Journal of Medicinal Chemistry
Article
(6) Swanson, C. J.; Bures, M.; Johnson, M. P.; Linden, A. M.; Monn, J.
A.; Schoepp, D. D. Metabotropic glutamate receptors as novel targets for
anxiety and stress disorders. Nat. Rev. Drug Discovery 2005, 4, 131−144.
(7) Kaneda, K.; Imanishi, M.; Nambu, A.; Shigemoto, R.; Takada, M.
Differential expression patterns of mGlu1 alpha in monkey nigral
dopamine neurons. NeuroReport 2003, 14, 947−950.
(8) Kaneda, K.; Tachibana, Y.; Imanishi, M.; Kita, H.; Shigemoto, R.;
Nambu, A.; Takada, M. Down-regulation of metabotropic glutamate
receptor 1alpha in globus pallidus and substantia nigra of parkinsonian
monkeys. Eur. J. Neurosci. 2005, 22, 3241−3254.
(9) Ribeiro, F. M.; Paquet, M.; Ferreira, L. T.; Cregan, T.; Swan, P.;
Cregan, S. P.; Ferguson, S. S. Metabotropic glutamate receptor-
mediated cell signaling pathways are altered in a mouse model of
Huntington’s disease. J. Neurosci. 2010, 30, 316−324.
(10) Werner, C. G.; Scartabelli, T.; Pancani, T.; Landucci, E.; Moroni,
F.; Pellegrini-Giampietro, D. E. Differential role of mGlu1 and mGlu5
receptors in rat hippocampal slice models of ischemic tolerance. Eur. J.
Neurosci. 2007, 25, 3597−3604.
emission tomography ligand for metabotropic glutamate receptor
subtype 1. Bioorg. Med. Chem. Lett. 2011, 21, 2998−3001.
(21) Yamasaki, T.; Fujinaga, M.; Kawamura, K.; Yui, J.; Hatori, A.;
Ohya, T.; Xie, L.; Wakizaka, H.; Yoshida, Y.; Fukumura, T.; Zhang, M.-
R. In vivo measurement of the affinity and density of metabotropic
glutamate receptor subtype 1 (mGluR1) in rat brain using 18F-FITM in
small-animal PET. J. Nucl. Med. 2012, 53, 1601−1607.
(22) Ametamey, S. M.; Kessler, L. J.; Honer, M.; Wyss, M. T.; Buck, A.;
Hintermann, S.; Auberson, Y. P.; Gasparini, F.; Schubiger, P. A.
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.
(23) Pike, V. W. PET radiotracers: crossing the blood−brain barrier
and surviving metabolism. Trends. Pharmacol. Sci. 2009, 30, 431−440.
(24) 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.
(25) Suzuki, M.; Doi, H.; Bjorkman, M.; Andersson, Y.; Langstrom, B.;
Watanabe, Y.; Noyori, R. Rapid coupling of methyl iodide with
aryltributylstannanes mediated by palladium(0) complexes: a general
protocol for the synthesis of 11CH3-labeled PET tracers. Chem.Eur. J.
1997, 3, 2039−2042.
(26) Koziorowski, J.; Henssen, C.; Weinreich, R. A new convenient
route to radioiodinated N-succinimidyl 3- and 4-iodobenzoate, two
reagents for radioiodination of proteins. Appl. Radiat. Isot. 1998, 49,
955−959.
(11) Zhou, M.; Xu, W.; Liao, G.; Bi, X.; Baudry, M. Neuroprotection
against neonatal hypoxia/ischemia-induced cerebral cell death by
prevention of calpain-mediated mGlu1alpha truncation. Exp. Neurol.
2009, 218, 75−82.
(12) Wang, J.; Maurer, L. Positron emission tomography: applications
in drug discovery and drug development. Curr. Top. Med. Chem. 2005, 5,
1053−1075.
(13) Fujinaga, M.; Maeda, J.; Yui, J.; Hatori, A.; Yamasaki, T.;
Kawamura, K.; Kumata, K.; Yoshida, Y.; Nagai, Y.; Higuchi, M.; Suhara,
T.; Fukumura, T.; Zhang, M.-R. Characterization of 1-(2-[18F]fluoro-3-
pyridyl)-4-(2-isopropyl-1-oxo-isoindoline-5-yl)-5-methyl-1H-1,2,3-tria-
zole, a PET ligand for imaging the metabotropic glutamate receptor type
1 in rat and monkey brains. J. Neurochem. 2012, 121, 115−124.
(14) Fujinaga, M.; Yamasaki, T.; Kawamura, K.; Kumata, K.; Hatori, A.;
Yui, J.; Yanamoto, K.; Yoshida, Y.; Ogawa, M.; Nengaki, N.; Maeda, J.;
Fukumura, T.; Zhang, M.-R. Synthesis and evaluation of 6-[1-(2-
[18F]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline for
positron emission tomography imaging of the metabotropic glutamate
receptor type 1 in brain. Bioorg. Med. Chem. 2011, 19, 102−110.
(15) Hostetler, E. D.; Eng, W.; Joshi, A. D.; Sanabria-Bohorquez, S.;
Kawamoto, H.; Ito, S.; O’Malley, S.; Krause, S.; Ryan, C.; Patel, S.;
Williams, M.; Riffel, K.; Suzuki, G.; Ozaki, S.; Ohta, H.; Cook, J.; Burns,
H. D.; Hargreaves, R. Synthesis, characterization, and monkey PET
studies of [18F]MK-1312, a PET tracer for quantification of mGluR1
receptor occupancy by MK-5435. Synapse 2011, 65, 125−135.
