Characterization of substituted phenylpropylamides as highly selective agonists at the melatonin mt2 receptor

Current Medicinal Chemistry

Volumn 20, Issue 2, 2013, Pages 289-300

  Chan, King H ^a   Hu, Yueqing ^a   Ho, Maurice K C ^a   Wong, Yung H ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

GPCR; Melatonin; MT1; MT2; Subtype selectivity

Indexed keywords

AMIDE; CROSS REACTING ANTIBODY; HORMONE RECEPTOR STIMULATING AGENT; MELATONIN 1 RECEPTOR; MELATONIN 2 RECEPTOR; MESSENGER RNA; PHENYLPROPYLAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; DOSE RESPONSE; DRUG POTENCY; FEMALE; HIGH THROUGHPUT SCREENING; IC 50; NONHUMAN; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION;

EID: 84877962180     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986713804806649     Document Type: Article

References (59)

1. Dubocovich, M.L., Melatonin receptors: role on sleep and circadian rhythm regulation. Sleep Med, 2007, 8 Suppl 3, 34-42. (Pubitemid 350131612)
2. Arendt, J., Melatonin and human rhythms. Chronobiol Int, 2006, 23, (1-2), 21-37. (Pubitemid 43739016)
3. Slominski, R.M.; Reiter, R.J.; Schlabritz-Loutsevitch, N.; Ostrom, R.S.; Slominski, A.T., Melatonin membrane receptors in peripheral tissues: Distribution and functions. Mol Cell Endocrinol, 2012.
4. Reppert, S.; Weaver, D.; Ebisawa, T., Cloning and characterization of a mammalian melatonin receptor that mediates reproductive and circadian responses. Neuron, 1994, 13, (5), 1177-1185. (Pubitemid 24372135)
5. Reppert, S.; Godson, C.; Mahle, C.; Weaver, D.; Slaugenhaupt, S.; Gusella, J., Molecular characterization of a second melatonin receptor expressed in human retina and brain: the Mel1b melatonin receptor. Proc Natl Acad Sci U S A, 1995, 92, (19), 8734-8738.
6. Rivera-Bermúdez, M.A.; Masana, M.I.; Brown, G.M.; Earnest, D.J.; Dubocovich, M.L., Immortalized cells from the rat suprachiasmatic nucleus express functional melatonin receptors. Brain Res, 2004, 1002, (1-2), 21-27. (Pubitemid 38251574)
7. Al-Ghoul, W.; Herman, M.; Dubocovich, M., Melatonin receptor subtype expression in human cerebellum. Neuroreport, 1998, 9, (18), 4063-4068. (Pubitemid 29030689)
8. Mazzucchelli, C.; Pannacci, M.; Nonno, R.; Lucini, V.; Fraschini, F.; Stankov, B.M., The melatonin receptor in the human brain: cloning experiments and distribution studies. Brain Res Mol Brain Res, 1996, 39, (1-2), 117-126. (Pubitemid 26179152)
9. Dubocovich, M.; Markowska, M., Functional MT1 and MT2 melatonin receptors in mammals. Endocrine, 2005, 27, (2), 101-110. (Pubitemid 41558442)
10. Masana, M.I.; Benloucif, S.; Dubocovich, M.L., Circadian rhythm of mt1 melatonin receptor expression in the suprachiasmatic nucleus of the C3H/HeN mouse. J Pineal Res, 2000, 28, (3), 185-192. (Pubitemid 30162451)
11. Tenn, C.; Niles, L.P., Physiological regulation of melatonin receptors in rat suprachiasmatic nuclei: diurnal rhythmicity and effects of stress. Mol Cell Endocrinol, 1993, 98, (1), 43-48. (Pubitemid 24016927)
12. Liu, C.; Weaver, D.; Jin, X.; Shearman, L.; Pieschl, R.; Gribkoff, V.; Reppert, S., Molecular dissection of two distinct actions of melatonin on the suprachiasmatic circadian clock. Neuron, 1997, 19, (1), 91-102. (Pubitemid 27332996)
13. Shibata, S.; Cassone, V.M.; Moore, R.Y., Effects of melatonin on neuronal activity in the rat suprachiasmatic nucleus in vitro. Neurosci Lett, 1989, 97, (1-2), 140-144. (Pubitemid 19048925)
14. Jin, X.; von Gall, C.; Pieschl, R.; Gribkoff, V.; Stehle, J.; Reppert, S.; Weaver, D., Targeted disruption of the mouse Mel(1b) melatonin receptor. Mol Cell Biol, 2003, 23, (3), 1054-1060. (Pubitemid 36133521)
