2-Iodomelatonin - CAS 93515-00-5
Category: Inhibitor
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Molecular Formula:
C13H15IN2O2
Molecular Weight:
358.18
COA:
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Targets:
Melatonin Receptor
Description:
2-Iodomelatonin is a potent agonist of the melatonin receptors 1 (MT1) with Ki value of 28 pM. It could be used to identify, characterize and localize melatonin binding sites in the brain and peripheral tissues. It inhibits forskolin-stimulated cAMP production in CHO cells expressing human MT1 30-fold more potently than melatonin. It has been used to characterize the role of MT1 in melatonin-mediated signaling. It is useful in receptor binding studies with radioactive iodomelatonin.
Purity:
≥98% by HPLC
Synonyms:
N-[2-(2-Iodo-5-methoxyindol-3-yl)ethyl]acetamide; N-Acetyl-2-iodo-5-methoxytryptamine
MSDS:
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InChIKey:
FJDDSMSDZHURBJ-UHFFFAOYSA-N
InChI:
InChI=1S/C13H15IN2O2/c1-8(17)15-6-5-10-11-7-9(18-2)3-4-12(11)16-13(10)14/h3-4,7,16H,5-6H2,1-2H3,(H,15,17)
Canonical SMILES:
CC(=O)NCCC1=C(NC2=C1C=C(C=C2)OC)I
1.Kinetic, thermodynamic and X-ray structural insights into the interaction of melatonin and analogues with quinone reductase 2.
Calamini B;Santarsiero BD;Boutin JA;Mesecar AD Biochem J. 2008 Jul 1;413(1):81-91. doi: 10.1042/BJ20071373.
Melatonin exerts its biological effects through at least two transmembrane G-protein-coupled receptors, MT1 and MT2, and a lower-affinity cytosolic binding site, designated MT3. MT3 has recently been identified as QR2 (quinone reductase 2) (EC 1.10.99.2) which is of significance since it links the antioxidant effects of melatonin to a mechanism of action. Initially, QR2 was believed to function analogously to QR1 in protecting cells from highly reactive quinones. However, recent studies indicate that QR2 may actually transform certain quinone substrates into more highly reactive compounds capable of causing cellular damage. Therefore it is hypothesized that inhibition of QR2 in certain cases may lead to protection of cells against these highly reactive species. Since melatonin is known to inhibit QR2 activity, but its binding site and mode of inhibition are not known, we determined the mechanism of inhibition of QR2 by melatonin and a series of melatonin and 5-hydroxytryptamine (serotonin) analogues, and we determined the X-ray structures of melatonin and 2-iodomelatonin in complex with QR2 to between 1.5 and 1.8 A (1 A=0.1 nm) resolution. Finally, the thermodynamic binding constants for melatonin and 2-iodomelatonin were determined by ITC (isothermal titration calorimetry).
2.Acute low doses of melatonin stimulate rat sex behavior: the role of serotonin neurotransmission.
Drago F;Busà L;Benelli A;Bertolini A Eur J Pharmacol. 1999 Nov 26;385(1):1-6.
Melatonin is known to inhibit male and female sex behavior, but this effect has been reported only after repeated administration of sustained doses of the hormone. The present experiments were performed in order to study the effects of acute treatment with low doses of melatonin on rat male and female sex behavior in a dose-response paradigm. After four mating tests with a receptive female, sexually active male rats of the Wistar strain were injected intraperitoneally (i.p.) with small doses of melatonin (10, 50 and 100 microg/kg) administered acutely 1 h before a 30-min mating test. Melatonin (50 and 100 ng/2 microl) or its analogs, 6-chloromelatonin (2 and 4 ng/2 microl) and 2-iodomelatonin (5 and 10 ng/2 microl) were also injected intracerebroventricularly (i.c.v.) 30 min before mating. Either treatments caused a reduction of the latency to the first mount, intromission and ejaculation. An increase in the frequency of mounts, intromissions and ejaculations was also observed. Inhibition of sexual activity was observed when a greater dose (1 mg/kg) of melatonin was repeatedly injected for 14 days. Female sex behavior, measured by the lordosis quotient in Wistar female rats, was not affected by acute treatment with the hormone, while it appeared to be inhibited by the repeated injection.
3.2-[125I]iodomelatonin binding sites in the quail liver: characterization and the effect of guanosine 5'-O-(3-thiotriphosphate).
Wan Q;Pang SF Biol Signals. 1995 Jan-Feb;4(1):24-31.
Melatonin receptors were studied in quail livers using the melatonin agonist 2-[125I]iodomelatonin ([125I]MEL) as the radioligand. The specific binding of [125I]MEL to membrane preparations of liver was rapid, stable, saturable, reversible and of high affinity. Scatchard analysis of the specific binding data indicated an equilibrium dissociation constant (Kd) of 19.4 +/- 1.01 pmol/l (n = 7) and a maximum number of binding sites (Bmax) of 1.16 +/- 0.19 fmol/mg protein (n = 7) in the quail liver collected at mid-light. The Hill coefficient approached 1.0, suggesting a single class of [125I]MEL binding sites in the quail liver. The diurnal variation study showed that the value of Kd was 64.4% higher (p < 0.05) at mid-dark compared to mid-light, with no significant change in Bmax. The kinetic analysis showed that the Kd value was 25.0 +/- 3.94 pmol/l at mid-light, which was comparable with values determined from saturation studies. Aside from 2-iodomelatonin, melatonin and 6-chloromelatonin, all indole analogs and neurotransmitters tested in inhibition studies had slight or no displacement of [125I]MEL binding. These studies demonstrated that [125I]MEL binding sites were highly specific for melatonin.
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CAS 93515-00-5 2-Iodomelatonin

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