Synthesis and in vivo evaluation of [ 18F]N-(2- benzofuranylmethyl)-N′-[4-(2-fluoroethoxy)benzyl]piperazine, a novel σ 1 receptor PET imaging agent

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 22, 2011, Pages 6820-6823

  Moussa, Iman A ^a   Banister, Samuel D ^a   Giboureau, Nicolas ^b   Meikle, Steven R ^b   Kassiou, Michael ^a,b  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Fluorine 18; Piperazines; Positron emission tomography; Sigma receptors

Indexed keywords

FLUORINE 18; HALOPERIDOL; N (2 BENZOFURANYLMETHYL) N' [4 (2 FLUOROETHOXY)BENZYL]PIPERAZINE F 18; RADIOPHARMACEUTICAL AGENT; SIGMA 1 OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BRAIN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VIVO STUDY; ISOTOPE LABELING; LIPOPHILICITY; NEUROIMAGING; NONHUMAN; PAPIO HAMADRYAS; POSITRON EMISSION TOMOGRAPHY; RADIOCHEMISTRY;

ANIMALS; BRAIN; FLUORINE RADIOISOTOPES; PAPIO; PIPERAZINES; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RECEPTORS, SIGMA;

ANIMALIA; PAPIO HAMADRYAS;

EID: 80054729314     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.09.028     Document Type: Article

References (46)

