Fully automated synthesis of PET TSPO radioligands [ 11C]DAA1106 and [ 18F]FEDAA1106

Applied Radiation and Isotopes

Volumn 70, Issue 6, 2012, Pages 965-973

  Wang, Min ^a   Gao, Mingzhang ^a   Zheng, Qi Huang ^a  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

11C DAA1106; 18F FEDAA1106; Automation; Positron emission tomography (PET); Radiosynthesis; Translocator protein 18kDa (TSPO)

Indexed keywords

[ 11C]DAA1106; [ 18F]FEDAA1106; AUTOMATED SYNTHESIS; NUCLEOPHILIC SUBSTITUTIONS; RADIOCHEMICAL YIELD; RADIOLIGANDS; RADIOSYNTHESIS; SPECIFIC ACTIVITY; TRANSLOCATORS;

ALKYLATION; AUTOMATION; POSITRON EMISSION TOMOGRAPHY;

PURIFICATION;

BENZODIAZEPINE RECEPTOR; CARBON N (2 METHOXY 5 METHOXYBENZYL) N (5 FLUORO 2 PHENOXYPHENYL)ACETAMIDE C 11; N (5 FLUORO 2 PHENOXYPHENYL) N [2 (2 FLUOROETHOXY) 5 METHOXYBENZYL]ACETAMIDE F 18; RADIOLIGAND; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; AUTOMATION; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENERGY YIELD; FLOW KINETICS; GAMMA RADIATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; METHYLATION; NUCLEOPHILICITY; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOACTIVITY;

ACETAMIDES; CARBON RADIOISOTOPES; CONTRAST MEDIA; FLUORINE RADIOISOTOPES; ISOTOPE LABELING; PHENYL ETHERS; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; ROBOTICS;

EID: 84860114490     PISSN: 09698043     EISSN: 18729800     Source Type: Journal    
DOI: 10.1016/j.apradiso.2012.03.011     Document Type: Article

References (38)

