Radiosynthesis of N-(4-chloro-3-[11C]methoxyphenyl)-2- picolinamide ([11C]ML128) as a PET radiotracer for metabotropic glutamate receptor subtype 4 (mGlu4)

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 19, 2013, Pages 5955-5962

  Kil, Kun Eek ^a   Zhang, Zhaoda ^a   Jokivarsi, Kimmo ^a   Gong, Chunyu ^a   Choi, Ji Kyung ^a   Kura, Sreekanth ^a   Brownell, Anna Liisa ^a  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

Author keywords

11C ML128; Metabotropic glutamate receptor subtype 4 (mGlu4); PET; Positive allosteric modulator

Indexed keywords

CARBON 11; METABOTROPIC RECEPTOR 4; N (4 CHLORO 3 HYDROXYPHENYL) 2 PICOLINAMIDE; N (4 CHLORO 3 METHOXYPHENYL) 2 PICOLINAMIDE; N (CHLORO 3 METHOXYPHENYL) 2 PICOLINAMIDE; N [3 (DIFLUOROMETHOXY)PHENYL] 2 PICOLINAMIDE; N [3 (DIFLUOROMETHOXY)PHENYL] 2 PICOLINAMIDE HYDROCHLORIDE SALT; PICOLINAMIDE; RADIOLIGAND; TRACER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BRAIN REGION; CEREBELLUM; CONTROLLED STUDY; CORPUS STRIATUM; DIAGNOSTIC IMAGING; EX VIVO STUDY; HIPPOCAMPUS; IN VIVO STUDY; MALE; NON INVASIVE PROCEDURE; NONHUMAN; OLFACTORY BULB; PARKINSON DISEASE; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; RAT; THALAMUS;

RATTUS;

METABOTROPIC GLUTAMATE RECEPTOR SUBTYPE 4 (MGLU(4)); PET; POSITIVE ALLOSTERIC MODULATOR; [(11)C]ML128;

ANILINE COMPOUNDS; ANIMALS; BRAIN CHEMISTRY; CARBON RADIOISOTOPES; MALE; PICOLINIC ACIDS; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, METABOTROPIC GLUTAMATE;

EID: 84883458105     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.07.046     Document Type: Article

References (28)

1. E.M. Hur, and K.T. Kim Cell Signal 14 2002 407
2. D.D. Schoepp, D.E. Jane, and J.A. Monn Neuropharmacology 38 1999 1431
3. J.P. Pin, and F. Acher Curr. Drug Targets CNS Neurol. Disord. 1 2002 297
4. P.J. Conn, and J.P. Pin Ann. Rev. Pharmacol. Toxicol. 37 1997 205
5. T. Muto, D. Tsuchiya, A. Morikawa, and H. Jingami Proc. Natl. Acad. Sci. U.S.A. 104 2007 3759
6. D.R. Hampson, E.M. Rose, and J.E. Antflick R.W. Gereau, G.T. Swanson, The Glutamate Receptors 2008 Human Press Totowa 363 386
7. R. Shigemoto, and N. Mizuno O.P. Otterson, J. Storm-Mathisen, Handbook of Chemical Neuroanatomy Vol. 18 2000 Elsevier, Amsterdam 63 98
8. S.R. Bradley, D.G. Standaert, K.J. Rhodes, H.D. Rees, C.M. Testa, A.I. Levey, and P.J. Conn J. Comp. Neurol. 407 1999 33
9. C. Corti, L. Aldegheri, P. Somogyi, and F. Ferraguti Neuroscience 110 2002 403
10. A. Kinoshita, H. Ohishi, S. Nomura, R. Shigemoto, S. Nakanishi, and N. Mizuno Neurosci. Lett. 207 1996 199
11. M.J. Marino, D.L. Williams Jr., J.A. O'Brian, O. Valenti, T.P. McDonald, M.K. Clements, R. Wang, A.G. DiLella, J.F. Hess, G.G. Kinney, and P.J. Conn Proc. Natl. Acad. Sci. U.S.A. 100 2003 13668
12. M.J. Marino, O. Valenti, and P.J. Conn Drugs Aging 20 2003 377
13. F. Blandini, G. Nappi, C. Tassorelli, and E. Martignoni Prog. Neurobiol. 62 2000 63
14. C.R. Hopkins, C.W. Lindsley, and C.M. Niswender Future Med. Chem. 1 2009 501
15. M. Maj, V. Bruno, Z. Dragic, R. Yamamoto, G. Battaglia, W. Inderbitzin, N. Stoehr, T. Stein, F. Gasparini, I. Vranesic, R. Kuhn, F. Nicoletti, and P.J. Flor Neuropharmacology 45 2003 895
16. D.W. Engers, C.M. Niswender, C.D. Weaver, S. Jadhav, U.N. Menon, R. Zamorano, P.J. Conn, C.W. Lindsley, and C.R. Hopkins J. Med. Chem. 52 2009 4115
17. J.Q. Wang, W. Tueckmantel, A. Zhu, D. Pellegrino, and A.-L. Brownell Synapse 67 2007 951
18. A.J. Robichaud, D.W. Engers, C.W. Lindsley, and C.R. Hopkins ACS Chem Neurosci. 2 2011 433
19. S.M. Ametamey, L.J. Kessler, M. Honer, M.T. Wyss, A. Buck, S. Hintermann, Y.P. Auberson, F. Gasparini, and P.A. Schubiger J. Nucl. Med. 47 2006 698
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. E.D. Hostetler, W. Eng, A.D. Joshi, S. Sanabria-Bohórquez, H. Kawamoto, S. Ito, S. O'Malley, S. Krause, C. Ryan, S. Patel, M. Williams, K. Riffel, G. Suzuki, S. Ozaki, H. Ohta, J. Cook, H.D. Burns, and R. Hargreaves Synapse 65 2011 125
22. The functional assay was generously provided by the National Institute of Mental Health's Psychoactive Drug Screening Program, Contract # HHSN-271-2008-00025-C (NIMH PDSP). The PDSP is directed by Bryan L. Roth, MD, PhD at the University of North Carolina at Chapel Hill and Project Officer Jamie Driscol at NIMH, Bethesda, MD, USA.
23. c Log P and tPSA were obtained by calculation program installed in ChemBioDraw 12.0.
24. A.K. Ghose, T. Herbertz, R.L. Hudkins, B.D. Dorsey, and J.P. Mallamo ACS Chem. Neurosci. 3 2012 50
25. H. Pajouhesh, and G.R. Lenz NeuroRx 2 2005 541
26. K.-E. Kil, A. Biegon, Y.-S. Ding, A. Fischer, R.A. Ferrieri, S.W. Kim, D. Pareto, M.J. Schueller, and J.S. Fowler Nucl. Med. Biol. 36 2009 215
27. N.D.P. Cosford, L. Tehrani, J. Roppe, E. Schweiger, N.D. Smith, J. Anderson, L. Bristow, J. Brodkin, X. Jiang, I. McDonald, S. Rao, M. Washburn, and M.A. Varney J. Med. Chem. 46 2003 204
28. G. Paxinos and C. Watson, The Rat Brain in Stereotaxic Coordinates - The New Coronal Set, 2004, Fifth Edition, Academic press, Amsterdam.