Nicotinic α4β2 receptor imaging agents. Part III. Synthesis and biological evaluation of 3-(2-(S)-azetidinylmethoxy)-5-(3'- 18F-fluoropropyl)pyridine ( 18F-nifzetidine)

Nuclear Medicine and Biology

Volumn 38, Issue 8, 2011, Pages 1183-1192

  Pichika, Rama ^a   Easwaramoorthy, Balu ^b   Christian, Bradley T ^c   Shi, Bingzhi ^d   Narayanan, Tanjore K ^d   Collins, Daphne ^e   Mukherjee, Jogeshwar ^e  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

^d KETTERING MEDICAL CENTER   (United States)

^e UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Autoradiography; Fluorine 18; Monkey PET; Nifene

Indexed keywords

CYTISINE; NICOTINIC RECEPTOR ALPHA4BETA2; NIFZETIDINE F 18; RADIOPHARMACEUTICAL AGENT; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN CORTEX; BRAIN HOMOGENATE; BRAIN SLICE; CEREBELLUM; CONTROLLED STUDY; CORPUS STRIATUM; DRUG RETENTION; DRUG SYNTHESIS; DRUG UPTAKE; FRONTAL CORTEX; IN VITRO STUDY; LATERAL GENICULATE BODY; MALE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PROTEIN LOCALIZATION; RAT; RECEPTOR BINDING; RHESUS MONKEY; SUBICULUM; TEMPORAL CORTEX; THALAMUS; TISSUE DISTRIBUTION;

ANIMALS; AZETIDINES; BRAIN; FLUORINE RADIOISOTOPES; MACACA MULATTA; MALE; NICOTINIC ANTAGONISTS; POSITRON-EMISSION TOMOGRAPHY; PYRIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, NICOTINIC; TISSUE DISTRIBUTION;

EID: 82655162155     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2011.05.005     Document Type: Article

References (26)

