Synthesis and evaluation of iodine-123 labelled tricyclic tropanes as radioligands for the serotonin transporter

Nuclear Medicine and Biology

Volumn 30, Issue 7, 2003, Pages 741-746

  Quinlivan, Mitchell ^a   Mattner, Filomena ^b   Papazian, Vahan ^b   Zhou, Jia ^c   Katsifis, Andrew ^b   Emond, Patrick ^d   Chalon, Sylvie ^d   Kozikowski, Alan ^c   Guilloteau, Denis ^d   Kassiou, Michael ^a,e  

^a University of Sydney   (Australia)

^b AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

^c GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

^d UNIVERSITÉ DE TOURS   (France)

^e ROYAL PRINCE ALFRED HOSPITAL   (Australia)

Author keywords

Iodine 123; Serotonin transporter; SPECT; Tricyclic tropanes

Indexed keywords

10 (BENZOYLOXYMETHYL) 9 (CHLORO 4 IODOBENZYLIDENE) 7 AZATRICYCLO[4.3.1.0 3,7 ]DECANE 1; 9 (3 CHLORO 4 IODOBENZYLIDENE) 7 AZATRICYCLO[4.3.1.0 3,7 ]DECANE 10 CARBOXYLIC ACID METHYL ESTER 2; ACID; CITALOPRAM; IODINE 123; OXIDIZING AGENT; RADIOLIGAND; SEROTONIN TRANSPORTER; TOSYLCHLORAMIDE SODIUM; TROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN REGION; CONTROLLED STUDY; DRUG BINDING; DRUG METABOLISM; DRUG SCREENING; DRUG SYNTHESIS; ENDOCRINE FUNCTION TEST; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INJECTION; ISOTOPE LABELING; LIPOPHILICITY; MALE; NONHUMAN; PRECURSOR; RADIOACTIVITY; RADIOCHEMISTRY; RADIOISOTOPE DISTRIBUTION; RAT;

EID: 10744226409     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(03)00076-3     Document Type: Article

References (24)

1. 123I]ADAM and SPECT. J Nucl Med. 42:2001;1556-1562.
2. 123I]IDAM. Eur J Nucl Med. 26:1999;854-861.
3. Bergstrom K., Halldin C., Hall H., Lundkvist C., Ginovart N., Swahn C., Farde L. In vitro and in vivo characterisation of nor-β-CIT: a potential radioligands for visualisation of the serotonin transporter in the brain. Eur J Nucl Med. 24:1997;596-601.
4. Blough B., Abraham P., Lewin A., Kuhar M., Boja J., Carroll F. Synthesis and transporter binding properties of 3β-(4′-alkyl-, 4′-alkenyl-, and 4′-alkynylphenyl)nortropane-2β-carboxylic acid methyl esters: serotonin transporter selective analogs. J Med Chem. 39:1996;4027-4035.
5. Blough B., Abraham P., Mills A., Lewin A., Boja J., Scheffel U., Kuhar M., Carroll F. 3β-(4-ethyl-3-iodophenyl)nortropane-2β-carboxylic acid methyl ester as a high affinity selective ligand for the serotonin transporter. J Med Chem. 40:1997;3861-3864.
6. Brust P., Scheffel U., Szabo Z. Radioligands for the study of the 5-HT transporter in vivo. IDrugs. 2:1999;129-145.
7. 3H]citalopram . Neuroscience. 54:1993;691-699.
8. 3H-paroxetine labeled serotonin uptake sites in rat brain. Synapse. 1:1987;488-496.
9. Emond P., Helfenbein J., Chalon S., Garreau L., Vercouillie J., Frangin Y., Besnard J., Guilloteau D. Synthesis of tropane and nortropane analogues with phenyl substitutions as serotonin transporter ligands. Bioorg Med Chem. 9:2001;1849-1855.
10. Ferris R., Brieaddy L., Mehta N., Hollingsworth E., Rigdon G., Wang C., Soroko F., Wastila W., Cooper B. Pharmacological properties of 403U76, a new chemical class of 5-hydroxytryptamine- and noradrenaline-reuptake inhibitor. J Pharm Pharmacol. 47:1995;775-781.
11. Helfenbein J., Sandell J., Halldin C., Chalon S., Emond P., Okubo Y., Chou Y., Frangin Y., Douziech L., Gareau L., Swahn C., Besnard J., Farde L., Guilloteau D. PET examination of three potent cocaine derivatives as specific radioligands for the serotonin transporter. Nucl Med Biol. 26:1999;491-499.
12. 11C]DASB. Eur J Nucl Med. 27:2000;1719-1722.
13. Jagust W., Eberling J., Biegon A., Taylor S., VanBrocklin H., Jordon S., Hanrahan S., Roberts J., Brennan K., Mathis C. Iodine-123-5-iodo-6-nitroquipazine SPECT radiotracer to image the serotonin transporter . J Nucl Med. 37:1996;1207-1214.
14. Kessler R., Ansari M., de Paulis T., Schmidt D., Clanton J., Smith H., Manning R., Gillespie D., Ebert M. High affinity dopamine D2 receptor radioligands. 1. Regional rat brain distribution of iodinated benzamides. J Nucl Med. 32:1991;1593-1600.
15. Leake A., Fairbairn A., McKeith I., Ferrier I. Studies on the serotonin uptake binging site in major depressive disorder and control post-mortem brain neurochemical and clinical correlates . Psychiatry Res. 39:1991;155-165.
16. McCann U., Szabo Z., Scheffel U., Dannals R., Ricaurte G. Positron emission tomographic evidence of toxic effect of MDMA ("Ecstasy") on brain serotonin neurons in human beings. Lancet. 352:1998;1433-1437.
17. 11C]DASB PET imaging study. Am J Psychiatry. 158:2001.
18. Oya S., Choi S., Hou C., Mu M., Kung M.-P., Acton P., Siciliano M., Kung H. 2-((2-((Dimethylamino)methyl)phenyl)thio)-5-iodophenylamine (ADAM) An improved serotonin transporter ligand . Nucl Med Biol. 27:2000;249-254.
19. 11C]McN5652. J Nucl Med. 41:2000;1465-1477.
20. Suehiro M., Scheffel U., Dannals R., Ravert H., Ricaurte G., Wagner H.J. A PET radiotracer for studying serotonin uptake sites Carbon-11 McN-5652Z . J Nucl Med. 34:1993;120-127.
21. 11C](+)McN5652. Synapse. 20:1995;37-43.
22. Tejani-Butt S., Yang J., Pawlky A. Altered serotonin transporter sites in Alzheimer's disease raphe and hippocampus. NeuroReport. 6:1995;1207-1210.
23. 123I]-1-(iodopropen-2-yl)-4-[(4-cyanophenoxy)methyl]piperidine . J Med Chem. 40:1997;1657-1667.
24. 3,7]decanes as a novel class of serotonin transporter inhibitors . J Med Chem. 45:2002;1930-1941.