Recent advances in the development of melatonin MT₁ and MT₂ receptor agonists

Bibliography

• Inouye ST, Kawamura H. Persistence of circadian rhythmicity in a mammalian hypothalamic “island” containing the suprachiasmatic nucleus. Proc Natl Acad Sci USA 1979;76:5962-6
   PubMed Web of Science ®Google Scholar
• Cardinali DP, Rosner JM. Metabolism of serotonin by the rat retina “in vitro”. J Neurochem 1971;18:1769-70
   PubMed Web of Science ®Google Scholar
• Tosini G, Menaker M. The clock in the mouse retina: melatonin synthesis and photoreceptor degeneration. Brain Res 1998;789:221-8
   PubMed Web of Science ®Google Scholar
• Carrillo-Vico A, Calvo JR, Abreu P, Evidence of melatonin synthesis by human lymphocytes and its physiological significance: possible role as intracrine, autocrine and/or paracrine substance. FASEB J 2004;18:537-9
   PubMed Web of Science ®Google Scholar
• Raikhlin NT, Kvetnoy IM. Melatonin and enterochromaffine cells. Acta Histochem 1976;55:19-24
   PubMed Web of Science ®Google Scholar
• Bubenik GA. Gastrointestinal melatonin: localization, function, and clinical relevance. Dig Dis Sci 2002;47:2336-48
   PubMed Web of Science ®Google Scholar
• Reiter RJ. The pineal and its hormones in the control of reproduction in mammals. Endocr Rev 1980;1:109-31
   PubMedGoogle Scholar
• Gillette MU, Tischkau SA. Suprachiasmatic nucleus: the brain's circadian clock. Recent Prog Horm Res 1999;54:33-58
   PubMedGoogle Scholar
• Shochat T, Luboshitzky R, Lavie P. Nocturnal melatonin onset is phase locked to the primary sleep gate. Am J Physiol 1997;273:R364-70
   Google Scholar
• Krauchi K, Wirz-Justice A. Circadian clues to sleep onset mechanism. Neuropsychopharmacology 2001;25:S92-6
   PubMed Web of Science ®Google Scholar
• Ferguson SA, Rajaratnam SMW, Dawson D. Melatonin agonists and insomnia. Expert Rev Neurother 2010;10:305-18
   PubMed Web of Science ®Google Scholar
• Rajaratnam SMW, Cohen DA, Rogers NL. Melatonin and melatonin analogues. Sleep Med Clin 2009;4:179-93
   Google Scholar
• Maestroni GJ. The immunotherapeutic potential of melatonin. Expert Opin Investig Drugs 2001;10:467-76
   PubMed Web of Science ®Google Scholar
• Arangino S, Cagnacci A, Angiolucci M, Effects of melatonin on vascular reactivity, catecholamine levels and blood pressure in healthy men. Am J Cardiol 1999;83:1417-9
   PubMed Web of Science ®Google Scholar
• Cagnacci A, Arangino S, Angiolucci M, Effect of exogenous melatonin on vascular reactivity and nitric oxide in postmenopausal women: role of hormone replacement therapy. Clin Endocrinol (Oxf) 2001;54:261-6
   PubMed Web of Science ®Google Scholar
• Ambriz-Tututi M, Rocha-González HI, Cruz SL, Granados-Soto V. Melatonin: a hormone that modulates pain. Life Sci 2009;84:489-98
   PubMed Web of Science ®Google Scholar
• Satomura K, Tobiume S, Tukoyama R, Melatonin at pharmacological doses enhances human osteoblastic differentiation in vitro and promotes mouse cortical bone formation in vivo. J Pineal Res 2007;42:231-9
   PubMed Web of Science ®Google Scholar
• Korkmaz A, Reiter RJ, Topal T, Melatonin: an established antioxidant worthy of use in clinical trials. Mol Med 2009;15:43-50
   PubMed Web of Science ®Google Scholar
• Dubocovich ML, Cardinali DP, Delagrange P, Melatonin receptors. The IUPHAR compendium of receptor characterization and classification. IUPHAR Media, London; 2001. p. 270-7
   Google Scholar
• Tan DX, Manchester LC, Terron MP, Melatonin as a naturally occurring co-substrate of quinone reductase-2, the putative MT3 melatonin membrane receptor: hypothesis and significance. J Pineal Res 2007;43:317-20
   PubMed Web of Science ®Google Scholar
