Synthesis and evaluation of nicotine α4β2 receptor radioligand, 5-(3′-18F-fluoropropyl)-3-(2-(S)- pyrrolidinylmethoxy)pyridine, in rodents and PET in nonhuman primate

Journal of Nuclear Medicine

Volumn 46, Issue 1, 2005, Pages 130-140

  Chattopadhyay, Sankha ^a   Xue, Baogang ^a   Collins, Daphne ^a   Pichika, Rama ^a   Bagnera, Rudy ^b   Leslie, Frances M ^b   Christian, Bradley T ^c   Shi, Bingzhi ^c   Narayanan, Tanjore K ^c   Potkin, Steven G ^a   Mukherjee, Jogeshwar ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c KETTERING MEDICAL CENTER   (United States)

Author keywords

4 2 nicotine receptors; 18F; Nifrolidine; PET

Indexed keywords

CYSTEINE; FLUORINE 18; IODINE 125; NICOTINE; NICOTINIC RECEPTOR; NIFROLIDINE F 18; RADIOLIGAND; TRACER; UNCLASSIFIED DRUG; 5 (3' FLUOROPROPYL) 3 (2 PYRROLIDINYLMETHOXY)PYRIDINE; 5-(3'-FLUOROPROPYL)-3-(2-PYRROLIDINYLMETHOXY)PYRIDINE; DIAGNOSTIC AGENT; NICOTINIC RECEPTOR ALPHA4BETA2; PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT;

ANESTHESIA; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BINDING AFFINITY; BRAIN REGION; BRAIN SLICE; DEPROTECTION REACTION; DRUG SCREENING; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; MALE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIMATE; PRIORITY JOURNAL; RADIOCHEMISTRY; RAT; RHESUS MONKEY; SCINTISCANNING; ANIMAL; BRAIN; CHEMISTRY; EVALUATION; MACACA; METABOLIC CLEARANCE RATE; METABOLISM; METHODOLOGY; PROTEIN BINDING; SPRAGUE DAWLEY RAT; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; BRAIN; ISOTOPE LABELING; MACACA MULATTA; MALE; METABOLIC CLEARANCE RATE; POSITRON-EMISSION TOMOGRAPHY; PROTEIN BINDING; PYRIDINES; PYRROLIDINES; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, NICOTINIC; TISSUE DISTRIBUTION;

