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Chemical Compound Review

IODOMELATONIN     N-[2-(2-iodo-5-methoxy-1H- indol-3...

Synonyms: Lopac-I-1899, Tocris-0737, CHEMBL289233, SureCN163451, AG-H-82210, ...
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Disease relevance of Tocris-0737


High impact information on Tocris-0737


Biological context of Tocris-0737


Anatomical context of Tocris-0737

  • Pretreating cultured cells for 24 h with 2-iodomelatonin or melatonin, but not with 5-methoxytryptamine, reduced subsequent 2-[125I]iodomelatonin binding [10].
  • During pharmacological screening administration of the agonists 2-iodomelatonin and 2-iodo-N-butanoyl-5-methoxytryptamine (IbMT) to the oocytes resulted in oscillatory membrane currents, whereas the administration of the MT3 agonist 5-methoxycarbonylamino-N-acetyltryptamine (GR135,531) exerted no detectable membrane currents [11].
  • Melatonin and melatonin receptor agonists 2-iodo-N-butanoyl-5-methoxytryptamine and 2-iodomelatonin (1.0-100 nM) increased enterocyte [Ca(2+)](i), EC(50) of melatonin being 17.0 +/- 2.6 nM [12].
  • Moreover, no superoxide anion scavenging effect of 2-iodomelatonin was observed in isolated mesenteric vascular muscle cells using lucigenin [9].
  • Most ligands exhibited reversed stereoselectivity when competing with 125I 2-iodomelatonin binding to chicken retinal (ML-1) and hamster brain (ML-2) membranes, further supporting the biochemical and pharmacological differences reported for these two sites [13].

Associations of Tocris-0737 with other chemical compounds


Gene context of Tocris-0737


Analytical, diagnostic and therapeutic context of Tocris-0737


  1. Melatonin mt1 and MT2 receptors stimulate c-Jun N-terminal kinase via pertussis toxin-sensitive and -insensitive G proteins. Chan, A.S., Lai, F.P., Lo, R.K., Voyno-Yasenetskaya, T.A., Stanbridge, E.J., Wong, Y.H. Cell. Signal. (2002) [Pubmed]
  2. Characterization and regulation of the human ML1A melatonin receptor stably expressed in Chinese hamster ovary cells. Witt-Enderby, P.A., Dubocovich, M.L. Mol. Pharmacol. (1996) [Pubmed]
  3. 2-iodomelatonin prevents apoptosis of cerebellar granule neurons via inhibition of A-type transient outward K+ currents. Hu, C.L., Liu, Z., Gao, Z.Y., Zhang, Z.H., Mei, Y.A. J. Pineal Res. (2005) [Pubmed]
  4. Melatonin receptor agonist 2-iodomelatonin prevents apoptosis of cerebellar granule neurons via K(+) current inhibition. Jiao, S., Wu, M.M., Hu, C.L., Zhang, Z.H., Mei, Y.A. J. Pineal Res. (2004) [Pubmed]
  5. Molecular modeling of human MT2 melatonin receptor: the role of Val204, Leu272 and Tyr298 in ligand binding. Mazna, P., Obsilova, V., Jelinkova, I., Balik, A., Berka, K., Sovova, Z., Ettrich, R., Svoboda, P., Obsil, T., Teisinger, J. J. Neurochem. (2004) [Pubmed]
  6. Melatonin receptors and signal transduction in photorefractory Siberian hamsters (Phodopus sungorus). Weaver, D.R., Provencio, I., Carlson, L.L., Reppert, S.M. Endocrinology (1991) [Pubmed]
  7. Potential involvement of mt1 receptor and attenuated sex steroid-induced calcium influx in the direct anti-proliferative action of melatonin on androgen-responsive LNCaP human prostate cancer cells. Xi, S.C., Tam, P.C., Brown, G.M., Pang, S.F., Shiu, S.Y. J. Pineal Res. (2000) [Pubmed]
  8. Melatonin agonists induce phosphoinositide hydrolysis in Xenopus laevis melanophores. Mullins, U.L., Fernandes, P.B., Eison, A.S. Cell. Signal. (1997) [Pubmed]
  9. Inhibitory effect of melatonin on alpha1-adrenergic-induced vasoconstriction in mesenteric beds of spontaneously hypertensive rats. Girouard, H., de Champlain, J. Am. J. Hypertens. (2004) [Pubmed]
  10. 5-Methoxytryptamine inhibits cyclic AMP accumulation in cultured retinal neurons through activation of a pertussis toxin-sensitive site distinct from the 2-[125I]iodomelatonin binding site. Iuvone, P.M., Gan, J., Alonso-Gómez, A.L. J. Neurochem. (1995) [Pubmed]
  11. Expression and functional characterization of the mt1 melatonin receptor from rat brain in Xenopus oocytes: evidence for coupling to the phosphoinositol pathway. Blumenau, C., Berger, E., Fauteck, J.D., Madeja, M., Wittkowski, W., Speckmann, E.J., Musshoff, U. J. Pineal Res. (2001) [Pubmed]
  12. Melatonin-induced calcium signaling in clusters of human and rat duodenal enterocytes. Sjöblom, M., Säfsten, B., Flemström, G. Am. J. Physiol. Gastrointest. Liver Physiol. (2003) [Pubmed]
  13. The high affinity melationin binding site probed with conformationally restricted ligand--I. Pharmacophore and minireceptor models. Jansen, J.M., Copinga, S., Gruppen, G., Molinari, E.J., Dubocovich, M.L., Grol, C.J. Bioorg. Med. Chem. (1996) [Pubmed]
  14. Human malignant melanoma cells express high-affinity receptors for melatonin: antiproliferative effects of melatonin and 6-chloromelatonin. Ying, S.W., Niles, L.P., Crocker, C. Eur. J. Pharmacol. (1993) [Pubmed]
  15. Iodinated melatonin: preparation and characterization of the molecular structure by mass and 1H NMR spectroscopy. Vakkuri, O., Lämsä, E., Rahkamaa, E., Ruotsalainen, H., Leppäluoto, J. Anal. Biochem. (1984) [Pubmed]
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