- Radioimmunoassay of N-acetyl-N-formyl-5-methoxykynuramine (AFMK): A melatonin oxidative metabolite
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N-acetyl-N-formyl-5-methoxykynuramine (AFMK) is a melatonin metabolite identified in rat brain by Hirata et al. (The Journal of Biological Chemistry 249 (1974) 1311). Since no assay has been described for its routine measurement, we have developed and val
- Harthe, Catherine,Claudy, Daniele,Dechaud, Henri,Vivien-Roels, Berthe,Pevet, Paul,Claustrat, Bruno
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Read Online
- Long term storage inducer
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PROBLEM TO BE SOLVED: To provide a long-term memory inducing agent.SOLUTION: A long-term memory inducing agent comprises a compound represented by the formula I, pharmaceutically acceptable salt thereof, or solvate thereof.SELECTED DRAWING: None
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- Oxidative coupling rearrangement product based on tryptamine skeleton and preparation method and application thereof
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The invention discloses an oxidative coupling rearrangement product based on a tryptamine skeleton and a preparation method and application thereof, wherein a corresponding dicarbonyl compound is obtained by oxidizing a color amine compound by using sodiu
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Paragraph 0069-0077
(2021/09/01)
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- Quinazoline and phthalazine derivatives as novel melatonin receptor ligands analogues of agomelatine
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For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and pharmacological results of a new family of melatonin receptor ligands. Issued from the introduction of quinazoline and phthalazine scaffolds carrying an ethyl amide lateral chain and a methoxy group as bioisosteric ligands analogues of previously developed Agomelatine. The biological activity of the prepared analogues was compared with that of Agomelatine. Quinazoline and phthalazine rings proved to be a versatile scaffold for easy feasible MT1 and MT2 ligands. Potent agonists with sub-micromolar binding affinity were obtained. However, the presence of two nitrogen atoms resulted in compounds with lower affinity for both MT1 and MT2, in comparison with the parent compound, balanced by the exhibition of good pharmacokinetic properties.
- Bolteau, Rapha?l,Descamps, Florian,Ettaoussi, Mohamed,Caignard, Daniel H.,Delagrange, Philippe,Melnyk, Patricia,Yous, Sa?d
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- LONG-TERM MEMORY INDUCING AGENT
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[Problem] To provide a method for inducing a long-term memory in a subject need thereof. [Solution to problem] A method for inducing a long-term memory, comprising a step of administering a compound represented by Formula I below, a pharmaceutically accep
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- Melatonin enhances photo-oxidation of 29, 79-dichlorodihydrofluorescein by an antioxidant reaction that renders N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK)
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The indolamine melatonin (MEL) is described as an antioxidant and a free radical scavenger. However occasionally, the indoleamine has been reported to increase free radicals with insufficient mechanistic explanation. In an attempt to find a reason for tho
- Hevia, David,Mayo, Juan C.,Tan, Dun-Xian,Rodriguez-Garcia, Aida,Sainz, Rosa M.
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- Online H/D exchange liquid chromatography as a support for the mass spectrometric identification of the oxidation products of melatonin
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The hydrogen-deuterium exchange of protonated melatonin and its in vitro oxidation end-products have been examined by liquid chromatography coupled with ion-trap mass spectrometry. Specific H/D scrambling of protons in the C2 and C4 positions of the indol
- Collin, Fabrice,Bonnefont-Rousselot, Dominique,Yous, Said,Marchetti, Catherine,Jore, Daniel,Gardes-Albert, Monique
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experimental part
p. 318 - 329
(2010/06/13)
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- Uses of melatonin in skin
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Melatonin, which can be produced in the skin, exerts a protective effect against damage induced by ultraviolet radiation (UVR). The present study investigated the effect of UVB, the most damaging component of UVR, on melatonin metabolism in HaCaT keratinocytes and in a cell-free system. Four metabolites were identified by HPLC and LC-MS: 6-hydroxymelatonin, AFMK, 2-hydroxymelatonin (the main intermediate between melatonin and AFMK) and 4-hydroxymelatonin. Concentrations of these photoproducts were directly proportional to UVR-dose and to melatonin substrate content, and their accumulation was time dependent. The UVR-dependent increase of AFMK and 2-hydroxymelatonin was also detected in keratinocytes, where it was accompanied by simultaneous consumption of intracellular melatonin. Of note, melatonin and its two major metabolites, 2-hydroxymelatonin and AFMK, were also detected in untreated keratinocytes, neither irradiated nor preincubated with melatonin. Thus, intracellular melatonin metabolism is enhanced under exposure to UVR. The additional biological activity of these individual melatonin metabolites increases the spectrum of potential actions of the recently identified cutaneous melatoninergic system.
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Page/Page column 2; 7-9; sheet 2; sheet 6
(2008/06/13)
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- Reactivity of peroxynitrite with melatonin as a function of pH and CO2 content
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Peroxynitrite is known to be a strong oxidant and a nitrating agent of aromatic phenolic or heterocyclic rings, depending on its form in aqueous solutions: the anion ONOO-, its conjugate acid ONOOH, or its CO2 adduct ONOOCO2-. Various reactions have been observed with melatonin (1), a tryptophan derivative, in phosphate-buffered solutions. Melatonin (1) is recognized as a scavenger of several strong oxidants (HO', H2O2,...) accounting for its biological and pharmacological effects. Here we describe two oxidation routes that give rise to indol-2-ones 2 (probably via a 2,3-epoxyindole) and kynuramines 6 (by cleavage of the pyrrole ring), attributable to reactions of ONOOH and ONOO-, respectively, according to the effects of pH and CO2 content. At pH = 7.6 and in the presence of CO2, an important conversion is the cyclization of the lateral amide function, giving 3-substituted pyrroloindoles 4. At neutral pH, therefore, all routes coexist, with a balance between indol-2-ones 2 and pyrroloindoles 4 on the one side and kynuramines 6 on the other, depending on the CO2 content. Furthermore, under specific conditions substitutions of the hydrogen atom on the pyrrole nitrogen atom, affording the 1-nitro-(5) and the unstable 1-nitrosomelatonin (7), are among the major transformations: formation of the nitrosation product, together with that of kynuramines 6, rises sharply when the pH of the medium increases, confirming the implication of ONOO-in their synthesis; conversely, both reaction yields decrease with increasing CO2 content, to favor 1-nitromelatonin (5). Finally, nitration by aromatic substitution occurring essentially on C-4 becomes important at acidic pH, and also at pH = 7.6 over a narrow range of CO2 concentrations. Most of the reactions are typical of the indole moiety, suggesting that melatonin (1) is a model of potential use for investigation of tryptophan chemistry with peroxynitrite. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Peyrot, Fabienne,Martin, Marie-Therese,Migault, Julie,Ducrocq, Claire
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p. 172 - 181
(2007/10/03)
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- The synthesis of the kynurenamines K1 and K2, metabolites of melatonin
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An efficient synthesis of the kynurenamines K1 and K2, the major brain and antioxidant metabolites of melatonin 1 is described. Regioselective lithiation of tert-butyl(4-methoxyphenyl) carbamate and iodination provided the (2-iodoary
- Amiet, Gary,Hügel, Helmut M.,Nurlawis, Faizul
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p. 495 - 497
(2007/10/03)
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