[11C]CURB: Evaluation of a novel radiotracer for imaging fatty acid amide hydrolase by positron emission tomography

Nuclear Medicine and Biology

Volumn 38, Issue 2, 2011, Pages 247-253

  Wilson, Alan A ^a   Garcia, Armando ^a   Parkes, Jun ^a   Houle, Sylvain ^a   Tong, Junchao ^b   Vasdev, Neil ^a  

^a CENTRE FOR ADDICTION AND MENTAL HEALTH   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Cannabinoid; Carbon 11; Ex vivo; FAAH; Positron emission tomography; Rats

Indexed keywords

CARBON 6 HYDRO [1,1' BIPHENYL] 3 YL CYCLOHEXYLCARBAMIC ACID C 11; FATTY ACID AMIDASE; TRACER; UNCLASSIFIED DRUG; AMIDASE; BIPHENYL DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBON; CARBONYL (11C) 6 HYDROXY (1,1' BIPHENYL) 3 YL CYCLOHEXYLCARBAMATE; CARBONYL-(11C)-6-HYDROXY-(1,1'-BIPHENYL)-3-YL CYCLOHEXYLCARBAMATE; DIAGNOSTIC AGENT; ENZYME INHIBITOR; FATTY-ACID AMIDE HYDROLASE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN REGION; BRAIN TISSUE; CEREBELLUM CORTEX; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG METABOLISM; DRUG POTENCY; DRUG SPECIFICITY; DRUG UPTAKE; EX VIVO STUDY; HYPOTHALAMUS NUCLEUS; ISOTOPE LABELING; MALE; MOLECULAR IMAGING; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; RAT; TISSUE DISTRIBUTION; ANIMAL; BLOOD; BRAIN; DRUG ANTAGONISM; ENZYME SPECIFICITY; METABOLISM; METHODOLOGY; SPRAGUE DAWLEY RAT;

AMIDOHYDROLASES; ANIMALS; BIPHENYL COMPOUNDS; BRAIN; CARBAMATES; CARBON RADIOISOTOPES; ENZYME INHIBITORS; MALE; POSITRON-EMISSION TOMOGRAPHY; RADIOACTIVE TRACERS; RATS; RATS, SPRAGUE-DAWLEY; SUBSTRATE SPECIFICITY;

EID: 79551684090     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.08.001     Document Type: Article

References (59)

