C, Martinez S, Maruani J, Neliat G and Caput D (1994) SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett 350:240-244.
26. Rothman B and Papermaster BW (1966) Membrane properties of living mammalian cells as studied by enzymatic hydrolysis of fluorogenic esters. Proc Natl Acad Sci USA 55:134-141.
27. Schaffer JE and Lodish HF (1994) Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein. Cell 79:427-436.
28. Takadate A, Irikura M, Suehiro T, Fujino H and Goya S (1984) New labeling reagents for alcohols in fluorescence high-performance liquid chromatography. Chem Pharm Bull 33:1164-1169.
29. Ueda N, Kurahashi Y, Yamamoto S and Tokunaga T (1995) Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J Biol Chem 270:23823-23827.
30. Vogel Z, Barg J, Levy R, Saya D, Heldman E and Mechoulam R (1993) Anandamide, a brain endogenous compound, interacts specifically with cannabinoid receptors and inhibits adenylate cyclase. J Neurochem 61:352-355.