An unambiguous assay for the cloned human sigma1 receptor reveals high affinity interactions with dopamine D4 receptor selective compounds and a distinct structure-affinity relationship for butyrophenones

European Journal of Pharmacology

Volumn 578, Issue 2-3, 2008, Pages 123-136

  Lee, Ivan T ^a   Chen, Shiuhwei ^a   Schetz, John A ^a  

^a UNIVERSITY OF NORTH TEXAS HEALTH SCIENCE CENTER   (United States)

Author keywords

Antipsychotics; N methyl d aspartate receptor; Neuroprotection; Opioid receptor; Psychostimulants; Psychotomimetics

Indexed keywords

1 PHENYLCYCLOHEXANECARBOXYLIC ACID 2 MORPHOLINOETHYL ESTER; 2 PHENYL 4 [4 (2 PYRIMIDINYL) 1 PIPERAZINYLMETHYL]IMIDAZOLE; 3 [[4 (4 CHLOROPHENYL) 1 PIPERAZINYL]METHYL] 1H PYRROLO[2,3 B]PYRIDINE; ALPHA (4 FLUOROPHENYL) 4 (5 FLUORO 2 PYRIMIDINYL) 1 PIPERAZINEBUTANOL; ANTIDEPRESSANT AGENT; BENPERIDOL; BROMPERIDOL; BUTYROPHENONE DERIVATIVE; CLOZAPINE; DOPAMINE 4 RECEPTOR; DROPERIDOL; FLUPHENAZINE; FLUVOXAMINE; HALOPERIDOL; L 741742; METHAMPHETAMINE; N [4 (2 CYANOPHENYL) 1 PIPERAZINYLMETHYL] 3 METHYLBENZAMIDE; N ALLYLNORMETAZOCINE; NEUROLEPTIC AGENT; NEUROSTEROID; PENFLURIDOL; PENTAZOCINE; PIMOZIDE; PROGESTERONE; RBI 257; SIGMA 1 OPIATE RECEPTOR; SIGMA OPIATE RECEPTOR; SIGMA RECEPTOR LIGAND; SPIPERONE; SPIPERONE DERIVATIVE; TRIFLUPERIDOL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; DRUG ABUSE; HUMAN; HUMAN CELL; LIGAND BINDING; MOLECULAR CLONING; PRIORITY JOURNAL; RECEPTOR AFFINITY; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

BINDING, COMPETITIVE; BUTYROPHENONES; CELL LINE, TUMOR; CENTRAL NERVOUS SYSTEM AGENTS; CLONING, MOLECULAR; DOPAMINE AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; FLUVOXAMINE; HALOPERIDOL; HUMANS; LIGANDS; METHAMPHETAMINE; MOLECULAR STRUCTURE; PENTAZOCINE; PROGESTERONE; PROTEIN BINDING; RADIOLIGAND ASSAY; RECEPTORS, DOPAMINE D4; RECEPTORS, SIGMA; REPRODUCIBILITY OF RESULTS; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION; TRITIUM;

EID: 37349052331     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2007.09.020     Document Type: Article

References (86)

