Synthesis and characterization of iodine-123 labeled 2β-carbomethoxy-3β-(4′-((Z)-2-iodoethenyl)phenyl)nortropane. A ligand for in vivo imaging of serotonin transporters by single-photon-emission tomography

Journal of Medicinal Chemistry

Volumn 46, Issue 6, 2003, Pages 925-935

  Goodman, Mark M ^a   Chen, Ping ^a   Plisson, Christophe ^a   Martarello, Laurent ^a   Galt, James ^a   Votaw, John R ^a   Kilts, Clinton D ^a   Malveaux, Gene ^a   Camp, Vernon M ^a   Shi, Bing ^a   Ely, Timothy D ^a   Howell, Leonard ^b   McConathy, Jon ^a   Nemeroff, Charles B ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2BETA CARBOMETHOXY 3BETA (4' 2 IODOETHENYL)PHENYL)NORTROPANE; 2BETA CARBOMETHOXY 3BETA (4' 2 TRIBUTYLSTANNYLETHENYL)PHENYL)NORTROPANE; 3BETA (4 CHLOROPHENYL) 2BETA TROPANECARBOXYLIC ACID PHENYL ESTER; 3BETA (4' (2 TRIMETHYLSTANNYLETHENYL)PHENYL)NORTROPANE; ALCOHOL; CITALOPRAM; DOPAMINE TRANSPORTER; FLUVOXAMINE; HYDROGEN PEROXIDE; IODINE 123; MONOAMINE OXIDASE INHIBITOR; NISOXETINE; NORADRENALIN TRANSPORTER; NORTROPANE DERIVATIVE; REBOXETINE; SEROTONIN TRANSPORTER; SODIUM IODIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN MAPPING; CONTROLLED STUDY; CORPUS STRIATUM; DIENCEPHALON; DRUG BINDING; DRUG DISTRIBUTION; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG SYNTHESIS; EMBRYO; FEMALE; HUMAN; HYPOTHALAMUS; IN VITRO STUDY; IN VIVO STUDY; MALE; MONKEY; NONHUMAN; PONS; PREFRONTAL CORTEX; RADIOACTIVITY; RAT; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STRUCTURE ANALYSIS;

ANIMALS; BINDING, COMPETITIVE; BRAIN; CARRIER PROTEINS; FEMALE; HELA CELLS; HUMANS; IODINE RADIOISOTOPES; ISOTOPE LABELING; LIGANDS; MACACA FASCICULARIS; MALE; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; NERVE TISSUE PROTEINS; NORTROPANES; RADIOLIGAND ASSAY; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; SEROTONIN; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 0037435050     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0100180     Document Type: Article

References (34)

