Development of a PET radioligand for the central 5-HT1B receptor: Radiosynthesis and characterization in cynomolgus monkeys of eight radiolabeled compounds

Nuclear Medicine and Biology

Volumn 38, Issue 2, 2011, Pages 261-272

  Andersson, Jan D ^a   Pierson, M Edward ^b   Finnema, Sjoerd J ^a   Gulyás, Balázs ^a   Heys, Richard ^b   Elmore, Charles S ^b   Farde, Lars ^c   Halldin, Christer ^a  

^a KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

^b ASTRAZENECA   (United Kingdom)

^c ASTRAZENECA R AND D   (Sweden)

Author keywords

5 HT1B; Positron emission tomography (PET); Radioligand development; Serotonin

Indexed keywords

CARBON 11; CARBON 5 METHYL 8 (4 METHYLPIPERAZIN 1 YL) N (4 MORPHOLINOPHENYL) 4 OXO 4H CHROMENE 2 CARBOXAMIDE C 11; CARBON 5 METHYL 8 (4 METHYLPIPERAZIN 1 YL) N (4 MORPHOLINOPHENYL)QUINOLINE 2 CARBOXAMIDE C 11; CARBON 6 FLUORO 8 (4 METHYLPIPERAZIN 1 YL) 4 OXO N [4 (4 PROPIONYLPIPERAZIN 1 YL)PHENYL] 4H CHROMENE 2 CARBOXAMIDE C 11; CARBON 8 (4 METHYLPIPERAZIN 1 YL) N (4 MORPHOLINOPHENYL) 4 OXO 4H CHROMENE 2 CARBOXAMIDE C 11; CARBON 8 (4 METHYLPIPERAZIN 1 YL) N (4 MORPHOLINOPHENYL)CHROMAN 2 CARBOXAMIDE C 11; CARBON METHYL 4 [4 [6 FLUORO 8 (4 METHYLPIPERAZIN 1 YL)CHROMAN 2 CARBOXAMIDO]PHENYL]PIPERAZINE 1 CARBOXYLIC ACID C 11; PIPERAZINE; RADIOLIGAND; RADIOPHARMACEUTICAL AGENT; SEROTONIN 1B RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CEREBELLUM CORTEX; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; EXPERIMENTAL MONKEY; FRONTAL CORTEX; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VIVO STUDY; ISOTOPE ANALYSIS; ISOTOPE LABELING; LIPOPHILICITY; METABOLITE; METHYLATION; NONHUMAN; OCCIPITAL CORTEX; POSITRON EMISSION TOMOGRAPHY; RACEMIC MIXTURE; RADIOCHEMISTRY; RADIOISOTOPE DECAY;

AMIDES; ANIMALS; BIOLOGICAL TRANSPORT; BRAIN; CARBON RADIOISOTOPES; HUMANS; ISOTOPE LABELING; LIGANDS; MACACA FASCICULARIS; POSITRON-EMISSION TOMOGRAPHY; RADIOCHEMISTRY; RECEPTOR, SEROTONIN, 5-HT1B; SUBSTRATE SPECIFICITY;

EID: 79551681945     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.08.006     Document Type: Article

References (33)