1. 1 receptor in the adult rat central nervous system. Neuroscience 97 (2000) 155-170
2. Aydar E., Palmer C.P., Klyachko V.A., and Jackson M.B. The sigma receptor as a ligand-regulated auxiliary potassium channel subunit. Neuron 34 (2002) 399-410
3. Bermack J.E., and Debonnel G. The role of sigma receptors in depression. J. Pharmacol. Sci. 97 (2005) 317-336
4. 2 receptor subtypes. Neuroscience 76 (1997) 467-477
5. Bowen W.D., Moses E.L., Tolentino P.J., and Walker J.M. Metabolites of haloperidol display preferential activity at sigma receptors compared to dopamine D-2 receptors. Eur. J. Pharmacol. 177 (1990) 111-118
6. 1 receptor agonists in the guinea-pig. Br. J. Pharmacol. 141 (2004) 233-240
7. 1 receptor. Biochemistry 46 (2007) 3532-3542
8. Cheng Y., and Prusoff W.H. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol. 22 (1973) 3099-3108
9. Debonnel G., and de Montigny C. Modulation of NMDA and dopaminergic neurotransmissions by sigma ligands: possible implications for the treatment of psychiatric disorders. Life Sci. 58 (1996) 721-734
10. 1 receptor modulation in the antidepressant action of venlafaxine. Neurosci. Lett. 420 (2007) 204-208
11. 1 receptor in inhibiting activity of fluvoxamine on marble-burying behavior: comparison with paroxetine. Eur. J. Pharmacol. 563 (2007) 149-154
12. Falkenstein E., Schmieding K., Lange A., Meyer C., Gerdes D., Welsch U., and Wehling M. Localization of a putative progesterone membrane binding protein in porcine hepatocytes. Cell. Mol. Biol. 44 (1998) 571-578
13. Floresco S.B., and Magyar O. Mesocortical dopamine modulation of executive functions: beyond working memory. Psychopharmacology 188 (2006) 567-585
14. Ganapathy M.E., Prasad P.D., Huang W., Seth P., Leibach F.H., and Ganapathy V. Molecular and ligand-binding characterization of the sigma-receptor in the Jurkat human T lymphocyte cell line. J. Pharmacol. Exp. Ther. 289 (1999) 251-260
15. Glase S.A., Akunne H.C., Georgic L.M., Heffner T.G., MacKenzie R.G., Manley P.J., Pugsley T.A., and Wise L.D. Substituted [(4-phenylpiperazinyl)-methyl]benzamides: selective dopamine D4 agonists. J. Med. Chem. 40 (1997) 1771-1772
16. 1) receptor binding: application of the "deconstruction-reconstruction-elaboration" approach. Mini Rev. Med. Chem. 5 (2005) 927-940
17. 1-binding site. Proc. Natl. Acad. Sci. U. S. A. 93 (1996) 8072-8077
18. Hashimoto K., and London E.D. Further characterization of [3H]ifenprodil binding to sigma receptors in rat brain. Eur. J. Pharmacol. 236 (1993) 159-163
19. Hashimoto K., Scheffel U., and London E.D. In vivo labeling of sigma receptors in mouse brain with [3H]4-phenyl-1-(4-phenylbutyl)piperidine. Synapse 20 (1995) 85-90
20. 1 receptors. Neuropsychopharmacology 32 (2007) 514-521
21. 1 receptors. Proc. Natl. Acad. Sci. U. S. A. 98 (2001) 491-496
22. 1 receptor ligands: potential in the treatment of neuropsychiatric disorders. CNS Drugs 18 (2004) 269-284
23. Hiramatsu M., and Hoshino T. Improvement of memory impairment by (+)- and (-)-pentazocine via sigma, but not kappa opioid receptors. Brain Res. 1057 (2005) 72-80
24. Inoue H., Ikeda N., Kudo K., Ishida T., Terada M., and Matoba R. Methamphetamine-related sudden death with a concentration which was of a 'toxic level'. Leg. Med. (Tokyo) 8 (2006) 150-155
25. Itzhak Y. Repeated methamphetamine-treatment alters brain sigma receptors. Eur. J. Pharmacol. 230 (1993) 243-244
26. Jbilo O., Vidal H., Paul R., De Nys N., Bensaid M., Silve S., Carayon P., Davi D., Galiegue S., Bourrie B., Guillemot J.C., Ferrara P., Loison G., Maffrand J.P., Le Fur G., and Casellas P. Purification and characterization of the human SR 31747A-binding protein. A nuclear membrane protein related to yeast sterol isomerase. J. Biol. Chem. 272 (1997) 27107-27115
