Radiosynthesis of [18F]PBR111, a selective radioligand for imaging the translocator protein (18 kDa) with PET

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 51, Issue 14, 2008, Pages 435-439

  Dollé, Frédéric ^a   Hinnen, Françoise ^a   Damont, Annelaure ^a   Kuhnast, Bertrand ^a   Fookes, Christopher ^b   Pham, Tien ^b   Tavitian, Bertrand ^a,c   Katsifis, Andrew ^b  

^a SERVICE HOSPITALIER FRÉDÉRIC JOLIOT   (France)

^b AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

^c INSERM   (France)

Author keywords

Fluorine 18; PBR; PBR111; TSPO

Indexed keywords

FLUORINE; FLUORINE COMPOUNDS; PROTEINS; SULFUR COMPOUNDS;

FLUORINE-18; HALF LIVES; HIGH AFFINITY LIGANDS; PBR; PBR111; RADIOLIGANDS; RADIOSYNTHESIS; SELECTIVE LIGANDS; TRANSLOCATORS; TSPO;

PURIFICATION;

2 [6 CHLORO 2 [4 (3 TOSYLOXYPROPOXY)PHENYL]IMIDAZO[1,2 A]PYRIDIN 3 YL] N,N DIETHYLACETAMIDE F 18; 2 [CHLORO 2 [4 (3 FLUOROPROPOXY)PHENYL]IMIDAZO[1,2 A]PYRIDIN 3 YL] N,N DIETHYLACETAMIDE F 18; ALIPHATIC COMPOUND; CARRIER PROTEIN; CRYPTAND 2.2.2; DIMETHYL SULFOXIDE; FLUORINE 18; NUCLEOPHILE; PBR 111; RADIOLIGAND; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; POSITRON EMISSION TOMOGRAPHY; PURIFICATION; RADIOACTIVITY; ROBOTICS; SUBSTITUTION REACTION;

EID: 57349108062     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1559     Document Type: Article

References (36)

