Reactions of melatonin and related indoles with free radicals: A computational study
Melatonin is being increasingly promoted as a therapeutic agent for the treatment of jet lag and insomnia and has been recently suggested to act as an efficient free-radical scavenger. In the present work, its mechanisms of action for scavenging hydroxyl radicals have been investigated using semiemp...
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1998
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| LEADER | 10871caa a22010457a 4500 | ||
|---|---|---|---|
| 001 | PAPER-2871 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203220.0 | ||
| 008 | 190411s1998 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0032505151 | |
| 024 | 7 | |2 cas |a Free Radical Scavengers; Hydroxyl Radical, 3352-57-6; Indoles; Melatonin, 73-31-4; Solutions; Superoxides, 11062-77-4; Water, 7732-18-5 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMCMA | ||
| 100 | 1 | |a Turjanski, A.G. | |
| 245 | 1 | 0 | |a Reactions of melatonin and related indoles with free radicals: A computational study |
| 260 | |c 1998 | ||
| 270 | 1 | 0 | |m Estrin, D.A.; Departamento de Quimica Inorganica, Facultad de Cie. Exactas/Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: dario@q1.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Barlow-Walden, L.R., Reiter, R.J., Abe, M., Pablos, M., Menendez-Pelaéz, A., Chen, L.D., Poeggeler, B., Melatonin Stimulates Brain Glutathione Peroxidase Activity (1995) Neurochem. Int., 26, pp. 497-502 | ||
| 504 | |a Antolin, I., Rodriguez, C., Sainz, R.M., Mayo, J.C., Uria, H., Koteer, M.L., Rodriguez-Colunga, M.J., Menendez-Pelaez, A., Neurohormone Melatonin Prevents Cell Damage: Effect on Gene Expression of Antioxidative Enzymes (1996) FASEB J., 10, pp. 882-890 | ||
| 504 | |a Tan, D.X., Poeggeler, B., Reiter, R.J., Chen, L.D., Chen, S., Manchester, L.C., Barlow-Walden, L.R., The Pineal Hormone Melatonin Inhibits DNA Adduct Formation Induced by the Chemical Carcinogen Safrole In Vivo (1993) Cancer Lett., 70, pp. 65-71 | ||
| 504 | |a Sewerynek, E., Melchiorri, D., Reiter, R.J., Ortiz, G.G., Lewinsy, A., Lipopolysaccharide-induced Hepatotoxicity is Inhibited by the Antioxidant Melatonin (1995) Eur. J. Pharmacol., 293, pp. 327-334 | ||
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| 504 | |a (1986) Phys. Rev., B34, p. 7406. , erratum | ||
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| 504 | |a Perez-Reyes, E., Mason, R.R., Characterization of the Structure and Reactions of Free Radicals from Serotonin and Related Indoles (1981) J. Biol. Chem., 10, pp. 2427-2432 | ||
| 504 | |a Tabor, M.W., Coats, E., Sainsbury, M., Shertzer, H.G., Antioxidation Potential of Indoles Compounds-Structure Activity Studies (1991) Biological Reactive Intermediates, 4, pp. 833-836. , Witmer, C. M., Jollow, D. D., Kalf, G. F., Kocsis, J. J., Sipes, I. G., Eds.; Plenum Press: New York | ||
| 504 | |a Simic, M., Jovanovic, S.V., Mechanism of Inactivation of Oxygen Radicals by Dietary Antioxidants and their Models (1990) Basic Life Sci., 52, pp. 127-137 | ||
| 504 | |a Jovanovic, S.V., Simic, M.G., Tryptophan Metabolites as Antioxidants (1985) Life Chem. Rep., 3, pp. 124-130 | ||
| 504 | |a Wrona, M.Z., Yang, Z., McAdams, M., Oçonnor-Coates, S., Dryhurst, G., Hydroxyl Radical-Mediated Oxidation of Serotonin: Potential Insights into the Neurotoxicity of Methamphetamine (1995) J. Neurochem., 64, pp. 1390-1400 | ||
| 504 | |a Matuszak, Z., Reszka, K.J., Chignell, C.F., Reaction of Melatonin and Related Indoles with Hydroxyl Radicals: EPR and Spin Trapping Investigations (1997) Free Radical Biol. Med., 3, pp. 367-372 | ||