27. Johansson E.D. Plasma levels of progesterone in pregnancy measured by a rapid competitive protein binding technique. Acta Endocrinol. 61 (1969) 607-617
28. John C.S., Bowen W.D., Fisher S.J., Lim B.B., Geyer B.C., Vilner B.J., and Wahl R.L. Synthesis, in vitro pharmacologic characterization, and preclinical evaluation of N-[2-(1′-piperidinyl)ethyl]-3-[125I]iodo-4-methoxybenzamide (P[125I]MBA) for imaging breast cancer. Nucl. Med. Biol. 26 (1999) 377-382
29. John C.S., Bowen W.D., Saga T., Kinuya S., Vilner B.J., Baumgold J., Paik C.H., Reba R.C., Neumann R.D., and Varma V.M. 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
30. Karasawa J., Takahashi S., and Horikomi K. Binding properties of [3H]MS-377, a novel sigma receptor ligand, to rat brain membranes. Eur. J. Pharmacol. 400 (2000) 51-57
31. Kekuda R., Prasad P.D., Fei Y.J., Leibach F.H., and Ganapathy V. Cloning and functional expression of the human type 1 sigma receptor (hSigmaR1). Biochem. Biophys. Res. Commun. 229 (1996) 553-558
32. Kula N.S., Tarazi F.I., Baldessarini R.J., Xu L., Bakthavachalam V., Pounds S., and True C.D. Neuropharmacological assessment of potential dopamine D4 receptor-selective radioligands. Eur. J. Pharmacol. 367 (1999) 139-142
33. Kulagowski J.J., Broughton H.B., Curtis N.R., Mawer I.M., Ridgill M.P., Baker R., Emms F., Freedman S.B., Marwood R., Patel S., Patel S., Ragan C.I., and Leeson P.D. 3-((4-(4-Chlorophenyl)piperazin-1-yl)-methyl)-1H-pyrrolo-2,3-b-pyridine: an antagonist with high affinity and selectivity for the human dopamine D4 receptor. J. Med. Chem. 39 (1996) 1941-1942
34. Largent B.L., Gundlach A.L., and Snyder S.H. Psychotomimetic opiate receptors labeled and visualized with (+)-[3H]3-(3-hydroxyphenyl)-N-(1-propyl)piperidine. Proc. Natl. Acad. Sci. U. S. A. 81 (1984) 4983-4987
35. Leitner M.L., Hohmann A.G., Patrick S.L., and Walker J.M. Regional variation in the ratio of sigma 1 to sigma 2 binding in rat brain. Eur. J. Pharmacol. 259 (1994) 65-69
36. Logan B.K. Methamphetamine - effects on human performance and behavior. Forens. Sci. Rev. 14 (2002) 133-151
37. Lupardus P.J., Wilke R.A., Aydar E., Palmer C.P., Chen Y., Ruoho A.E., and Jackson M.B. Membrane-delimited coupling between sigma receptors and K+ channels in rat neurohypophysial terminals requires neither G-protein nor ATP. J. Physiol. 526 (2000) 527-539
38. Martin W.R., Eades C.G., Thompson J.A., Huppler R.E., and Gilbert P.E. The effects of morphine- and nalorphine-like drugs in the nondependent and morphine-dependent chronic spinal dog. J. Pharmacol. Exp. Ther. 197 (1976) 517-532
39. Martin-Fardon, R., Maurice, T., Aujla, H., Bowen, W.D., Weiss, F., 2007. Differential Effects of sigma(1) Receptor Blockade on Self-Administration and Conditioned Reinstatement Motivated by Cocaine vs Natural Reward. Neuropsychopharmacology [Electronic publication].
40. Massai R., Miranda P., Valdes P., Lavin P., Zepeda A., Casado M.E., Silva M.A., Fetis G., Bravo C., Chandia O., Peralta O., Croxatto H.B., and Diaz S. Preregistration study on the safety and contraceptive efficacy of a progesterone-releasing vaginal ring in Chilean nursing women. Contraception 60 (1999) 9-14
41. Matsumoto R.R., Bowen W.D., Tom M.A., Vo V.N., Truong D.D., and De Costa B.R. Characterization of two novel sigma receptor ligands: antidystonic effects in rats suggest sigma receptor antagonism. Eur. J. Pharmacol. 280 (1995) 301-310
42. Matsumoto R.R., and Pouw B. Correlation between neuroleptic binding to sigma(1) and sigma(2) receptors and acute dystonic reactions. Eur. J. Pharmacol. 401 (2000) 155-160
43. Maurice T., and Lockhart B.P. Neuroprotective and anti-amnesic potentials of sigma (sigma) receptor ligands. Prog. Neuro-psychopharmacol. Biol. Psychiatry 21 (1997) 69-102
