Novel sigma receptor ligands: Synthesis and biological profile

Journal of Medicinal Chemistry

Volumn 50, Issue 5, 2007, Pages 951-961

  Prezzavento, Orazio ^a   Campisi, Agata ^a   Ronsisvalle, Simone ^a   Li Volti, Giovanni ^b   Marrazzo, Agostino ^a   Bramanti, Vincenzo ^d   Cannavò, Giuseppe ^d   Vanella, Luca ^a   Cagnotto, Alfredo ^c   Mennini, Tiziana ^c   Ientile, Riccardo ^d   Ronsisvalle, Giuseppe ^a  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF BRESCIA   (Italy)

^c MARIO NEGRI INSTITUTE FOR PHARMACOLOGICAL RESEARCH   (Italy)

^d UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHOXYCARBONYL 1 PHENYL 2 CYCLOPROPYLMETHYLAMINE DERIVATIVE; 1 PHENYL 2 CYCLOPROPYLMETHYLAMINE DERIVATIVE; 4 PHENYLPIPERIDIN 4 OL; CITALOPRAM; CYCLOPROPYLMETHYLAMINE DERIVATIVE; DIZOCILPINE; DOPAMINE 1 RECEPTOR; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; HALOPERIDOL; HISTAMINE H1 RECEPTOR; IBOGAINE; KETANSERIN; MESULERGINE; N [2 (2,3 DICHLOROPHENYL)ETHYL] 2 DIMETHYLAMINO N METHYLETHYLAMINE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; PENTAZOCINE; PRAZOSIN; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; SEROTONIN 3 RECEPTOR; SEROTONIN 4 RECEPTOR; SEROTONIN 6 RECEPTOR; SIGMA 1 OPIATE RECEPTOR; SIGMA 1 OPIATE RECEPTOR AGONIST; SIGMA 2 OPIATE RECEPTOR; SIGMA 2 OPIATE RECEPTOR AGONIST; SIGMA OPIATE RECEPTOR; SPIPERONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANALGESIA; ANIMAL CELL; ARTICLE; ASTROCYTE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; NONHUMAN; RAT; SEROTONIN RELEASE; SUBSTITUTION REACTION;

ANIMALS; ASTROCYTES; BRAIN; CASPASE 3; CELLS, CULTURED; CYCLOPROPANES; DNA FRAGMENTATION; GTP-BINDING PROTEINS; GUINEA PIGS; LIGANDS; PIPERIDINES; RADIOLIGAND ASSAY; RATS; RATS, WISTAR; RECEPTORS, SIGMA; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSGLUTAMINASES;

EID: 33847778872     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0611197     Document Type: Article

References (44)

