Nicotinic α4β2 receptor imaging agents. Part II. Synthesis and biological evaluation of 2-[18F]fluoro-3-[2-((S)-3-pyrrolinyl)methoxy]pyridine (18F-nifene) in rodents and imaging by PET in nonhuman primate

Nuclear Medicine and Biology

Volumn 33, Issue 3, 2006, Pages 295-304

  Pichika, Rama ^a   Easwaramoorthy, Balasubramaniam ^a   Collins, Daphne ^a   Christian, Bradley T ^b   Shi, Bingzhi ^b   Narayanan, Tanjore K ^b   Potkin, Steven G ^a   Mukherjee, Jogeshwar ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b KETTERING MEDICAL CENTER   (United States)

Author keywords

4 2 Nicotinic receptors; Autoradiography; Fluorine 18; Nifene; PET imaging

Indexed keywords

2 FLUORO 3 [2 (3 PYRROLINYL)METHOXY]PYRIDINE F 18; CYTISINE; NICOTINE; NICOTINIC ALPHA4 BETA2 RECEPTOR; NICOTINIC RECEPTOR; NIFENE F 18; RADIOPHARMACEUTICAL AGENT; TRITIUM; UNCLASSIFIED DRUG; NICOTINIC RECEPTOR ALPHA4BETA2; NIFENE; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE;

ANALYTICAL EQUIPMENT; ANESTHESIA; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BINDING AFFINITY; BINDING SITE; BIOLOGICAL ACTIVITY; BRAIN CORTEX; BRAIN HOMOGENATE; BRAIN REGION; BRAIN SLICE; CEREBELLUM; CINGULATE GYRUS; COMPARATIVE STUDY; CONTROLLED STUDY; CORPUS STRIATUM; DRUG ACTIVITY; DRUG DISTRIBUTION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; EVALUATION; HIPPOCAMPUS; IMAGING SYSTEM; IN VITRO STUDY; INJECTION PAIN; ISOTOPE LABELING; LATERAL GENICULATE NUCLEUS; MALE; MEASUREMENT; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIMATE; PROTEIN LOCALIZATION; RADIOCHEMISTRY; RADIOISOTOPE DECAY; RAT; RHESUS MONKEY; RODENT; SUBICULUM; TEMPORAL CORTEX; THALAMUS; THALAMUS NUCLEUS; THALAMUS VENTRAL NUCLEUS; ANIMAL; BRAIN; MACACA; METABOLISM; SCINTISCANNING; SPRAGUE DAWLEY RAT; SYNTHESIS;

ANIMALS; BRAIN; MACACA MULATTA; MALE; POSITRON-EMISSION TOMOGRAPHY; PYRIDINES; PYRROLES; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, NICOTINIC;

EID: 33646046816     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2005.12.017     Document Type: Article

References (28)