• Benitez-King G, Huerto-Delgadillo L, Anton-Tay F. Binding of 3H-melatonin to calmodulin. Life Sci 1993;53:201-7
   PubMedGoogle Scholar
• Romero MP, Garcia-Perganeda A, Guerrero JM, Osuna C. Membrane-bound calmodulin in Xenopus laevis oocytes as a novel binding site for melatonin. FASEB J 1998;12:1401-08
   PubMedGoogle Scholar
• Hardeland R. Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors 2009;35:183-92
   PubMed Web of Science ®Google Scholar
• Witt-Enderby PA, Bennett J, Jarzynka MJ, Melatonin receptors and their regulation: biochemical and structural mechanisms. Life Sci 2003;72:2183-98
   PubMed Web of Science ®Google Scholar
• Weaver DR, Reppert SM. The Mel1a melatonin receptor gene is expressed in human suprachiasmatic nuclei. Neuroreport 1996;8:109-12
   PubMed Web of Science ®Google Scholar
• Savaskan E, Ayoub MA, Jockers R, Reduced hippocampal MT2 melatonin receptor expression in Azheimer's disease. J Pineal Res 2005;38:10-6
   PubMed Web of Science ®Google Scholar
• Uz T, Arslan AD, Imbesi M, The regional and cellular expression profile of the melatonin receptor MT1 in the central dopaminergic system. Brain Res Mol Brain Res 2005;136:45-53
   PubMedGoogle Scholar
• Ekmekcioglu C, Thalhammer T, Humpeler S, The melatonin receptor subtype MT2 is present in the human cardiovascular system. J Pineal Res 2003;35:40-4
   PubMed Web of Science ®Google Scholar
• Savaskan E, Wirz-Justice A, Olivieri G, Distribution of melatonin MT1 receptor immunoreactivity in human retina. J Histochem Cytochem 2002;50:519-26
   PubMed Web of Science ®Google Scholar
• Maestroni GJ, Sulli A, Pizzorni C, Melatonin in rheumatoid arthritis: synovial macrophages show melatonin receptors. Ann NY Acad Sci 2002;966:271-5
   PubMedGoogle Scholar
• Jin X, von Gall C, Pieschl RL, Targeted disruption of mouse Mel1b melatonin receptor. Mol Cell Biol 2003;23:1054-60
   PubMed Web of Science ®Google Scholar
• von Gall C, Garabette ML, Kell CA, Rhythmic gene expression in pituitary depends on heterologous sensitization by the neurohormone melatonin. Nat Neurosci 2002;5:234-38
   PubMed Web of Science ®Google Scholar
• Drazen DL, Bilu D, Bilbo SD, Nelson RJ. In vitro melatonin enhancement of splenocyte proliferation is attenuated in mice by luzindole, a melatonin receptor antagonist. Am J Physiol 2001;280:R1476-82
   PubMed Web of Science ®Google Scholar
• Dubocovich ML, Masana MI, Iacob S, Sauri DM. Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor. Naunyn-Schmied Arch Pharmacol 1997;355:365-75
   PubMed Web of Science ®Google Scholar
• Ersahin C, Masana MI, Dubocovich ML. Constitutively active melatonin MT1 receptors in male rat caudal artieries. Eur J Pharmacol 2002;439:171-2
   PubMedGoogle Scholar
• Masana MI, Doolen S, Ersahin C, MT2 melatonin receptors are present and functional in rat caudal artery. J Pharmacol Exp Ther 2002;302:1295-302
   PubMed Web of Science ®Google Scholar
• Srinivasan V, Pandi-Perumal SR, Trahkt I, Melatonin and melatonergic drugs on sleep: possible mechanisms of action. Int J Neurosci 2009;119:821-46
   PubMed Web of Science ®Google Scholar
• Lewy AJ. Circadian misalignment in mood disturbances. Curr Psychiatry Rep 2009;11:459-65
   PubMed Web of Science ®Google Scholar
• Hirsch-Rodriguez E, Imbesi M, Manev R, The pattern of melatonin receptor expression in the brain may influence antidepressant treatment. Med Hypotheses 2006;69:120-4
   Web of Science ®Google Scholar
• Solmaz I, Gurkanlar D, Gokcil Z, Antiepileptic activity of melatonin in guinea pigs with pentylenetetrazol-induced seizures. Neurol Res 2009;31:989-95
   PubMed Web of Science ®Google Scholar
