A 18F-Labeled Fluorobutyl-Substituted Spirocyclic Piperidine Derivative as a Selective Radioligand for PET Imaging of Sigma1 Receptors

ChemMedChem

Volumn 6, Issue 8, 2011, Pages 1401-1410

  Maisonial, Aurélie ^a   GroßeMaestrup, Eva ^b   Fischer, Steffen ^a   Hiller, Achim ^a   Scheunemann, Matthias ^a   Wiese, Christian ^b   Schepmann, Dirk ^b   Steinbach, Jörg ^a   Deuther Conrad, Winnie ^a   Wünsch, Bernhard ^b   Brust, Peter ^a  

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

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Fluorinated ligands; Positron emission tomography; Radiochemistry; Sigma1 receptors; Spirocyclic piperidines

Indexed keywords

1' BENZYL 3 (4 FLUORBUTYL) 3H SPIRO[(2)]BENZOFURAN 1,4' PIPERIDINE; FLUORINE 18; PIPERIDINE DERIVATIVE; RADIOLIGAND; SIGMA 1 OPIATE RECEPTOR; UNCLASSIFIED DRUG; FLUORINE; HALOPERIDOL; PIPERIDINE; RADIOPHARMACEUTICAL AGENT; SIGMA OPIATE RECEPTOR; SPIRO COMPOUND;

ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BINDING AFFINITY; BRAIN TISSUE; ENANTIOSELECTIVITY; EX VIVO STUDY; FACIAL NERVE NUCLEUS; ISOTOPE LABELING; MOLECULAR STABILITY; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOCHEMISTRY; RADIOISOTOPE DISTRIBUTION; RECEPTOR DENSITY; ANIMAL; BRAIN; CHEMISTRY; DRUG ANTAGONISM; FEMALE; METABOLISM; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; AUTORADIOGRAPHY; BRAIN; FEMALE; FLUORINE RADIOISOTOPES; HALOPERIDOL; ISOTOPE LABELING; MICE; PIPERIDINES; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RECEPTORS, SIGMA; SPIRO COMPOUNDS; TISSUE DISTRIBUTION;

EID: 79960688328     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201100108     Document Type: Article

References (50)