EID: 15044345704     PISSN: 01615505     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Romanelli MN, Gualtieri F. Cholinergic nicotinic receptors: competitive ligands, allosteric modulators, and their potential applications. Med Res Rev. 2003;23:393-426.
2. Lukas RJ. Diversity and patterns of regulation of nicotinic receptor subtypes. Ann NY Acad Sci. 1995;757:153-168.
3. Levin ED. Nicotine receptor subtypes and cognitive function. J Neurobiol. 2002;53:633-640.
4. Paterson D, Nordberg A. Neuronal nicotinic receptors in the human brain. Prog Neurobiol. 2000;61:75-111.
5. Benowitz NL. Pharmacology of nicotine: addiction and therapeutics. Annu Rev Pharmacol Toxicol. 1996;36:597-613.
6. 3H]nicotine binding sites in human brain. J Neurochem. 1988;50:1243-1247.
7. 11C-nicotine in the human brain: difficulties in visualizing specific receptor binding in vivo. Psychopharmacology. 1994;115:31-36.
8. Badio B, Daly JW. Epibatidine, a potent analgetic and nicotinic agonist. Mol Pharmacol. 1994;45:563-569.
9. Sihver W, Nordberg A, Langstrom B, et al. Development of ligands for in vivo imaging of cerebral nicotinic receptors. Behav Brain Res. 2000;113:143-157.
10. 11C]methyl-2-(S)- pyrrolidinylmethoxy)pyridine, a high affinity ligand for studying nicotinic acetylcholine receptors by positron emission tomography. Bioorg Med Chem. 2001;9:3055-3058.
11. 11C-methyl-A- 85380 as an imaging agent as an imaging agent for PET investigations of brain nicotinic acetylcholine receptors. J Nucl Med. 2004;45:878-884.
12. 2 receptor imaging with PET. Bioorg Med Chem. 2003;11:5333-5343.
13. 123I-5-I-A85380 in healthy human subjects. Eur J Nucl Med. 2002;29:183-190.
14. 18F]F-A-85380: PET imaging of brain nicotinic acetylcholine receptors and whole body distribution in humans. FASEBJ. 2003;17:1331-1333.
15. 18F-fluoro-A-85380 in healthy volunteers. J Nucl Med. 2003;44:596-601.
16. 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.
17. Lena C, Changeaux J-P. Allosteric modulations of the nicotinic acetylcholine receptor. Trends Neurosci. 1993;16:181-186.
18. Ochoa ELM, Chattopadhyay A, McNamee MG. Desensitization of the nicotinic acetylcholine receptor: molecular mechanisms and effect of modulators. Cell Mol Neurobiol. 1989;9:141-178.
19. Lin NH, Gunn DE, Li Y, et al. Synthesis and structure-activity relationships of pyridine modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy] pyridine, A-84543: a potent nicotinic acetylcholine receptor agonist. Bioorg Med Chem Lett. 1998;8:249-254.
20. Lin NH, Li Y, He Y, et al. Synthesis and structure-activity relationships of 5-substituted pyridine analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543: a potent nicotine receptor ligand. Bioorg Med Chem Lett. 2001;11:631-633.
21. Abreo MA, Lin NH, Garvey DS, et al. Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors. J Med Chem. 1996;39:817-825.
22. 18F]FA binding to nicotinic acetylcholine receptors in rhesus monkey brain. Synapse. 2003;48:25-34.
23. 123I-5- Iiodo-3-pyridyl ethers: synthesis and binding to neuronal nicotinic acetylcholine receptors. Nucl Med Biol. 2001;28:911-921.
24. Lin N-H, He Y, Holladay MW, Ryther K, Li Y, inventors; Abbott Laboratories assignee. 3-Pyridyloxymethyl heterocyclic ether compounds useful in controlling chemical synaptic transmission. US patent 5 629 325. May 13, 1997.
25. Comins DL, Killpack DL. Lithiation of methoxypyridines directed by a-amino alkoxides. J Org Chem. 1990;55:69-73.
26. Perry DC, Xiao Y, Nguyen HN, Musachio JL, Davila-Garcia MI, Kellar KJ. Measuring nicotinic receptors with characterisitcs of α4β2, α3β2 and α3β4 subtypes in rat tissues by autoradiography. J Neurochem. 2002;82:468-481.
27. Ospina JA, Broide RS, Acevedo D, Robertson RT, Leslie FM. Calcium regulation of agonist binding to a7-type nicotinic acetylcholine receptors in adult and fetal rat hippocampus. J Neurochem. 1998;70:1061-1068.
28. 11C-(R,S)-5-hydroxy-2-(di-n-propylamino)tetralin in rodents and nonhuman primate. Synapse. 2000;37:64-70.
29. Mukherjee J, Yang ZY, Das MK, Brown T. Fluorinated benzamide neuroleptics-3: development of (S)-N-[(1-allyl-2-pyrrolidinyl)methyl]-5-(3-[F- 18]fluoropropyl)-2,3-dimethoxybenzamide as an improved dopamine D-2 receptor tracer. Nucl Med Biol. 1995;22:283-296.
30. 18F-fluorophenylthio)benzylamine as a serotonin transporter imaging agent. Appl Radiat Isot. 2003;58:183-191.
31. 125I-a-bungaratoxin binding sites in the brain of Macca mulatta. J Comp Neurol. 2003;461:49-60.
32. Carroll FI, Lee JR., Navarro HA, et al. Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-exo-2-(2′,3′-disubstituted-5′-pyridinyl)-7-azabicyclo[2.2.1] heptanes: epibatidine analogues. J Med Chem. 2002;45: 4755-4761.
33. 18F-A85380). J Labelled Compds Radiopharm. 1998;41:309-318.
34. Dolle F, Dolci L, Valette H, et al. Synthesis and nicotinic acetylcholine receptor 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. 1999;42:2251-2259.