1. Breese C.R., Lee M.J., Adams C.E., Sullivan B., Logel J., Gillen K.M., et al. Abnormal regulation of high affinity nicotinic receptors in subjects with schizophrenia. Neuropsychopharmacology 23 (2000) 351-364
2. Clementi F., Fornasari D., and Gotti C. Neuronal nicotinic acetylcholine receptors: from structure to therapeutics. Trends Pharmacol Sci 21 (2000) 35-37
3. Dani J.A. Overview of nicotinic receptors and their roles in the central nervous system. Biol Psychiatry 49 (2001) 166-174
4. Paterson D., and Nordberg A. Neuronal nicotinic receptors in the human brain. Prog Neurobiol 61 (2000) 75-111
5. Sacco K.A., Bannon K.L., and George T.P. Nicotinic receptor mechanisms and cognition in normal states and neuropsychiatric disorders. J Psychopharmacol 18 (2004) 457-474
6. Sihver W., Nordberg A., Langstrom B., Mukhin A.G., Koren A.O., Kimes A.S., et al. Development of ligands for in vivo imaging of cerebral nicotinic receptors. Behav Brain Res 113 (2000) 143-157
7. 18F]fluoro-A-85380, a high-affinity ligand for α4β2 nicotinic acetylcholine receptors. Synapse 55 (2005) 89-97
8. 18F-fluoropropyl)-3-(2-(S)-pyrrolidinylmethoxy)pyridine, in rodents and PET in nonhuman primate. J Nucl Med 46 (2005) 130-140
9. 18F]F-A-85380: PET imaging of brain nicotinic acetylcholine receptors and whole body distribution in humans. FASEB J 17 (2003) 1331-1333
10. 18F-fluoro-A-85380 in healthy volunteers. J Nucl Med 44 (2003) 596-601
11. 123I-5-IA85380 SPET. Eur J Nucl Med 30 (2003) 1620-1629
12. 18F]FA binding to nicotinic acetylcholine receptors in rhesus monkey brain. Synapse 48 (2003) 25-34
13. Abreo M.A., Lin N.-H., Garvey D.S., Gunn D.E., Hettinger A.M., Wasicak J.T., et al. Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors. J Med Chem 39 (1996) 817-825
14. Pichika R., Collins D., Christian B.T., Shi B., Narayanan T.K., and Mukherjee J. PET imaging agents for thalamic and extrathalamic α4β2 nicotinic receptors. J Label Compd Radiopharm 48 (2005) S9
15. Brown L., Chefer S., Pavlova O., Vaupel D.B., Koren A.O., Kimes A.S., et al. Evaluation of 5-(2-(4-pyridinyl)vinyl)-6-chloro-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine and its analogues as PET radioligands for imaging nicotine acetylcholine receptors. J Neurochem 91 (2004) 600-612
16. Lin N.-H., Gunn D.E., Li Y., He Y., Bai H., Ryther K.B., et al. Synthesis and structure-activity relationships of pyridine-modified analogs of 3-[2-(S)-pyrrolidinyl)pyridine], A-84543. A potent nicotinic acetylcholine receptor agonist. Bioorg Med Chem 8 (1998) 249-254
17. 3H]Cytisine binding to nicotinic cholinergic receptors in brain. Mol Pharmacol 39 (1991) 9-12
18. Cheng Y.-C., and Prusoff W.H. Relationship between the inhibition constant and the concentration of inhibitor which cause 50 percent of an enzymatic reaction. Biochem Pharmacol 22 (1973) 3099-3108
19. Smulders C.J.G.M., Zwart R., Bermudez I., van Kleef R.G.D.M., Groot-Kormelink P.J., and Vijverberg H.P.M. Cholinergic drugs potentiate human nicotinic α4β2 acetylcholine receptors by a competitive mechanism. Eur J Pharmacol 509 (2005) 97-108
20. Dolle F., Dolci L., Valette H., Hinnen F., Vaufrey F., Guenther I., et al. Synthesis and nicotinic acetylcholine receptors in vivo binding properties of 2-fluoro-3-[2(S)-2-azetidinylmethoxy]pyridine: a new positron emission tomography ligand for nicotinic receptors. J Med Chem 42 (1999) 2251-2259
21. Hughes D.L. Organic reactions vol. 42 (1992), John Wiley & Sons, Inc, New York 335-656
22. Perry D.C., Xiao Y., Nguyen H.N., Musachio J.L., Davila-Garcia M.I., and Kellar K.J. Measuring nicotinic receptors with characteristics of α4β2, α3β2 and α3β4 subtypes in rat tissues by autoradiography. J Neurochem 82 (2002) 468-481
23. 18F]Fluoro-A-85380, a new PET tracer for the nicotinic acetylcholine receptor: studies in the human brain and in vivo demonstration of specific binding in the white matter. Synapse 53 (2004) 184-189
24. 18F]A-85380). J Label Compd Radiopharm 35 (1998) 309-318
25. Valette H., Bottlaender M., Dolle F., Coulon C., Ottaviani M., and Syrota A. Long-lasting occupancy of central nicotinic acetylcholine receptors after smoking: a PET study in monkeys. J Neurochem 84 (2003) 105-111
26. 125I-a-bungaratoxin binding sites in the brain of Macca mulatta. J Comp Neurol 461 (2003) 49-60
27. Perry D.C., Davila-Garcia M.I., Stockmeier C.A., and Kellar K.J. Increased nicotinic receptors in brains from smokers: membrane binding and autoradiography studies. J Pharmacol Exp Ther 289 (1999) 1545-1552
28. 18F-A85380: optimized synthesis and in vitro evaluation in Alzheimer's disease. Appl Radiat Isot 61 (2004) 1235-1240