1. 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. 1982, 223, 284-290.
2. Quirion, R.; Chicheportiche, R.; Contreras, P. C.; Johnson, K. M.; Lodge, D.; Tam, S. W.; Woods, J. H.; Zukin, S. R. Classification and nomenclature of phencyclidine and sigma receptors sites. Trends Neurosci. 1987, 10, 444-446.
3. Quirion, R.; Bowen, W. D.; Itzhak, Y.; Junien, J. L.; Musacchio, J. M.; Rothman, R. B.; Su, T. P.; Tam, S. W.; Taylor, D. P. A proposal for the classification of sigma binding sites. Trends Pharmacol. Sci. 1992, 13, 85-86.
4. Hellewell, S. B.; Bowen, W. D. A sigma-like binding site in rat pheochromocytoma (PC12) cells: decreased affinity for (+)-benzo-morphans and lower molecular weight suggest a different sigma receptor form from that of guinea pig brain. Brain Res. 1990, 527, 244-253.
5. 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.
6. McCann, D. J.; Weissman, A. D.; Su, T. P. Sigma-1 and sigma-2 sites in rat brain: comparison of regional, ontogenetic, and subcellular patterns. Synapse 1994, 17, 182-189.
7. Hanner, M.; Moebius, F. F.; Flandorfer, A.; Knaus, H. G.; Striessnig, J.; Kempner, E.; Glossmann, H. Purification, molecular cloning, and expression of the mammalian sigma1-binding site. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8072-8077.
8. Su, T. P.; Hayashi, T. Understanding the molecular mechanism of sigma-1 receptors: towards a hypothesis that sigma-1 receptors are intracellular amplifiers for signal transduction. Curr. Med. Chem. 2003, 10, 2073-2080.
9. Zhang, H.; Cuevas, J. Sigma receptor activation blocks potassium channels and depresses neuroexcitability in rat intracardiac neurons. J. Pharmacol. Exp. Ther. 2005, 313, 1387-1396.
10. 2+: clinical and therapeutic relevance. Biol. Cell 2005, 97, 873-883.
11. Monnet, F. P.; Debonnel, G.; Junien, J. L.; De Montigny, C. N-Methyl-D-aspartate-induced neuronal activation is selectively modulated by sigma receptors. Eur. J. Pharmacol. 1990, 179, 441-445.
12. Peeters, M.; Romieu, P.; Maurice, T.; Su, T. P.; Maloteaux, J. M.; Hermans, E. Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine. Eur. J. Neurosci. 2004, 19, 2212-2220.
13. Kobayashi, T.; Matsuno, K.; Mita, S. Regional differences of the effect of sigma receptor ligands on the acetylcholine release in the rat brain. J. Neural Transm. 1996, 103, 661-669.
14. Bowen, W. D. Sigma receptors: recent advances and new clinical potentials. Pharm. Acta Helv. 2000, 74, 211-218.
15. Lesort, M.; Tucholski, J.; Miller, M. L.; Johnson, G. V. Tissue transglutaminase: a possible role in neurodegenerative diseases. Prog. Neurobiol. 2000, 61, 439-463.
16. Tucholski, J.; Johnson, G. V. Tissue transglutaminase differentially modulates apoptosis in a stimuli-dependent manner. J. Neurochem. 2002, 81, 780-791.
17. Nakaoka, H.; Perez, D. M.; Baek, K. J.; Das, T.; Husain, A.; Misono, K.; Im, M. J.; Graham, R. M. Gh: a GTP-binding protein with transglutaminase activity and receptor signaling function. Science 1994, 264, 1593-1596.
18. Slife, C. W.; Dorsett, M. D.; Bouquett, G. T.; Register, A.; Taylor, E.; Conroy, S. Subcellular localization of a membrane-associated transglutaminase activity in rat liver. Arch. Biochem. Biophys. 1985, 241, 329-336.
19. Mishra, S.; Murphy, L. J. The p53 oncoprotein is a substrate for tissue transglutaminase kinase activity. Biochem. Biophys. Res. Commun. 2006, 339, 726-730.
20. Gentile, V.; Cooper, A. J. Transglutaminases, possible drug targets in human diseases. Curr. Drug Targets: CNS Neurol. Disord. 2004, 3, 99-104.
21. Campisi, A.; Caccamo, D.; Raciti, G.; Cannavo, G.; Macaione, V.; Curro, M.; Macaione, S.; Vanella, A.; Ientile, R. Glutamate-induced increases in transglutaminase activity in primary cultures of astroglial cells. Brain Res. 2003, 978, 24-30.
22. Ronsisvalle, G.; Prezzavento, O.; Pasquinucci, L.; Pappalardo, M. S.; Marrazzo, A.; Vittorio, F.; Carboni, L.; Spampinato, S. Synthesis of (+)-(1′R,2′S) and (1′S,2′R)- 6,11-dimethyl-1,2,3,4,5,6-hexahydro-3-[[2′-(alkoxycarbonyl) -2′-phenylcyclopropyl]methyl]-2,6-methano-3-benzazocin-8-ol. Comparison of the affinities for sigma 1 and opioid receptors within the diastereoisomeric MPCB and CCB. Farmaco 1997, 52, 471-476.
23. Casadio, S.; Cousse, H.; Mouzin, G.; Stenger, A.; Charveron, M.; Vilain, P.; Lauressergues, H. New beta-phenethylamine derivatives: Synthesis and pharmacologic properties. Boll. Chim. Farm. 1978, 117, 83-89.