1. Horti A.G., Gao Y., Kuwabara H., Dannals R.F. Development of radioligands with optimized imaging properties for quantification of nicotinic acetylcholine receptors by positron emission tomography. Life Sci 2010, 86:575-584.
2. Levin E.D. Nicotinic receptor subtypes and cognitive function. J Neurobiol 2002, 53:633-640.
3. Paterson D., Nordberg A. Neuronal nicotinic receptors in the human brain. Prog Neurobiol 2000, 61:75-111.
4. Benowitz N.L. Pharmacology of nicotine: addiction and therapeutics. Annu Rev Pharmacol Toxicol 1996, 36:597-613.
5. 3H]nicotine binding sites in human brain. J Neurochem 1988, 50:1243-1247.
6. Brown L., Chefer S., Pavlova O., Vaupel D.B., Koren A.O., Kimes A.S., Horti A.G., Mukhin A.G. Evaluation of 5-(2-(4-pyridinyl)vinyl)-6-chloro-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine and its analogues as PET radioligands for imaging nicotinic acetylcholine receptors. J Neurochem 2004, 91:600-612.
7. Iida Y., Ogawa M., Ueda M., Tominaga A., Kawashima H., Magata Y., Nishiyama S., Tsukada H., Mukai T., Saji H. Evaluation of 5-11C-methyl-A-85380 as an imaging agent for PET investigations of brain nicotinic acetylcholine receptors. J Nuc Med 2004, 45:878-884.
8. Roger G., Lagnel B., Rouden J., Besret L., Valette H., Demphel S., Gopisetti J.M., Coulon C., Ottaviani M., Wrenn L.A., Letchworth S.R., Bohme G.A., Benavides J., Lasne M.C., Bottlaender M., Dolle F. Synthesis of a [2-pyridinyl-18F]-labelled fluoro derivative of (-)-cytisine as a candidate radioligand for brain nicotinic α4β2 receptor imaging with PET. Bioorg. Med Chem 2003, 11:5333-5343.
9. Fujita M., Ichise M., van Dyck C.H., Zoghbi S.S., Tamagnan G., Mukhin A.G., Bozkurt A., Seneca N., Tipre D., DeNucci C.C., Iida H., Vaupel D.B., Horti A.G., Koren A.O., Kimes A.S., London E.D., Seibyl J.P., Baldwin R.M., Innis R.B. Quantification of nicotinic acetylcholine receptors in human brain using 123I-5-IA85380 SPET. Eur J Nucl Med 2003, 30:1620-1629.
10. Kimes A.S., Horti A.G., London E.D., Chefer S.I., Contoreggi C., Ernst M., Friello P., Koren A.O., Kurian V., Matochik J.A., Pavlova O., Vaupel D.B., Mukhin A.G. 2-[18F]F-A-85380: PET imaging of brain nicotinic acetylcholine receptors and whole body distribution in humans. FASEB J 2003, 17:1331-1333.
11. Bottlaender M., Valette H., Roumenov D., Dolle F., Coulon C., Ottaviani M., Hinnen F., Ricard M. Biodistribution and radiation dosimetry of 18F-fluoro-A-85380 in healthy volunteers. J Nucl Med 2003, 44:596-601.
12. Ding Y.S., Fowler J., Logan J., Wang G.J., Telang F., Garza V., Biegon A., Pareto D., Rooney W., Shea C., Alexoff D., Volkow N.D., Vocci F. 6-[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 2004, 53:184-189.
13. 18F-nifene) in rodents and imaging by PET in nonhuman primate. Nucl. Med. Biol 2006, 33:295-304.
14. Lin N.H., Li Y., He Y., Holladay M.W., Kuntzweiler T., Anderson D.J., Campbell J.E., Arneric S.P. Synthesis and structure-activity relationships of 5-substituted pyridine analogues of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543: a potent nicotinic receptor ligand. Bioorg Med Chem Lett 2001, 11:631-633.
15. Lin N.H., Gunn D.E., Li Y., He Y., Bai H., Ryther K.B., Kuntzweiler T., Donnelly-Roberts D.L., Anderson D.J., Campbell J.E., Sullivan J.P., Armeric S.P., Holladay M.W. 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 Lett 1998, 8:249-254.
16. 18F-fluoropropyl)-3-(2-(S)-pyrrolidinylmethoxy)pyridine, in rodents and PET in nonhuman primate. J Nucl Med 2005, 46:130-140.
17. Pabreza L.A., Dhawan S., Kellar K.J. [3H]Cytisine binding to nicotinic cholinergic receptors in brain. Mol. Pharmacol 1991, 39:9-12.
18. Smulders C.J.G.M., Awart R., Bermudez I., van Kleef R.G.D.M., Groot-Kormelink P.J., Vijverberg H.P.M. Cholinergic drugs potentiate human nicotinic A4B2 acetylcholine receptors by a competitive mechanism. Eur J Pharmacol 2005, 509:97-108.
19. Hughes D.L. Organic reactions 1992, Vol. 42:335-656. John Wiley & Sons, Inc, New York.
20. Kosugi M., Sasazawa K., Shimizu Y., Migita T. Reactions of allyltin compounds III. Allylation of aromatic halides with allyltributyltin in the presence of tetrakis(triphenylphosphine)palladium (0). Chem Letts 1977, 301-302.
21. Middleton W.J., Bingham E.M. Diethylaminosulfur trifluoride. Organic Synth 1977, 57.
22. Cox P., Terpinski J., Lawrynowicz W. Anhydrous tetrabutylammonium fluoride: a mild but highly efficient source of nucleophilic fluoride ion. J Org Chem 1984, 49:3216.
23. Sihver W., Nordberg A., Langstrom B., Mukhin A.G., Koren A.O., Kimes A.S., London E.D. Development of ligands for in vivo imaging of cerebral nicotinic receptors. Behav Brain Res 2000, 113:143-157.
24. Chefer S.I., London E.D., Koren A.O., Pavlova O.A., Kurian V., Kimes A.S., Horti A.G., Mukhin A.G. Graphical analysis of 2-[18F]FA binding to nicotinic acetylcholine receptors in rhesus monkey brain. Synapse 2003, 48:25-34.
25. Pichika R., Easwaramoorthy B., Collins D., Potkin S., Mukherjee J. 18F-nifrolene: a new PET imaging agent for a4b2 nAChR nicotinic receptors. J Nucl Med 2006, (47 Suppl):27P.
26. 18F-nifrolene microPET studies of nicotinic a4b2 receptors. J Nucl Med 2010, 51(Suppl 2):219.