(16) Prabhakaran, J.; Majo, V. J.; Milak, M. S.; Kassir, S. A.; Palner, M.;
Savenkova, L.; Mali, P.; Arango, V.; Mann, J. J.; Parsey, R. V.; Kumar, J. S.
Synthesis, in vitro and in vivo evaluation of [11C]MMTP: a potential
PET ligand for mGlu1 receptors. Bioorg. Med. Chem. Lett. 2011, 20,
3499−3501.
(17) Yanamoto, K.; Konno, F.; Odawara, C.; Yamasaki, T.; Kawamura,
K.; Hatori, A.; Yui, J.; Wakizaka, H.; Nengaki, N.; Takei, M.; Zhang, M.-
R. Radiosynthesis and evaluation of [11C]YM-202074 as a PET ligand
for imaging the metabotropic glutamate receptor type 1. Nucl. Med. Biol.
2010, 37, 615−624.
(18) Fujinaga, M.; Yamasaki, T.; Yui, J.; Hatori, A.; Xie, L.; Kawamura,
K.; Asagawa, C.; Kumata, K.; Yoshida, Y.; Ogawa, M.; Nengaki, N.;
Fukumura, T.; Zhang, M.-R. Synthesis and evaluation of novel
radioligands for positron emission tomography imaging of metabotropic
glutamate receptor subtype 1 (mGluR1) in rodent brain. J. Med. Chem.
2012, 55, 2342−2352.
(27) Kaderavek, J.; Kozempel, J.; Sticha, M.; Petrasek, J.; Jirsa, M.;
Taimr, P.; Leseticky, L. Vitamin a derivatives labelled with 131I-potential
agents for liver scintigraphy. Czech. J. Phys. 2006, 56, D711−D717.
(28) Suzuki, K.; Inoue, O.; Hashimoto, K.; Yamasaki, T.; Kuchiki, M.;
Tamate, K. Computer-controlled large scale production of high specific
activity [11C]Ro 15-1788 for PET studies of benzodiazepine receptors.
Int. J. Appl. Radiat. Isot. 1985, 36, 971−976.
(29) Lavreysen, H.; Wouters, R.; Bischoff, F.; Nobrega Pereira, S.;
Langlois, X.; Blokland, S.; Somers, M.; Dillen, L.; Lesage, A. S.
JNJ16259685, a highly potent, selective and systemically active mGlu1
receptor antagonist. Neuropharmacology 2004, 47, 961−972.
(30) Fotuhi, M.; Sharp, A. H.; Glatt, C. E.; Hwang, P. M.; von Krosigk,
M.; Snyder, S. H.; Dawson, T. M. 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.
(31) Lavreysen, H.; Pereira, S. N.; Leysen, J. E.; Langlois, X.; Lesage, A.
S. Metabotropic glutamate 1 receptor distribution and occupancy in the
rat brain: a quantitative autoradiographic study using [3H]R214127.
Neuropharmacology 2004, 46, 609−619.
(32) Innis, R. B.; Cunningham, V. J.; Delforge, J.; Fujita, M.; Gjedde,
A.; Gunn, R. N.; Holden, J.; Houle, S.; Huang, S. C.; Ichise, M.; Iida, H.;
Ito, H.; Kimura, Y.; Koeppe, R. A.; Knudsen, G. M.; Knuuti, J.;
Lammertsma, A. A.; Laruelle, M.; Logan, J.; Maguire, R. P.; Mintun, M.
A.; Morris, E. D.; Parsey, R.; Price, J. C.; Slifstein, M.; Sossi, V.; Suhara,
T.; Votaw, J. R.; Wong, D. F.; Carson, R. E. Consensus nomenclature for
in vivo imaging of reversibly binding radioligands. J. Cereb. Blood Flow
Metab. 2007, 27, 1533−1539.
(33) Logan, J.; Fowler, J. S.; Volkow, N. D.; Wang, G. J.; Ding, Y. S.;
Alexoff, D. L. Distribution volume ratios without blood sampling from
graphical analysis of PET data. J. Cereb. Blood Flow Metab. 1996, 16,
834−840.
(34) Yui, J.; Maeda, J.; Kumata, K.; Kawamura, K.; Yanamoto, K.;
Hatori, A.; Yamasaki, T.; Nengaki, N.; Higuchi, M.; Zhang, M.-R. 18F-
FEAC and 18F-FEDAC: PET of the monkey brain and imaging of
translocator protein (18 kDa) in the infarcted rat brain. J. Nucl. Med.
2010, 51, 1301−1309.
(35) Lammertsma, A. A.; Hume, S. P. Simplified reference tissue model
for PET receptor studies. NeuroImage 1996, 4, 153−158.
(36) Takei, M.; Kida, T.; Suzuki, K. Sensitive measurement of positron
emitters eluted from HPLC. Appl. Radiat. Isot. 2001, 55, 229−234.
(19) Yamasaki, T.; Fujinaga, M.; Maeda, J.; Kawamura, K.; Yui, J.;
Hatori, A.; Yoshida, Y.; Nagai, Y.; Tokunaga, M.; Higuchi, M.; Suhara,
T.; Fukumura, T.; Zhang, M.-R. Imaging for metabotropic glutamate
receptor subtype 1 in rat and monkey brains using PET with [18F]FITM.
Eur. J. Nucl. Med. Mol. Imaging 2011, 39, 632−641.
(20) Yamasaki, T.; Fujinaga, M.; Yoshida, Y.; Kumata, K.; Yui, J.;
Kawamura, K.; Hatori, A.; Fukumura, T.; Zhang, M.-R. 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
11051
dx.doi.org/10.1021/jm301597s | J. Med. Chem. 2012, 55, 11042−11051