Nitrosation of melatonin by nitric oxide: A computational study

Melatonin is being increasingly promoted as a therapeutic agent for the treatment of jet lag and insomnia, and is an efficient free radical scavenger. We have recently characterized a product for the reaction of melatonin with nitric oxide (NO), N-nitrosomelatonin. In the present work, reaction path...

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Autores principales:	Turjanski, A.G., Sáenz, D.A., Doctorovich, F., Estrin, D.A., Rosenstein, R.E.
Formato:	JOUR
Materias:	AM1 Free radicals Melatonin Nitric oxide hydrogen melatonin n nitrosomelatonin nitric oxide nitrogen nitroso derivative nitrosonium ion scavenger unclassified drug aqueous solution article calculation chemical interaction chemical reaction insomnia jet lag nitrosation Animals Binding Sites Free Radicals Humans Ions Models, Chemical Nitric Oxide Thermodynamics
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_07423098_v31_n2_p97_Turjanski
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_07423098_v31_n2_p97_Turjanski
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spelling	todo:paper_07423098_v31_n2_p97_Turjanski2023-10-03T15:38:23Z Nitrosation of melatonin by nitric oxide: A computational study Turjanski, A.G. Sáenz, D.A. Doctorovich, F. Estrin, D.A. Rosenstein, R.E. AM1 Free radicals Melatonin Nitric oxide hydrogen melatonin n nitrosomelatonin nitric oxide nitrogen nitroso derivative nitrosonium ion scavenger unclassified drug aqueous solution article calculation chemical interaction chemical reaction insomnia jet lag nitrosation Animals Binding Sites Free Radicals Humans Ions Melatonin Models, Chemical Nitric Oxide Thermodynamics Melatonin is being increasingly promoted as a therapeutic agent for the treatment of jet lag and insomnia, and is an efficient free radical scavenger. We have recently characterized a product for the reaction of melatonin with nitric oxide (NO), N-nitrosomelatonin. In the present work, reaction pathways with N1, C2, C4, C6 and C7 as possible targets for its reaction with NO that yield the respective nitroso derivatives have been investigated using semiempirical AM1 computational tools, both in vacuo and aqueous solution. Specifically, two different pathways were studied: a radical mechanism involving the hydrogen atom abstraction to yield a neutral radical followed by NO addition, and an ionic mechanism involving addition of nitrosonium ion to the indolic moiety. Our results show that the indolic nitrogen is the most probable site for nitrosation by the radical mechanism, whereas different targets are probable considering the ionic pathway. These results are in good agreement with previous experimental findings and provide a coherent picture for the interaction of melatonin with NO. Fil:Turjanski, A.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Sáenz, D.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Doctorovich, F. 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. Fil:Rosenstein, R.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_07423098_v31_n2_p97_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	AM1 Free radicals Melatonin Nitric oxide hydrogen melatonin n nitrosomelatonin nitric oxide nitrogen nitroso derivative nitrosonium ion scavenger unclassified drug aqueous solution article calculation chemical interaction chemical reaction insomnia jet lag nitrosation Animals Binding Sites Free Radicals Humans Ions Melatonin Models, Chemical Nitric Oxide Thermodynamics
spellingShingle	AM1 Free radicals Melatonin Nitric oxide hydrogen melatonin n nitrosomelatonin nitric oxide nitrogen nitroso derivative nitrosonium ion scavenger unclassified drug aqueous solution article calculation chemical interaction chemical reaction insomnia jet lag nitrosation Animals Binding Sites Free Radicals Humans Ions Melatonin Models, Chemical Nitric Oxide Thermodynamics Turjanski, A.G. Sáenz, D.A. Doctorovich, F. Estrin, D.A. Rosenstein, R.E. Nitrosation of melatonin by nitric oxide: A computational study
topic_facet	AM1 Free radicals Melatonin Nitric oxide hydrogen melatonin n nitrosomelatonin nitric oxide nitrogen nitroso derivative nitrosonium ion scavenger unclassified drug aqueous solution article calculation chemical interaction chemical reaction insomnia jet lag nitrosation Animals Binding Sites Free Radicals Humans Ions Melatonin Models, Chemical Nitric Oxide Thermodynamics
description	Melatonin is being increasingly promoted as a therapeutic agent for the treatment of jet lag and insomnia, and is an efficient free radical scavenger. We have recently characterized a product for the reaction of melatonin with nitric oxide (NO), N-nitrosomelatonin. In the present work, reaction pathways with N1, C2, C4, C6 and C7 as possible targets for its reaction with NO that yield the respective nitroso derivatives have been investigated using semiempirical AM1 computational tools, both in vacuo and aqueous solution. Specifically, two different pathways were studied: a radical mechanism involving the hydrogen atom abstraction to yield a neutral radical followed by NO addition, and an ionic mechanism involving addition of nitrosonium ion to the indolic moiety. Our results show that the indolic nitrogen is the most probable site for nitrosation by the radical mechanism, whereas different targets are probable considering the ionic pathway. These results are in good agreement with previous experimental findings and provide a coherent picture for the interaction of melatonin with NO.
format	JOUR
author	Turjanski, A.G. Sáenz, D.A. Doctorovich, F. Estrin, D.A. Rosenstein, R.E.
author_facet	Turjanski, A.G. Sáenz, D.A. Doctorovich, F. Estrin, D.A. Rosenstein, R.E.
author_sort	Turjanski, A.G.
title	Nitrosation of melatonin by nitric oxide: A computational study
title_short	Nitrosation of melatonin by nitric oxide: A computational study
title_full	Nitrosation of melatonin by nitric oxide: A computational study
title_fullStr	Nitrosation of melatonin by nitric oxide: A computational study
title_full_unstemmed	Nitrosation of melatonin by nitric oxide: A computational study
title_sort	nitrosation of melatonin by nitric oxide: a computational study
url	http://hdl.handle.net/20.500.12110/paper_07423098_v31_n2_p97_Turjanski
work_keys_str_mv	AT turjanskiag nitrosationofmelatoninbynitricoxideacomputationalstudy AT saenzda nitrosationofmelatoninbynitricoxideacomputationalstudy AT doctorovichf nitrosationofmelatoninbynitricoxideacomputationalstudy AT estrinda nitrosationofmelatoninbynitricoxideacomputationalstudy AT rosensteinre nitrosationofmelatoninbynitricoxideacomputationalstudy
_version_	1807314665797058560

Nitrosation of melatonin by nitric oxide: A computational study

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