An improved synthesis of 4-[18F]-ADAM, a potent serotonin transporter imaging agent

Applied Radiation and Isotopes

Volumn 67, Issue 6, 2009, Pages 1063-1067

  Huang, Ya Yao ^a,b   Huang, Wen Sheng ^a   Chu, Tieh Chi ^b   Shiue, Chyng Yann ^a  

^a TRI SERVICE GENERAL HOSPITAL   (Taiwan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

4 18F ADAM; 18F; Improved synthesis; Serotonin transporters imaging agent

Indexed keywords

4-[18F]-ADAM; 18F; BENZAMIDE; BENZYLAMINE; IMPROVED SYNTHESIS; MOLECULAR ORBITAL CALCULATIONS; RADIOCHEMICAL YIELDS; RADIOLIGAND; SEROTONIN TRANSPORTERS IMAGING AGENT; SPECIFIC ACTIVITIES; SYNTHESIS TIME; SYNTHETIC METHODS;

AMIDES; AMINES; MOLECULAR ORBITALS;

SYNTHESIS (CHEMICAL);

BENZAMIDE DERIVATIVE; BENZYLAMINE DERIVATIVE; CONTRAST MEDIUM; FLUORINE 18; N,N DIMETHYL 2 (2 AMINO 4 FLUOROPHENYLTHIO)BENZYLAMINE F 18; N,N DIMETHYL 2 (2 NITRO 4 TRIMETHYLAMMONIUMTRIFLUOROMETHANESULFONYLPHENYLTHIO)BENZAMIDE; N,N DIMETHYL 2 (2,4 DINITROPHENYLTHIO)BENZYLAMINE; RADIOLIGAND; RADIOPHARMACEUTICAL AGENT; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOTRON; DIAGNOSTIC IMAGING; POSITRON EMISSION TOMOGRAPHY; PRECURSOR; PRIORITY JOURNAL; RADIOCHEMISTRY; SYNTHESIS;

BENZYLAMINES; FLUORINE RADIOISOTOPES; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS;

EID: 64449083090     PISSN: 09698043     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apradiso.2009.02.090     Document Type: Article

References (27)

1. Brust P., Hesse S., Muller U., and Szabo Z. Neuroimaging of the serotonin transporter-possibilities and pitfalls. Curr. Psychiatry Rev. 2 (2006) 111-149
2. 11C](+)McN-5652: assessment of methods. J. Cereb. Blood Flow Metab. 20 (2000) 253-262
3. Ferris R.M., Brieaddy L., Mehta N., Hollingsworth E., Rigdon G., Wang C., et al. Pharmacological properties of 403U76, a new chemical class of 5-hydroxytryptamine and noradrenaline-reuptake inhibitor. J. Pharm. Pharmacol. 47 (1995) 775-781
4. Frazer A. Antidepressants. J. Clin. Psychiatry 58 Suppl. 6 (1997) 9-25
5. 11C]DASB binding to the human serotonin transporter: modeling strategies. J. Cereb. Blood Flow Metab. 21 (2001) 1342-1353
6. 18F] GBR-13119. J. Labelled Compd. Radiopharm. 27 (1988) 823-833
7. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley, New York
8. Horschitz S., Hummerich R., and Schloss P. Down-regulation of the rat serotonin transporter upon exposure to a selective serotonin reuptake inhibitor. NeuroReport 12 (2001) 2181-2184
9. 11C]AFM). Nucl. Med. Biol. 31 (2004) 543-556
10. Huang Y., Bae S.A., Zhu Z., Guo N., Roth B.L., and 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. 48 (2005) 2559-2570
11. 18F-ADAM PET in healthy and drug-naïve depressant subjects. J. Nucl. Med. 48 Suppl. 2 (2007) 261p
12. 18F]-ADAM, a serotonin transporter imaging agent. In: 2008 World Molecular Imaging Congress, Abstract #1667, Nice, France, September 10-13.
13. Jilek J., Sindelar K., Pomykcek J., Kmonicek V., Sedivy Z., Hrubantova M., et al. Potential antidepressants: 2-(methoxy- and hydroxy-phenylthio)-benzylamines as selective inhibitors of 5 hydroxytryptamine re-uptake in the brain. Collect. Czech. Chem. Commun. 54 (1989) 3294-3328
14. 11C-MADAM binding to the serotonin transporter in the human brain. J Nucl Med 46 (2005) 1505-1515
15. 18F] ADAM as a SERT imaging agent using micro-PET and autoradiography. NeuroImage 45 (2009) 687-693
16. Mann J.J. Role of the serotonergic system in the pathogenesis of major depression and suicidal behavior. Neuropsychopharmacology 21 (1999) 99S-105S
17. Meltzer C.C., Smith G., DeKosky S.T., Pollock B.G., Mathis C.A., Moore R.Y., et al. Serotonin in aging, late-life depression, and Alzheimer's disease: the emerging role of functional imaging. Neuropsychopharmacology 18 (1998) 407-430
18. 11C]AFM provides high specific binding signals in humans. J. Nucl. Med. 49 suppl (2008) 80p
19. 18F]ACF (2-[(2-amino-4-chloro-5-fluorophenyl)thio]-N,N- dimethyl-benzenmethanamine). J. Med. Chem. 45 (2002) 4716-4723
20. 18F]-ADAM) for imaging serotonin transporters. Appl. Radiat. Isot. 66 (2008) 625-631
21. 18F]-ADAM): an improved PET radioligand for serotonin transporters. J. Nucl. Med. 44 (2003) 1890-1897
22. 18F]fluorophenylthio)benzylamine as a serotonin transporter imaging agent. Appl. Radiat. Isot. 58 (2003) 183-191
23. 11C]McN-5652-Z. J. Labelled Compd. Radiopharm. 31 (1992) 841-848
24. 11C]McN-5652. Synapse 20 (1995) 37-43
25. Tarkiainen J., Vercouillie J., Emond P., Sandell J., Hiltunen J., Frangin Y., et al. Carbon-11 labelling of MADAM in two different positions: a highly selective PET radioligand for the serotonin transporter. J. Labelled Compd. Radiopharm. 44 (2001) 1013-1023
26. 18F]fluoropr opoxy)-phenylthio)benzene-amine for positron emission tomography imaging of serotonin transporters. Nucl. Med. Biol. 35 (2008) 447-458
27. 11C-labeled 2-(phenylthio)araalkylamines. J. Med. Chem. 43 (2000) 3103-3110