Synthesis and comparison of 4-[18F]F-ADAM, 2-[18F]F-ADAM, N-Desmethyl-4-[18F]F-ADAM and [18F]F-AFM as serotonin transporter imaging agents

Applied Radiation and Isotopes

Volumn 70, Issue 10, 2012, Pages 2298-2307

  Huang, Ya Yao ^a,b   Huang, Wen Sheng ^a   Ma, Kuo Hsing ^c   Chou, Ta Kai ^a   Kuo, Yu Yeh ^c   Cheng, Cheng Yi ^a   Shiue, Chyng Yann ^a,b  

^a TRI SERVICE GENERAL HOSPITAL   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY HOSPITAL   (Taiwan)

^c NATIONAL DEFENSE MEDICAL CENTER   (Taiwan)

Author keywords

2 18F F ADAM; 4 18F F ADAM; 18F F AFM; N Desmethyl 4 18F F ADAM; PET; Serotonin transporter imaging agents

Indexed keywords

2-[18F]F-ADAM; 4-[18F]F-ADAM; [18F]F-AFM; IMAGING AGENT; N-DESMETHYL-4-[18F]F-ADAM;

POLYETHYLENE TEREPHTHALATES; RADIATION;

ISOTOPES;

2 (2 FLUORO 4 AMINOPHENYLTHIO)BENZOIC ACID; 2 (4 BROMO 2 NITROPHENYLTHIO)BENZOIC ACID; 2 (4 FLUORO 2 NITROPHENYLTHIO)BENZOIC ACID; 2 [[2 AMINO 4 (FLUOROMETHYL)PHENYL]THIO] N,N DIMETHYLBENZENE METHANAMINE F 18; DIAGNOSTIC AGENT; N METHYL 2 (2 AMINO 4 FLUOROPHENYLTHIO)BENZYLAMINE; N METHYL 2 (2 AMINO 4 FLUOROPHENYLTHIO)BENZYLAMINE F 18; N METHYL 2 (4 BROMO 2 NITROPHENYLTHIO)BENZAMIDE; N METHYL 2 (4 BROMO 2 NITROPHENYLTHIO)BENZYLAMINE; N METHYL 2 (ALPHA FLUORO 2 NITROPHENYLTHIO)BENZAMIDE; N METHYL N TERT BUTOXYCARBONYL 2 (4 BROMO 2 NITROPHENYLTHIO)BENZYLAMINE; N,N DIMETHYL 2 (2 AMINO 4 FLUOROPHENYLTHIO)BENZYLAMINE F 18; N,N DIMETHYL 2 (2 FLUORO 4 AMINOPHENYLTHIO)BENZAMIDE; N,N DIMETHYL 2 (2 FLUORO 4 AMINOPHENYLTHIO)BENZYLAMINE; N,N DIMETHYL 2 (2 FLUORO 4 AMINOPHENYLTHIO)BENZYLAMINE F 18; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; DRUG BINDING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; ENERGY YIELD; IN VIVO STUDY; MALE; MESENCEPHALON; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOACTIVITY; RAT;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORINE RADIOISOTOPES; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; RATS; RATS, SPRAGUE-DAWLEY; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS;

EID: 84864500152     PISSN: 09698043     EISSN: 18729800     Source Type: Journal    
DOI: 10.1016/j.apradiso.2012.06.005     Document Type: Article

References (52)