1. X. Guitart, X. Codony, X. Monroy, Psychopharmacology 2004, 174, 301-319.
2. T. Hayashi, T. P. Su, Cell 2007, 131, 596-610.
3. T. P. Su, T. Hayashi, T. Maurice, S. Buch, A. E. Ruoho, Trends Pharmacol. Sci. 2010, 31, 557-566.
4. A. vanWaarde, N. K. Ramakrishnan, A. A. Rybczynska, P. H. Elsinga, K. Ishiwata, I. M. Nijholt, P. G. Luiten, R. A. Dierckx, Behav. Brain. Res. 2011, 221, 543-554.
5. E. Aydar, C. P. Palmer, V. A. Klyachko, M. B. Jackson, Neuron 2002, 34, 399-410.
6. R. Kekuda, P. D. Prasad, Y. J. Fei, F. H. Leibach, V. Ganapathy, Biochem. Biophys. Res. Commun. 1996, 229, 553-558.
7. K. Kitaichi, J. G. Chabot, F. F. Moebius, A. Flandorfer, H. Glossmann, R. Quirion, J. Chem. Neuroanat. 2000, 20, 375-387.
8. G. Alonso, V. Phan, I. Guillemain, M. Saunier, A. Legrand, M. Anoal, T. Maurice, Neuroscience 2000, 97, 155-170.
9. T. Maurice, T. P. Su, Pharmacol. Ther. 2009, 124, 195-206;
10. T. LeeCollier, R. N. Waterhouse, M. Kassiou, Curr. Pharm. Des. 2007, 13, 51-72.
11. M. Ishikawa, K. Hashimoto, J. Recept. Ligand Channel Res. 2010, 3, 25-36.
12. R. R. Matsumoto, Y. Liu, M. Lerner, E. W. Howard, D. J. Brackett, Eur. J. Pharmacol. 2003, 469, 1-12.
13. J. L. Díaz, D. Zamanillo, J. Corbera, J. M. Baeyens, R. Maldonado, M. A. Pericàs, J. M. Vela, A. Torrens, Cent. Nerv. Syst. Agents Med. Chem. 2009, 9, 172-183.
14. S. Y. Tsai, T. Hayashi, T. Mori, T. P. Su, Cent. Nerv. Syst. Agents Med. Chem. 2009, 9, 184-189.
15. T. Hayashi, T. P. Su, CNS Drugs 2004, 18, 269-284.
16. J. A. Fishback, M. J. Robson, Y. T. Xu, R. R. Matsumoto, Pharmacol. Ther. 2010, 127, 271-282.
17. T. Hayashi, Z. Justinova, E. Hayashi, G. Cormaci, T. Mori, S. Y. Tsai, C. Barnes, S. R. Goldberg, T. P. Su, J. Pharmacol. Exp. Ther. 2010, 332, 1054-1063.
18. T. Hiranita, P. L. Soto, G. Tanda, J. L. Katz, J. Pharmacol. Exp. Ther. 2010, 332, 515-524.
19. M. Mishina, K. Ishiwata, K. Ishii, S. Kitamura, Y. Kimura, K. Kawamura, K. Oda, T. Sasaki, O. Sakayori, M. Hamamoto, S. Kobayashi, Y. Katayama, Acta Neurol. Scand. 2005, 112, 103-107.
20. M. Mishina, M. Ohyama, K. Ishii, S. Kitamura, Y. Kimura, K. Oda, K. Kawamura, T. Sasaki, S. Kobayashi, Y. Katayama, K. Ishiwata, Ann. Nucl. Med. 2008, 22, 151-156.
21. V. Villard, J. Espallergues, E. Keller, T. Alkam, A. Nitta, K. Yamada, T. Nabeshima, A. Vamvakides, T. Maurice, Neuropsychopharmacology 2009, 34, 1552-1566.
22. V. Villard, J. Espallergues, E. Keller, A. Vamvakides, T. Maurice, J. Psychopharmacol. 2010, DOI: .
23. K. Kawamura, K. Ishiwata, Y. Shimada, Y. Kimura, T. Kobayashi, K. Matsuno, Y. Homma, M. Senda, Ann. Nucl. Med. 2000, 14, 285-292.
24. K. Kawamura, K. Ishiwata, H. Tajima, S. Ishii, K. Matsuno, Y. Homma, M. Senda, Nucl. Med. Biol. 2000, 27, 255-261.
25. K. Kawamura, H. Tsukada, K. Shiba, C. Tsuji, N. Harada, Y. Kimura, K. Ishiwata, Nucl. Med. Biol. 2007, 34, 571-577.
26. R. H. Mach, H. D. Gage, N. Buchheimer, Y. Huang, R. Kuhner, L. Wu, T. E. Morton, R. L. Ehrenkaufer, Synapse 2005, 58, 267-274.
27. C. Y. Shiue, G. G. Shiue, S. X. Zhang, S. Wilder, J. H. Greenberg, F. Benard, J. A. Wortman, A. A. Alavi, Nucl. Med. Biol. 1997, 24, 671-676.
28. R. N. Waterhouse, T. L. Collier, Nucl. Med. Biol. 1997, 24, 127-134.
29. I. A. Moussa, S. D. Banister, C. Beinat, N. Giboureau, A. J. Reynolds, M. Kassiou, J. Med. Chem. 2010, 53, 6228-6239.
30. J. Toyohara, M. Sakata, K. Ishiwata, Cent. Nerv. Syst. Agents Med. Chem. 2009, 9, 190-196.
31. J. R. Lever, J. L. Gustafson, R. Xu, R. L. Allmon, S. Z. Lever, Synapse 2006, 59, 350-358.
32. K. Shiba, K. Ogawa, K. Ishiwata, K. Yajima, H. Mori, Bioorg. Med. Chem. 2006, 14, 2620-2626.
33. F. Berardi, S. Ferorelli, N. A. Colabufo, M. Leopoldo, R. Perrone, V. Tortorella, Bioorg. Med. Chem. 2001, 9, 1325-1335.
34. C. A. Maier, B. Wünsch, J. Med. Chem. 2002, 45, 438-448.
35. T. Schläger, D. Schepmann, E. U. Wüthwein, B. Wünsch, Bioorg. Med. Chem. 2008, 16, 2992-3001.
36. C. Oberdorf, D. Schepmann, J. M. Vela, J. L. Diaz, J. Holenz, B. Wünsch, J. Med. Chem. 2008, 51, 6531-6537.
37. C. A. Maier, B. Wünsch, J. Med. Chem. 2002, 45, 4923-4930.
38. E. GroßeMaestrup, C. Wiese, D. Schepmann, A. Hiller, S. Fischer, M. Scheunemann, P. Brust, B. Wünsch, Bioorg. Med. Chem. 2009, 17, 3630-3641.
39. A. Jasper, D. Schepmann, K. Lehmkuhl, J. M. Vela, H. Buschmann, J. Holenz, B. Wünsch, Eur. J. Med. Chem. 2009, 44, 4306-4314.
40. C. Wiese, E. GroßeMaestrup, D. Schepmann, J. M. Vela, J. Holenz, H. Buschmann, B. Wünsch, J. Pharm. Pharmacol. 2009, 61, 631-640.
41. E. GroßeMaestrup, S. Fischer, C. Wiese, D. Schepmann, A. Hiller, W. Deuther-Conrad, J. Steinbach, B. Wünsch, P. Brust, J. Med. Chem. 2009, 52, 6062-6072.
42. E. GroßeMaestrup, C. Wiese, D. Schepmann, P. Brust, B. Wünsch, Bioorg. Med. Chem. 2011, 19, 393-405.
43. S. Fischer, C. Wiese, E. GroßeMaestrup, A. Hiller, W. Deuther-Conrad, M. Scheunemann, D. Schepmann, J. Steinbach, B. Wünsch, P. Brust, Eur. J. Nucl. Med. Mol. Imaging 2011, 38, 540-551.
44. C. A. Maier, B. Wünsch, Eur. J. Org. Chem. 2003, 714-720.
45. OECD (2004), HPLC Method, OECD Guidelines for the Testing of Chemicals, Section 1: Physical-Chemical Properties, OECD Publishing, DOI: .
46. J. L. Musachio, U. Scheffel, M. Stathis, H. T. Ravert, W. B. Mathews, R. F. Dannals, Life Sci. 1994, 55, PL225-232.
47. M. M. Bradford, Anal. Biochem. 1976, 72, 248-254.
48. D. L. DeHaven-Hudkins, L. C. Fleissner, F. Y. Ford-Rice, Eur. J. Pharmacol. 1992, 227, 371-378.
49. R. H. Mach, C. R. Smith, S. R. Childers, Life Sci. 1995, 57, PL57-62.
50. Y. C. Cheng, W. H. Prusoff, Biochem. Pharmacol. 1973, 22, 3099-3108.