Radiosynthesis and evaluation of [11C]YM-202074 as a PET ligand for imaging the metabotropic glutamate receptor type 1

Nuclear Medicine and Biology

Volumn 37, Issue 5, 2010, Pages 615-624

  Yanamoto, Kazuhiko ^a   Konno, Fujiko ^a   Odawara, Chika ^a   Yamasaki, Tomoteru ^a   Kawamura, Kazunori ^a   Hatori, Akiko ^a   Yui, Joji ^a   Wakizaka, Hidekatsu ^a   Nengaki, Nobuki ^a,b   Takei, Makoto ^a,c   Zhang, Ming Rong ^a  

^a NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

^b Japan   (Japan)

^c Department of Engineering and Environment   (Japan)

Author keywords

11C YM 202074; Autoradiography; MGluR1; PET

Indexed keywords

GLUTAMATE RECEPTOR 1; RADIOLIGAND; RADIOPHARMACEUTICAL AGENT; TRACER; UNCLASSIFIED DRUG; YM 202074 C 11; BENZIMIDAZOLE DERIVATIVE; DIAGNOSTIC AGENT; LIGAND; METABOTROPIC GLUTAMATE RECEPTOR TYPE 1; METABOTROPIC RECEPTOR; N CYCLOHEXYL 6 (((2 METHOXYETHYL)(METHYL)AMINO)METHYL) N METHYLTHIAZOLO(3,2 A)BENZIMIDAZOLE 2 CARBOXAMIDE; N-CYCLOHEXYL-6-(((2-METHOXYETHYL)(METHYL)AMINO)METHYL)-N-METHYLTHIAZOLO(3,2-A)BENZIMIDAZOLE-2-CARBOXAMIDE; THIAZOLE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; CEREBELLUM; HIPPOCAMPUS; IN VITRO STUDY; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIATION DOSE DISTRIBUTION; RAT; SYNTHESIS; THALAMUS; ANIMAL; BRAIN; CHEMISTRY; DRUG SCREENING; ENZYME SPECIFICITY; MALE; METABOLISM; METHODOLOGY; MOUSE; NUCLEAR MAGNETIC RESONANCE IMAGING; SCINTISCANNING;

ANIMALS; BENZIMIDAZOLES; BRAIN; DRUG EVALUATION, PRECLINICAL; LIGANDS; MAGNETIC RESONANCE IMAGING; MALE; MICE; POSITRON-EMISSION TOMOGRAPHY; RATS; RECEPTORS, METABOTROPIC GLUTAMATE; SUBSTRATE SPECIFICITY; THIAZOLES;

EID: 77953810321     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.03.002     Document Type: Article

References (29)

