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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Autores principales:	Turjanski, Adrián Gustavo, Rosenstein, Ruth Estela, Estrin, Dario Ariel
Publicado:	1998
Materias:	antioxidant free radical indole derivative melatonin antioxidant activity aqueous solution article hormone action insomnia jet lag scavenging system thermodynamics Computer Simulation Free Radical Scavengers Hydroxyl Radical Indoles Melatonin Models, Biological Quantum Theory Solutions Superoxides Thermodynamics Vacuum Water
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v41_n19_p3684_Turjanski http://hdl.handle.net/20.500.12110/paper_00222623_v41_n19_p3684_Turjanski
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00222623_v41_n19_p3684_Turjanski
record_format	dspace
spelling	paper:paper_00222623_v41_n19_p3684_Turjanski2023-06-08T14:48:35Z Reactions of melatonin and related indoles with free radicals: A computational study Turjanski, Adrián Gustavo Rosenstein, Ruth Estela Estrin, Dario Ariel antioxidant free radical indole derivative melatonin antioxidant activity aqueous solution article hormone action insomnia jet lag scavenging system thermodynamics Computer Simulation Free Radical Scavengers Hydroxyl Radical Indoles Melatonin Models, Biological Quantum Theory Solutions Superoxides Thermodynamics Vacuum Water 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. Fil:Turjanski, A.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Rosenstein, R.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Estrin, D.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1998 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v41_n19_p3684_Turjanski http://hdl.handle.net/20.500.12110/paper_00222623_v41_n19_p3684_Turjanski
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	antioxidant free radical indole derivative melatonin antioxidant activity aqueous solution article hormone action insomnia jet lag scavenging system thermodynamics Computer Simulation Free Radical Scavengers Hydroxyl Radical Indoles Melatonin Models, Biological Quantum Theory Solutions Superoxides Thermodynamics Vacuum Water
spellingShingle	antioxidant free radical indole derivative melatonin antioxidant activity aqueous solution article hormone action insomnia jet lag scavenging system thermodynamics Computer Simulation Free Radical Scavengers Hydroxyl Radical Indoles Melatonin Models, Biological Quantum Theory Solutions Superoxides Thermodynamics Vacuum Water Turjanski, Adrián Gustavo Rosenstein, Ruth Estela Estrin, Dario Ariel Reactions of melatonin and related indoles with free radicals: A computational study
topic_facet	antioxidant free radical indole derivative melatonin antioxidant activity aqueous solution article hormone action insomnia jet lag scavenging system thermodynamics Computer Simulation Free Radical Scavengers Hydroxyl Radical Indoles Melatonin Models, Biological Quantum Theory Solutions Superoxides Thermodynamics Vacuum Water
description	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.
author	Turjanski, Adrián Gustavo Rosenstein, Ruth Estela Estrin, Dario Ariel
author_facet	Turjanski, Adrián Gustavo Rosenstein, Ruth Estela Estrin, Dario Ariel
author_sort	Turjanski, Adrián Gustavo
title	Reactions of melatonin and related indoles with free radicals: A computational study
title_short	Reactions of melatonin and related indoles with free radicals: A computational study
title_full	Reactions of melatonin and related indoles with free radicals: A computational study
title_fullStr	Reactions of melatonin and related indoles with free radicals: A computational study
title_full_unstemmed	Reactions of melatonin and related indoles with free radicals: A computational study
title_sort	reactions of melatonin and related indoles with free radicals: a computational study
publishDate	1998
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v41_n19_p3684_Turjanski http://hdl.handle.net/20.500.12110/paper_00222623_v41_n19_p3684_Turjanski
work_keys_str_mv	AT turjanskiadriangustavo reactionsofmelatoninandrelatedindoleswithfreeradicalsacomputationalstudy AT rosensteinruthestela reactionsofmelatoninandrelatedindoleswithfreeradicalsacomputationalstudy AT estrindarioariel reactionsofmelatoninandrelatedindoleswithfreeradicalsacomputationalstudy
_version_	1768544898018967552

Reactions of melatonin and related indoles with free radicals: A computational study

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