1. Cravatt B.F., Giang D.K., Mayfield S.P., Boger D.L., Lerner R.A., Gilula N.B. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 1996, 384:83-87.
2. Giang D.K., Cravatt B.F. Molecular characterization of human and mouse fatty acid amide hydrolases. Proc Natl Acad Sci U S A 1997, 94:2238-2242.
3. McKinney M.K., Cravatt B.F. Structure and function of fatty acid amide hydrolase. Annu Rev Biochem 2005, 74:411-432.
4. Bracey M.H., Hanson M.A., Masuda K.R., Stevens R.C., Cravatt B.F. Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling. Science 2002, 298:1793-1796.
5. Egertova M., Giang D.K., Cravatt B.F., Elphick M.R. A new perspective on cannabinoid signalling: complementary localization of fatty acid amide hydrolase and the CB1 receptor in rat brain. Proc Biol Sci 1998, 265:2081-2085.
6. Thomas E.A., Cravatt B.F., Danielson P.E., Gilula N.B., Sutcliffe J.G. Fatty acid amide hydrolase, the degradative enzyme for anandamide and oleamide, has selective distribution in neurons within the rat central nervous system. J Neurosci Res 1997, 50:1047-1052.
7. Marsicano G., Kuner R. Anatomical distribution of receptors, ligands and enzymes in the brain and in the spinal cord: circuitries and neurochemistry. Cannabinoids Brain 2008, 161-201.
8. Naidu P.S., Kinsey S.G., Guo T.L., Cravatt B.F., Lichtman A.H. Regulation of inflammatory pain by inhibition of fatty acid amide hydrolase. J Pharmacol Exp Ther 2010, 334:182-190.
9. Schlosburg J.E., Kinsey S.G., Lichtman A.H. Targeting fatty acid amide hydrolase (FAAH) to treat pain and inflammation. AAPS J 2009, 11:39-44.
10. Fowler C.J., Naidu P.S., Lichtman A., Onnis V. The case for the development of novel analgesic agents targeting both fatty acid amide hydrolase and either cyclooxygenase or TRPV1. Br J Pharmacol 2009, 156:412-419.
11. Ahn K., Johnson D.S., Mileni M., Beidler D., Long J.Z., McKinney M.K., et al. Discovery and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain. Chem Biol 2009, 16:411-420.
12. Jayamanne A., Greenwood R., Mitchell V.A., Aslan S., Piomelli D., Vaughan C.W. Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models. Br J Pharmacol 2006, 147:281-288.
13. Pillarisetti S., Alexander C.W., Khanna I. Pain and beyond: fatty acid amides and fatty acid amide hydrolase inhibitors in cardiovascular and metabolic diseases. Drug Discov Today 2009, 14:1098-1111.
14. Battista N., Bari M., Tarditi A., Mariotti C., Bachoud-Levi A.C., Zuccato C., et al. Severe deficiency of the fatty acid amide hydrolase (FAAH) activity segregates with the Huntington's disease mutation in peripheral lymphocytes. Neurobiol Dis 2007, 27:108-116.
15. Malone D.T., Kearn C.S., Chongue L., Mackie K., Taylor D.A. Effect of social isolation on CB1 and D2 receptor and fatty acid amide hydrolase expression in rats. Neuroscience 2008, 152:265-272.
16. Moreira F.A., Kaiser N., Monory K., Lutz B. Reduced anxiety-like behaviour induced by genetic and pharmacological inhibition of the endocannabinoid-degrading enzyme fatty acid amide hydrolase (FAAH) is mediated by CB1 receptors. Neuropharmacology 2008, 54:141-150.
17. Bambico F.R., Duranti A., Tontini A., Tarzia G., Gobbi G. Endocannabinoids in the treatment of mood disorders: evidence from animal models. Curr Pharm Des 2009, 15:1623-1646.
18. Bambico F.R., Cassano T., Dominguez-Lopez S., Katz N., Walker C.D., Piomelli D., et al. Genetic deletion of fatty acid amide hydrolase alters emotional behavior and serotonergic transmission in the dorsal raphe, prefrontal cortex, and hippocampus. Neuropsychopharmacology 2010, 35:2083-2100.
19. Parolaro D., Realini N., Vigano D., Guidali C., Rubino T. The endocannabinoid system and psychiatric disorders. Exp Neurol 2010, 224:3-14.