1. Conn P.J., Pin J.P. Pharmacology and functions of metabotropic glutamate receptors. Annu Rev Pharmacol Toxicol 1997, 37:205-237.
2. Nakanishi S. Metabotropic glutamate receptors: synaptic transmission, modulation, and plasticity. Neuron 1994, 13:1031-1037.
3. Ferraguti F., Crepaldi L., Nicoletti F. Metabotropic glutamate 1 receptor: current concepts and perspectives. Pharmacol Rev 2008, 60:536-581.
4. Annoura H., Fukunaga A., Uesugi M., Tatsuoka T., Horikawa Y. A novel class of antagonists for metabotropic glutamate receptors, 7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxylates. Bioorg Med Chem Lett 1996, 6:763-766.
5. Litschig S., Gasparini F., Rueegg D., Stoehr N., Flor P.J., Vranesic I., et al. CPCCOEt, a noncompetitive metabotropic glutamate receptor 1 antagonist, inhibits receptor signaling without affecting glutamate binding. Mol Pharmacol 1999, 55:453-461.
6. Carroll F.Y., Stolle A., Beart P.M., Voerste A., Brabet I., Mauler F., et al. BAY36-7620: a potent non-competitive mGlu1 receptor antagonist with inverse agonist activity. Mol Pharmacol 2001, 59:965-973.
7. 3H]R214127: a novel high-affinity radioligand for the mGlu1 receptor reveals a common binding site shared by multiple allosteric antagonists. Mol Pharmacol 2003, 63:1082-1093.
8. Lavreysen H., Wouters R., Bischoff F., Nóbrega Pereira S., Langlois X., Blokland S., et al. JNJ16259685, a highly potent, selective and systemically active mGlu1 receptor antagonist. Neuropharmacology 2004, 47:961-972.
9. Suzuki G., Kimura T., Satow A., Kaneko N., Fukuda J., Hikichi H., et al. Pharmacological characterization of a new, orally active and potent allosteric metabotropic glutamate receptor 1 antagonist, 4-[1-(2-fluoropyridin-3-yl)-5-methyl-1H-1,2,3-triazol-4-yl]-N-isopropyl-N-methyl-3,6-dihydropyridine-1(2H)-carboxamide (FTIDC). J Pharmacol Exp Ther 2007, 321:1144-1153.
10. Kohara A., Toya T., Tamura S., Watabiki T., Nagakura Y., Shitaka Y., et al. Radioligand binding properties and pharmacological characterization of 6-amino-N-cyclohexyl-N,3-dimethylthiazolo[3,2-a]benzimidazole-2-carboxamide (YM-298198), a high-affinity, selective, and noncompetitive antagonist of metabotropic glutamate receptor type 1. J Pharmacol Exp Ther 2005, 315:163-169.
11. Kohara A., Takahashi M., Yatsugi S., Tamura S., Shitaka Y., Hayashibe S., et al. Neuroprotective effects of the selective type 1 metabotropic glutamate receptor antagonist YM-202074 in rat stroke models. Brain Res 2008, 1191:168-179.
12. Yu M., Tueckmantel W., Wang X., Zhu A., Kozikowski A.P., Brownell A.L. Methoxyphenylethynyl, methoxypyridylethynyl and phenylethynyl derivatives of pyridine: synthesis, radiolabeling and evaluation of new PET ligands for metabotropic glutamate subtype 5 receptors. Nucl Med Biol 2005, 32:631-640.
13. 11C-ABP688 as a probe for imaging the metabotropic glutamate receptor subtype 5. J Nucl Med 2006, 47:698-705.
14. 18F]-FE-DABP688 as a PET radioligand for the metabotropic glutamate receptor subtype 5. Nucl Med Biol 2007, 34:973-980.
15. Hamill T.G., Krause S., Ryan C., Bonnefous C., Govek S., Seiders T.J., et al. Synthesis, characterization, and first successful monkey imaging studies of metabotropic glutamate receptor subtype 5 (mGluR5) PET radiotracers. Synapse 2005, 56:205-216.
16. 18F-labeling of 3-fluoro-5-(2-(2-(fluoromethyl)thiazol-4-yl)ethynyl)benzonitrile as a high affinity radioligand for imaging monkey brain metabotropic glutamate subtype-5 receptors with positron emission tomography. J Med Chem 2007, 50:3256-3266.
17. 11C]methyl-6-quinolinyl)(cis-4-methoxycyclohexyl)methanone. J Med Chem 2005, 48:5096-5099.
18. 18F]MK-1312: a PET tracer for quantification of mGluR1 receptor occupancy by MK-5435. J Label Compd Radiopharm 2009, 52:S84.
19. Hayashibe S., Itahana H., Okada M., Kohara A., Maeno K., Yahiro K., et al. Yamanouchi Pharmaceutical Co., Ltd., Novel thiazolobenzimidazole derivatives 2000, World Patent 2000; WO00/59913.
20. 11C]RO 15-1788 for PET studies of benzodiazepine receptors. Int J Appl Radiat Isot 1985, 36:971-976.
21. Bao Q., Newport D., Chen M., Stout D.B., Chatziioannou A.F. Performance evaluation of the inveon dedicated PET preclinical tomograph based on the NEMA NU-4 standards. J Nucl Med 2009, 50:401-408.
22. Visser E.P., Disselhorst J.A., Brom M., Laverman P., Gotthardt M., Oyen W.J., et al. Spatial resolution and sensitivity of the Inveon small-animal PET scanner. J Nucl Med 2009, 50:139-147.
23. Fotuhi M., Sharp A.H., Glatt C.E., Hwang P.M., von Krosigk M., Snyder S.H., et al. Differential localization of phosphoinositide-linked metabotropic glutamate receptor (mGluR1) and the inositol 1,4,5-trisphosphate receptor in rat brain. J Neurosci 1993, 13:2001-2012.
24. 3H]R214127. Neuropharmacology 2004, 46:609-619.
25. 11C]FLB 457 PET. J Cereb Blood Flow Metab 2007, 27:369-377.
26. 2 receptor ligands. Int J Rad Appl Instrum B 1990, 17:347-356.
27. 1-dopamine receptors. J Nucl Med 1998, 39:2061-2068.
28. 11C-DASB in healthy humans. Synapse 2005, 55:164-175.
29. Suzuki G., Kawagoe-Takaki H., Inoue T., Kimura T., Hikichi H., Murai T., et al. Correlation of Receptor Occupancy of Metabotropic Glutamate Receptor Subtype 1 (mGluR1) in Mouse Brain With In Vivo Activity of Allosteric mGluR1 Antagonists. J Pharmacol Sci 2009, 110:315-325.