1. S.B. Hellewell, and W.D. Bowen Brain Res. 527 1990 244
2. R. Quirion, W.D. Bowen, Y. Itzhak, J.L. Junien, J.M. Musacchio, R.B. Rothman, T.-P. Su, S.W. Tam, and D.P. Taylor Trends Pharmacol. Sci. 13 1992 85
3. J.M. Walker, W.D. Bowen, S.R. Goldstein, A.H. Roberts, S.L. Patrick, A.G. Hohmann, and B. DeCosta Brain Res. 581 1992 33
4. S.B. Hellewell, A. Bruce, G. Feinstein, J. Orringer, W. Williams, and W.D. Bowen Eur. J. Pharmacol., Mol. Pharmacol. Sect. 268 1994 9
5. T. Maurice, and T.-P. Su Pharmacol. Ther. 124 2009 195
6. T. Maurice Pharmacopsychiatry 37 2004 171
7. E.J. Cobos, J.M. Entrena, F.R. Nieto, C.M. Cendan, and E.D. Pozo Curr. Neuropharmacol. 6 2008 344
8. P.D. Prasad, H.W. Li, Y.-J. Fei, M.E. Ganapathy, T. Fujita, L.H. Plumely, T.L. Yang-Feng, F.H. Leibach, and V. Ganapathy J. Neurochem. 70 1998 443
9. T. Hayashi, and T.-P. Su Cell 131 2007 596
10. S.-Y. Tsai, T. Hayashi, T. Mori, and T.-P. Su Cent. Nerv. Syst. Agents Med. Chem. 9 2009 184
11. T. Hayashi, T. Maurice, and T.-P. Su J. Pharmacol. Exp. Ther. 293 2000 788
12. E. Aydar, C.P. Palmer, V.A. Klyachko, and M.B. Jackson Neuron 34 2002 399
13. H. Zhang, and J. Cuevas J. Neurophysiol. 87 2002 2867
14. S.K. Kulkarni, and A. Dhir Expert Rev. Neurother. 9 2009 1021
15. M. Takebayashi, T. Hayashi, and T.P. Su Pharmacopsychiatry 37 2004 208
16. V. Villard, J. Meunier, N. Chevallier, and T. Maurice J. Pharmacol. Sci. 115 2011 279
17. T. Hayashi, and T.-P. Su CNS Drugs 18 2004 269
18. Y. Chen, A.R. Hajipour, M.K. Sievert, M. Arbabian, and A.E. Ruoho Biochemistry 46 2007 3532
19. R.R. Matsumoto, K.A. McCracken, B. Pouw, Y. Zhang, and W.D. Bowen Neuropharmacology 42 2002 1043
20. P. Romieu, R.M. Martin-Fardon, and T. Maurice NeuroReport 11 2000 2885
21. J. Kitanaka, N. Kitanaka, T. Tatsuta, F. Hall, G. Uhl, K. Tanaka, N. Nishiyama, Y. Morita, and M. Takemura Psychopharmacology 203 2009 781
22. M.A. Paquette, E.G. Brudney, D.B. Putterman, C.K. Meshul, S.W. Johnson, and S.P. Berger NeuroReport 19 2008 111
23. T. Maurice Drug News Perspect. 15 2002 617
24. T.L. Collier, R.N. Waterhouse, and M. Kassiou Curr. Pharm. Des. 13 2007 51
25. K. Hashimoto, and K. Ishiwata Curr. Pharm. Des. 12 2006 3857
26. T.L. Collier, J.C. O'Brien, and R.N. Waterhouse J. Labelled Compd. Radiopharm. 38 1996 785
27. R.N. Waterhouse, M.G. Stabin, and J.G. Page Nucl. Med. Biol. 30 2003 555
28. R.N. Waterhouse, M. Slifstein, P. Talbot, F. Dumont, A. Sultana, Y. Sudo, R. Narendran, L. Hackett, and M. Laruelle Mol. Imaging Biol. 4 2002 S35
29. R.N. Waterhouse, M. Slifstein, P. Talbot, F. Dumont, A. Sultana, Y. Sudo, R. Narenjen, L. Hackett, and M. Laruelle NeuroImage 16 2002 S6
30. J. Zhao, R.C. Chang, P. Carambot, and R.N. Waterhouse J. Labelled Compd. Radiopharm. 48 2005 547
31. R.N. Waterhouse, R.C. Chang, J. Zhao, and P.E. Carambot Nucl. Med. Biol. 33 2006 211
32. R.N. Waterhouse, J. Zhao, M.G. Stabin, H. Ng, J. Schindler-Horvat, R.C. Chang, and J.C. Mirsalis Mol. Imaging Biol. 8 2006 284
33. C.-Y. Shiue, G.G. Shiue, S.X. Zhang, S. Wilder, J.H. Greenberg, F. Benard, J.A. Wortman, and A.A. Alavi Nucl. Med. Biol. 24 1997 671
34. S. Fischer, C. Wiese, E. Große Maestrup, A. Hiller, W. Deuther-Conrad, M. Scheunemann, D. Schepmann, J. Steinbach, B. Wünsch, and P. Brust Eur. J. Nucl. Med. Mol. Imaging 38 2011 540
35. K. Kawamura, P.H. Elsinga, T. Kobayashi, S.-I. Ishii, W.-F. Wang, K. Matsuno, W. Vaalburg, and K. Ishiwata Nucl. Med. Biol. 30 2003 273
36. P.H. Elsinga, H. Tsukada, N. Harada, T. Kakiuchi, K. Kawamura, W. Vaalburg, Y. Kimura, T. Kobayashi, and K. Ishiwata Synapse 52 2004 29
37. A. van Waarde, A. Rixt Buursma, G.A.P. Hospers, K. Kawamura, T. Kobayashi, K. Ishii, K. Oda, K. Ishiwata, W. Vaalburg, and P.H. Elsinga J. Nucl. Med. 45 2004 1939
38. A. van Waarde, L.B. Been, K. Ishiwata, R.A. Dierckx, and P.H. Elsinga J. Nucl. Med. 47 2006 1538
39. K.T. Wheeler, L.M. Wang, C.A. Wallen, S.R. Childers, J.M. Cline, P.C. Keng, and R.H. Mach Br. J. Cancer 82 2000 1223
40. A. van Waarde, P.L. Jager, K. Ishiwata, R.A. Dierckx, and P.H. Elsinga J. Nucl. Med. 47 2006 150
41. I.A. Moussa, S.D. Banister, C. Beinat, N. Giboureau, A.J. Reynolds, and M. Kassiou J. Med. Chem. 53 2010 6228
42. S. Banister, D. Roeda, F. Dolle, and M. Kassiou Curr. Radiopharm. 3 2010 68
43. C. Halldin, B. Gulyas, O. Langer, and L.Q. Farde J. Nucl. Med. 45 2001 139
44. K.A. Yousef, N.D. Volkow, D.J. Schlyer, J.S. Fowler, A.P. Wolf, G.-J. Wang, M.R. Smith, J.D. Brodie, and D. Warner Synapse 19 1995 14
45. D.-R. Hwang, L.S. Kegeles, and M. Laruelle Nucl. Med. Biol. 27 2000 533
46. R.H. Mach, H.D. Gage, N. Buchheimer, Y. Huang, R. Kuhner, L. Wu, T.E. Morton, and R.L. Ehrenkaufer Synapse 58 2005 267