Radiosynthesis and preliminary evaluation of 4-[18F]fluoro-N-[4- [6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide as a new positron emission tomography ligand for metabotropic glutamate receptor subtype 1

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 10, 2011, Pages 2998-3001

  Yamasaki, Tomoteru ^a,b   Fujinaga, Masayuki ^a   Yoshida, Yuichiro ^c   Kumata, Katsushi ^a   Yui, Joji ^a   Kawamura, Kazunori ^a   Hatori, Akiko ^a   Fukumura, Toshimitsu ^a   Zhang, Ming Rong ^a  

^a NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c 141 0032   (Japan)

Author keywords

mGluR1; PET

Indexed keywords

4 FLUORO N [4 [6 (ISOPROPYLAMINO)PYRIMIDIN 4 YL] 1,3 THIAZOL 2 YL]N METHYLBENZAMIDE F 18; CRYPTAND 2.2.2; METABOTROPIC RECEPTOR 1; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AUTORADIOGRAPHY; CEREBELLUM; CORPUS STRIATUM; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; EX VIVO STUDY; FLUORINATION; HIPPOCAMPUS; IMAGING SYSTEM; IN VITRO STUDY; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOCHEMISTRY; THALAMUS;

ANIMALS; BENZAMIDES; BRAIN; INHIBITORY CONCENTRATION 50; LIGANDS; MOLECULAR STRUCTURE; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RATS; RECEPTORS, METABOTROPIC GLUTAMATE; THIAZOLES;

RATTUS;

EID: 79955556415     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.03.046     Document Type: Article

References (31)

