Synthesis and biological evaluation of 18F labeled fluoro-oligo-ethoxylated 4-benzylpiperazine derivatives for sigma-1 receptor imaging

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 1, 2013, Pages 215-222

  Wang, Xia ^a   Li, Yan ^a   Deuther Conrad, Winnie ^b   Xie, Fang ^a   Chen, Xin ^a   Cui, Meng Chao ^a   Zhang, Xiao Jun ^c   Zhang, Jin Ming ^c   Steinbach, Jörg ^b   Brust, Peter ^b   Liu, Bo Li ^a   Jia, Hong Mei ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

^b INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

^c CHINESE PLA GENERAL HOSPITAL   (China)

Author keywords

1 Receptor; 4 Benzylpiperazine; F 18; Fluoro oligo ethoxylated

Indexed keywords

1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 (4 (2 FLUOROETHOXY)BENZYL)PIPERAZINE; 1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 (4 (2 FLUOROETHOXY)BENZYL)PIPERAZINE F 18; 1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 (4 HYDROXYBENZYL)PIPERAZINE; 1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 [4 [2 (2 FLUOROETHOXY)ETHOXY]BENZYL]PIPERAZINE; 1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 [4 [2 (4 METHYLBENZYLSULFONYLOXY)ETHOXY]BENZYL]PIPERAZINE; 1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 [4 [2 [2 (2 FLUOROETHOXY)ETHOXY]ETHOXY]BENZYL]PIPERAZINE; 1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 [4 [2 [2 (2 HYDROXYETHOXY)ETHOXY]ETHOXY]BENZYL]PIPERAZINE; 1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 [4 [2 [2 (2 HYDROXYETHOXY)ETHOXY]ETHOXY]BENZYL]PIPERAZINE F 18; 1 (1,3 BENZODIOXOL 5 YLMETHYL) 4 [4 [2 [2 [2 (4 METHYLBENZYLSULFONYLOXY)ETHOXY]ETHOXY]ETHOXY]BENZYL]PIPERAZINE; FLUORINE 18; FLUORO OLIGO ETHOXYLATED 4 BENZYLPIPERAZINE DERIVATIVE; HALOPERIDOL; RADIOLIGAND; SIGMA 1 OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BINDING AFFINITY; BINDING COMPETITION; BRAIN; CONTROLLED STUDY; DEFLUORINATION; DRUG DISTRIBUTION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TISSUE LEVEL; DRUG UPTAKE; EX VIVO STUDY; HEART; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; ISOTOPE LABELING; KIDNEY; LUNG; MALE; MOUSE; NONHUMAN; PROTEIN EXPRESSION; RADIOCHEMISTRY; RECEPTOR AFFINITY; SPLEEN;

ANIMALS; AUTORADIOGRAPHY; FLUORINE RADIOISOTOPES; MALE; MICE; MOLECULAR IMAGING; PIPERAZINES; RADIOLIGAND ASSAY; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, SIGMA; TISSUE DISTRIBUTION;

MUS; RATTUS;

EID: 84870866060     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.10.038     Document Type: Article

References (30)