1. H. Kettenmann, G. A. Burton, U. J. Moenning in Neuroinflammation - From Bench to Bedside (Ed.: Ernst Schering Research Foundation), Springer, Berlin, Heidelberg, 2002, pp. 1-234.
2. S. Venneti, B. J. Lopresti, C. A. Wiley, Prog. Neurobiol. 2006, 80, 308-322.
3. J. J. Bourguignon, Endogenous and synthetic ligands of mitochondrial benzodiazepine receptors: structure-affinity relationships, in Peripheral Benzodiazepine Receptors (Ed.: E. Giesen-Crouse), Academic Press, London, 1993, pp. 59-85.
4. V. Papadopoulos, M. Baraldi, T. R. Guilarte, T. B. Knudsen, J.-J. Lacapère, P. Lindemann, M. D. Norenberg, D. Nutt, A. Weizman, M.-R. Zhang, M. Gavish, Trends Pharmacol. Sci. 2006, 27, 402-409.
5. R. Camsonne, C. Crouzel, D. Comar, M. Mazière, C. Prenant, J. Sastre, M. A. Moulin, A. Syrota, J. Label. Compds. Radiopharm. 1984, 21, 985-991.
6. F. Chauveau, H. Boutin, N. Van Camp, F. Dollé, B. Tavitian, Eur. J. Nucl. Med. Mol. Imag. 2008, in press. DOI: 10.1007/s002 59-008-0908-9.
7. M. L. James, S. Selleri, M. Kassiou, Curr. Med. Chem. 2006, 13, 1991-2001.
8. M. Kassiou, S. R. Meikle, R. B. Banati, Brain Res. Rev. 2005, 48, 207-210.
9. M. R. Zhang, J. Maeda, K. Furutsuka, Y. Yoshida, M. Ogawa, T. Suhara, K. Suzuki, Bioorg. Med. Chem. Lett. 2003, 13, 201-204.
10. M. R. Zhang, T. Kida, J. Noguchi, K. Furutsuka, J. Maeda, T. Suhara, K. Suzuki, Nucl. Med. Biol. 2003, 30, 513-519.
11. M. R. Zhang, J. Maeda, M. Ogawa, J. Noguchi, T. Ito, Y. Yoshida, T. Okauchi, S. Obayashi, T. Suhara, K. Suzuki, J. Med. Chem. 2004, 47, 2228-2235.
12. J. Maeda, T. Suhara, M. R. Zhang, T. Okauchi, F. Yasuno, Y. Ikoma, M. Inaji, Y. Nagai, A. Takano, S. Obayashi, K. Suzuki, Synapse 2004, 52, 283-291.
13. E. Briard, J. Shah, J. L. Musachio, S. S. Zoghbi, M. Fujita, M. Imaizumi, V. Croplay, R. B. Innis, V. W. Pike, J. Label. Compds. Radiopharm. 2005, 48(suppl 1), S4.
14. M. R. Zhang, M. Ogawa, J. Maeda, T. Ito, J. Noguchi, K. Kumata, T. Okauchi, T. Suhara, K. Suzuki, J. Med. Chem. 2006, 49, 2735-2742.
15. Y. Fujimura, Y. Ikoma, F. Yasuno, T. Suhara, M. Ota, R. Matsumoto, S. Nozaki, A. Takano, J. Kosaka, M. R. Zhang, R. Nakao, K. Suzuki, N. Kato, H. Ito, J. Nucl. Med. 2006, 47, 43-50.
16. K. C. Probst, D. Izquierdo, R. J. Davies, J. L. E. Bird, T. D. Fryer, H. K. Richards, J. C. Clark, E. A. Warburton, P. L. Weissberg, F. I. Aigbirhio, J. Label. Compds. Radiopharm. 2007, 50, 561-562.
17. M. Shidahara, Y. Ikoma, C. Seki, Y. Fujimura, M. Naganawa, H. Ito, T. Suhara, I. Kanno, Y. Kimura, Eur. J. Nucl. Med. Mol. Imaging 2008, 35, 416-423.
18. T. Pham, F. Mattner, C. Fookes, I. Greguric, P. Berghofer, P. Ballantyne, X. Liu, R. Shepherd, T. Jackson, A. Katsifis, J. Label. Compds. Radiopharm. 2007, 50(suppl 1), S377.
19. M. James, R. Fulton, J. Vercouillie, D. Henderson, L. Garreau, S. Eberl, S. Chalon, S. Selleri, F. Dollé, D. Guilloteau, M. Kassiou, J. Label. Compds. Radiopharm. 2007, 50(suppl 1), S25.
20. J. Doorduin, H. C. Klein, M. James, M. Kassiou, R. A. Dierckx, E. F. J. De Vries. J. Label. Compds. Radiopharm. 2007, 50(suppl 1), S333.
21. M. James, R. Fulton, J. Vercouillie, D. Henderson, L. Garreau, S. Chalon, F. Dollé, S. Selleri, D. Guilloteau, M. Kassiou, J. Nucl. Med. 2008, 49, 814-822.
22. A. Damont, F. Hinnen, B. Kuhnast, M.-A. Schöllhorn-Peyronneau, M. James, C. Luus, B. Tavitian, M. Kassiou, F. Dollé, J. Label. Compds. Radiopharm. 2008, 51, 286-292.
23. F. Mattner, T. Pham, C. Fookes, I. Greguric, P. Berghofer, P. Ballantyne, X. Liu, T. Jackson, B. Dikic, R. Shepherd, A. Katsifis, J. Label. Compds. Radiopharm. 2007, 50(suppl 1), S76.
24. T. Pham, C. Fookes, X. Liu, I. Greguric, T. Bourdier, A. Katsifis, J. Label. Compds. Radiopharm. 2007, 50(suppl 1), S204.
25. C. Fookes, T. Pham, F. Mattner, I. Greguric, C. Loc'h, X. Liu, P. Berghofer, R. Shepherd, M.-C. Grégoire, A. Katsifis, J. Med. Chem. 2008, 51, 3700-3712.
26. M. R. Kilbourn, Fluorine-18 labeling of radiopharmaceuticals, in Nuclear Science Series (Ed.: M. R. Kilbourn), National Academy Press, Washington, DC, 1990, pp. 1-149.
27. +-emitting compounds based on fluorine-18, in Topics in Current Chemistry, Vol. 222 (Ed.: W. Krause), Springer, Berlin, Heidelberg, 2002, pp. 201-258.
28. M. J. Welch, C. S. Redvanly in Handbook of Radiopharmaceuticals - Radiochemistry and Applications (Eds.: M. J. Welch, C. S. Redvanly), Wiley, New York, Chichester, Brisbane, Toronto, 2003, pp. 1-848.
29. P. A. Schubiger, L. Lehmann, M. Friebe in PET Chemistry: The Driving Force in Molecular Imaging, (Ed.: Ernst Schering Research Foundation), Springer, Berlin, Heidelberg, 2007, pp. 1-339.
30. F. Dollé, D. Roeda, B. Kuhnast, M.-C. Lasne, Fluorine-18 chemistry for molecular imaging with positron emission tomography, in Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals (Eds.: A. Tressaud, G. Haufe), Elsevier, Amsterdam, Boston, Heidelberg, London, New York, Oxford, Paris, San Diego, San Francisco, Singapore, Sydney, Tokyo, 2008, pp. 3-65.
31. L. Cai, S. Lu, V. W. Pike, Eur. J. Org. Chem. 2008, 17, 2853-2873.
32. H. H. Coenen, B. Klatte, A. Knoechel, M. Schueller, G. Stöcklin, J. Label. Compds. Radiopharm. 1986, 23, 455-467.
33. K. Hamacher, H. H. Coenen, G. Stöcklin, J. Nucl. Med. 1986, 27, 235-238.
34. H. Boutin, F. Chauveau, C. Thominiaux, B. Kuhnast, M.-C. Grégoire, S. Jan, V. Brulon, Y. Fontyn, R. Trebossen, Ph. Hantraye, F. Dollé, B. Tavitian, A. Katsifis, Glia 2007, 55, 1459-1468.
35. H. Boutin, F. Chauveau, C. Thominiaux, B. Kuhnast, M.-C. Grégoire, M. James, S. Jan, V. Brulon, Y. Fontyn, R. Trebossen, Ph. Hantraye, F. Dollé, B. Tavitian, M. Kassiou, J. Nucl. Med. 2007, 48, 573-581.
36. C. Lemaire, A. Plenevaux, J. Aerts, G. Del Fiore, C. Brihaye, D. Le Bars, D. Comar, A. Luxen, J. Label. Compds. Radiopharm. 1999, 42, 63-75.