Synthesis and evaluation of novel 18F-labeled spirocyclic piperidine derivatives as σ1 receptor ligands for positron emission tomography imaging

Journal of Medicinal Chemistry

Volumn 56, Issue 9, 2013, Pages 3478-3491

  Li, Yan ^a   Wang, Xia ^a   Zhang, Jinming ^b   Deuther Conrad, Winnie ^c   Xie, Fang ^a   Zhang, Xiaojun ^b   Liu, Jian ^b   Qiao, Jinping ^a   Cui, Mengchao ^a   Steinbach, Jörg ^c   Brust, Peter ^c   Liu, Boli ^a   Jia, Hongmei ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

^b CHINESE PLA GENERAL HOSPITAL   (China)

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

Author keywords

[No Author keywords available]

Indexed keywords

1' (4 (2 FLUOROETHOXY)BENZYL) 3H SPIRO[2 BENZOFURAN 1,4' PIPERIDINE]; FLUORINE 18; PIPERIDINE DERIVATIVE; SIGMA RECEPTOR LIGAND; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; AUTORADIOGRAPHY; BINDING ASSAY; BRAIN REGION; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; EX VIVO STUDY; ISOTOPE LABELING; LIPOPHILICITY; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOCHEMISTRY; RAT; RECEPTOR AFFINITY;

ANIMALS; BINDING, COMPETITIVE; BRAIN; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; DRUG STABILITY; FLUORINE RADIOISOTOPES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; ISOTOPE LABELING; LIGANDS; MALE; MICE; MICROSOMES, LIVER; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PIPERIDINES; POSITRON-EMISSION TOMOGRAPHY; RATS; RECEPTORS, SIGMA; SPIRO COMPOUNDS;

EID: 84877715641     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301734g     Document Type: Article

References (57)

