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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2001
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paper:paper_07423098_v31_n2_p97_Turjanski2023-06-08T15:44:43Z Nitrosation of melatonin by nitric oxide: A computational study Turjanski, Adrián Gustavo Saenz, Daniel Alberto Doctorovich, Fabio Ariel Estrin, Dario Ariel Rosenstein, Ruth Estela 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. 2001 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07423098_v31_n2_p97_Turjanski 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, Adrián Gustavo Saenz, Daniel Alberto Doctorovich, Fabio Ariel Estrin, Dario Ariel Rosenstein, Ruth Estela 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. |
| author |
Turjanski, Adrián Gustavo Saenz, Daniel Alberto Doctorovich, Fabio Ariel Estrin, Dario Ariel Rosenstein, Ruth Estela |
| author_facet |
Turjanski, Adrián Gustavo Saenz, Daniel Alberto Doctorovich, Fabio Ariel Estrin, Dario Ariel Rosenstein, Ruth Estela |
| author_sort |
Turjanski, Adrián Gustavo |
| 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 |
| publishDate |
2001 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07423098_v31_n2_p97_Turjanski http://hdl.handle.net/20.500.12110/paper_07423098_v31_n2_p97_Turjanski |
| work_keys_str_mv |
AT turjanskiadriangustavo nitrosationofmelatoninbynitricoxideacomputationalstudy AT saenzdanielalberto nitrosationofmelatoninbynitricoxideacomputationalstudy AT doctorovichfabioariel nitrosationofmelatoninbynitricoxideacomputationalstudy AT estrindarioariel nitrosationofmelatoninbynitricoxideacomputationalstudy AT rosensteinruthestela nitrosationofmelatoninbynitricoxideacomputationalstudy |
| _version_ |
1768544737214595072 |