15. Hunt, A.; Al-Ghoul, W.; Gillette, M.; Dubocovich, M., Activation of MT(2) melatonin receptors in rat suprachiasmatic nucleus phase advances the circadian clock. Am J Physiol Cell Physiol, 2001, 280, (1), C110-118. (Pubitemid 32523404)
16. Dubocovich, M.; Hudson, R.; Sumaya, I.; Masana, M.; Manna, E., Effect of MT1 melatonin receptor deletion on melatonin-mediated phase shift of circadian rhythms in the C57BL/6 mouse. J Pineal Res, 2005, 39, (2), 113-120. (Pubitemid 41140748)
17. Drazen, D.L.; Klein, S.L.; Yellon, S.M.; Nelson, R.J., In vitro melatonin treatment enhances splenocyte proliferation in prairie voles. J Pineal Res, 2000, 28, (1), 34-40. (Pubitemid 30066050)
18. Drazen, D.; Nelson, R., Melatonin receptor subtype MT2 (Mel 1b) and not mt1 (Mel 1a) is associated with melatonin-induced enhancement of cellmediated and humoral immunity. Neuroendocrinology, 2001, 74, (3), 178-184. (Pubitemid 32786217)
19. Arendt, J.; Skene, D., Melatonin as a chronobiotic. Sleep Med Rev, 2005, 9, (1), 25-39. (Pubitemid 40092916)
20. Cardinali, D.; Furio, A.; Reyes, M.; Brusco, L., The use of chronobiotics in the resynchronization of the sleep-wake cycle. Cancer Causes Control, 2006, 17, (4), 601-609.
21. Claustrat, B.; Brun, J.; Chazot, G., The basic physiology and pathophysiology of melatonin. Sleep Med Rev, 2005, 9, (1), 11-24. (Pubitemid 40092915)
22. Nonno, R.; Lucini, V.; Pannacci, M.; Mazzucchelli, C.; Angeloni, D.; Fraschini, F.; Stankov, B., Pharmacological characterization of the human melatonin Mel1a receptor following stable transfection into NIH3T3 cells. Br J Pharmacol, 1998, 124, (3), 485-492. (Pubitemid 28254504)
23. Mulchahey, J.; Goldwater, D.; Zemlan, F., A single blind, placebo controlled, across groups dose escalation study of the safety, tolerability, pharmacokinetics and pharmacodynamics of the melatonin analog betamethyl-6-chloromelatonin. Life Sci, 2004, 75, (15), 1843-1856. (Pubitemid 39070497)
24. Uchikawa, O.; Fukatsu, K.; Tokunoh, R.; Kawada, M.; Matsumoto, K.; Imai, Y.; Hinuma, S.; Kato, K.; Nishikawa, H.; Hirai, K.; Miyamoto, M.; Ohkawa, S., Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists. J Med Chem, 2002, 45, (19), 4222-4239. (Pubitemid 35025570)
25. Bourin, M.; Mocaër, E.; Porsolt, R., Antidepressant-like activity of S 20098 (agomelatine) in the forced swimming test in rodents: involvement of melatonin and serotonin receptors. J Psychiatry Neurosci, 2004, 29, (2), 126-133. (Pubitemid 38570217)
26. Millan, M.; Gobert, A.; Lejeune, F.; Dekeyne, A.; Newman-Tancredi, A.; Pasteau, V.; Rivet, J.; Cussac, D., The novel melatonin agonist agomelatine (S20098) is an antagonist at 5-hydroxytryptamine2C receptors, blockade of which enhances the activity of frontocortical dopaminergic and adrenergic pathways. J Pharmacol Exp Ther, 2003, 306, (3), 954-964. (Pubitemid 37025301)
27. Hardeland, R., Tasimelteon, a melatonin agonist for the treatment of insomnia and circadian rhythm sleep disorders. Curr Opin Investig Drugs, 2009, 10, (7), 691-701.
28. Hu, Y.; Ho, M.; Chan, K.; New, D.; Wong, Y., Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT(2)-selective melatonin ligands. Bioorg Med Chem Lett, 2010, 20, (8), 2582-2585.
29. Mody, S.; Ho, M.; Joshi, S.; Wong, Y., Incorporation of Galpha(z)-specific sequence at the carboxyl terminus increases the promiscuity of galpha(16) toward G(i)-coupled receptors. Mol Pharmacol, 2000, 57, (1), 13-23. (Pubitemid 30033255)