20. Falenski K.W., Thorpe A.J., Schlosburg J.E., Cravatt B.F., Abdullah R.A., Smith T.H., et al. FAAH-/- mice display differential tolerance, dependence, and cannabinoid receptor adaptation after delta 9-tetrahydrocannabinol and anandamide administration. Neuropsychopharmacology 2010, 35:1775-1787.
21. Tyndale R.F., Payne J.I., Gerber A.L., Sipe J.C. The fatty acid amide hydrolase C385A (P129T) missense variant in cannabis users: studies of drug use and dependence in Caucasians. Am J Med Genet B Neuropsychiatr Genet 2007, 144B:660-666.
22. Flanagan J.M., Gerber A.L., Cadet J.L., Beutler E., Sipe J.C. The fatty acid amide hydrolase 385 A/A (P129T) variant: haplotype analysis of an ancient missense mutation and validation of risk for drug addiction. Hum Genet 2006, 120:581-588.
23. Sipe J.C., Chiang K., Gerber A.L., Beutler E., Cravatt B.F. A missense mutation in human fatty acid amide hydrolase associated with problem drug use. Proc Natl Acad Sci U S A 2002, 99:8394-8399.
24. Schacht J.P., Selling R.E., Hutchison K.E. Intermediate cannabis dependence phenotypes and the FAAH C385A variant: an exploratory analysis. Psychopharmacology (Berl) 2009, 203:511-517.
25. Sipe J.C., Waalen J., Gerber A., Beutler E. Overweight and obesity associated with a missense polymorphism in fatty acid amide hydrolase (FAAH). Int J Obes (Lond) 2005, 29:755-759.
26. Monteleone P., Tortorella A., Martiadis V., Di Filippo C., Canestrelli B., Maj M. The cDNA 385C to A missense polymorphism of the endocannabinoid degrading enzyme fatty acid amide hydrolase (FAAH) is associated with overweight/obesity but not with binge eating disorder in overweight/obese women. Psychoneuroendocrinology 2008, 33:546-550.
27. Filbey F.M., Schacht J.P., Myers U.S., Chavez R.S., Hutchison K.E. Individual and additive effects of the CNR1 and FAAH genes on brain response to marijuana cues. Neuropsychopharmacology 2010, 35:967-975.
28. Hariri A.R., Gorka A., Hyde L.W., Kimak M., Halder I., Ducci F., et al. Divergent effects of genetic variation in endocannabinoid signaling on human threat- and reward-related brain function. Biol Psychiatry 2009, 66:9-16.
29. Glaser S.T., Gatley S.J., Gifford A.N. Ex vivo imaging of fatty acid amide hydrolase activity and its inhibition in the mouse brain. J Pharmacol Exp Ther 2006, 316:1088-1097.
30. 123I-labeled anandamide analogues for mapping brain FAAH. Bioorg Med Chem 2009, 17:49-56.
31. wyffels L., Muccioli G.G., De Bruyne S., Moerman L., Sambre J., Lambert D.M., et al. Synthesis, in vitro and in vivo evaluation, and radiolabeling of aryl anandamide analogues as candidate radioligands for in vivo imaging of fatty acid amide hydrolase in the brain. J Med Chem 2009, 52:4613-4622.
32. 11C-labelled URB597 analogue. Nucl Med Biol 2010, 37:665-675.
33. Seierstad M., Breitenbucher J.G. Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors. J Med Chem 2008, 51:7327-7343.
34. Piomelli D., Tarzia G., Duranti A., Tontini A., Mor M., Compton T.R., et al. Pharmacological profile of the selective FAAH inhibitor KDS-4103 (URB597). CNS Drug Rev 2006, 12:21-38.
35. Manwell L.A., Satvat E., Lang S.T., Allen C.P., Leri F., Parker L.A. FAAH inhibitor, URB-597, promotes extinction and CB(1) antagonist, SR141716, inhibits extinction of conditioned aversion produced by naloxone-precipitated morphine withdrawal, but not extinction of conditioned preference produced by morphine in rats. Pharmacol Biochem Behav 2009, 94:154-162.
36. Mor M., Rivara S., Lodola A., Plazzi P.V., Tarzia G., Duranti A., et al. Cyclohexylcarbamic acid 3'- or 4'-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies. J Med Chem 2004, 47:4998-5008.