1. J.N.C. Kew Pharmacol. Ther. 104 2004 223
2. M.J. Marino, and P.J. Conn Curr. Opin. Pharmacol. 6 2006 1
3. C.J. Swanson, M. Bures, M.P. Johnson, A.-M. Linden, J.A. Monn, and D.D. Schoepp Nat. Rev. Drug Disc. 4 2005 131
4. G.J. Marek Curr. Med. Chem. Cent. Nervous Syst. Agents 2 2002 29
5. F. Gasparini, R. Kuhn, and J.-P. Pin Curr. Opin. Pharmacol. 2 2002 43
6. S.M. Ametamey, L.J. Kessler, M. Honer, M.T. Wyss, A. Buck, S. Hintermann, Y.P. Auberson, F. Gasparini, and P.S. Schubiger J. Nucl. Med. 47 2006 698
7. D. Pellegrino, F. Cicchetti, X. Wang, A. Zhu, M. Yu, M. Saint-Pierre, and A.L. Brownell J. Nucl. Med. 48 2007 1147
8. V. Treyer, J. Streffer, M.T. Wyss, A. Bettio, S.M. Ametamey, U. Fischer, M. Schmidt, F. Gasparini, C. Hock, and A. Buck J. Nucl. Med. 48 2007 1207
9. H. Annoura, A. Fukunaga, M. Uesugi, T. Tatsuoka, and Y. Horikawa Bioorg. Med. Chem. Lett. 6 1996 763
10. S. Litschig, F. Gasparini, D. Rueegg, N. Stoehr, P.J. Flor, I. Vranesic, L. Prezeau, J.P. Pin, C. Thomen, and R. Kuhn Mol. Pharmacol. 55 1999 453
11. F.Y. Carroll, A. Stolle, P.M. Beart, A. Voerste, I. Brabet, F. Mauler, C. Joly, H. Antonicek, J. Bockaert, T. Muller, J.P. Pin, and L. Prezeau Mol. Pharmacol. 59 2001 965
12. H. Lavreysen, C. Janssen, F. Bischoff, X. Langlois, J.E. Leysen, and A.S. Lesage Mol. Pharmacol. 63 2003 1082
13. H. Lavreysen, R. Wouters, F. Bischoff, S. Nobrega Pereira, H. Langlois, S. Blokland, M. Somers, L. Dillen, and A.S. Lesage Neuropharmacology 47 2004 961
14. G. Suzuki, T. Kimura, A. Satow, N. Kaneko, J. Fukuda, H. Hikichi, N. Sakai, S. Maehara, H. Kawagoe-Takaki, M. Hata, T. Azunma, S. Ito, H. Kawamoto, and H. Ohta J. Pharmacol. Exp. Ther. 321 2007 1144
15. A. Kohara, M. Takahashi, S. Yatsugi, S. Tamura, Y. Shitaka, S. Hayashibe, S. Kawabata, and M. Okada Brain Res. 1191 2008 168
16. Y. Huang, R. Narendran, F. Bischoff, N. Guo, A. Zhu, S.A. Bae, A.S. Lesage, and M. Laruelle J. Med. Chem. 48 2005 5096
17. M. Ohgami, T. Haradahira, N. Takai, M.R. Zhang, K. Kawamura, T. Yamasaki, and K. Yanamoto Eur. J. Nucl. Med. Mol. Imaging 36 2009 S310
18. E.D. Hostetler, W. Eng, A.D. Joshi, S. Sanabria-Bohorquez, H. Kawamoto, S. Ito, S. O'Malley, S. Krause, C. Ryan, S. Patel, M. Williams, K. Riffel, G. Suzuki, H. Ohta, J. Cook, H.D. Burns, and R. Hargreaves Synapse 65 2011 125
19. J. Prabhakaran, V.J. Majo, M.S. Milak, S.A. Kassir, M. Palner, L. Savenkova, P. Mali, V. Arango, J.J. Mann, R.V. Parsey, and J.S. Kumar Bioorg. Med. Chem. Lett. 20 2010 3499
20. K. Yanamoto, F. Konno, C. Odawara, T. Yamasaki, K. Kawamura, A. Hatori, J. Yui, H. Wakizaka, N. Nengaki, M. Takei, and M.R. Zhang Nucl. Med. Biol. 37 2010 615
21. S. Ito, Y. Hirata, Y. Nagatomi, A. Satoh, G. Suzuki, T. Kimura, A. Satow, S. Maehara, H. Hikichi, M. Hata, H. Ohta, and H. Kawamoto Bioorg. Med. Chem. Lett. 19 2009 5310
22. F. Ferraguti, L. Crepaldi, and F. Nicoletti Pharmacol. Rev. 60 2008 536
23. C. Shaffer, M.L. Guo, E.E. Fibuch, L.M. Mao, and J.Q. Wang Brain Res. 1326 2010 184
24. A. Satoh, Y. Nagatomi, Y. Hirata, S. Ito, G. Suzuki, T. Kimura, S. Maehara, H. Hikichi, A. Satow, M. Hata, H. Ohta, and H. Kawamoto Bioorg. Med. Chem. Lett. 19 2009 5464
25. 3) δ: 1.29 (d, J = 6.6 Hz, 6H), 3.72 (s, 3H), 4.10 (br, 1H), 4.83 (br, 1H), 7.02 (s, 1H), 7.76 (d, J = 8.8 Hz, 2H), 7.97 (s, 1H), 8.39 (d, J = 8.4 Hz, 2H), 8.57 (s, 1H); GCMS (EI), m/z: 399.
26. M. Fujinaga, T. Yamasaki, K. Kawamura, K. Kumata, A. Hatori, J. Yui, K. Yanamoto, Y. Yoshida, M. Ogawa, N. Nengaki, J. Maeda, T. Fukumura, and MR. Zhang Bioorg. Med. Chem. 19 2011 102
27. 18F]4 with n-octanol (3.0 g) and sodium phosphate buffer (PBS, 3.0 g; 0.1 M, pH 7.4) in a test tube. The tube was vortexed for 3 min at room temperature, followed by centrifugation at 3500 rpm for 5 min. An aliquot of 1 mL PBS and 1 mL n-octanol was removed, weighed, and counted. Samples from the remaining organic layer were removed and re-partitioned until consistent Log D values were obtained. The Log D value was calculated by comparing the ratio of the count per minute (cpm)/g of n-octanol to that of PBS and expressed as Log D = Log[cpm/g (n-octanol)/cpm/g(PBS)]. All assays were performed in triplicate.
28. Animal experiments were performed according to the recommendations of the Committee for the Care and Use of Laboratory Animals, National Institute of Radiological Sciences (Chiba, Japan).
29. 18F]4 in the presence or absence of 1 mg/kg JNJ16259685 (ENZO, USA) through the tail vein. At 30 min after the injection of radioactivity, rats were sacrificed by cervical dislocation, and their brains were removed quickly and frozen on powder dry ice. Brain sagittal sections (20 μm) were cut on a cryostat microtone (HM560; Carl Zeiss, Germany) and thaw-mounted on glass slides. Autoradiographic images were obtained by the method described above.
30. R. Kuhn, A. Pagano, I. Vranesic, PJ. Flor, K. Lingenhohl, W. Spooren, C. Gentsch, A. Vassout, A. Pilic, and F. Gasparini Amino Acids 23 2002 207
31. M. Fotuhi, AH. Sharp, CE. Glatt, PM. Hwang, M. von Krosigk, and SH. Snyder J. Neurosci. 13 1993 2001