30. Liu, A.; Ho, M.; Wong, C.; Chan, J.; Pau, A.; Wong, Y., Galpha(16/z) chimeras efficiently link a wide range of G protein-coupled receptors to calcium mobilization. J Biomol Screen, 2003, 8, (1), 39-49.
31. New, D.; Wong, Y., Characterization of CHO cells stably expressing a G alpha 16/z chimera for high throughput screening of GPCRs. Assay Drug Dev Technol, 2004, 2, (3), 269-280. (Pubitemid 39069633)
32. Wong, Y., Gi assays in transfected cells. Methods Enzymol, 1994, 238, 81-94.
33. Liu, A.; Wong, Y., G16-mediated activation of nuclear factor kappaB by the adenosine A1 receptor involves c-Src, protein kinase C, and ERK signaling. J Biol Chem, 2004, 279, (51), 53196-53204. (Pubitemid 40051822)
34. Browning, C.; Beresford, I.; Fraser, N.; Giles, H., Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors. Br J Pharmacol, 2000, 129, (5), 877-886. (Pubitemid 30142898)
35. Charlton, S.J.; Vauquelin, G., Elusive equilibrium: the challenge of interpreting receptor pharmacology using calcium assays. Br J Pharmacol, 2010, 161, (6), 1250-1265.
36. Lai, F.; Mody, S.; Yung, L.; Kam, J.; Pang, C.; Pang, S.; Wong, Y., Molecular determinants for the differential coupling of Galpha(16) to the melatonin MT1, MT2 and Xenopus Mel1c receptors. J Neurochem, 2002, 80, (5), 736-745. (Pubitemid 34809225)
37. Bondi, C.; McKeon, R.; Bennett, J.; Ignatius, P.; Brydon, L.; Jockers, R.; Melan, M.; Witt-Enderby, P., MT1 melatonin receptor internalization underlies melatonin-induced morphologic changes in Chinese hamster ovary cells and these processes are dependent on Gi proteins, MEK 1/2 and microtubule modulation. J Pineal Res, 2008, 44, (3), 288-298. (Pubitemid 351392943)
38. Chan, A.; Lai, F.; Lo, R.; Voyno-Yasenetskaya, T.; Stanbridge, E.; Wong, Y., Melatonin mt1 and MT2 receptors stimulate c-Jun N-terminal kinase via pertussis toxin-sensitive and -insensitive G proteins. Cell Signal, 2002, 14, (3), 249-257. (Pubitemid 34102454)
39. Witt-Enderby, P.; Dubocovich, M., Characterization and regulation of the human ML1A melatonin receptor stably expressed in Chinese hamster ovary cells. Mol Pharmacol, 1996, 50, (1), 166-174. (Pubitemid 26250088)
40. Maestroni, G.; Sulli, A.; Pizzorni, C.; Villaggio, B.; Cutolo, M., Melatonin in rheumatoid arthritis: synovial macrophages show melatonin receptors. Ann N Y Acad Sci, 2002, 966, 271-275. (Pubitemid 34729185)
41. García-Maurio, S.; Pozo, D.; Calvo, J.; Guerrero, J., Correlation between nuclear melatonin receptor expression and enhanced cytokine production in human lymphocytic and monocytic cell lines. J Pineal Res, 2000, 29, (3), 129-137.
42. Carrillo-Vico, A.; Lardone, P.; Fernández-Santos, J.; Martín-Lacave, I.; Calvo, J.; Karasek, M.; Guerrero, J., Human lymphocyte-synthesized melatonin is involved in the regulation of the interleukin-2/interleukin-2 receptor system. J Clin Endocrinol Metab, 2005, 90, (2), 992-1000. (Pubitemid 40279225)
43. Lardone, P.; Carrillo-Vico, A.; Naranjo, M.; De Felipe, B.; Vallejo, A.; Karasek, M.; Guerrero, J., Melatonin synthesized by Jurkat human leukemic T cell line is implicated in IL-2 production. J Cell Physiol, 2006, 206, (1), 273-279. (Pubitemid 41740741)
44. Garratt, P.J.; Travard, S.; Vonhoff, S.; Tsotinis, A.; Sugden, D., Mapping the melatonin receptor. 4. Comparison of the binding affinities of a series of substituted phenylalkyl amides. J Med Chem, 1996, 39, (9), 1797-1805. (Pubitemid 26142822)
45. Rivara, S.; Mor, M.; Silva, C.; Zuliani, V.; Vacondio, F.; Spadoni, G.; Bedini, A.; Tarzia, G.; Lucini, V.; Pannacci, M.; Fraschini, F.; Plazzi, P., Three-dimensional quantitative structure-Activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation. J Med Chem, 2003, 46, (8), 1429-1439. (Pubitemid 36512705)
