In vivo characterization of radioiodinated (+)-2-[4-(4-iodophenyl) piperidino] cyclohexanol as a potential σ-1 receptor imaging agent

Nuclear Medicine and Biology

Volumn 34, Issue 6, 2007, Pages 697-702

  Akhter, Nasima ^a   Shiba, Kazuhiro ^a   Ogawa, Kazuma ^a   Kinuya, Seigo ^a   Nakajima, Kenichi ^a   Mori, Hirofumi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

1 receptor; (+) p Iodovesamicol; Biodistribution; Radioligand

Indexed keywords

1 (3,4 DIMETHOXYPHENETHYL) 4 (3 PHENYLPROPYL)PIPERAZINE; 2 [4 (4 IODOPHENYL)PIPERIDINO]CYCLOHEXANOL I 125; HALOPERIDOL; PENTAZOCINE; RADIOLIGAND; SIGMA 1 OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BINDING AFFINITY; CENTRAL NERVOUS SYSTEM; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG DISTRIBUTION; DRUG RECEPTOR BINDING; EX VIVO STUDY; ISOTOPE LABELING; MALE; MOLECULAR IMAGING; NONHUMAN; RADIOIODINATION; RAT; RECEPTOR BINDING;

ANIMALS; AUTORADIOGRAPHY; BIOTRANSFORMATION; BRAIN; CENTRAL NERVOUS SYSTEM; CHEMISTRY, PHYSICAL; CYCLOHEXANOLS; HALOPERIDOL; IODINE RADIOISOTOPES; ISOTOPE LABELING; MALE; NARCOTIC ANTAGONISTS; NOOTROPIC AGENTS; PENTAZOCINE; PIPERAZINES; PIPERIDINES; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, SIGMA; STEREOISOMERISM; TISSUE DISTRIBUTION;

EID: 34547830387     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2007.05.005     Document Type: Article

References (40)