| 504 | |a Menendez-Pelaez, A., Poeggeler, B., Reiter, R.J., Barlow-Walden, L.R., Pablos, M.I., Tan, D.X., Nuclear Localization of Melatonin in Different Mammalian Tissues. Immunocytochemical and Radioimmunoassay Evidence (1993) J. Cell Biochem., 53, pp. 372-382 | ||
| 504 | |a Faillace, M.P., Cutrera, R., Keller Sarmiento, M.I., Rosenstein, R.E., Evidence for Local Synthesis of Melatonin in Golden Hamster Retina (1995) Neuroreport, 6, pp. 2093-2095 | ||
| 504 | |a Marshall, K.A., Reiter, R.J., Poeggeler, B., Aruoma, O.I., Halliwell, B., Evaluation of the Antioxidant Activity of Melatonin In Vitro (1996) Free Radical Biol. Med., 3, pp. 307-315 | ||
| 520 | 3 | |a Melatonin is being increasingly promoted as a therapeutic agent for the treatment of jet lag and insomnia and has been recently suggested to act as an efficient free-radical scavenger. In the present work, its mechanisms of action for scavenging hydroxyl radicals have been investigated using semiempirical AM1 and density functional theory (DFT) computational tools. Two different reactions were proposed as follows: one involving the abstraction of an indolic hydrogen to yield a neutral radical and another involving the addition of the hydroxyl radical to the indolic moiety. Our results show that, from a thermodynamical standpoint, melatonin may directly scavenge hydroxyl radicals both in vacuum and in aqueous solution. The structural requirements for free-radical-tapping ability have been examined comparing melatonin with related indoles. Computational data suggest that 5- methoxy and N-acetyl groups of melatonin do not significantly affect its thermodynamical capacity of free-radical trapping. The present results support experimental data on the potential of melatonin as a physiological or pharmacological antioxidant agent. |l eng | |
| 593 | |a Depto. Quim. Inorg., Analitica y Q., Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, 1428 Buenos Aires, Argentina | ||
| 593 | |a Departamento de Fisiología, Facultad de Medicina, Universidad de Buenos Aires, Paraguay 2155, 7 P Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ANTIOXIDANT |
| 690 | 1 | 0 | |a FREE RADICAL |
| 690 | 1 | 0 | |a INDOLE DERIVATIVE |
| 690 | 1 | 0 | |a MELATONIN |
| 690 | 1 | 0 | |a ANTIOXIDANT ACTIVITY |
| 690 | 1 | 0 | |a AQUEOUS SOLUTION |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a HORMONE ACTION |
| 690 | 1 | 0 | |a INSOMNIA |
| 690 | 1 | 0 | |a JET LAG |
| 690 | 1 | 0 | |a SCAVENGING SYSTEM |
| 690 | 1 | 0 | |a THERMODYNAMICS |
| 690 | 1 | 0 | |a COMPUTER SIMULATION |
| 690 | 1 | 0 | |a FREE RADICAL SCAVENGERS |
| 690 | 1 | 0 | |a HYDROXYL RADICAL |
| 690 | 1 | 0 | |a MELATONIN |
| 690 | 1 | 0 | |a MODELS, BIOLOGICAL |
| 690 | 1 | 0 | |a QUANTUM THEORY |
| 690 | 1 | 0 | |a SOLUTIONS |
| 690 | 1 | 0 | |a SUPEROXIDES |
| 690 | 1 | 0 | |a THERMODYNAMICS |
| 690 | 1 | 0 | |a VACUUM |
| 690 | 1 | 0 | |a WATER |
| 650 | 1 | 7 | |2 spines |a INDOLES |
| 700 | 1 | |a Rosenstein, R.E. | |
| 700 | 1 | |a Estrin, D.A. | |
| 773 | 0 | |d 1998 |g v. 41 |h pp. 3684-3689 |k n. 19 |p J. Med. Chem. |x 00222623 |w (AR-BaUEN)CENRE-686 |t Journal of Medicinal Chemistry | |
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| 856 | 4 | 0 | |u https://doi.org/10.1021/jm980117m |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00222623_v41_n19_p3684_Turjanski |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v41_n19_p3684_Turjanski |y Registro en la Biblioteca Digital |
| 961 | |a paper_00222623_v41_n19_p3684_Turjanski |b paper |c PE | ||
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