1. T. Hayashi, and T.-P. Su Cell 131 2007 596
2. J.L. Katz, T.-P. Su, T. Hiranita, T. Hayashi, G. Tanda, T. Kopajtic, and S.Y. Tsai Pharmaceuticals 4 2011 880
3. T. Hayashi, S.Y. Tsai, T. Mori, M. Fujimoto, and T.-P. Su Expert Opin. Ther. Targets 15 2011 557
4. S.Y. Tsai, T. Hayashi, B.K. Harvey, Y. Wang, W.W. Wu, R.F. Shen, Y. Zhang, K.G. Becker, B.J. Hoffer, and T.-P. Su Proc. Natl. Acad. Sci. U.S.A. 106 2009 22468
5. T.S. Yi, R.R. Kyle, and S.T. Ping Synapse (N. Y., NY) 66 2012 42
6. T. Maurice, and T.P. Su Pharmacol. Ther. 124 2009 195
7. B. Bourrie, E. Bribes, J.M. Derocq, H. Vidal, and P. Casellas Curr. Opin. Investig. Drugs 5 2004 1158
8. V. Megalizzi, M. Le Mercier, and C. Decaestecker Med. Res. Rev. 32 2012 410
9. K. Ito, Y. Hirooka, R. Matsukawa, and M. Nakano Cardiovasc. Res. 93 2012 33
10. M. Mishina, K. Ishiwata, K. Ishii, S. Kitamura, Y. Kimura, K. Kawamura, K. Oda, T. Sasaki, O. Sakayori, M. Hamamoto, S. Kobayashi, and Y. Katayama Acta Neurol. Scand. 112 2005 103
11. M. Mishina, M. Ohyama, K. Ishii, S. Kitamura, Y. Kimura, K. Oda, K. Kawamura, T. Sasaki, S. Kobayashi, Y. Katayama, and K. Ishiwata Ann. Nucl. Med. 22 2008 151
12. R.N. Waterhouse, M.S. Nobler, Y. Zhou, R.C. Chang, O. Morales, H. Kuwabara, A. Kumar, R.L. VanHeertum, D.F. Wong, and H.A. Sackeim Neuroimage 22 2004 T29
13. J.M. Stone, E. Arstad, K. Erlandsson, R.N. Waterhouse, P.J. Ell, and L.S. Pilowsky Synapse 60 2006 109
14. R.N. Waterhouse, R.C. Chang, N. Atuehene, and T.L. Collier Synapse 61 2007 540
15. K. Shiba, K. Ogawa, K. Ishiwata, K. Yajima, and H. Mori Bioorg. Med. Chem. 14 2006 2620
16. F. Berardi, S. Ferorelli, N.A. Colabufo, M. Leopoldo, R. Perrone, and V. Tortorella Bioorg. Med. Chem. 9 2001 1325
17. F.F. Moebius, R.J. Reiter, M. Hanner, and H. Glossmann Br. J. Pharmacol. 121 1997 1
18. F.F. Moebius, R.J. Reiter, K. Bermoser, H. Glossmann, S.Y. Cho, and Y.-K. Paik Mol. Pharmacol. 54 1998 591
19. K. Ishiwata, K. Kawamura, K. Yajima, Q.G.L. Tu, H. Mori, and K. Shiba Nucl. Med. Biol. 33 2006 543
20. J. Toyohara, M. Sakata, and K. Ishiwata Nucl. Med. Biol. 39 2012 1049
21. S. Fischer, C. Wiese, E.G. 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
22. Z.-J. Li, H.-Y. Ren, M.-C. Cui, W. Deuther-Conrad, R.-K. Tang, J. Steinbach, P. Brust, B.-L. Liu, and H.-M. Jia Bioorg. Med. Chem. 19 2011 2911
23. K. Kopka, A. Faust, P. Keul, S. Wagner, H.-J. Breyholz, C. Höltke, O. Schober, M. Schäfers, and B. Levkau J. Med. Chem. 49 2006 6704
24. K.M. Bonger, R.J.B.H.N. van den Berg, L.H. Heitman, J. Oosterom, C.M. Timmers, H.S. Overkleeft, and G.A. van der Marel Bioorg. Med. Chem. 15 2007 4841
25. D.Y. Kim, H.J. Kim, K.H. Yu, and J.J. Min Bioorg. Med. Chem. Lett. 22 2012 319
26. N. Kotera, L. Delacour, T. Traore, N. Tassali, P. Berthault, D.-A. Buisson, J.-P. Dognon, and B. Rousseau Org. Lett. 13 2011 2153
27. Y.-S. Kim, C.-T. Yang, J. Wang, L. Wang, Z.-B. Li, X. Chen, and S. Liu J. Med. Chem. 51 2008 2971
28. R.-Q. Chen, Y. Li, Q.-Y. Zhang, H.-M. Jia, W. Deuther-Conrad, D. Schepmann, J. Steinbach, P. Brust, B. Wünschs, and B.-L. Liu J. Labelled Compd. Radiopharm. 53 2010 569
29. C. Fan, H. Jia, W. Deuther-Conrad, P. Brust, J. Steinbach, and B. Liu Sci. China, Ser. B: Chem. 49 2006 169
30. K. Kawamura, K. Ishiwata, Y. Shimada, Y. Kimura, T. Kobayashi, K. Matsuno, Y. Homma, and M. Senda Ann. Nucl. Med. 14 2000 285