46. Faust, R.; Garratt, P.J.; Jones, R.; Yeh, L.K.; Tsotinis, A.; Panoussopoulou, M.; Calogeropoulou, T.; Teh, M.T.; Sugden, D., Mapping the melatonin receptor. 6. Melatonin agonists and antagonists derived from 6Hisoindolo[ 2,1-A]indoles, 5,6-dihydroindolo[2,1-A]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-A]indoles. J Med Chem, 2000, 43, (6), 1050-1061. (Pubitemid 30173731)
47. Teh, M.; Sugden, D., Comparison of the structure-Activity relationships of melatonin receptor agonists and antagonists: lengthening the N-Acyl sidechain has differing effects on potency on Xenopus melanophores. Naunyn Schmiedebergs Arch Pharmacol, 1998, 358, (5), 522-528. (Pubitemid 28518314)
48. Miyamoto, M., Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders. CNS Neurosci Ther, 2009, 15, (1), 32-51.
49. Audinot, V.; Mailliet, F.; Lahaye-Brasseur, C.; Bonnaud, A.; Le Gall, A.; Amossé, C.; Dromaint, S.; Rodriguez, M.; Nagel, N.; Galizzi, J.; Malpaux, B.; Guillaumet, G.; Lesieur, D.; Lefoulon, F.; Renard, P.; Delagrange, P.; Boutin, J., New selective ligands of human cloned melatonin MT1 and MT2 receptors. Naunyn Schmiedebergs Arch Pharmacol, 2003, 367, (6), 553-561. (Pubitemid 36829452)
50. Dubocovich, M.L.; Yun, K.; Al-Ghoul, W.M.; Benloucif, S.; Masana, M.I., Selective MT2 melatonin receptor antagonists block melatonin-mediated phase advances of circadian rhythms. FASEB J, 1998, 12, (12), 1211-1220. (Pubitemid 28418951)
51. Pfeffer, M.; Rauch, A.; Korf, H.W.; von Gall, C., The Endogenous Melatonin (MT) Signal Facilitates Reentrainment of the Circadian System to Light-Induced Phase Advances by Acting Upon MT2 Receptors. Chronobiol Int, 2012, 29, (4), 415-429.
52. Wallez, V.; Durieux-Poissonnier, S.; Chavatte, P.; Boutin, J.; Audinot, V.; Nicolas, J.; Bennejean, C.; Delagrange, P.; Renard, P.; Lesieur, D., Synthesis and structure-Affinity-Activity relationships of novel benzofuran derivatives as MT(2) melatonin receptor selective ligands. J Med Chem, 2002, 45, (13), 2788-2800. (Pubitemid 34627649)
53. Pfeffer, M.; Rauch, A.; Korf, H.W.; von Gall, C., The endogenous melatonin (MT) signal facilitates reentrainment of the circadian system to light-induced phase advances by acting upon MT2 receptors. Chronobiol Int, 2012, 29, (4), 415-429.
54. Ochoa-Sanchez, R.; Comai, S.; Lacoste, B.; Bambico, F.R.; Dominguez-Lopez, S.; Spadoni, G.; Rivara, S.; Bedini, A.; Angeloni, D.; Fraschini, F.; Mor, M.; Tarzia, G.; Descarries, L.; Gobbi, G., Promotion of non-rapid eye movement sleep and activation of reticular thalamic neurons by a novel MT2 melatonin receptor ligand. J Neurosci, 2011, 31, (50), 18439-18452.
55. Simko, F.; Pechanova, O., Potential roles of melatonin and chronotherapy among the new trends in hypertension treatment. J Pineal Res, 2009, 47, (2), 127-133.
56. Mühlbauer, E.; Albrecht, E.; Hofmann, K.; Bazwinsky-Wutschke, I.; Peschke, E., Melatonin inhibits insulin secretion in rat insulinoma -cells (INS-1) heterologously expressing the human melatonin receptor isoform MT2. J Pineal Res, 2011.
57. Hardeland, R., Investigational melatonin receptor agonists. Expert Opin Investig Drugs, 2010, 19, (6), 747-764.
58. Mody, S.; Hu, Y.; Ho, M.; Wong, Y., In search of novel and therapeutically significant melatoninergic ligands. Recent Pat CNS Drug Discov, 2007, 2, (3), 241-245. (Pubitemid 350200295)
59. Rivara, S.; Mor, M.; Bedini, A.; Spadoni, G.; Tarzia, G., Melatonin receptor agonists: SAR and applications to the treatment of sleep-wake disorders. Curr Top Med Chem, 2008, 8, (11), 954-968.