• Lin HW, Lee EJ. Effects of melatonin in experimental stroke models in acute, sub-acute, and chronic stages. Neuropsychiatr Dis Treat 2009;5:157-62
   PubMed Web of Science ®Google Scholar
• Kiefer TL, Ram PT, Yuan L, Hill SM. Melatonin inhibits estrogen receptor transactivation and cAMP levels in breast cancer cells. Breast Cancer Res Treat 2002;71:37-45
   PubMed Web of Science ®Google Scholar
• Garcia-Navarro A, Gonzalez-Puga C, Escames G, Cellular mechanisms involved in the melatonin inhibition of HT-29 human colon cancer cell proliferation in culture. J Pineal Res 2007;43:195-205
   PubMedGoogle Scholar
• Spadoni G, Bedini A, Mor M, Rivara S. The rationale for the development of melatonin receptor ligands. In: Pandi-Perumal SR, Verster JC, Monti JM, , editors, Sleep disorders: diagnosis and therapeutics. Informa Healthcare, London; 2008
   Google Scholar
• Steinhilber D, Carlberg C. Melatonin receptor ligands. Expert Opin Ther Patents 1999;9:281-90
   Web of Science ®Google Scholar
• Hardeland R. Investigational melatonin receptor agonists. Expert Opin Investig Drugs 2010;19:747-64
   PubMed Web of Science ®Google Scholar
• Rajaratnam SM, Polymeropoulos MH, Fisher DM, Melatonin agonist tasimelteon (VEC-162) for transient insomnia after sleep-time shift: two randomised controlled multicentre trials. Lancet 2009;373:482-91
   PubMed Web of Science ®Google Scholar
• Available from: www.vandapharma.com/development.html
   Google Scholar
• Zemlan FP, Mulchahey JJ, Scharf MB, The efficacy and safety of the melatonin agonist beta-methyl-6-chloromelatonin in primary insomnia: a randomized, placebo-controlled, crossover clinical trial. J Clin Psychiatry 2005;66:384-90
   PubMed Web of Science ®Google Scholar
• Tarzia G, Mor M, Rivara S, Melatonin receptor agonists: SAR and application to the treatment of sleep-wake disorders. Curr Top Med Chem 2008;8:954-68
   PubMedGoogle Scholar
• Zlotos DP. Recent advances in melatonin receptor ligands. Arch Pharm (Weinheim) 2005;338:229-47
   PubMed Web of Science ®Google Scholar
• Davies DJ, Faust R, Garratt PJ, Binding affinity and biological activity of oxygen and sulfur isosteres at melatonin receptors as a function of their hydrogen bonding capability. Bioorg Chem 2004;32:1-12
   PubMedGoogle Scholar
• Les Laboratoires Servier. Novel indole derivatives, process for their preparation thereof and pharmaceutical compositions containing them. WO2008049997; 2008
   Google Scholar
• Elsner J, Boeckler F, Davidson K, Bicyclic melatonin receptor agonists containing a ring-junction nitrogen: synthesis, biological evaluation, and molecular modeling of the putative bioactive conformation. Bioorg Med Chem 2006;14:1949-58
   PubMed Web of Science ®Google Scholar
• Tsotinis A, Panoussopoulou M, Sivananthan S, Sugden D. Synthesis of new tricyclic melatoninergic ligands. Farmaco 2001;56:725-9
   PubMedGoogle Scholar
• Tsotinis A, Panoussopoulou M, Hough K, Synthesis and biological evaluation of new beta,beta'-disubstituted 6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl ethylamido melatoninergic ligands. Eur J Pharm Sci 2003;18:297-304
   PubMedGoogle Scholar
• Spadoni G, Balsamini C, Diamantini G, Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study. J Med Chem 1997;40:1990-2002
   PubMed Web of Science ®Google Scholar
• Rivara S, Diamantini G, Di Giacomo B, Reassessing the melatonin pharmacophore – enantiomeric resolution, pharmacological activity, structure analysis, and molecular modeling of a constrained chiral melatonin analogue. Bioorg Med Chem 2006;14:3383-91
   PubMed Web of Science ®Google Scholar
• Cognetix, Inc. Subtype selective melatonergics. WO0200215; 2002
   Google Scholar