1. Boja J.W., Kuhar M.J., Kopajtic T., Yang E., Abraham P., Lewin A.H., Carroll F.I. Secondary Amine Analogs of 3. beta.-(4'-Substituted phenyl) tropane-2. beta.-carboxylic Acid Esters and N-Norcocaine Exhibit Enhanced Affinity for Serotonin and Norepinephrine Transporters. J Med Chem. 1994, 37(8):1220-1223.
2. Brucke T., Kornhuber J., Angelberger P., Asenbaum S., Frassine H., Podreka I. SPECT imaging of dopamine and serotonin transporters with [123I]beta-CIT. Binding kinetics in the human brain. J Neural Transm Gen Sect 1993, 94(2):137-146.
3. 18F] fluoromethyl)-(+)-McN5652. Synapse 2003, 47(2):143-151.
4. 18F] fluoromethyl)-(+)-McN5652. Neuropsychopharmacology 2003, 28(11):2010-2019.
5. Brust P., Hesse S., Mueller U., Szabo Z. Neuroimaging of the Serotonin Transporter: Possibilities and Pitfalls. Curr Psychiatry Rev 2006, 2(1):111-149.
6. 11C](+)McN-5652: assessment of methods. J Cereb Blood Flow Metab. 2000, 20(2):253-262.
7. Emond P., Vercouillie J., Innis R., Chalon S., Mavel S., Frangin Y., Halldin C., Besnard J.C., Guilloteau D. Substituted diphenyl sulfides as selective serotonin transporter ligands: synthesis and in vitro evaluation. J Med Chem. 2002, 45(6):1253-1258.
8. 18F]-ADAM) as a serotonin transporter imaging agent. Appl Radiat Isot 2004, 61(6):1247-1254.
9. Frazer A. Antidepressants. J Clin Psychiatry 1997, 58(Suppl. 6):9-25.
10. 18F]fluorobenzyl) methylamino) methylphenylsulfanyl) benzonitrile, an F-18 fluorobenzyl analogue of DASB: synthesis, in vitro binding, and in vivo biodistribution studies. Bioconjug Chem. 2007, 18(5):1612-1618.
11. 11C]-DASB binding to the human serotonin transporter: modeling strategies. J Cereb Blood Flow Metab. 2001, 21(11):1342-1353.
12. 11C] cyanoimipramine. Int J Rad Appl Instrum B 1987, 14(6):587-592.
13. Hesse, S., Brust, P., Mäding, P., Becker, G.A., Patt, M., Seese, A., Sorger, D., Zessin, J., Meyer, P.M. and Lobsien, D., 2012. Imaging of the brain serotonin transporters (SERT) with 18F-labelled fluoromethyl-McN5652 and PET in humans. Eur J Nucl Med Mol Imaging, Published online: 17 February 2012.
14. Horschitz S., Hummerich R., Schloss P. Down-regulation of the rat serotonin transporter upon exposure to a selective serotonin reuptake inhibitor. Neuroreport 2001, 12(10):2181-2184.
15. 18F-ADAM PET in healthy and drug-naïve depressant subjects. J Nucl Med 2007, 48(Suppl. 2):261P.
16. 11C]AFM). Nucl Med Biol. 2004, 31(5):543-556.
17. Huang Y., Bae S.A., Zhu Z., Guo N., Roth B.L., Laruelle M. Fluorinated diaryl sulfides as serotonin transporter ligands: synthesis, structure-activity relationship study, and in vivo evaluation of fluorine-18-labeled compounds as PET imaging agents. J Med Chem. 2005, 48(7):2559-2570.
18. Huang Y., Zheng M.Q., Gerdes, J.M. Development of effective PET and SPECT imaging agents for the serotonin transporter: has a twenty-year journey reached its destination?. Curr Top Med Chem. 2010, 10(15):1499-1526.
19. 18F]-ADAM,a potent serotonin transporter imaging agent. Appl. Radiat. Isot 2009, 67(6):1063-1067.
20. 18F]AFM as Sert Imaging Agents in Rats Using μPET. J Nucl Med. 2009, 52(Suppl. 2):358P.
21. 18F]-ADAM in rats and monkeys Eur J Nucl Med Mol Imaging 2010, 37(3):545-555.
22. Hume S., Pascali C., Pike V., Turton D., Ahier R., Myers R., Bateman D., Cremer J., Manjil L., Dolan R. Citalopram: labelling with carbon-11 and evaluation in rat as a potential radioligand for in vivo PET studies of 5-HT re-uptake sites. Int J Rad Appl Instrum B 1991, 18(3):339-351.
23. Jarkas N., Votaw J.R., Voll R.J., Williams L., Camp V.M., Owens M.J., Purselle D.C., Bremner J.D., Kilts C.D., Nemeroff C.B. Carbon-11 HOMADAM: A novel PET radiotracer for imaging serotonin transporters. Nucl Med Biol. 2005, 32(3):211-224.
24. 18F]fluoromethyl)-(+)-McN5652. Eur Neuropsychopharmacology 2003, 13(5):387-397.
