Efficient microwave-assisted direct radiosynthesis of [18F]PR04.MZ and [18F]LBT999: Selective dopamine transporter ligands for quantitative molecular imaging by means of PET

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 22, 2009, Pages 7630-7634

  Riss, Patrick J ^a   Roesch, Frank ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Direct aliphatic radiofluorination; Dopamine transporter; Microwave irradiation; PET

Indexed keywords

8 (4 FLUOROBUT 2 ENYL) 3B TOLYL 8 AZABICYCLO[3.2.1]OCTANE 2B CARBOXYLIC ACID METHYL ESTER; 8 (4 FLUOROBUT 2 ENYL) 3B TOLYL 8 AZABICYCLO[3.2.1]OCTANE 2B CARBOXYLIC ACID METHYL ESTER F 18; 8 (4 FLUOROBUT 2 YNYL) 3 TOLYL 8 AZABICYCLO[3.2.1]OCTANE 2 CARBOXYLIC ACID METHYL ESTER; 8 (4 FLUOROBUT 2 YNYL) 3 TOLYL 8 AZABICYCLO[3.2.1]OCTANE 2 CARBOXYLIC ACID METHYL ESTER F 18; CESIUM; CESIUM FLUORIDE F 18; COCAINE DERIVATIVE; CRYPTAND 2.2.2; CRYPTAND 2.2.2 FLUORINE F 18; DOPAMINE TRANSPORTER; DOPAMINE UPTAKE INHIBITOR; FLUORINE 18; KRYPTOFIX 222; LBT 999; PR 04 MZ; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM FLUORIDE F 18; UNCLASSIFIED DRUG;

ARTICLE; FLUORINATION; ISOTOPE LABELING; MICROWAVE RADIATION; MOLECULAR IMAGING; POSITRON EMISSION TOMOGRAPHY; RADIOCHEMISTRY;

CESIUM; COCAINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; FLUORIDES; FLUORINE RADIOISOTOPES; ISOTOPE LABELING; LIGANDS; MICROWAVES; MODELS, CHEMICAL; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; TROPANES;

EID: 71749093755     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.09.054     Document Type: Article

References (31)

1. Bergström K.A., Tupala E., and Tiihonen J. Pharmacol. Toxicol. 88 (2001) 287
2. Marshall V., and Grosset D. Mov. Disord. 18 (2003) 1415
3. Laakso A., and Hietala J. Curr. Pharm. Des. 6 (2000) 1611
4. Laakso A., Bergman J., Haaparanta M., Vilkman H., Solin O., Syvalahti E., and Hietala J. Schizophr. Res. 52 (2001) 115
5. Volkow N.D., Fowler J.S., Wang G.J., Baler R., and Telang F. Neuropharmacology 56 (2009) 3
6. Fowler J.S., Volkow N.D., Wolf A.P., Dewey S.L., Schlyer D.J., Macgregor R.R., Hitzemann R., Logan J., Bendriem B., Gatley S.J., and Christman D. Synapse 4 (1989) 371
7. Sulzer D. Clin. Neurosci. Res. 5 (2005) 117
8. Aquilonius S.M., Bergström K., Eckernas S.A., Hartvig P., Leenders K.L., Lundquist H., Antoni G., Gee A., Rimland A., Uhlin J., and Langström B. Acta Neurol. Scand. 76 (1987) 283
9. Kilbourn M.R., Carey J.E., Koeppe R.A., Haka M.S., Hutchins G.A., Sherman P.S., and Kuhl D.E. Nucl. Med. Biol. 16 (1989) 569
10. Ding Y.-S., Fowler J.S., Volkow N.D., Logan J., Gatley S.J., and Sugano Y. J. Nucl. Med. 36 (1995) 2298
11. Rinne J.O., Bergman J., Ruottinen H., Haaparanta M., Eronen E., Oikonen V., Sonninen P., and Solin O. Synapse 31 (1999) 119
12. Sulzer D. Clin. Neurosci. Res. 5 (2005) 117
13. Chesselet M.F., and Delfs J.M. Trends Neurosci. 19 (1996) 417
14. Müller L., Halldin C., Lundquist C., Swahn C.-G., Foged C., Hall H., Karlsson P., Ginovart N., Nakashima Y., Suhara T., and Farde L. J. Radioanal. Nucl. Chem. 206 (1996) 133
15. Abi-Dargham A., Gandelman M.S., DeErausquin G.A., Zea-Ponce Y., Zoghbi S.S., Baldwin R.M., Laruelle M., Charney D.S., Hoffer P.B., and Neumeyer J.L. J. Nucl. Med. 37 (1996) 1129
16. Cai L., Lu S., and Pike V.W. Eur. J. Org. Chem. (2008) 2853
17. Dollé F., Helfenbein J., Hinnen F., Mavel S., Mincheva Z., Saba W., Schöllhorn-Peyronneau M.-A., Valette H., Garreau L., Chalon S., Halldin C., Madelmont J.-C., Deloye J.-B., Bottlaender M., Legailliard J., Guilloteau D., and Emond P. J. Labelled Compd. Radiopharm. 50 (2007) 717
18. Dollé F., Emond P., Mavel S., Demphel S., Hinnen F., Mincheva Z., Saba W., Valette H., Chalon S., Halldin C., Helfenbein J., Legaillard J., Madelmont J.-C., Deloye J.-B., Bottlaender M., and Guilloteau D. Bioorg. Med. Chem. 14 (2006) 1115
19. Dollé F., Hinnen F., Emond P., Mavel S., Mincheva Z., Saba W., Schöllhorn-Peyronneau M.-A., Valette H., Garreau L., Chalon S., Halldin C., Helfenbein J., Legaillard J., Madelmont J.-C., Deloye J.-B., Bottlaender M., and Guilloteau D. J. Labelled Compd. Radiopharm. 49 (2006) 687
20. Klok R.P., Klein P.J., Herscheid J.D.M., and Windhorst A.D. J. Labelled Compd. Radiopharm. 49 (2006) 77
21. Wuest F., Berndt M., Strobel K., van den Hoff J., Peng X., Neumeyer J.L., and Bergmann R. Bioorg. Med. Chem. 15 (2007) 4511
22. Chalon S., Hall H., Saba W., Garreau L., Dollé F., Halldin C., Emond P., Bottlaender M., Deloye J.-B., Helfenbein J., Madelmont J.-C., Bodard S., Mincheva Z., Besnard J.-C., and Guilloteau D. J. Pharmacol. Exp. Ther. 317 (2006) 147
23. Riss P.J., Hummerich R., and Schloss P. Org. Biomol. Chem. 7 (2009) 2688
24. Riss P.J., Debus F., Hummerich R., Schmidt U., Lueddens H., Schloss P., and Roesch F. ChemMedChem 4 (2009) 1480
25. Riss P.J., Hooker M.J., Alexoff D., Kim S.-W., Fowler J.S., and Rösch F. Bioorg. Med. Chem. Lett. 19 (2009) 4343
26. Elander N., Jones J.R., Lu S.-Y., and Stone-Elander S. Chem. Soc. Rev. 29 (2000) 239
27. Dollé F. Curr. Pharm. Des. 11 (2005) 3221
28. Hayes B. Microwave Synthesis (2002), CEM Publishing, Matthews
29. Lidström P., Tierney J., Wathey B., and Westman J. Tetrahedron 57 (2001) 9225
30. Meltzer P.C., Liang A.Y., Brownell A.L., Elmaleh D.R., and Madras B.K. J. Med. Chem. 36 (1993) 855
31. Xu L., and Trudell M.L. J. Heterocycl. Chem. 33 (1996) 2037