Derivatives of WAY 100635 as potential imaging agents for 5-HT(1A) receptors: Syntheses, radiosyntheses, and in vitro and in vivo evaluation

Nuclear Medicine and Biology

Volumn 25, Issue 8, 1998, Pages 769-776

  Wilson, Alan A ^a,b   Inaba, Ted ^a   Fischer, Nancy ^a   Dixon, Lori M ^a   Nobrega, José ^a   DaSilva, Jean N ^a   Houle, Sylvain ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b CENTRE FOR ADDICTION AND MENTAL HEALTH   (Canada)

Author keywords

5 HT(1A); Carbon 11; Liver metabolism; PET; Receptors; WAY 100635

Indexed keywords

CARBON 11; N [2 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL]ETHYL] N (2 PYRIDYL)CYCLOHEXANECARBOXAMIDE; SEROTONIN 1A RECEPTOR;

ANIMAL EXPERIMENT; CONFERENCE PAPER; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ISOTOPE LABELING; LIVER METABOLISM; MALE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RAT; RECEPTOR AFFINITY;

ANIMALS; BLOOD-BRAIN BARRIER; BRAIN; CARBON RADIOISOTOPES; HUMANS; ISOTOPE LABELING; LIGANDS; LIVER; MALE; PIPERAZINES; PYRIDINES; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, SEROTONIN; RECEPTORS, SEROTONIN, 5-HT1; SEROTONIN ANTAGONISTS; TOMOGRAPHY, EMISSION-COMPUTED;

EID: 0032212714     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(98)00020-1     Document Type: Conference Paper

References (56)