1. 1-binding site Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 8072-8077
2. Aydar, E.; Palmer, C. P.; Klyachko, V. A.; Jackson, M. B. The sigma receptor as a ligand-regulated auxiliary potassium channel subunit Neuron 2002, 34, 399-410
3. 2+ signaling and cell survival Cell 2007, 131, 596-610
4. Walker, J. M.; Bowen, W. D.; Walker, F. O.; Matsumoto, R. R.; De Costa, B.; Rice, K. C. Sigma receptors: biology and function Pharmacol. Rev. 1990, 42, 355-402
5. 1 receptor Biochem. Pharmacol. 2001, 62, 349-355
6. Kim, F. J.; Kovalyshyn, I.; Burgman, M.; Neilan, C.; Chien, C. C.; Pasternak, G. W. Sigma 1 receptor modulation of G-protein-coupled receptor signaling: potentiation of opioid transduction independent from receptor binding Mol. Pharmacol. 2010, 77, 695-703
7. Guitart, X.; Codony, X.; Monroy, X. Sigma receptors: biology and therapeutic potential Psychopharmacology 2004, 174, 301-319
8. Hayashi, T.; Tsai, S. Y.; Mori, T.; Fujimoto, M.; Su, T. P. Targeting ligand-operated chaperone sigma-1 receptors in the treatment of neuropsychiatric disorders Expert Opin. Ther. Targets 2011, 15, 557-577
9. Maurice, T.; Su, T. P. The pharmacology of sigma-1 receptors Pharmacol. Ther. 2009, 124, 195-206
10. Feher, A.; Juhasz, A.; Laszlo, A.; Kalman, J., Jr.; Pakaski, M.; Kalman, J.; Janka, Z. Association between a variant of the sigma-1 receptor gene and Alzheimer's disease Neurosci. Lett. 2012, 517, 136-139
11. Ishikawa, M.; Hashimoto, K. The role of sigma-1 receptors in the pathophysiology of neuropsychiatric diseases J. Recept. Ligand Channel Res. 2010, 3, 25-36
12. Van Waarde, A.; Rybczynska, A. A.; Ramakrishnan, N.; Ishiwata, K.; Elsinga, P. H.; Dierckx, R. A. Sigma receptors in oncology: therapeutic and diagnostic applications of sigma ligands Curr. Pharm. Des. 2010, 16, 3519-3537
13. Megalizzi, V.; Le Mercier, M.; Decaestecker, C. Sigma receptors and their ligands in cancer biology: overview and new perspectives for cancer therapy Med. Res. Rev. 2012, 32, 410-427
14. Ito, K.; Hirooka, Y.; Matsukawa, R.; Nakano, M.; Sunagawa, K. Decreased brain sigma-1 receptor contributes to the relationship between heart failure and depression Cardiovasc. Res. 2012, 93, 33-40
15. 1 receptors in Parkinson's disease Acta Neurol. Scand. 2005, 112, 103-107
16. 1 receptors in early Alzheimer's disease Ann. Nucl. Med. 2008, 22, 151-156
17. 11C]SA4503 Cent. Nerv. Syst. Agents Med. Chem. 2009, 9, 190-196
18. 11C]SA4503 Int. J. Neuropsychopharmacol. 2009, 12, 1127-1131
19. 11C]SA4503 NeuroImage 2007, 35, 1-8
20. 18F] FPS) in healthy humans NeuroImage 2004, 22, T29-T30
21. 18F]FPS Synapse 2007, 61, 540-546
22. 123I]TPCNE-a novel SPET tracer for the sigma-1 receptor: first human studies and in vivo haloperidol challenge Synapse 2006, 60, 109-117
23. 1 receptor agonist Eur. J. Pharmacol. 1996, 306, 271-279
24. Maier, C. A.; Wünsch, B. Novel spiropiperidines as highly potent and subtype selective sigma-receptor ligands. Part 1 J. Med. Chem. 2002, 45, 438-448
25. Maier, C. A.; Wünsch, B. Novel sigma receptor ligands. Part 2. SAR of spiro[[2]benzopyran-1,4′-piperidines] and spiro[[2]benzofuran-1, 4′-piperidines] with carbon substituents in position 3 J. Med. Chem. 2002, 45, 4923-4930
26. 1 receptor ligand 1′-benzyl-3-methoxy-3 H-spiro[[2]benzofuran-1,4′-piperidine] J. Pharm. Pharmacol. 2009, 61, 631-640
27. 1 receptor ligands as potential PET radiotracers, structure-affinity relationships and in vitro metabolic stability Bioorg. Med. Chem. 2009, 17, 3630-3641
28. 1 receptor binding and biotransformation of the spirocyclic PET tracer 1′-benzyl-3-(3- fluoropropyl)-3H-spiro[[2]benzofuran-1,4′-piperidine] Chirality 2011, 23, 148-154
29. 1 receptors ChemMedChem 2011, 6, 1401-1410
30. 1 receptor ligands for neuroimaging with positron emission tomography J. Med. Chem. 2009, 52, 6062-6072
31. 18F]fluspidine Eur. J. Nucl. Med. Mol. Imaging 2011, 38, 540-551