25. 123I]Β-CIT binding to dopamine transporters in healthy human subjects. J Cereb Blood Flow Metab. 1994, 14(6):982-994.
26. Li I.H., Huang W.S., Shiue C.Y., Huang Y.Y., Liu R.S., Chyueh S.C., Hu S.H., Liao M.H., Shen L.H., Liu J.C., Ma K.H. Study on the neuroprotective effect of fluoxetine against MDMA-induced neurotoxicity on the serotonin transporter in rat brain using micro-PET. NeuroImage. 2009, 49(2):1259-1270.
27. 11C-MADAM binding to the serotonin transporter in the human brain. J. Nucl. Med. 2005, 46(9):1505-1515.
28. 18F]-ADAM as a SERT imaging agent using micro-PET and autoradiography. Neuroimage 2009, 45(3):687-693.
29. Mann J.J. Role of the serotonergic system in the pathogenesis of major depression and suicidal behavior. Neuropsychopharmacology 1999, 21(2 Suppl):99S-105S.
30. 18F]fluoromethyl-(+)-McN5652, a PET tracer for the serotonin transporter: Evaluation in rats. Synapse 2003, 47(1):45-53.
31. Meltzer C.C., Smith G., DeKosky S.T., Pollock B.G., Mathis C.A., Moore R.Y., Kupfer D.J., Reynolds C.F. Serotonin in aging, late-life depression, and Alzheimer's disease: the emerging role of functional imaging. Neuropsychopharmacology 1998, 18(6):407-430.
32. 18F-fluoxetine in the rodent brain: an in vitro and in vivo study. Nucl Med Biol 1998, 25(7):605-610.
33. 11C] AFM provides high specific binding signals in humans. J Nucl Med. 2008, 49(Supp 1):80P.
34. 123I-ADAM: a serotonin transporter imaging agent. J Nucl Med. 2004, 45(5):834-841.
35. 11C-HOMADAM binding to the serotonin transporter in the healthy human brain. J Nucl Med. 2008, 49(12):2018-2025.
36. 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 transporter ligand. Nucl Med Biol. 2000, 27(3):249-254.
37. 18F]ACF (2-[(2-amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine). J Med Chem 2002, 45(21):4716-4723.
38. Parhi A.K., Wang J.L., Oya S., Choi S.R., Kung M.P., Kung H.F. 2-(2'-((dimethylamino) methyl)-4'-(fluoroalkoxy)-phenylthio) benzenamine derivatives as serotonin transporter imaging agents. J Med Chem. 2007, 50(26):6673-6684.
39. Paxinos G., Watson C. The rat brain in stereotaxic coordinates 1998, Academic Press, San Diego, CA.
40. 18F]-ADAM) for imaging serotonin transporters. Appl Radiat Isot 2008, 66(5):625-631.
41. 11C]fluoxetine in a monkey brain. Nucl Med Biol. 1995, 22(5):613-616.
42. 18F]fluorophenylthio)benzylamine as a serotonin transporter imaging agent. Appl Radiat Isot 2003, 58(2):183-191.
43. 18F]-ADAM): an improved PET radioligand for serotonin transporters. J Nucl Med. 2003, 44(12):1890-1897.
44. Silver I.S., Wurm R.M., Welch R.M., Harrelson J.C. A High Performance Liquid Chromato-Graphic Method for a Novel Serotonin Reuptake Inhibitor 5-Chloro-2-[[2-(dimethylamino) methyl] phenyl] benzyl Alcohol (403U76). J Liq Chrom & Rel Technol 1996, 19(7):1117-1126.
45. 18F] fluoropropyl) paroxetine as a radiotracer for in vivo labeling of serotonin uptake sites by PET. Int J Rad Appl Instrum B 1991, 18(7):791-796.
46. 11C]McN-5652-Z. J Labelled Comp Radiopharm 1992, 31(10):841-848.
47. 18F]fluoroethyl analog of McN5652. Nucl Med Biol. 1996, 23(4):407-412.
48. Tarkiainen J., Vercouillie J., Emond P., Sandell J., Hiltunen J., Frangin Y., Guilloteau D., Halldin C. Carbon-11 labelling of MADAM in two different positions: a highly selective PET radioligand for the serotonin transporter. J Labelled Cpd Radiopharm 2001, 44(14):1013-1023.
49. Waterhouse R.N. Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents. Mol Imaging Biol 2003, 5(6):376-389.
50. Wilson A.A., Houle S. Radiosynthesis of Carbon-11 labelled N-methyl-2-(arylthio) benzylamines: Potential radiotracers for the serotonin reuptake receptor. J Labelled Cpd. Radiopharm 1999, 42(13):1277-1288.
51. 11C-labeled 2-(phenylthio) araalkylamines. J Med Chem. 2000, 43(16):3103-3110.
52. 18F] fluoromethyl)-(+)-McN5652 as a potential PET radioligand for the serotonin transporter. Nucl Med Biol. 2001, 28(7):857-863.