1. Andrade R., Nicoll R.A. Novel anxiolytics discriminate between postsynaptic serotonin receptors mediating different physiological responses on single neurons of the rat hippocampus. Naunyn Scmeideberg's Arch. Pharmacol. 336:1987;5-10.
2. Bowen D.M., Francis P.T., Pangalos M.N., Stephens P.H., Procter A.W. Treatment strategies for Alzheimer's disease. Lancet. 339:1992;132-133.
3. Bowen D.M., Najlerahim A., Procter A.W., Francis P.T., Murphy E. Circumscribed changes of the cerebral cortex in neuropsychiatric disorders of later life. Proc. Natl. Acad. Sci. USA. 86:1989;9504-9508.
4. 2A receptor mRNAs and binding site densities are differentially altered in schizophrenia. Neuropsychopharmacology. 15:1996;442-455.
5. 3H]8-OH-DPAT and demonstration of increased binding in the frontal cortex in schizophrenia . Neurochem. Int. 30:1997;565-574.
6. Campbell M.E., Grant D.G., Inaba T., Kalow W. Biotransformation of caffeine, paraxanthine, theophylline and theobromine by polycyclic aromatic hydrocarbon inducible cytochrome P-450 in human liver microsomes. Drug Metab. Dispos. 15:1987;237-249.
7. 1A antagonist research. Drugs Future. 18:1993;631-642.
8. Crouzel C., Guillame M., Barre L., Lemaire C., Pike V. Ligands and tracers for PET studies of the 5HT system - Current status. Nucl. Med. Biol. 19:1992;857-870.
9. 11C]methyl iodide. Appl. Radiat. Isot. Int. J. Appl. Instrum. Part A. 38:1987;601-603.
10. 1A binding sites with G regulatory proteins. Biochem. Pharmacol. 39:1990;7.
11. 1A receptor antagonist. Br. J. Pharmacol. 112:1994;91P.
12. 1A receptor antagonists Utility as research tools and therapeutic agents . Trends Pharmacol. Sci. 14:1993;441-448.
13. Francis P.T., Sims N.R., Proctor A.W., Bowen D.M. (1993) Cortical pyramidal neurone loss may cause glutamatergic hypoactivity and cognitive impairment in Alzheimer's disease Investigative and therapeutic perspectives. J. Neurochem., 1589-1564.
14. Glaser T., Traber J. Buspirone Action on serotonin receptors in calf hippocampus . Eur. J. Pharmacol. 88:1983;137-138.
15. 1A serotonin agonists and antagonist. Drug Dev. Res. 26:1992;251-274.
16. Goldberg H.L., Finnerty R.J. The comparative effect of buspirone and diazepam in the treatment of anxiety. Am. J. Psychiatry. 136:1979;1184-1187.
17. 3H]-PAT . Nature. 305:1983;140-142.
18. 1A receptors in rat brain membranes. Eur. J. Pharmacol. 288:1995;173-186.
19. Gurevich E.V., Joyce J.N. Alterations in the cortical serotonergic system in schizophrenia A postmortem study . Biol. Psychiatry. 42:1997;529-545.
20. 1A agonist for PET. J. Labelled Compd. Radiopharm. 35:1994;494-495.
21. 1A receptors in prefrontal and temporal cortices of brains from patients with chronic schizophrenia. Life Sci. 48:1991;355-363.
22. 1A radioligand [O-methyl-C-11]WAY 100635 [abstract]. Canadian Association of Nuclear Medicine Scientific Meeting, Quebec City, P37.
23. 1A receptors in rat brain. Eur. J. Pharmacol. 271:1994;515-523.
24. 3-hydroxylation . Drug Metab. Dispos. 16:1988;605-608.
25. 1A presynaptic but not postsynaptic receptor-mediated responses Relationship to anti-depressant-like action . Eur. J. Pharmacol. 138:1987;53-60.
26. Khawaja X., Evans N., Reilly Y., Ennis C., Minchin M.C.W. Characterisation of the binding of [H-3]WAY-100635, a novel 5-hydroxytryptamine(1A) receptor antagonist, to rat brain. J. Neurochem. 64:1995;2716-2726.
27. Kobilka B. Adrenergic receptors as models for G protein-coupled receptors. Ann. Rev. Neurosci. 15:1992;87.
28. 2-receptor selectivity of flesinoxan and analogous N4-substituted N1-arylpiperazines. J. Med. Chem. 40:1997;300-312.
29. 1A receptor ligands. J. Med. Chem. 38:1995;1942-1954.
30. 1A receptors in rat brain. Synapse. 18:1994;359-366.
31. 1A receptors by [H-3]WAY 100635 in the mouse. Eur. J. Pharmacol. 271:1994;505-514.
32. Mathis C.A., Simpson N.R., Mahmood K., Kinahan P.E., Mintun M.A. [C-11]WAY 100635 A radioligand for imaging 5-HT(1A) receptors with positron emission tomography . Life Sci. 55:1994;403-407.
33. Mazière B., Coenen H., Halldin C., Nagren K., Pike V. PET radioligands for dopamine receptors and re-uptake sites Chemistry and biochemistry . Nucl. Med. Biol. 19:1992;497-512.
34. 1A receptor radioligand, [carbonyl-C-11]WAY-100635, via C-11- carboxylation of an immobilized Grignard reagent. J. Labelled Compds. Radiopharm. 38:1996;941-953.
35. McKittrick C.R., Blanchard D.C., Blanchard R.J., McEwen B.S., Sakai R.R. Serotonin receptor binding in a colony model of chronic social stress. Biol. Psychiatry. 37:1995;383-393.
36. 2 receptor affinity for N-[3[(4-aryl-1-piperazinyl)propyl] derivatives of 3,4-dihydroquinolin-2(1H)-one and its isomeric isoquinolines. Med. Chem. Res. 2:1992;82-87.
37. 1A agonists . Arch. Pharmacol. 328:1995;770-774.
38. 1A receptor ligands with reduced alpha(1)-adrenergic activity. Synthesis and structure-affinity relationships. J. Med. Chem. 38:1995;1273-1277.
39. 1A receptor radioligand, [O-methyl-C-11]WAY- 100635, in monkey and human plasma by HPLC Comparison of the behaviour of an identified radioactive metabolite with parent radioligand in monkey using PET . Nucl. Med. Biol. 23:1996;627-634.
40. 1A agonists - A comparative review. CNS Drugs. 2:1994;234-251.
41. Perrone R., Berardi F., Colabufo N.A., Leopoldo M., Tortorella V., Fiorentini F., Olgiati V., Ghiglieri A., Govoni S. High affinity and selectivity on 5-HT(1A) receptor of 1-aryl-4-[1-tetralin)alkyl]piperazines .2. J. Med. Chem. 38:1995;942-949.
42. Pike V.W., Halldin C., Crouzel C., Barré L., Nutt D.J., Osman S., Shah F., Turton D.R., Waters S.L. Radioligands for PET studies of central benzodiazepine receptors and PK (peripheral benzodiazepine) binding sites - Current status. Nucl. Med. Biol. 20:1993;503-525.
43. 1A receptors in vivo. J. Nucl. Med. 36:1995;58P.
44. 11C]WAY-100635. Med. Chem. Res. 5:1994;208-227.
45. 1-adrenergic affinity. J. Med. Chem. 34:1991;2633-2638.
46. 1A receptors in ventral prefrontal cortex in schizophrenia. Biol. Psychiatry. 39:1996;919-928.
47. 1A receptors are increased in postmortem prefrontal cortex in schizophrenia. Brain Res. 708:1996;209-214.
48. 11C]-8-hydroxy-2-(di-N-propylamino)tetralin. J. Labelled Compd. Radiopharm. 35:1994;496.
49. 1A receptor ligands, 1. Heterobicyclic phenylpiperazines with N4-alkyl substituents. J. Med. Chem. 36:1993;2751-2760.
50. 11C]ORG-13502 . J. Labelled Compd. Radiopharm. 37:1995;280-282.
51. 3]-carbomethoxy-3β-aryltropanes Radiotracers for the dopamine transporter . J. Labelled Compd. Radiopharm. 34:1994;759-765.
52. 18F]-labelled cocaine analogues as potential dopamine transporter ligands for positron emission tomography. Nucl. Med. Biol. 23:1996;141-146.
53. 11C]WAY 100635. J. Labelled Compds. Radiopharm. 38:1996;149-154.
54. 1A receptors by positron emission tomography (PET) [abstract]. Proc. XIIth Intl. Symp. Radiopharm. Chem. 1:1997;531-533.
55. 1A Ligands. J. Med. Chem. 37:1994;4572-4575.
56. 1A receptor ligand . J. Med. Chem. 36:1993;3161-3165.