1. Moret C., Briley M. The possible role of 5-HT(1B/D) receptors in psychiatric disorders and their potential as a target for therapy. Eur J Pharmacol 2000, 404(1-2):1-12.
2. Engel G., Gothert M., Hoyer D., Schlicker E., Hillenbrand K. Identity of inhibitory presynaptic 5-hydroxytryptamine (5-HT) autoreceptors in the rat brain cortex with 5-HT1B binding sites. Naunyn Schmiedebergs Arch Pharmacol 1986, 332(1):1-7.
3. Stenfors C., Hallerback T., Larsson L.G., Wallsten C., Ross S.B. Pharmacology of a novel selective 5-hydroxytryptamine1B receptor antagonist, AR-A000002. Naunyn Schmiedebergs Arch Pharmacol 2004, 369(3):330-337.
4. Schlicker E., Fink K., Molderings G.J., Price G.W., Duckworth M., Gaster L., et al. Effects of selective h5-HT1B (SB-216641) and h5-HT1D (BRL-15572) receptor ligands on guinea-pig and human 5-HT auto- and heteroreceptors. Naunyn Schmiedebergs Arch Pharmacol 1997, 356(3):321-327.
5. Bruinvels A.T., Landwehrmeyer B., Gustafson E.L., Durkin M.M., Mengod G., Branchek T.A., et al. Localization of 5-HT1B, 5-HT1D alpha, 5-HT1E and 5-HT1F receptor messenger RNA in rodent and primate brain. Neuropharmacology 1994, 33(3-4):367-386.
6. Peterlin B.L., Rapoport A.M. Clinical pharmacology of the serotonin receptor agonist, zolmitriptan. Expert Opin Drug Metab Toxicol 2007, 3(6):899-911.
7. Clitherow J.W., Scopes D.I., Skingle M., Jordan C.C., Feniuk W., Campbell I.B., et al. Evolution of a novel series of [(N,N-dimethylamino)propyl]- and piperazinylbenzanilides as the first selective 5-HT1D antagonists. J Med Chem 1994, 37(15):2253-2257.
8. Gaster L.M., Blaney F.E., Davies S., Duckworth D.M., Ham P., Jenkins S., et al. The selective 5-HT1B receptor inverse agonist 1μ-methyl-5-[[2μ-methyl-4μ-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydro-spiro[furo[2,3-f]indole-3,4μ-piperidine] (SB-224289) potently blocks terminal 5-HT autoreceptor function both in vitro and in vivo. J Med Chem 1998, 41(8):1218-1235.
9. 3H]5-carboxamidotryptamine. Eur J Pharmacol 1997, 327(2-3):247-256.
10. Lee C.M., Farde L. Using positron emission tomography to facilitate CNS drug development. Trends Pharmacol Sci 2006, 27(6):310-316.
11. Halldin C., Gulyas B., Farde L. PET studies with carbon-11 radioligands in neuropsychopharmacological drug development. Curr Pharm Des 2001, 7(18):1907-1929.
12. 11C]raclopride. Synapse 2006, 59(5):260-269.
13. Ahlgren C., Eriksson A., Tellefors P., Ross S.B., Stenfors C., Malmberg A. In vitro characterization of AR-A000002, a novel 5-hydroxytryptamine(1B) autoreceptor antagonist. Eur J Pharmacol 2004, 499(1-2):67-75.
14. 11C]AZ10419369: a selective 5-HT1B receptor radioligand suitable for positron emission tomography (PET). Characterization in the primate brain. Neuroimage 2008, 41(3):1075-1085.
15. 1B receptors in human brain. J Cereb Blood Flow Metab 2010, [Epub ahead of print] doi:10.1038/jcbfm.2010.55.
16. Finnema S.J., Varrone A., Hwang T.J., Gulyas B., Pierson M.E., Halldin C., et al. Fenfluramine-induced serotonin release decreases [(11)C]AZ10419369 binding to 5-HT(1B)-receptors in the primate brain. Synapse 2010, 64(7):573-577.
17. Larsen P., Ulin J., Dahlstrom K., Jensen M. Synthesis of C-11 iodomethane by iodination of C-11 methane. Appl Radiat Isot 1997, 48(2):153-157.
18. 11C]methane: Increased specific radioactivity. Appl Radiat Isot 2009, 67(1):106-110.
19. 11C]methyl triflate. Nucl Med Biol 1995, 22(2):235-239.
20. Clark J.D., Gebhart G.F., Gonder J.C., Keeling M.E., Kohn D.F. Special Report: The 1996 Guide for the Care and Use of Laboratory Animals. ILAR J 1997, 38(1):41-48.
21. 1-dopamine receptor. Psychopharmacology (Berl) 1993, 113:149-156.
22. Wienhard K., Dahlbom M., Eriksson L., Michel C., Bruckbauer T., Pietrzyk U., et al. The ECAT EXACT HR: performance of a new high resolution positron scanner. J Comput Assist Tomogr 1994, 18(1):110-118.
23. 11C]raclopride binding. J Cereb Blood Flow Metab 1998, 18(9):941-950.
24. Varnas K., Hall H., Bonaventure P., Sedvall G. Autoradiographic mapping of 5-HT(1B) and 5-HT(1D) receptors in the post mortem human brain using [(3)H]GR 125743. Brain Res 2001, 915(1):47-57.
25. 2-dopamine receptors studied by PET - a comparison to the equilibrium analysis. J Cereb Blood Flow Metab 1989, 9:696-708.
26. Innis R.B., Cunningham V.J., Delforge J., Fujita M., Gjedde A., Gunn R.N., et al. Consensus nomenclature for in vivo imaging of reversibly binding radioligands. J Cereb Blood Flow Metab 2007, 27(9):1533-1539.
27. Lammertsma A.A., Hume S.P. Simplified reference tissue model for PET receptor studies. Neuroimage 1996, 4(3 Pt 1):153-158.
28. 11C]Az10419369 binding to 5-HT1B receptors in the human brain. Neuroimage 2008, 41:T58-T200.
29. Halldin C., Swahn C.G., Farde L., Sedvall G. Radioligand disposition and metabolism - key information in early drug development. PET for drug development and evaluation 1995, 55-65. Kluwer Academic Publishers, Dordrecht. D. Comar (Ed.).
30. Yamazaki M., Neway W.E., Ohe T., Chen I., Rowe J.F., Hochman J.H., et al. In vitro substrate identification studies for p-glycoprotein-mediated transport: species difference and predictability of in vivo results. J Pharmacol Exp Ther 2001, 296(3):723-735.
31. Maier D.L., Sobotka-Briner C., Ding M., Powell M.E., Jiang Q., Hill G., et al. [N-Methyl-3H3]AZ10419369 binding to the 5-HT1B receptor: in vitro characterization and in vivo receptor occupancy. J Pharmacol Exp Ther 2009, 330(1):342-351.
32. 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(6):376-389.
33. Passchier J., Gee A., Willemsen A., Vaalburg W., van Waarde A. Measuring drug-related receptor occupancy with positron emission tomography. Methods 2002, 27(3):278-286.