• Faust R, Garratt PJ, Jones R, Mapping the melatonin receptor. 6. Melatonin agonists and antagonists derived from 6H-isoindolo[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;43:1050-61
   PubMed Web of Science ®Google Scholar
• Fisher SP, Sugden D. Sleep-promoting action of IIK7, a selective MT2 melatonin receptor agonist in the rat. Neurosci Lett 2009;457:93-6
   PubMed Web of Science ®Google Scholar
• Ferrer Internacional S.A. Compounds of 2,3-dihydro-benzofuran. WO2009053444; 2009
   Google Scholar
• Ferrer Internacional S.A. Indane compounds. WO2009053443; 2009
   Google Scholar
• Ferrer Internacional S.A. Indoline compounds. WO2009053440; 2009
   Google Scholar
• Glaxo Group, Ltd. Indoline derivatives, method of preparation and use. US5633276; 1997
   Google Scholar
• Epperson JR, Bruce MA, Catt JD, Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]-propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides. Bioorg Med Chem 2004;12:4601-11
   PubMedGoogle Scholar
• Bristol-Myers Squibb Co. Polycyclic ethyl alkylamide melatonergic agents. US5948817; 1999
   Google Scholar
• Bristol-Myers Squibb Co. Spirocyclopropyl fluorenes as melatonergic agents. US6028112; 2000
   Google Scholar
• Concert Pharmaceuticals, Inc. Naphtyl(ethyl) acetamides. WO2008137461; 2008
   Google Scholar
• Les Laboratoires Servier. Novel naphthalene derivatives, process for the preparation thereof and pharmaceutical compositions containing same. WO2009022062; 2009
   Google Scholar
• Les Laboratoires Servier. Novel naphthalene derivatives, process for the preparation thereof and pharmaceutical compositions containing same. WO2009022066; 2009
   Google Scholar
• Les Laboratoires Servier. Novel naphthalene derivatives, process for the preparation thereof and pharmaceutical compositions containing same. WO2009022064; 2009
   Google Scholar
• Les Laboratoires Servier. Novel naphthalene derivatives, process for the preparation thereof and pharmaceutical compositions containing same. WO2009022063; 2009
   Google Scholar
• Les Laboratoires Servier. Novel naphthalene derivatives, process for the preparation thereof and pharmaceutical compositions containing same. WO2009022065; 2009
   Google Scholar
• Jellimann C, Mathe-Allainmat M, Andrieux J, Synthesis of phenalene derivatives as new conformationally restricted ligands for melatonin receptors. J Med Chem 2000;43:4051-62
   PubMedGoogle Scholar
• Mesangeau C, Peres B, Descamp-Francois C, Design, synthesis and pharmacological evaluation of novel naphthalenic derivatives as selective MT1 melatoninergic ligands. Bioorg Med Chem 2010;18:3426-36
   PubMedGoogle Scholar
• Adir et Compagnie. Substituted dimeric compounds. US6319930; 2001
   Google Scholar
• Audinot V, Mailliet F, Bonnaud A, New selective ligands of human cloned melatonin MT1 and MT2 receptors. Naunyn-Schmied Arch Pharmacol 2003;367:553-61
   PubMed Web of Science ®Google Scholar
• Les Laboratoires Servier. Novel bicyclic alkyl derivatives, method for production of and pharmaceutical compositions comprising the same. WO2005012229; 2005
   Google Scholar
• Mattson RJ, Catt JD, Keavy D, Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett 2003;13:1199-202
   PubMedGoogle Scholar
• Les Laboratoires Servier. Substituted (dihydro)benzoxazine and (dihydro)benzothiazine compounds. US6620809; 2003
   Google Scholar
• Wyeth. Dihydrobenzofuran derivatives and uses thereof. WO2006116136; 2006
   Google Scholar
• The Hong Kong University of Science and Technology. Isoquinolone compounds as subtype-selective agonists for melatonin receptors MT1 and MT2. WO2008092292; 2008
   Google Scholar
