Design and synthesis of naphthalenic dimers as selective MT1 melatoninergic ligands

Journal of Medicinal Chemistry

Volumn 46, Issue 7, 2003, Pages 1127-1129

  Descamps François, Carole ^a   Yous, Saïd ^a   Chavatte, Philippe ^a   Audinot, Valérie ^b   Bonnaud, Anne ^b   Boutin, Jean A ^b   Delagrange, Philippe ^b   Bennejean, Caroline ^b   Renard, Pierre ^b   Lesieur, Daniel ^a  

^a UNIV LILLE   (France)

^b INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AGOMELATINE; DIMER; MELATONIN; MELATONIN DERIVATIVE; MELATONIN RECEPTOR;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHO CELL; CLINICAL TRIAL; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN;

ACETAMIDES; ANIMALS; CELL LINE; CRICETINAE; DIMERIZATION; DRUG DESIGN; HUMANS; LIGANDS; MELATONIN; NAPHTHALENES; RADIOLIGAND ASSAY; RECEPTORS, CELL SURFACE; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RECEPTORS, MELATONIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037468868     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0255872     Document Type: Article

References (29)

1. Reiter, R. J. Pineal melatonin: cell biology of its synthesis and of its physiological interactions. Endocr. Rev. 1991, 12, 151-180.
2. Mahle, C. D.; Watson, A. J. Melatonin receptors: potential targets for central nervous system disorders. Expert Opin. Invest. Drugs 1997, 6, 399-406.
3. Li, P. K.; Witt-Enderby, P. A. Melatonin receptors as potential targets for drug discovery. Drugs Future 2000, 25, 945-957.
4. Reppert, S. M.; Weaver, D. R.; Ebisawa, T. Cloning and characterisation of a mammalian melatonin receptor that mediates reproductive and circadian responses. Neuron 1994, 13, 1177-1185.
5. Reppert, S. M.; Godson, C.; Mahle, C. D.; Weaver, D. R.; Slaugenhaupt, S. A.; Gusella, J. F. Molecular characterisation of a second melatonin receptor expressed in human retina and brain: The Mel1b melatonin receptor. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8734-8738.
6. Dubocovich, M. L.; Cardinali, D. P.; Delagrange, P.; Krause, D. N.; Strosberg, A. D.; Sugden, D.; Yocca, F. D. The IUPHAR Compendium of Receptor Characterisation and Classification; IUPHAR Media: London, 2000; pp 271-277.
7. 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, 117-126.
8. 1a melatonin receptor gene is expressed in human suprachiasmatic nuclei. NeuroReport 1996, 8, 109-112.
9. Al-Ghoul, W. M.; Herman, M. D.; Dubocovich, M. L. Melatonin receptor subtype expression in human cerebellum. NeuroReport 1998, 9, 4063-4068.
10. 1a subtype localised primarily to the basolateral membrane of the proximal tubule. FASEB J. 1997, 11, 93-100.
11. Brydon, L.; Petit, L.; Delagrange, P.; Strosberg, A. D.; Jockers, R. Functional expression of mt2 (mel1b) melatonin receptors in human paz6 adipocytes. Endocrinology 2001, 142, 4264-4271.
12. Morgan, P. J.; Barrett, P.; Howell, H. E.; Helliwell, R. Melatonin receptors: localization, molecular pharmacology and physiological significance. Neurochem. Int. 1994, 24, 101-146.
13. Doolen, S.; Krause, D. N.; Dubocovich, M. L.; Duckles, S. P. Melatonin mediates two distinct responses in vascular smooth muscle. Eur. J. Pharmacol. 1998, 345, 67-69.
14. Dubocovich, M. L.; Masana, M. I.; Iacob, S.; Sauri, D. M. 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-Schmiedeberg's Arch. Pharmacol. 1997, 355, 365-375.