1. Owens, M. J.; Nemeroff, C. B. The Serotonin Transporter and Depression. Depression Anxiety 1998, 8 (Suppl. 1), 5-6.
2. Perry, E. K.; Marshall, E. F.; Blesses, G.; Tomlinson, B. E.; Perry, R. H. Decreased Imipramine Binding in the Brains of Patients with Depressive Illness. Br. J. Psychiatry 1983, 142, 188-192.
3. 3H]imipramine Binding Sites Are Decreased in the Frontal Cortex of Suicides. Science 1982, 216, 1337-1339.
4. Leake, A.; Fairbairn, A. F.; McKeith, I. G.; Ferrier, I. N. Studies on the Serotonin Uptake Binding Site in Major Depressive Disorder and Control Post-Mortem Brain: Neurochemical and Clinical Correlates. Psychiatry Res. 1991, 39, 31-35.
5. Owens, M. J.; Nemeroff, C. B. Role of Serotonin in the Pathophysiology of Depression: Focus on the Serotonin Transporter. Clin. Chem. 1994, 40, 288-295.
6. Palmer, A. M.; Francis, P. T.; Benton, J. S.; et al. Presynaptic Serotonergic Dysfunction in Patients with Alzheimer's Disease. J. Neurochem. 1987, 48, 8-15.
7. 3H]-Imipramine Binding Sites in Control and Parkinsonian Brain. Eur. J. Pharmacol. 1985, 117, 71-80.
8. 3H]Citalopram. Neuroscience 1993, 54, 691-699.
9. Squier, M. V.; Jalloh, S.; Hilton-Joneees, D.; Series, H. Death After Ectasy Ingestion: Neuropathological Findings. J. Neurol., Neurosurg. Psychiatry 1995, 58, 756.
10. Ritz, M. C.; Lamb, R. J.; Goldberg, S. R.; Kuhar, M. J. Cocaine Receptors on Dopamine Tranporters Are Related to Self-Administration of Cocaine. Science 1987, 237, 1219-1223.
11. Chumpradit, S.; Kung, M. P.; Panyachotipun, C.; Prapansiri, V.; Foulon, C.; Brooks, B. P.; Szabo, S. A.; Tejan-Buut, S.; Frazer, A.; Kung, H. F. Iodinated Tomoxetine Derivatives as Selective Ligands for Serotonin and Norepinephrine Uptake Sites. J. Med. Chem. 1994, 37, 1220-1223.
12. Kung, M. P.; Chumpradit, S.; Billings, J.; Kung, H. F. 4-Iodtomoxetine: A novel ligand for serotonin uptake sites. Life Sci. 1992, 51, 95-106.
13. 3H]6-Nitroquipazine Binding Sites in Rat Brain. Eur. J. Pharmacol. 1990, 180, 273-281.
14. 3H]6-Nitroquipazine to Cortical Membranes in the Rat: Inhibition by 5-Hydroxytryptamine and 5-Hydroxytryptamine Uptake Inhibitors. Neuropharmacology 1991, 30, 113-117.
15. 3H]6-Nitroquipazine. J. Pharmacol. Exp. Ther. 1990, 255, 146-153.
16. 123I]-5-Iodo-6-nitroquipazine. Eur. J. Pharmacol. 1993, 242, 189-193.
17. Jagust, W. J.; Eberling, J. L.; Biegon, A.; Taylor, S.; VanBrocklin, H.; Jordon, S.; Hanrahan, S. M.; Roberts, J. A.; Brennan, K. M.; Mathis, C. A. Iodine-123 5-Iodo-6-nitroquipazine: SPECT radiotracer to image the serotonin transporter. J. Nucl. Med. 1996, 37, 1207-1214.
18. Oya, S.; Choi, S. R.; Hou, C.; Mu, M.; Kung, M.-P.; Acton, P. D.; Siciliano, M.; Kung, H. F. 2-((2-((Dimethylamino)methyl)-phenyl)thio)-5-iodophenylamine (ADAM): An Improved Serotonin Transporters Ligand. Nucl. Med. Biol. 2000, 27, 249-254.
19. 125I]ADAM to Serotonin Transporters in Rat Brain. Synapse 2000, 38, 403-412.
20. 123I]ADAM and SPECT. J. Nucl. Med. 2001, 42, 1556-1562.
21. Boja, J. W.; Kuhar, M. J.; Kopajtic, T.; Yang, E.; Abraham, P.; Lewin, A. H.; Carroll, F. I. Secondary Amine Analogues of 3β-(4′-Substituted phenyl)tropane-2β-carboxylic Acid Esters and N-Norcocaine Exhibit Enhanced Affinity for Serotonin and Norepinephrine Transporters. J. Med. Chem. 1994, 37, 1220-1223.
22. 123I]beta-CIT Binding to Dopamine and Serotonin Transporters. Eur. J. Nucl. Med. 1996, 23, 431-436.
23. Kuikka, J. T.; Tiihonen, J.; Bergstron, K. A.; Karhu, J.; Haartikainen, P.; Viinamaki, H.; Lansimies, E.; Lehtonen, J.; Hakola, P. Imaging of Serotonin and Dopamine Transporters in the Living Human Brain. Eur. J. Nucl. Med. 1995, 222, 3346-350.
24. Booij, J.; Knol, R. J.; Reneman, L.; de Bruin, K.; Janssen, A. G. M.; Royen, E. A. Iodine-123 labelled nor-β-CIT binds to the serotonin transporter in vivo as assessed by biodistribution studies in rats. Eur. J. Nucl. Med. 1998, 25, 1666-1669.
25. Davies, H. M.; Kuhn, L. A.; Thornley, C.; Matasi, J. J.; Sexton, T.; Childers, S. R. Synthesis of 3β-Aryl-8-azabicyclo [3.2.1]octanes with High Binding Affinities and Selectivities for the Serotonin Transporter Site. J. Med. Chem. 1996, 39, 2554-2558.
26. Blough, B. E.; Abraham, P.; Mills, A. C.; Lewin, A. H.; Boja, J. W.; Scheffel, U.; Kuhar, M. J.; Carroll, F. I. 3β-(4-Ethyl-3-iodophenyl)nortropane-2β-carboxylic acid methyl ester as a high-affinity selective ligand for the serotonin transporter. J. Med. Chem. 1996, 39, 4027-4035.
27. Brent, D. A.; Sabatka, J. A.; Minick, D. J.; Henry, D. W. A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships. J. Med. Chem. 1982, 26, 1014-1020.
28. Moerlein, S. M.; Laufer, P.; Stocklin, G. Effect of lipophilicity on the in vivo localization of radiolabeled spiperone analogues. Int. J. Nucl. Biol. 1985, 12, 353-356.
29. 18F]Fluoroethyl)-spiperone: A novel ligand for cerebral dopamine receptor studies with PET. Life Sci. 1987, 40, 81-88.
30. 18F labeled spiperone analog for positron emission tomographic studies of the dopamine receptor. Nucl. Med. Biol. 1988, 1, 83-97.
31. 2 radioligands 1. Regional rat brain distribution of iodinated benzamides. J. Nucl. Med. 1991, 32, 1593-1600.
32. 11C-labeled 2-(phenylthio)araalkylamines. J. Med. Chem. 2000, 43, 3103-3110.
33. 18F-Labeled FECNT: A selective dopamine transporter radioligand for PET. Nucl. Med. Biol. 2000, 27, 1-12.
34. Zea-Ponce, Y.; Baldwin, R. M.; Laurelle, M.; Wang, S.; Neumeyer, J. L.; Innis, R. B. Simplified multidose preparation of iodine-123-β-CIT: A marker for dopamine transporters. J. Nucl. Med. 1995, 36, 525-529.