32. 1 receptors and comparison with fluoroalkyl homologs Bioorg. Med. Chem. 2012, 20, 257-269
33. 1 receptor imaging agent J. Labelled Compd. Radiopharm. 2010, 53, 569-574
34. Kubota, H.; Fujii, M.; Ikeda, K.; Takeuchi, M.; Shibanuma, T.; Isomura, Y. Spiro-substituted piperidines as neurokinin receptor antagonists. I. Design and synthesis of (±)-N-[2-(3,4-dichlorophenyl)-4-(spiro [isobenzofuran-1(3H), 4′piperidin]-1′-yl)butyl]-N-methylbenzamide, YM-35375, as a new lead compound for novel neurokinin receptor antagonists Chem. Pharm. Bull. 1998, 46, 351-354
35. 18F labeled fluoro-oligo-ethoxylated 4-benzylpiperazine derivatives for sigma-1 receptor imaging Bioorg. Med. Chem. 2013, 21, 215-222
36. Holtke, C.; von Wallbrunn, A.; Kopka, K.; Schober, O.; Heindel, W.; Schafers, M.; Bremer, C. A fluorescent photoprobe for the imaging of endothelin receptors Bioconjugate Chem. 2007, 18, 685-694
37. 1 receptor ligand as a potential tumor imaging agent Sci. China, Ser. B: Chem. 2006, 49, 169-176
38. 18F-labeled fluoroacetylmorpholino derivative of vesamicol for neuroimaging of the vesicular acetylcholine transporter Nucl. Med. Biol. 2008, 35, 185-195
39. OECD Guidelines for Testing of Chemicals; OECD Publishing: Paris, France, 1989; http://www.oecd.org/dataoecd/17/36/1948177.pdf.
40. 1 receptors Nucl. Med. Biol. 2000, 27, 255-261
41. Fishback, J. A.; Robson, M. J.; Xu, Y. T.; Matsumoto, R. R. Sigma receptors: potential targets for a new class of antidepressant drug Pharmacol. Ther. 2010, 127, 271-282
42. 1 receptor ligands with exocyclic amino moiety (increased distance 1) Bioorg. Med. Chem. 2011, 19, 3141-3151
43. 1) receptor binding: application of the " deconstruction-reconstruction-elaboration " approach Mini-Rev. Med. Chem. 2005, 5, 927-940
44. Laruelle, M.; Slifstein, M.; Huang, Y. Relationships between radiotracer properties and image quality in molecular imaging of the brain with positron emission tomography Mol. Imaging Biol. 2003, 5, 363-375
45. Patel, S.; Gibson, R. In vivo site-directed radiotracers: a mini-review Nucl. Med. Biol. 2008, 35, 805-815
46. 1 receptors in the cat brain Ann. Nucl. Med. 2000, 14, 285-292
47. Leysen, J. E.; Janssen, P. M.; Gommeren, W.; Wynants, J.; Pauwels, P. J.; Janssen, P. A. In vitro and in vivo receptor binding and effects on monoamine turnover in rat brain regions of the novel antipsychotics risperidone and ocaperidone Mol. Pharmacol. 1992, 41, 494-508
48. 35S] binding J. Pharmacol. Exp. Ther. 1998, 285, 119-126
49. Kroeze, W. K.; Hufeisen, S. J.; Popadak, B. A.; Renock, S. M.; Steinberg, S.; Ernsberger, P.; Jayathilake, K.; Meltzer, H. Y.; Roth, B. L. H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs Neuropsychopharmacology 2003, 28, 519-526
50. Cobos, E. J.; del Pozo, E.; Baeyens, J. M. Irreversible blockade of sigma-1 receptors by haloperidol and its metabolites in guinea pig brain and SH-SY5Y human neuroblastoma cells J. Neurochem. 2007, 102, 812-825
51. 1 and EBP sites Bioorg. Med. Chem. 2001, 9, 1325-1335
52. Shiba, K.; Ogawa, K.; Ishiwata, K.; Yajima, K.; Mori, H. Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor Bioorg. Med. Chem. 2006, 14, 2620-2626
53. Elfving, B.; Bjornholm, B.; Knudsen, G. M. Interference of anaesthetics with radioligand binding in neuroreceptor studies Eur. J. Nucl. Med. Mol. Imaging 2003, 30, 912-915
54. Zhao, F.; Jin, T.; Wang, P.; Kim, S. G. Isoflurane anesthesia effect in functional imaging studies NeuroImage 2007, 38, 3-4
55. 18F-labeled 1-[2-(4-alkoxy-3-methoxyphenyl)ethyl]- 4-(3-phenylpropyl)piperazines as sigma receptor ligands for positron emission tomography studies Nucl. Med. Biol. 2003, 30, 273-284
56. Sheldrick, G. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1996.
57. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure from Diraction Data; University of Göttingen: Göttingen, Germany, 1997.