1. 11C labelled radiotracers synthesis. Curr. Med. Chem. 2008, 15:235-277.
2. Batarseh A., Papadopoulos V. Regulation of translocator protein 18kDa (TSPO) expression in health and disease states. Mol. Cell Endocrinol. 2010, 327:1-12.
3. 11C-labeled aryloxyanilide ligands for imaging brain peripheral benzodiazepine receptors in vivo. J. Med. Chem. 2008, 51:17-30.
4. 18F-labeled ligand for imaging brain peripheral benzodiazepine receptors with PET. J. Med. Chem. 2009, 52:688-699.
5. 18F-N-fluoroacetyl-N-(2,5-dimethoxybenzyl)-2-phenoxyaniline. J. Nucl. Med. 2010, 52:107-114.
6. 11C]PK11195 challengers. Eur. J. Nucl. Med. Mol. Imaging 2008, 35:2304-2319.
7. Dhir A., Rogawski M.A. Role of neurosteroids in the anticonvulsant activity of midazolam. Br. J. Pharmacol. 2011, 10.1111/j.1476-5381.2011.01733.x.
8. 3 receptor radioligands. Appl. Radiat. Isot. 2008, 66:1891-1897.
9. 18F]fallypride. Appl. Radiat. Isot. 2010, 68:1079-1086.
10. 1AR. Appl. Radiat. Isot. 2012, 70:498-504.
11. 18F-fluoroethylcholine for cancer imaging with PET: synthesis, biochemistry, and prostate cancer imaging. J. Nucl. Med. 2002, 43:187-199.
12. Howell W.C., Millington J.E., Pattison F.L.M. Toxic fluorine compounds. VII. ω-Fluoroalkyl thiocyanates and ω-fluoroalkyl mercaptans. J. Am. Chem. Soc. 1956, 78:3843-3846.
13. 11C]methyl triflate. Int. J. Rad. Appl. Instrum. A 1992, 43:1383-1385.
14. 18F]Fallypride on a TRACERLab FX-FN synthesizer. J. Labelled Compd. Radiopharm. 2009, 52:S286.
15. Kumar S.K., Amador M., Hidalgo M., Bhat S.V., Khan S.R. Design, synthesis and biological evaluation of novel ricardiphenol analogs. Bioorg. Med. Chem. 2005, 13:2873-2880.
16. 18F]Fallypride in a micro-reactor: rapid optimization and multiple-production in small doses for micro-PET studies. Curr. Radiopharm. 2009, 2:49-55.
17. Luus C., Hanani R., Reynolds A., Kassiou M. The development of PET radioligands for imaging the translocator protein (18kDa): what have we learned?. J. Labelled Compd. Radiopharm. 2010, 53:501-510.
18. 11C]methyl triflate. Nucl. Med. Biol. 1999, 26:467-471.
19. Mock B.H., Glick-Wilson B.E., Zheng Q.-H., DeGrado T.R. Automated measurement of specific activity of radiolabeled ligands during synthesis. J. Labelled Compd. Radiopharm. 2005, 48:S224.
20. 11C-radio-synthesis system. J. Labelled Compd. Radiopharm. 2005, 48:S225.
21. Okubo T., Yoshikawa R., Chaki S., Okuyama S., Nakazato A. Design, synthesis and structure-affinity relationship of arylxoyanilide derivatives as novel peripheral benzodiazepine receptor ligands. Bioorg. Med. Chem. 2004, 12:423-438.
22. Owen D.R., Gunn R.N., Rabiner E.A., Bennacef I., Fujita M., Kreisl W.C., Innis R.B., Pike V.W., Reynolds R., Matthews P.M., Parker C.A. Mixed-affinity binding in humans with 18kDa translocator protein ligands. J. Nucl. Med. 2011, 52:24-32.
23. Papadopoulos V., Baraldi M., Guilarte T.R., Knudsen T.B., Lacapère J.J., Lindemann P., Norenberg M.D., Nutt D., Weizman A., Zhang M.R., Gavish M. Translocator protein (18kDa): new nomenclature for the peripheral-type benzodiazepine receptor based on its structure and molecular function. Trends Pharmacol. Sci. 2006, 27:402-409.
24. 11C]DAA1106. Nucl. Med. Biol. 2007, 34:439-446.
25. Rupprecht R., Papadopoulos V., Rammes G., Baghai T.C., Fan J., Akula N., Groyer G., Adams D., Schumacher M. Translocator protein (18kDa) (TSPO) as a therapeutic target for neurological and psychiatric disorders. Nat. Rev. Drug Discov. 2010, 9:971-988.
26. 11C]PIB PET in patients with Alzheimer's disease, mild cognitive impairment, and older adults with cognitive complaints. Alzheimer's Dement 2010, 6(4, Suppl. 1):S3-S4.
27. Scarf A.M., Kassiou M. The translocator protein. J. Nucl. Med. 2011, 52:677-680.
28. 18F]FEDAA1106: a human whole-body PET study. Eur. J. Nucl. Med. Mol. Imaging 2011, 38:2058-2065.
29. 11C]FEDAA1106 as a new PET imaging probe for peripheral benzodiazepine receptor expression. Eur. J. Med. Chem. 2009, 44:2748-2753.
30. 11C]PBR28. Bioorg. Med. Chem. Lett. 2009, 19:5636-5639.
31. 18F]PBR06 as agents for positron emission tomographic (PET) imaging of the translocator protein (TSPO). Steroids 2011, 76:1331-1340.
32. Wyatt S.K., Manning H.C., Bai M., Bailey S.N., Gallant P., Ma G., Mclntosh L., Bornhop D.J. Molecular imaging of the translocator protein (TSPO) in a pre-clinical model of breast cancer. Mol. Imaging Biol. 2009, 12:349-358.
33. 11C]PBR28. NeuroImage 2010, 52(Suppl. 1):S33-S34.
34. 11C]DAA1106: radiosynthesis and in vivo binding to peripheral benzodiazepine receptors in mouse brain. Nucl. Med. Biol. 2003, 30:513-519.
35. 18F]FEDAA1106: two positron-emitter labeled ligands for peripheral benzodiazepine receptor (PBR). Bioorg. Med. Chem. Lett. 2003, 13:201-204.
36. 18F]fluoroethyl-5-methoxybenzyl)acetamide, for pet imaging of peripheral benzodiazepine receptor in primate brain. J. Med. Chem. 2004, 47:2228-2235.
37. 131I]iodo-5-methoxybenzyl)acetamide: a potent iodinated radioligand for the peripheral-type benzodiazepine receptor in brain. J. Med. Chem. 2007, 50:848-855.
38. Zheng Q.-H., Mock B.H. Purification of carbon-11 PET radiotracers from unlabeled precursors by preparative HPLC and SPE. Biomed. Chromatogr. 2005, 19:671-676.