44. 1) receptor: pharmacological evidence and therapeutic opportunities. Jpn. J. Pharmacol. 81 (1999) 125-155
45. 2 sites in rat brain: comparison of regional, ontogenetic, and subcellular patterns. Synapse 17 (1994) 182-189
46. 1 receptor. Biochem. Pharmacol. 62 (2001) 349-355
47. 1) receptor agonist of the learning and memory deficits induced by a prenatal restraint stress in juvenile rats. Br. J. Pharmacol. 142 (2004) 689-700
48. 1 receptor. Br. J. Pharmacol. 149 (2006) 998-1012
49. Moller H.J. Antidepressive effects of traditional and second generation antipsychotics: a review of the clinical data. Eur. Arch. Psychiatry Clin. Neurosci. 255 (2005) 83-93
50. Morin-Surun M.P., Collin T., Denavit-Saubie M., Baulieu E.E., and Monnett F.P. Intracellular s1 receptor modulates phospholipase C and protein kinase C activities in the brainstem. Proc. Natl. Acad. Sci. U. S. A. 14 (1999) 8196-8199
51. Mukherjee A., Prasad T.K., Rao N.M., and Banerjee R. Haloperidol-associated stealth liposomes: a potent carrier for delivering genes to human breast cancer cells. J. Biol. Chem. 280 (2005) 15619-15627
52. Narita N., Hashimoto K., Tomitaka S., and Minabe Y. Interactions of selective serotonin reuptake inhibitors with subtypes of sigma receptors in rat brain. Eur. J. Pharmacol. 307 (1996) 117-119
53. Nguyen E.C., McCracken K.A., Liu Y., Pouw B., and Matsumoto R.R. Involvement of sigma (sigma) receptors in the acute actions of methamphetamine: receptor binding and behavioral studies. Neuropharmacology 49 (2005) 638-645
54. 1-receptor in oligodendrocytes in the rat central nervous system. Brain Res. 961 (2003) 92-99
55. Patel S., Freedman S., Chapman K.L., Emms F., Fletcher A.E., Knowles M., Marwood R., Mcallister G., Myers J., Curtis N., Kulagowski J.J., Leeson P.D., Ridgill M., Graham M., Matheson S., Rathbone D., Watt A.P., Bristow L.J., Rupniak N.M., Baskin E., Lynch J.J., and Ragan C.I. Biological profile of l-745,870, a selective antagonist with high affinity for the dopamine D4 receptor. J. Pharmacol. Exp. Ther. 283 (1997) 636-647
56. Pfeiffer U.J., and Fendt M. Prefrontal dopamine D4 receptors are involved in encoding fear extinction. NeuroReport 17 (2006) 847-850
57. 1) receptor expression and behavioral efficacy in the aged C57BL/6 mouse. Neurobiol. Aging 24 (2003) 865-881
58. Quirion R., Bowen W.D., Itzhak Y., Junien J.L., Musacchio J.M., Rothman R.B., Su T.P., Tam S.W., and Taylor D.P. A proposal for the classification of sigma binding sites. Trends Pharmacol. Sci. 13 (1992) 85-86
59. Quirion R., and Chicheportiche R. Classification and nomenclature of phencyclidine and sigma receptor sites. Trends Pharmacol. Sci. 10 (1987) 444-446
60. Ramamoorthy J.D., Ramamoorthy S., Mahesh V.B., Leibach F.H., and Ganapathy V. Cocaine-sensitive sigma-receptor and its interaction with steroid hormones in the human placental syncytiotrophoblast and in choriocarcinoma cells. Endocrinology 136 (1995) 924-932
61. Rowley M., Broughton H.B., Collins I., Baker R., Emms F., Marwood R., Patel S., Patel S., Ragan C.I., Freedman S.B., and Leeson P.D. 5-(4-Chlorophenyl)-4-methyl-3-(1-(2-phenylethyl)piperidin-4-yl)isoxazole: a potent, selective antagonist at human cloned dopamine D4 receptors. J. Med. Chem. 39 (1996) 1943-1945
62. Rummel C., Kissling W., and Leucht S. Antidepressants as add-on treatment to antipsychotics for people with schizophrenia and pronounced negative symptoms: a systematic review of randomized trials. Schizophr. Res. 80 (2005) 85-97
63. Seth P., Leibach F.H., and Ganapathy V. Cloning and structural analysis of the cDNA and the gene encoding the murine type 1 sigma receptor. Biochem. Biophys. Res. Commun. 241 (1997) 535-540
64. Seth P., Fei Y.J., Li H.W., Huang W., Leibach F.H., and Ganapathy V. Cloning and functional characterization of a sigma receptor from rat brain. J. Neurochem. 70 (1998) 922-931
