Synthesis and characterization in monkey of [11C]SP203 as a radioligand for imaging brain metabotropic glutamate 5 receptors

European Journal of Nuclear Medicine and Molecular Imaging

Volumn 39, Issue 12, 2012, Pages 1949-1958

  Siméon, Fabrice G ^a   Liow, Jeih San ^a   Zhang, Yi ^a   Hong, Jinsoo ^a   Gladding, Robert L ^a   Zoghbi, Sami S ^a   Innis, Robert B ^a   Pike, Victor W ^a  

^a NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

Author keywords

Carbon 11; MGluR5; PET; Radioligand; SP203

Indexed keywords

3 FLUORO 5 [2 [2 (FLUOROMETHYL)THIAZOL 4 YL]ETHYNYL]BENZONITRILE C 11; 3 FLUORO 5 [2 [2 (FLUOROMETHYL)THIAZOL 4 YL]ETHYNYL]BENZONITRILE F 18; CARBON 11; FLUORINE 18; METABOTROPIC RECEPTOR 5; TRACER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG SYNTHESIS; NEUROIMAGING; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RHESUS MONKEY;

ANIMALS; BRAIN; CARBON RADIOISOTOPES; HUMANS; LIGANDS; MACACA MULATTA; MALE; NITRILES; RADIOACTIVE TRACERS; RADIOPHARMACEUTICALS; RECEPTORS, METABOTROPIC GLUTAMATE; THIAZOLES;

EID: 84869092552     PISSN: 16197070     EISSN: 16197089     Source Type: Journal    
DOI: 10.1007/s00259-012-2205-x     Document Type: Article

References (31)