• Bristol-Myers Squibb Co. Benzofuran and dihydrobenzofuran melatonergic agents. US5856529; 1999
   Google Scholar
• Bristol-Myers Squibb Co. Benzopyran derivatives as melatonergic agents. US6060506; 2000
   Google Scholar
• Bristol-Myers Squibb Co. Benzodioxa alkylene ethers as melatonergic agents. US5981571; 1999
   Google Scholar
• Bristol-Myers Squibb Co. Heterocyclic cis cyclopropane derivatives as melatonergic agents. WO9962515; 1999
   Google Scholar
• Bristol-Myers Squibb Co. Arylalkylbenzofuran derivatives as melatonergic agents. US6569894; 2003
   Google Scholar
• Sun L-Q, Takaki K, Chen J, (R)-2-(4-Phenylbutyl)dihydrobenzofuran derivatives as melatoninergic agents. Bioorg Med Chem Lett 2005;15:1345-49
   PubMedGoogle Scholar
• Sun L-Q, Takaki K, Chen J, N-{2-[2-(4-Phenylbutyl)benzofuran-4-yl]cyclopropylmethyl}-acetamide: an orally bioavailable melatonin receptor agonist. Bioorg Med Chem Lett 2004;14:5157-60
   PubMedGoogle Scholar
• Bristol-Myers Squibb Co. Benzoxazole derivatives as novel melatonergic agents. US6737431; 2004
   Google Scholar
• Sun L-Q, Chen J, Takaki K, Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands. Bioorg Med Chem Lett 2004;14:1197-200
   PubMed Web of Science ®Google Scholar
• Sun L-Q, Chen J, Bruce M, Synthesis and structure-activity relationship of novel benzoxazole derivatives as melatonin receptor agonists. Bioorg Med Chem Lett 2004;14:3799-802
   PubMed Web of Science ®Google Scholar
• Bristol-Myers Squibb. Heterocyclic aminopyrrolidine derivatives as melatonergic agents. US6211225; 2001
   Google Scholar
• Luo G, Sun L-Q, Chen J, Heterocyclic aminopyrrolidine derivatives as melatoninergic agents. Bioorg Med Chem Lett 2003;13:4381-4
   PubMedGoogle Scholar
• Vanda Pharmaceuticals, Inc. Treatment for depressive disorders. WO2007137247; 2007
   Google Scholar
• Takeda Pharmaceutical Co., Ltd. Bicyclic compound and pharmaceutical use thereof. WO2008136382; 2008
   Google Scholar
• Takeda Pharmaceutical Co., Ltd. Tricyclic compound and medical use thereof. WO2008069311; 2008
   Google Scholar
• Takeda Pharmaceutical Co., Ltd. Tricyclic compound and pharmaceutical use thereof. WO2008084717; 2008
   Google Scholar
• Ferrer Internacional S.A. 1,6-dihydro-2H-3-oxa-6-aza-as-indacene compounds. WO2010012789; 2010
   Google Scholar
• Takeda Chemical Industries, Ltd. Tricyclic compounds, their production and use. US6034239; 2000
   Google Scholar
• Takeda Pharmaceutical Co., Ltd. Tricyclic compound and pharmaceutical use thereof. WO2007148808; 2007
   Google Scholar
• Bristol-Myers Squibb Co. N-acyl-2-arylcyclopropylmethylamine derivatives as melatonergics. US5889031; 1999
   Google Scholar
• Ferrer Internacional S.A. Phenylpyrrolidine compounds. WO2009053441; 2009
   Google Scholar
• Bristol-Myers Squibb Co. Aryloxyanilides and related compounds. WO9948859; 1999
   Google Scholar
• Epperson JR, Deskus JA, Gentile AJ, 4-substituted anilides as selective melatonin MT2 receptor agonists. Bioorg Med Chem Lett 2004;14:1023-6
   PubMedGoogle Scholar
• McGill University, Università degli Studi di Parma, Università degli Studi di Milano, Università degli Studi di Urbino. Novel melatonin ligands having antidepressant activity as well as sleep inducing properties. WO2007079593; 2007
   Google Scholar
• Rivara S, Lodola A, Mor M, N-(substituted-anilinoethyl)amides: design, synthesis, and pharmacological characterization of a new class of melatonin receptor ligands. J Med Chem 2007;50:6618-26
   PubMed Web of Science ®Google Scholar
• Hu Y, Ho MKC, Chan KH, Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT2-selective melatonin ligands. Bioorg Med Chem Lett 2010;20:2582-85
   PubMedGoogle Scholar