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Chemical Compound Review:

Lopac-C-0331 N-[2-(6-chloro-5-methoxy-1H- indol-3...

Synonyms: Tocris-0443, CHEMBL34730, SureCN677517, SureCN677518, AG-J-38755, ...

Lanoix, D. et al., Popova, J.S. et al., Roberts, J.E. et al., Kennaway, D.J. et al., Vacas, M.I. et al., et al.

Roberts, Hu, Martinez, Chignell,

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Disease relevance of BRN 0410191

This effect of 6-chloromelatonin on forskolin-stimulated HCG-beta secretion was abolished by pertussis toxin (PTX), suggesting that melatonin regulates hCG-beta production by an action involving an inhibitory Gi/o protein [1].

High impact information on BRN 0410191

Pharmacological characterization showed that these binding sites were highly specific to 2-iodomelatonin, melatonin, 6-hydroxymelatonin, and 6-chloromelatonin [2].
Melatonin (0.1-2.0 mM) and its analog, 6-chloromelatonin (0.1-0.5 mM) depressed evoked potentials (EPSP and the population spike) in a concentration-dependent manner [3].
Using flash photolysis, we determined that melatonin and its membrane receptor agonist 6-chloromelatonin (Mel(1a-b), Lilly, Indianapolis, IN) produced very little singlet oxygen (psidelta = 0.073 and psidelta = 0.01, respectively) [4].
Direct stimulation of membrane phospholipase C by 6-chloromelatonin (10 microM) in isolated myo-[2-3H]inositol-prelabeled optic tectum membranes was dependent on the presence of guanosine-5'-O-(3-thio)triphosphate (1 microM), thus suggesting that G protein(s) link melatonin receptor activation to phospholipase C stimulation [5].
6-Chloromelatonin (1-30 mg/kg, i.p.) significantly retarded the alpha-MpT-induced decrease in NE levels in the hypothalamus, but not in hippocampus and frontal cortex [6].

Biological context of BRN 0410191

Melatonin (5-OCH3-N-acetyltryptamine) and 6-chloromelatonin were equipotent in inhibiting the calcium-dependent release of [3H]dopamine (IC50 = 40 pM) [7].
The effects of 6-chloromelatonin and 6-fluoromelatonin on ovulation and LH and prolactin release in rats were determined [8].

Anatomical context of BRN 0410191

In male Fisher rat caudal artery denuded of endothelium, melatonin was 10 times more potent than 6-chloromelatonin to potentiate contraction to phenylephrine, suggesting activation of smooth muscle MT(1) melatonin receptors [9].
5-Methoxytryptol, 5-methoxytryptamine, melatonin and 6-chloromelatonin (10(-8)-10(-6) M) depressed significantly the K+-stimulated increase in Ca2+-uptake, without affecting the basal, unstimulated Ca2+-uptake by synaptosomes [10].

Associations of BRN 0410191 with other chemical compounds

Among the indoles tested only 6-chloromelatonin, melatonin and N-acetylserotonin had significant affinities to the [125I]iodomelatonin binding site [11].
Plasma cholesterol levels were elevated only in hamsters receiving 6-chloromelatonin injections [12].

Gene context of BRN 0410191

Melatonin, 6-chloromelatonin, 2,3-dihydromelatonin and 6-chloro-2,3-dihydromelatonin decreased plasma prolactin to 31, 45, 54 and 48% of control levels respectively when administered daily (100 micrograms at 1600 h) for 21 days [13].

Analytical, diagnostic and therapeutic context of BRN 0410191

Furthermore, enzyme-linked immunosorbent assay showed that 6-chloromelatonin (a melatonin agonist) inhibits, in a dose-dependent manner, forskolin-stimulated hCG-beta secretion in JEG-3 (P < 0.001) and BeWo (P < 0.05) cells but had no effect on basal human chorionic gonadotrophin (hCG-beta) levels [1].

References

Expression of melatoninergic receptors in human placental choriocarcinoma cell lines. Lanoix, D., Ouellette, R., Vaillancourt, C. Hum. Reprod. (2006) [Pubmed]
2-[125I]iodomelatonin-binding sites in the human kidney and the effect of guanosine 5'-O-(3-thiotriphosphate). Song, Y., Tam, P.C., Poon, A.M., Brown, G.M., Pang, S.F. J. Clin. Endocrinol. Metab. (1995) [Pubmed]
The modulation of neuronal activity by melatonin: in vitro studies on mouse hippocampal slices. Hogan, M.V., El-Sherif, Y., Wieraszko, A. J. Pineal Res. (2001) [Pubmed]
Photophysical studies on melatonin and its receptor agonists. Roberts, J.E., Hu, D.N., Martinez, L., Chignell, C.F. J. Pineal Res. (2000) [Pubmed]
Melatonin receptor-mediated stimulation of phosphoinositide breakdown in chick brain slices. Popova, J.S., Dubocovich, M.L. J. Neurochem. (1995) [Pubmed]
Activation of melatonin receptor sites retarded the depletion of norepinephrine following inhibition of synthesis in the C3H/HeN mouse hypothalamus. Fang, J.M., Dubocovich, M.L. J. Neurochem. (1990) [Pubmed]
Luzindole (N-0774): a novel melatonin receptor antagonist. Dubocovich, M.L. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
Inhibition of luteinizing hormone release and ovulation by 6-chloro- and 6-fluoromelatonin. Clemens, J.A., Flaugh, M.E., Parli, J., Sawyer, B.D. Neuroendocrinology (1980) [Pubmed]
MT(2) melatonin receptors are present and functional in rat caudal artery. Masana, M.I., Doolen, S., Ersahin, C., Al-Ghoul, W.M., Duckles, S.P., Dubocovich, M.L., Krause, D.N. J. Pharmacol. Exp. Ther. (2002) [Pubmed]
Pineal methoxyindoles depress calcium uptake by rat brain synaptosomes. Vacas, M.I., Keller Sarmiento, M.I., Cardinali, D.P. Brain Res. (1984) [Pubmed]
Retinal [125I]iodomelatonin binding sites in the tree shrew (Tupaiidae). Lu, Y., Yuan, H., Pang, S.F. Neurosci. Lett. (1991) [Pubmed]
Natural and synthetic analogues of melatonin and related compounds. II. Effects on plasma thyroid hormones and cholesterol levels in male Syrian hamsters. Vaughan, M.K., Richardson, B.A., Johnson, L.Y., Petterborg, L.J., Powanda, M.C., Reiter, R.J., Smith, I. J. Neural Transm. (1983) [Pubmed]
Prolactin response in Border-Leicester x merino ewes to administration of melatonin, melatonin analogues, a melatonin metabolite and 6-methoxybenzoxazolinone. Kennaway, D.J., Royles, P., Dunstan, E.A., Hugel, H.M. Aust. J. Biol. Sci. (1986) [Pubmed]

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