37. Vacondio F., Silva C., Lodola A., Fioni A., Rivara S., Duranti A., et al. Structure-property relationships of a class of carbamate-based fatty acid amide hydrolase (FAAH) inhibitors: chemical and biological stability. ChemMedChem 2009, 4:1495-1504.
38. Clapper J.R., Vacondio F., King A.R., Duranti A., Tontini A., Silva C., et al. A second generation of carbamate-based fatty acid amide hydrolase inhibitors with improved activity in vivo. ChemMedChem 2009, 4:1505-1513.
39. 11C-carbonyl]-methylcarbamates. Org Biomol Chem 2010, 8:428-432.
40. 11C]-URB694 for FAAH PET imaging: a novel radiotracer for a new target. Neuroimage 2010, 52:S24.
41. Ueda N., Puffenbarger R.A., Yamamoto S., Deutsch D.G. The fatty acid amide hydrolase (FAAH). Chem Phys Lipids 2000, 108:107-121.
42. 11C]l-deprenyl in living baboon brain. J Neurochem 1988, 51:1524-1534.
43. 11C]-l-deprenyl in mice: potential for measurement of functional monoamine oxidase activity in brain using positron emission tomography. Biochem Pharmacol 1985, 34:3207-3210.
44. Hilton J., Yokoi F., Dannals R.F., Ravert H.T., Szabo Z., Wong D.F. Column-switching HPLC for the analysis of plasma in PET imaging studies. Nucl Med Biol 2000, 27:627-630.
45. Fowler J.S., Logan J., Volkow N.D., Wang G.J., MacGregor R.R., Ding Y.S. Monoamine oxidase: radiotracer development and human studies. Methods 2002, 27:263-277.
46. 11C-labelled MAO-A inhibitors and their in vivo uptake kinetics in rhesus monkey brain. Nucl Med Biol 1997, 24:381-388.
47. 11C]-harmine binding to monoamine oxidase-A in the human brain. J Cereb Blood Flow Metab 2006, 26:330-344.
48. Iyo M., Namba H., Fukushi K., Shinotoh H., Nagatsuka S., Suhara T., et al. Measurement of acetylcholinesterase by positron emission tomography in the brains of healthy controls and patients with Alzheimer's disease. Lancet 1997, 349:1805-1809.
49. 11C]PMP). Synapse 1996, 22:123-131.
50. 18F]fluoro-d-glucose for metabolic studies: current status. Int J Radiat Appl Instrum Part A Appl Radiat Isot 1986, 37:663-668.
51. Fowler J.S., Wang G.J., Logan J., Xie S., Volkow N.D., Macgregor R.R., et al. Selective reduction of radiotracer trapping by deuterium substitution: comparison of carbon-11-l-deprenyl and carbon-11-deprenyl-D2 for MAO B mapping. J Nucl Med 1995, 36:1255-1262.
52. Waterhouse R.N. Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents. Mol Imaging Biol 2003, 5:376-389.
53. Alexander J.P., Cravatt B.F. Mechanism of carbamate inactivation of FAAH: implications for the design of covalent inhibitors and in vivo functional probes for enzymes. Chem Biol 2005, 12:1179-1187.
54. Mileni M., Kamtekar S., Wood D.C., Benson T.E., Cravatt B.F., Stevens R.C. Crystal structures of fatty acid amide hydrolase bound to the carbamate inhibitor URB597: discovery of a deacylating water molecule and insight into enzyme inactivation. J Mol Biol 2010, 400:743-754.
55. 2 into carbamates. Angew Chem Int Ed Engl 2009, 48:3482-3485.
56. Wilson AA, Garcia A, Houle S, Vasdev N. The synthesis and application of isocyanates radiolabeled with carbon-11. Chem Eur J. Submitted for publication.
57. Zhang D., Saraf A., Kolasa T., Bhatia P., Zheng G.Z., Patel M., et al. Fatty acid amide hydrolase inhibitors display broad selectivity and inhibit multiple carboxylesterases as off-targets. Neuropharmacology 2007, 52:1095-1105.
58. Ahn K., Johnson D.S., Fitzgerald L.R., Liimatta M., Arendse A., Stevenson T., et al. Novel mechanistic class of fatty acid amide hydrolase inhibitors with remarkable selectivity. Biochemistry 2007, 46:13019-13030.
59. Wilson A.A., Jin L., Garcia A., DaSilva J.N., Houle S. An admonition when measuring the lipophilicity of radiotracers using counting techniques. Appl Radiat Isot 2001, 54:203-208.