1. Conn PJ, Pin J-P. Pharmacology and functions of metabotropic glutamate receptors. Annu Rev Pharmacol Toxicol. 1997;37:205-37. (Pubitemid 27238875)
2. Zhu CZ, Wilson SG, Mikusa JP, Wismer CT, Gauvin DM, Lynch JJ, et al. Assessing the role of metabotropic glutamate receptor 5 in multiple nociceptive modalities. Eur J Pharmacol. 2004;506:107-18. (Pubitemid 39592907)
3. Cosford NDP, Tehrani L, Roppe J, Schweiger E, Smith ND, Anderson J, et al. 3-[(2-Methyl-1, 3-thiazol-4-yl) ethynyl]-pyridine: a potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity. J Med Chem. 2003;46:204-6. (Pubitemid 36078139)
4. Pietraszek M, Nagel J, Gravius A, Schafer D, Danysz W. The role of group I metabotropic glutamate receptors in schizophrenia. Amino Acids. 2007;32:173-8. (Pubitemid 46198740)
5. Tessari M, Pilla M, Andreoli M, Hutcheson DM, Heidbreder CA. Antagonism at metabotropic glutamate 5 receptor inhibits nicotineand cocaine-taking behaviors and prevents nicotine-triggered relapse to nicotine seeking. Eur J Pharmacol. 2004;499:121-3.
6. Chiamulera C, Epping-Jordan MP, Zocchi A, Marcon C, Cottiny C, Tacconi S, et al. Reinforcing and locomotor stimulant effects of cocaine are absent in mGluR5 null mutant mice. Nat Neurosci. 2001;4:873-4. (Pubitemid 32801588)
7. Maccarrone M, Rossi S, Bari M, De Chiara V, Rapino C, Musella A, et al. Abnormal mGlu5 receptor/endocannabinoid coupling in mice lacking FMRP and BC1 RNA. Neuropsychopharmacology. 2010;35:1500-9.
8. Gravius A, Pietraszek M, Dekundy A, Danysz W. Metabotropic glutamate receptors as therapeutic targets for cognitive disorders. Curr Topics Med Chem. 2010;10:187-206.
9. Siméon FG, Brown AK, Zoghbi SS, Patterson VM, Innis RB, Pike VW. Synthesis and simple 18F-labeling of a high affinity 2-(fluoromethyl) thiazole derivative ([18F]SP203) as a radioligand for imaging brain metabotropic glutamate subtype-5 receptors with PET. J Med Chem. 2007;50:3256-66. (Pubitemid 47065974)
10. Brown AK, Kimura Y, Zoghbi SS, Siméon FG, Liow JS, Kreisl WC, et al. Metabotropic glutamate subtype-5 (mGluR5) receptors quantified in human brain with a novel radioligand for positron emission tomography. J Nucl Med. 2008;49:2042-8.
11. Kimura Y, Siméon FG, Hatazawa J, Mozley PD, Pike VW, Innis RB, et al. Biodistribution and radiation dosimetry of a positron emission tomography ligand, 18F-SP203, to image metabotropic glutamate subtype 5 (mGluR5) receptor in humans. Eur J Nucl Med Mol Imaging. 2010;37:1943-9.
12. Kimura Y, Siméon FG, Zoghbi SS, Zhang Y, Hatazawa J, Pike VW, et al. Quantification of metabotropic glutamate receptor subtype 5 receptors in the brain by an equilibrium method using 18F-SP203. Neuroimage. 2012;59:2124-30.
13. Shetty HU, Zoghbi SS, Siméon FG, Liow JS, Brown AK, Kannan P, et al. Radiodefluorination of 3-fluoro-5-(2-(2-([18F]fluoromethyl) thiazol-4-yl) ethynyl) benzonitrile ([18F]SP203), a radioligand for imaging brain mGluR5 in vivo, occurs by glutathionylation in rat brain. J Pharmacol Exp Ther. 2008;327:727-35.
14. Gopinathan MB, Jin C, Rehder KS. A short and efficient synthesis of 3-{2-[2-(bromomethyl) thiazol-4-yl]ethynyl}-5-fluorobenzonitrile: a precursor for PET radioligand [18F]SP203. Synthesis Stuttgart. 2009;12:1979-82.
15. Iwata R, Ido T, Takahashi T, Nakanishi H, Iida S. Optimization of [11C]HCN production and no-carrier-Added [1-11C]amino acid synthesis. Appl Radial Isot. 1987;38:97-102. (Pubitemid 17034510)
16. Christman DR, Finn RD, Karlström KI, Wolf AP. Production of ultra high activity 11C-labeled hydrogen-cyanide, carbon-dioxide, carbon-monoxide and methane via 14N (p, α) 11C reaction. Int J Appl Radiat Isot. 1975;26:435-42.
17. Bjurling P, Reineck R, Westerberg G, Gee AD, Sutcliffe J, Långström B. Proceedings of the 6th Workshop on Targetry and Target Chemistry, TRIUMF, 1995, p. 282-284.
18. Clark J, Baldwin R, Bayne K, Brown MJ, Gebhart GF, Gonder JC, et al. Guide for the care and use of laboratory animals. Washington, DC: Institute of Laboratory Animal Resources, National Research Council; 1996.
19. Cosford NDP, Tehrani L, Arruda J, King C, McDonald IA, Munoz B, et al. 3-[(2-Methyl-1, 3-thiazol-4-yl) ethynyl]pyridine (MTEP): design and synthesis of a potent and highly selective metabotropic glutamate subtype 5 (mGlu5) receptor antagonist with anxiolytic activity. Neuropharmacology. 2002;43:282-3.
20. Yasuno F, Brown AK, Zoghbi SS, Krushinski JH, Chernet E, Tauscher J, et al. The PET radioligand [11C]MePPEP binds reversibly and with high specific signal to cannabinoid CB1 receptors in nonhuman primate brain. Neuropsychopharmacology. 2008;33:259-69. (Pubitemid 350243344)
21. Zoghbi SS, Shetty UH, Ichise M, Fujita M, Imaizumi M, Liow JS, et al. PET imaging of the dopamine transporter with [18F]FECNT: a polar radiometabolite confounds brain radioligand measurements. J Nucl Med. 2006;47:520-7. (Pubitemid 46768495)
22. Airaksinen AJ, Andersson J, Truong P, Karlsson O, Halldin C. Radiosynthesis of [11C]ximelagatran via palladium catalyzed [11C] cyanation. J Label Compds Radiopharm. 2007;51:1-5.
23. Andersson J, Truong P, Halldin C. In-target produced [11C] methane: increased specific radioactivity. Appl Radiat Isot. 2009;67:106-10.
24. Hamill TG, Krause S, Ryan C, Bonnefous C, Govek S, Sieders TJ, et al. Synthesis, characterization, and first successful monkey imaging studies of metabotropic glutamate receptor subtype 5 (mGluR5) PET radiotracers. Synapse. 2005;56:205-16. (Pubitemid 40656643)
25. Andersson Y, Långström B. Transition metal-mediated reactions using [11C]cyanide in synthesis of 11C-labeled aromaticcompounds. J Chem Soc Perkin Trans 1. 1994;11:1395-400.
26. Lindsley CW, Bates BS, Menon UN, Jadhav SB, Kane AS, Jones CK, et al. (3-Cyano-5-fluorophenyl) biaryl negative allosteric modulators of mGlu5: discovery of a new tool compound with activity in the OSS mouse model of addiction. ACS Chem Neurosci. 2011;2:471-82.
27. Zoghbi SS, Anderson KB, Jenko KJ, Luckenbaugh DA, Innis RB, Pike VW. On quantitative relationships between drug-like compound lipophilicity and plasma free fraction in monkey and human. J Pharm Sci. 2012;101:1028-39.
28. Okamura T, Kikuchi T, Okada M, Toramatsu C, Fukushi K, Takei M, et al. Noninvasive and quantitative assessment of the function of multidrug resistance-Associated protein 1 in the living brain. J Cereb Blood Flow Metab. 2009;29:504-11.
29. Ametamey SM, Kessler LJ, Honer M, Wyss MT, Buck A, Hintermann S, et al. Radiosynthesis and preclinical evaluation of 11C-ABP688 as a probe for imaging the metabotropic glutamate receptor subtype 5. J Nucl Med. 2006;47:698-705. (Pubitemid 46768472)
30. DeLorenzo C, Milak MS, Brennan KG, Kumar JSD, Mann JJ, Parsey RV. In vivo positron emission tomography imaging with [11C]ABP688: binding variability and specificity for the metabotropic glutamate receptor subtype 5 in baboons. Eur J Nucl Med Mol Imaging. 2011;38:1083-94.
31. Ametamey SM, Treyer V, Streffer J, Wys MT, Schmidt M, Blagoev M, et al. Human PET studies of metabotropic glutamate receptor subtype 5 with 11C-ABP688. J Nucl Med. 2007;48:247-52. (Pubitemid 47555351)