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  • Title: 7-Substituted-melatonin and 7-substituted-1-methylmelatonin analogues: effect of substituents on potency and binding affinity.
    Author: Faust R, Garratt PJ, Trujillo Pérez MA, Piccio VJ, Madsen C, Stenstrøm A, Frølund B, Davidson K, Teh MT, Sugden D.
    Journal: Bioorg Med Chem; 2007 Jul 01; 15(13):4543-51. PubMed ID: 17459711.
    Abstract:
    A series of 7-substituted melatonin and 1-methylmelatonin analogues were prepared and tested against human and amphibian melatonin receptors. 7-Substituents reduced the agonist potency of all the analogues in the Xenopus laevis melanophore assay, 7-bromomelatonin (5d) and N-butanoyl 7-bromo-5-methoxytryptamine (5f) being the most active compounds, but both were 42-fold less potent than melatonin (1). Whereas all the analogues bind with lower affinity at the human MT(1) receptor than melatonin, 5d, 5f and N-propanoyl 7-bromo-5-methoxytryptamine (5e) show a similar binding affinity to melatonin at the MT(2) receptor and consequently show some MT(2) selectivity. These results suggest that the receptor pocket around C-7 favours binding by an electronegative group, suggesting an electropositive region in this area of the receptor.
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