65. Seth P., Ganapathy M.E., Conway S.J., Bridges C.D., Smith S.B., Casellas P., and Ganapathy V. Expression pattern of the type 1 sigma receptor in the brain and identity of critical anionic amino acid residues in the ligand-binding domain of the receptor. Biochim. Biophys. Acta 1540 (2001) 59-67
66. Su T.P. Evidence for sigma opioid receptor: binding of [3H]SKF-10047 to etorphine-inaccessible sites in guinea-pig brain. J. Pharmacol. Exp. Ther. 223 (1982) 284-290
67. Su T.P., London E.D., and Jaffe J.H. Steroid binding at sigma receptors suggests a link between endocrine, nervous, and immune systems. Science 240 (1988) 219-221
68. 1 receptors are intracellular amplifiers for signal transduction. Curr. Med. Chem. 10 (2003) 2073-2080
69. Takahashi S., Miwa T., and Horikomi K. Involvement of sigma 1 receptors in methamphetamine-induced behavioral sensitization in rats. Neurosci. Lett. 289 (2000) 21-24
70. Tallman J.F., Primus R.J., Brodbeck R., Cornfield L., Meade R., Woodruff K., Ross P., Thurkauf A., and Gallager D.W. I. NGD 94-1: identification of a novel, high-affinity antagonist at the human dopamine D4 receptor. J. Pharmacol. Exp. Ther. 282 (1997) 1011-1019
71. Tam S.W. Naloxone-inaccessible sigma receptor in rat central nervous system. Proc. Natl. Acad. Sci. U. S. A. 80 (1983) 6703-6707
72. Tam S.W., and Cook L. Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc. Natl. Acad. Sci. U. S. A. 81 (1984) 5618-5621
73. Trotter A., Muck K., Grill H.J., Schirmer U., Hannekum A., and Lang D. Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children. Crit. Care 5 (2001) 343-348
74. Ujike H., Okumura K., Zushi Y., Akiyama K., and Otsuki S. Persistent supersensitivity of sigma receptors develops during repeated methamphetamine treatment. Eur. J. Pharmacol. 211 (1992) 323-328
75. Vaupel D.B. Naltrexone fails to antagonize the sigma effects of PCP and SKF 10,047 in the dog. Eur. J. Pharmacol. 92 (1983) 269-274
76. 2 receptors are expressed in a wide variety of human and rodent tumor cell lines. Cancer Res. 55 (1995) 408-413
77. Volz H.P., and Stoll K.D. Clinical trials with sigma ligands. Pharmacopsychiatry 3 (2004) S214-S220 37 Suppl
78. Walker J.M., Bowen W.D., Walker F.O., Matsumoto R.R., De Costa B., and Rice K.C. Sigma receptors: biology and function. Pharmacol. Rev. 42 (1990) 355-402
79. Wang B., Rouzier R., Albarracin C.T., Sahin A., Wagner P., Yang Y., Smith T.L., Meric-Bernstam F., Marcelo Aldaz C., Hortobagyi G.N., and Pusztai L. Expression of sigma 1 receptor in human breast cancer. Breast Cancer Res. Treat. 87 (2004) 205-214
80. Wang, J., Mack, A.L., Coop, A., Matsumoto, R.R., 2007. Novel sigma (sigma) receptor agonists produce antidepressant-like effects in mice. Eur. Neuropsychopharmacol. [Electronic publication].
81. Weigl, M., Wunsch, B., 2007. Synthesis of bridged piperazines with sigma receptor affinity. Eur. J. Med. Chem. [Electronic publication].
82. Xu R., Lever J.R., and Lever S.Z. Synthesis and in vitro evaluation of tetrahydroisoquinolinyl benzamides as ligands for sigma receptors. Bioorg. Med. Chem. Lett. 17 (2007) 2594-2597
83. 1 receptors the brain-derived neurotrophic factor-induced signaling for glutamate release. J. Biol. Chem. 281 (2006) 12941-12949
84. Yamamoto H., Yamamoto T., Sagi N., Klenerova V., Goji K., Kawai N., Baba A., Takamori E., and Moroji T. Sigma ligands indirectly modulate the NMDA receptor-ion channel complex on intact neuronal cells via sigma 1 site. J. Neurosci. 15 (1995) 731-736
85. Zukin S.R. Differing stereospecificities distinguish opiate receptor subtypes. Life Sci. 31 (1982) 1307-1310
86. Zukin S.R., Brady K.T., Slifer B.L., and Balster R.L. Behavioral and biochemical stereoselectivity of sigma opiate/PCP receptors. Brain Res. 294 (1984) 174-177