N-substituted analogs of 2β-carbomethoxy-3β-(4′-iodophenyl)tropane (β-CIT) with selective affinity to dopamine or serotonin transporters in rat forebrain

Journal of Medicinal Chemistry

Volumn 39, Issue 2, 1996, Pages 543-548

  Neumeyer, John L ^a   Tamagnan, Gilles ^a   Wang, Shaoyin ^a   Gao, Yigong ^a   Milius, Richard A ^a   Kula, Nora S ^b   Baldessarini, Ross J ^b  

^a Research Biochemicals International   (United States)

^b MASSACHUSETTS GENERAL HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 (BENZHYDRYLOXY)ETHYL] 4 (3 PHENYLPROPYL)PIPERAZINE; 1 [2 [BIS(4 FLUOROPHENYL)METHOXY]ETHYL] 4 (3 PHENYLALLYL)PIPERAZINE DIMESILATE; 3BETA (4 IODOPHENYL) 2BETA TROPANECARBOXYLIC ACID METHYL ESTER; COCAINE DERIVATIVE; DOPAMINE RECEPTOR; MAZINDOL; N (2 FLUOROETHYL) 3BETA (4 IODOPHENYL) 2BETA NORTROPANECARBOXYLIC ACID METHYL ESTER; N (3 FLUOROPROPYL) 3BETA (4 IODOPHENYL) 2BETA NORTROPANECARBOXYLIC ACID METHYL ESTER; NOMIFENSINE; PAROXETINE; SEROTONIN RECEPTOR; TROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DEPRESSION; DOPAMINE RELEASE; DOPAMINERGIC NERVE CELL; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; FOREBRAIN; MOUSE; NERVE DEGENERATION; NEUROTRANSMISSION; NONHUMAN; PARKINSON DISEASE; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; CARRIER PROTEINS; COCAINE; DOPAMINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; MOLECULAR PROBES; NERVE TISSUE PROTEINS; PROSENCEPHALON; RADIOLIGAND ASSAY; RATS; SEROTONIN; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 0030070681     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9505324     Document Type: Article

References (33)