1. Martin W.R., Eades C.G., Thompso J.A., Huppler R.E., and Gilber P.E. The effects of morphine and morphine-like drugs in the nondependent and morphine-dependent chronic spinal dog. J Pharmacol Exp Ther 197 (1976) 517-532
2. Manallack D.T., Beart P.M., and Gundlach A.L. Psychotomimetic σ-opiates and PCP. Trends Pharmacol Sci 7 (1986) 448-451
3. 3H]-1-[1-(2-thienyl)cyclohexyl] piperidine. J Pharmacol Exp Ther 238 (1986) 739-748
4. Quirion R., Bowen W.D., Itzhak Y., Junien J.L., Musacchio J.M., Rothman R., et al. A proposal for the classification of σ-binding sites. Trends Pharmacol Sci 13 (1992) 85-86
5. Su T.-P. Delineating biochemical and functional properties of sigma receptors: emerging concepts. Crit Rev Neurobiol 7 (1993) 187-203
6. Weissman A.D., Su T.-P., Hedreen J.C., and London E.D. Sigma receptors in post-mortem human brains. J Pharmacol Exp Ther 247 (1988) 29-33
7. Ciarlegio A.E., and Mash D.C. Autoradiographic localization of putative sigma receptors in the primate and human brain. Soc Neurosci Abst 16 (1990) 1140
8. Weissman E.D., Casanova M.F., Kleinman J.E., London E.D., and De Souza E.B. Selective loss of cerebral cortical sigma, but not PCP binding sites in schizophrenia. Biol Psychiat 29 (1991) 41-54
9. Simpson M.D.C., Slater P., Royston M.C., and Deakin J.F.W. Alterations in phencyclidine and sigma binding sites in schizophrenic brains. Effects of disease process and neuroleptic medication. Schizophr Res 6 (1992) 41-48
10. Matsuno K., Matsunaga K., Senda T., and Mita S. Increase in extracellular acetylcholine level by sigma ligands in rat frontal cortex. J Pharmacol Exp Ther 265 (1993) 851-859
11. Early B., Burke M., Leonard B.E., Gouret C.J., and Junien J.L. Evidence for anti-amnesic effect of JO1784 in the rat: a potent and selective ligand for the sigma receptor. Brain Res 546 (1991) 282-286
12. Matsuno K., Senda T., Matsunaga K., and Mita S. Ameliorating effects of σ receptor ligands on the impairment of passive avoidance tasks in mice: involvement in the central acetylcholinergic system. Eur J Pharmacol 261 (1994) 43-51
13. Maurice T., Hiramatsu M., Itoh J., Kameyama T., and Nabeshima T. Behavioral evidence for a modulating role of sigma ligands in memory processes: I. Attenuation of diazocilpine (MK-801)-induced amnesia. Brain Res 647 (1994) 44-56
14. Jansen K.L., Faull R.L., Storey P., and Leslie R.A. Loss of sigma binding sites in the CA1 area of the anterior hippocampus in Alzheimer's disease correlates with CA1 pyramidal cell loss. Brain Res 623 (1993) 299-302
15. John C.S., Bowen W.D., Saga T., Kinuya S., Vilner B.J., et al. A malignant melanoma imaging agent: synthesis, characterization, in vitro binding and biodistribution of iodine-125-(2-piperidinylaminoethyl)-4-iodobenzamide. J Nucl Med 34 (1993) 2169-2175
16. Choi S.R., Yang B., Plossl K., Chumpradit S., Wey S., Acton P.D., et al. Development of a Tc-99m labeled sigma-2 receptor-specific ligand as a potential breast tumor imaging agent. Nucl Med Biol 28 (2001) 657-666
17. 123I]-1-(iodopropen-2-yl)-4-[(4-cyanophenoxy)methyl]piperidine. J Med Chem 40 (1997) 1657-1667
18. 123I]1-(4-cyanobenzyl)-4-[(trans-iodopropen-2-yl) oxymethyl]piperidine: a novel high affinity sigma receptor radioligand for SPECT. Nucl Med Biol 24 (1997) 45-51
19. 123I-labeled piperidine-based sigma receptor ligands as potential melanoma imaging agents: initial studies in mouse tumor models. Nucl Med Biol 24 (1997) 587-593
20. 123I]TPCNE - a novel SPET tracer for the sigma-1 receptor: first human studies and in vivo haloperidol challenge. Synapse 60 (2006) 109-117
21. 18F]-1-(3-fluoropropyl)-4-(4-cyanophenoxymethyl)piperidine: a potential sigma - a receptor radioligand for PET. J Labelled Compd Radiopharm 38 (1996) 785-794
22. 18F]-1-(3-fluoropropyl)-4-(4-cyanophenoxymethyl)piperidine: a selective sigma-1 receptor radioligand for PET. Nucl Med Biol 24 (1997) 127-134
23. 18F] labeled benzamides: high affinity sigma receptor ligands for PET imaging. Nucl Med Biol 24 (1997) 333-340
24. 18F]fluoro-benzamide: a potential ligand for PET imaging of σ receptors. Nucl Med Biol 24 (1997) 671-676
25. 11C]NE-100 labeled in two different positions as a PET σ receptor ligand. Nucl Med Biol 2 (1998) 195-202
26. 11C]SA4503: radiation dosimetry, in vivo selectivity and PET imaging of sigma-1 receptors in the cat brain. Ann Nucl Med 14 (2000) 285-292
27. 11C]methoxy-1,2,3,4-tetrahydrochromeno[3,4-c]pyridine-5-one: a PET tracer for imaging sigma-1 receptors. Nucl Med Biol 29 (2002) 469-476
28. 18F]FBFPA): a potential fluorine-18 labeled PET radiotracer for imaging sigma-1 receptors in the CNS. Synapse 58 (2005) 267-274
29. 18F]1-(2-fluoroethyl)-4-[(4-cyanophenoxy)methyl]piperidine as a potential radiotracer for PET assessment of CNS sigma-1 receptors. Nucl Med Biol 33 (2006) 211-215
30. Shiba K., Yano T., Sato W., Mori H., and Tonami N. Characterization of radioiodinated (-)-ortho-iodovesamicol binding in rat brain preparations. Life Sci 71 13 (2002) 1591-1598
31. Shiba K., Ogawa K., and Mori H. Characterization of radioiodinated (+)-2-[4-(4-iodophenyl) piperidino]cyclohexanol [(+)-pIV] as a sigma receptor ligand. Bioorg Med Chem 13 (2005) 1095-1099
32. Shiba K., Mori H., Matsuda H., Ichikawa A., and Tonami N. Radioiodinated 2-(4-phenylpiperidino) cyclohexanol: a potential radioligand for mapping presynaptic cholinergic neurons. Nucl Med Commun 17 (1996) 485-492
33. Shiba K., Ogawa K., Ishiwata K., Yajima K., and Mori H. Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor. Bioorg Med Chem 14 (2006) 2620-2626
34. Matsuno K., Nakazawa M., Okamoto K., Kawashima Y., and Mita S. Binding properties of SA4503 a novel and selective σ-1 receptor agonist. Eur J Pharmacol 306 (1996) 1-9
35. Matsuno K., and Mita S. SA4503: a novel sigma-1 receptor agonist. CNS Drug Rev 4 (1998) 1-24
36. Lever J.R., Gustafson J.L., Xu R., Allmon R.L., and Level S.Z. Sigma 1 and sigma 2 receptor binding affinity and selectivity of SA4503 and fluoroethyl SA4503. Synapse 59 (2006) 350-358
37. McLean S., and Weber E. Autoradiographic visualization of haloperidol-sensitive sigma receptors in guinea brain. Neuroscience 25 (1988) 259-269
38. 3H-3-(3-hydroxyphenyl)-N-(1-propyl)piperidine. J Neuroscience 6 (1986) 1757-1770
39. 18F]FPS. Nucl Med Biol 30 (2003) 555-563
40. 11C]SA4503. Nucl Med Biol 30 (2006) 543-548