24. Schaus, J. M.; Bymaster, F. P. Dopaminergic approches to anthipsychotic agents. Annu. Rep. Med. Chem. 1998, 33, 1-10.
25. Glennon, R. A.; Ablordeppey, S. Y.; Ismaiel, A. M.; el Ashmawy, M. B.; Fischer, J. B.; Howie, K. B. Structural features important for sigma 1 receptor binding. J. Med. Chem. 1994, 37, 1214-1219.
26. Bowen, W. D.; Vilner, B. J.; Williams, W.; Bertha, C. M.; Kuehne, M. E.; Jacobson, A. E. Ibogaine and its congeners are sigma 2 receptor-selective ligands with moderate affinity. Eur. J. Pharmacol. 1995, 279, R1-R3.
27. Danso-Danquah, R.; Bai, X.; Zhang, X.; Mascarella, S. W.; Williams, W.; Sine, B.; Bowen, W. D.; Carroll, F. I. Synthesis and sigma binding properties of 2′-substituted 5,9-alpha-dimethyl-6,7-benzo-morphans. J. Med. Chem. 1995, 38, 2978-2985.
28. Jaen, J. C.; Caprathe, B. W.; Pugsley, T. A.; Wise, L. D.; Akunne, H. Evaluation of the effects of the enantiomers of reduced haloperidol, azaperol, and related 4-amino-1-arylbutanols on dopamine and sigma receptors. J. Med. Chem. 1993, 36, 3929-3936.
29. Mach, R. H.; Smith, C. R.; Childers, S. R. Ibogaine possesses a selective affinity for sigma 2 receptors. Life Sci. 1995, 57, L57-L62.
30. Colabufo, N. A.; Berardi, F.; Contino, M.; Niso, M.; Abate, C.; Perrone, R.; Tortorella, V. Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines. Naunyn-Schmiedeberg's Arch. Pharmacol. 2004, 370, 106-113.
31. Zambon, A. C.; De Costa, B. R.; Kanthasamy, A. G.; Nguyen, B. Q.; Matsumoto, R. R. Subchronic administration of N-[2-(3,4-dichlorophenyl) ethyl]-N-methyl-2-(dimethylamino)ethylamine (BD1047) alters sigma 1 receptor binding. Eur. J. Pharmacol. 1997, 324, 39-47.
32. Matsumoto, R. R.; Bowen, W. D.; Tom, M. A.; Vo, V. N.; Truong, D. D.; De Costa, B. R. Characterization of two novel sigma receptor ligands: antidystonic effects in rats suggest sigma receptor antagonism. Eur. J. Pharmacol. 1995, 280, 301-310.
33. Milakovic, T.; Tucholski, J.; McCoy, E.; Johnson, G. V. Intracellular localization and activity state of tissue transglutaminase differentially impacts cell death. J. Biol. Chem. 2004, 279, 8715-8722.
34. Gavrieli, Y.; Sherman, Y.; Ben Sasson, S. A. Identification of programmed cell death in situ via specific labeling of nuclear DNA fragmentation. J. Cell Biol. 1992, 119, 493-501.
35. Colabufo, N. A.; Berardi, F.; Abate, C.; Contino, M.; Niso, M.; Perrone, R. Is the sigma2 receptor a histone binding protein? J. Med. Chem. 2006, 49, 4153-4158.
36. Kim, J. H.; Nam, K. H.; Kwon, O. S.; Kim, I. G.; Bustin, M.; Choy, H. E.; Park, S. C. Histone cross-linking by transglutaminase. Biochem. Biophys. Res. Commun. 2002, 293, 1453-1457.
37. Crawford, K. W.; Bowen, W. D. Sigma-2 receptor agonists activate a novel apoptotic pathway and potentiate antineoplastic drugs in breast tumor cell lines. Cancer Res. 2002, 62, 313-322.
38. Vilner, B. J.; Bowen, W. D. Modulation of cellular calcium by sigma-2 receptors: release from intracellular stores in human SK-N-SH neuroblastoma cells. J. Pharmacol. Exp. Ther. 2000, 292, 900-911.
39. DeHaven-Hudkins, D. L.; Fleissner, L. C.; Ford-Rice, F. Y. Characterization of the binding of [3H](+)-pentazocine to sigma recognition sites in guinea pig brain. Eur. J. Pharmacol. 1992, 227, 371-378.
40. Boess, F. G.; Monsma, F. J., Jr.; Carolo, C.; Meyer, V.; Rudler, A.; Zwingelstein, C.; Sleight, A. J. Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells. Neuropharmacology 1997, 36, 713-720.
41. Gobbi, M.; Crespi, D.; Foddi, M. C.; Fracasso, C.; Mancini, L.; Parotti, L.; Mennini, T. Effects of chronic treatment with fluoxetine and citalopram on 5-HT uptake, 5-HT1B autoreceptors, 5-HT3 and 5-HT4 receptors in rats. Naunyn-Schmiedeberg's Arch. Pharmacol. 1997, 356, 22-28.
42. Mennini, T.; Bernasconi, P.; Fiori, M. G. Neurotoxicity of nonionic low-osmolar contrast media. A receptor binding study. Invest. Radiol. 1993, 28, 821-827.
43. Campisi, A.; Renis, M.; Russo, A.; Sorrenti, V.; Di Giacomo, C.; Castorina, C.; Vanella, A. Transglutaminase activity in primary and subcultured rat astroglial cells. Neurochem. Res. 1992, 17, 1201-1205.
44. Klouz, A.; Tillement, J. P.; Boussard, M. F.; Wierzbicki, M.; Berezowski, V.; Cecchelli, R.; Labidalle, S.; Onteniente, B.; Morin, D. [3H]BHDP as a novel and selective ligand for sigma1 receptors in liver mitochondria and brain synaptosomes of the rat. FEBS Lett. 2003, 553, 157-162.