1. 3H]cocaine binding in central nervous system of mouse. Life Sci. 1980, 27, 1055-1062.
2. Kenney, L. T.; Hanbauer, I. Sodium-sensitive cocaine binding to rat striatum membrane: possible relationship to dopamine uptake sites. J. Neurochem. 1983, 41, 172-178.
3. Calligaro, D. O.; Elderfrawi, M. E. Central and peripheral cocaine receptors. J. Pharmacol. Exp. Ther. 1987, 243, 61-67.
4. 3H]cocaine in striatum and its relationship to the dopamine transporter. Membr. Biochem. 1988, 7, 87-106.
5. 3H]Cocaine binding sites in caudate-putamen. J. Pharmacol. Exp. Ther. 1989, 251, 131-141.
6. Reith, M. E.; Meisler, B. E.; Sershen, H.; Lajtha, A. Structure requirements for cocaine congeners to interact with dopamine and serotonin uptake sites in mouse brain and to induce stereotyped behavior. Biochem. Pharmacol. 1986, 35, 1123-1129.
7. Ritz, M. C.; Lamb, R. J.; Goldberg, S. R.; Kuhar, M. J. Cocaine receptors on dopamine transporters are related to self-administration of cocaine. Science 1987, 237, 1219-1223.
8. Bergman, J.; Madras, B. K.; Spealman, R. D. Effects of cocaine and related drugs in nonhuman primates. III. Self-administration by squirrel monkeys. J. Pharmacol. Exp. Ther. 1989, 251, 150-155.
9. 3H]cocaine binding associated with dopamine uptake sites in the rat striatum and human putamen decrease after dopaminergic denervation and in Parkinson's disease. Naunyn-Schmiedeberg's Arch. Pharmacol. 1985, 329, 227-235.
10. 123I]-2β-carbomethoxy-3β-(4-iodophenyl)tropane: High affinity SPECT radiotracer of monoamine reuptake sites in brain. J. Med. Chem. 1991, 34, 3144-3146.
11. 123I]-CIT. Eur. J. Pharmacol. 1991, 200, 369-370.
12. 123I]β-CIT: pharmacological characterization of brain uptake in nonhuman primates, Synapse 1993, 13, 295-309.
13. 123I]β-CIT) in non-uman primates: Pharmacokinetics, biodistribution and SPECT brain imaging coregistered with MRI. Nucl. Med. Biol. 1993, 20, 597-606.
14. Shaya, E. K.; Schettel, U.; Dannals, R. F.; Ricaurte, G. A.; Carroll, F. I.; Wagner, H. N.; Kuhar, M. J. In vivo imaging of dopamine reuptake sites in the primate brain using single photon emission computed tomography (SPECT) and iodine-123 labeled RTI-55. Synapse 1992, 10, 1169-1172.
15. 11C]CFT. Synapse 1993, 15, 130-142.
16. Carroll, F. I.; Gao, Y.; Rahman, M. A.; Abraham, P.; Lewin, A. H.; Parham, K A.; Boja, J. W.; Kuhar, M. J. Synthesis, Ligand binding, QSAR, and CoMFA study of 3β-(p-substitued phenyl)-tropane-2β-carboxylic acid methyl ester. J. Med. Chem. 1992, 35, 2719-2725.
17. 11C]WIN 35,428 reveals marked declines in mild Parkinson's disease. Ann. Neurol. 1993, 34, 423-431.
18. Innis, R. B.; Seibyl, J. B.; Scanley, B. E.; Laurelle, M.; Abi-Dargham, A.; Wallance, E.; Baldwin, R. M.; Zea-Ponce, Y.; Zoghbi, S.; Wang, S.; Gao, Y.; Neumeyer, J. L.; Charney, D. S.; Hoffer, P. B.; Marek, K. L. SPECT Imaging demonstrates loss of striatal monoamine transporters in Parkinson's disease. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11965-11969.
19. Neumeyer, J. L.; Wang, S.; Gao, Y.; Milius, R. A.; Kula, N. S.; Campbell, A.; Baldessarini, R. J.; Zea-Ponce, Y.; Baldwin, R. M.; Innis, R. B. N-ω-fluoroalkyl analogs of (1R)-2β-carbomethoxy3β-(4-iodophenyl)tropane (β-CIT): Radiotracers for PET and SPECT imaging of dopamine transporters. J. Med. Chem. 1994, 37, 1558-1561.
20. 18F-labelled analogues of β-CIT labelling in different positions and PET evaluation in cynomolgus monkeys. Abstract submitted for Eleventh International Symposium on Radiopharmaceutical Chemistry in Vancouver, BC, Canada, August 13-17, 1995.
21. 11C]β-CIT-FP, a potential PET radioligand for quantilation of the dapamine transporter, preparation, autoradiography, metabolite studies and PET examinations. Nucl. Med. Biol. 1995, in press.
22. Kuikka, J. T.; Bergstrom, K. A.; Ahonen, A.; Hiltunen, J.; Haukka, J.; Lansimies, E.; Wang, S.; Neumeyer, J. L. Comparison of iodine-123 labeled 2β-carbomethoxy-3β-(4-iodophenyl)-tropane and 2β-carbomethoxy-3β-(4-iodophenyl)-N-(3-fluoropropyl)nortropane for imaging of the dopamine transporter in the living human brain. Eur. J. Nucl. Med. 1995, 22, 356-360.
23. 123I]N-ω-fluoroalkyl-2β-carboxy-3β-(4-iodophenyl) nortropane esters in baboons. Nucl. Med. Biol. 1995, 22, 211-219.
24. 3H]GBR-12935 binding in vitro to rat striatial membranes: Labeling of the dopamine uptake complex. J. Neurochem. 1987, 48, 1887-1896.
25. Kula, N. S.; Baldessarini, R. J. Lack of increase in dopamine transporter binding or function in rat brain tissue after treatment with blockers of neuronal uptake of dopamine. Neuropharmacology 1991, 30, 89-92.
26. 3H]paroxetine binding to rat cortical membranes. Eur. J. Pharmacol. 1985, 118, 107-114.
27. 3H]Nisoxetine: A radioligand for quantitation of norepinephrine uptake sites by autoradiography or by homogenate binding. J. Pharmacol. Exp. Ther. 1992, 260, 427-436.
28. Baldessarini, R. Drugs and the treatment of psychiatric disorders: Antimanic and antidepressant agents. In Goodman and Gilman's The Pharmacologic Basis of Therapeutics, 9th Ed.; Harden, W., Rudin, W., Molinoff, P. B., Rall, T., Eds.; McGraw-Hill Press: New York, 1995; Chapter 19.
29. Abraham, P.; Pitner, J. B.; Lewin, A. H.; Kuhar, M. J.; Carroll, F. I. N-Modified analogues of cocaine: Synthesis and inhibition of binding to the cocaine receptor. J. Med. Chem. 1992, 35, 141-144.
30. Kozikowski, A. P.; Saiah, M. K. E.; Bergmann, J. S.; Johnson, K. M. Structure-activity relationship studies of N-sulfonyl analogs of cocaine of ionic interaction in cocaine binding. J. Med. Chem. 1994, 37, 3440-3442.
31. DeLean, A.; Munson, P. J.; Rodbard, D. Simultaneous analysis of families of sigmoid curves: Application to bioassay, radioligand, and physiological dose-response curves. Am. J. Physiol. 1978, 4, E97-E102.
32. Teicher, M. H. Med-65, ALLFIT, GRAFIT (Applesoft); Vanderbilt University Biomedical Computing Technology Information Center: Nashville, TN, 1983.
33. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.