15. Teh, M.; Sugden, D. Comparison of the structure - activity relationships of melatonin receptor agonists and antagonists: lengthening the N-acyl side-chain has differing effects on potency on Xenopus melanophores. Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 358, 522-528.
16. Sugden, D.; Yeh, L. K.; Teh, M. T. Design of subtype selective melatonin receptor agonists and antagonists. Reprod., Nutr., Dev. 1999, 39, 335-44.
17. Faust, R.; Garratt, P. J.; Jones, R.; Yeh, L. K.; Tsotinis, A.; Panoussoupolou, M.; Calogeropoulou, T.; Teh, M. T.; Sugden, D. Mapping the melatonin receptor. 6. Melatonin agonists and antagonists derived from 6H-isoindolo[2,1-α]indoles, 5,6-dihydroindolo[2,1-α]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-α]indoles. J. Med. Chem. 2000, 43, 1050-1061.
18. 2-selective melatonin antagonists. J. Med. Chem. 2001, 44, 2900-2912.
19. Masana, M. I.; Dubocovich, M. L. Melatonin receptor signaling: finding the path through the dark. Sci. STKE 2001, 6, 107.
20. 2 melatonin receptor selective ligands. J. Med. Chem. 2002, 45, 2788-2800.
21. Portoghese, P. S.; Ronsisvalle, G.; Larson, D. L.; Yim, C. B.; Sayre, L. M.; Takemori, A. E. Opioid agonist and antagonist bivalent ligands as receptor probes. Life Sci. 1982, 31, 1283-1286.
22. Erez, M.; Takemori, A. E.; Porthoghese, P. S. Narcotic antagonist potency of bivalent ligands which contain β-naltrexamine. Evidence for bridging between proximal recognition sites. J. Med. Chem. 1982, 25, 847-849.
23. Turnheim, K.; Kraupp, O. Pulmonary and systemic circulatory effect and β-adrenergic selectivity of hexaprenaline, salbutamol, oxyfedrine and isoproterenol. Eur. J. Pharmacol. 1971, 15, 231-239.
24. Fisher, L. E.; Rosenkranz, R. P.; Clark, R. D.; Muchowski, J. M.; McClelland, D. L.; Michel, A.; Caroon, J. M.; Galeazi, E.; Eylen, R.; Whiting, R. L. N,N-6-Bis-[2-(3,4-dihydroxybenzyl)- pyrrolidinyl]hexane, a potent, selective, orally active dopamine analog with hypotensive and diuretic activity. Bioorg. Med. Chem. Lett. 1995, 5, 2371-2376.
25. Le Boulluec, K.; Matson, R. J.; Mable, C. D.; McGovern, R. T.; Nowak, H. P.; Gentile, A. J. Bivalent indoles exhibiting serotoninergic binding affinity. Bioorg. Med. Chem. Lett. 1995, 5, 123-126.
26. Yous, S.; Andrieux, J.; Howell, H. E.; Morgan, P. J.; Renard, P.; Pfeiffer, B.; Lesieur, D.; Guardiola-Lemaître, B. Novel naphthalenic ligands with high affinity for melatonin receptor. J. Med. Chem. 1992, 35, 1484-1486.
27. Depreux, P.; Lesieur, D.; Mansour, H. A.; Morgan, P.; Howell, H. E.; Renard, P.; Caignard, D.-H.; Pfeiffer, B.; Delagrange, P.; Guardiola, B.; Yous, S.; Demarque, A.; Adam, G.; Andrieux, J. Synthesis and structure - activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands. J. Med. Chem. 1994, 37, 3231-3239.
28. Lesieur, D.; Leclerc, V.; Chavatte, P.; Marot, C.; Renard, P.; Guardiola-Lemaître, B. La mélatonine, prototype pertinent pour l'innovation thérapeutique (Melatonin, a pertinent prototype for therapeutic innovation). Therapie 1998, 53, 429-437.
29. Ayoub, M. A.; Couturier, C.; Lucas-Meunier, E.; Angers, S.; Fossier, P.; Bouvier, M.; Jockers, R. Monitoring of ligand- independent dimerization and ligand-induced conformational changes of melatonin receptors in living cells by bioluminescence resonance energy transfer. J. Biol. Chem. 2002, 277, 21522-21528.