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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| Veröffentlicht in: | Journal of pineal research 2001-09, Vol.31 (2), p.97-101 |
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| container_title | Journal of pineal research |
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| creator | Turjanski, Adrián G. Sáenz, Daniel A. Doctorovich, Fabio Estrin, Darío A. Rosenstein, Ruth E. |
| 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 ion 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. |
| doi_str_mv | 10.1034/j.1600-079x.2001.310201.x |
| format | Article |
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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 ion 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. 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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 ion 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.</description><subject>AM1</subject><subject>Animals</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>free radicals</subject><subject>Free Radicals - metabolism</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hormones and neuropeptides. Regulation</subject><subject>Humans</subject><subject>Hypothalamus. Hypophysis. Epiphysis. Urophysis</subject><subject>In Vitro Techniques</subject><subject>Ions</subject><subject>melatonin</subject><subject>Melatonin - analogs & derivatives</subject><subject>Melatonin - chemistry</subject><subject>Melatonin - metabolism</subject><subject>Models, Chemical</subject><subject>nitric oxide</subject><subject>Nitric Oxide - metabolism</subject><subject>Thermodynamics</subject><subject>Vertebrates: endocrinology</subject><issn>0742-3098</issn><issn>1600-079X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkE1LxDAQhoMoun78BakHvXWdfLRpvKgsuiqiIoriJaRtAln7sTYtdv-9Wbvq1dME5pk3Mw9CBxjGGCg7no1xDBACF_2YAOAxxUB86dfQ6Kfzuo5GwBkJKYhkC207NwOAJEniTbSFcRRFOKYjdHpn26Z2qrV1FdQmKHWh2rqyVZAugsr3bBbUvc31SaCCrC7nXfvNqiJwbZcvdtGGUYXTe6u6g54vL54mV-Ht_fR6cn4bZiwROBRxmkfKGL8BAOMgMIkINWA4pXEGPMZ5HulccJMSEjFqsBZCKROblKeEa7qDjobceVN_dNq1srQu00WhKl13TnKMOWGceVAMYObPco02ct7YUjULiUEu7cmZXDqSS3tyaU8O9mTvZ_dXn3RpqfO_yZUuDxyuAOUyVZhGVZl1fxzDIBglnjsbuE9b6MX_N5A3D9fD20eEQ4R1re5_I1TzLmNOeSRf7qaSvV29Cv44lZx-AQ7smnU</recordid><startdate>200109</startdate><enddate>200109</enddate><creator>Turjanski, Adrián G.</creator><creator>Sáenz, Daniel A.</creator><creator>Doctorovich, Fabio</creator><creator>Estrin, Darío A.</creator><creator>Rosenstein, Ruth E.</creator><general>Munksgaard International Publishers</general><general>Blackwell</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>200109</creationdate><title>Nitrosation of melatonin by nitric oxide: a computational study</title><author>Turjanski, Adrián G. ; Sáenz, Daniel A. ; Doctorovich, Fabio ; Estrin, Darío A. ; Rosenstein, Ruth E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4891-96bd5aff00800470912523f0f7336c0761dd5ed97fb22543f1e99aaf6fb7b27e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>AM1</topic><topic>Animals</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>free radicals</topic><topic>Free Radicals - metabolism</topic><topic>Fundamental and applied biological sciences. 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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 ion 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. 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| subjects | AM1 Animals Binding Sites Biological and medical sciences free radicals Free Radicals - metabolism Fundamental and applied biological sciences. Psychology Hormones and neuropeptides. Regulation Humans Hypothalamus. Hypophysis. Epiphysis. Urophysis In Vitro Techniques Ions melatonin Melatonin - analogs & derivatives Melatonin - chemistry Melatonin - metabolism Models, Chemical nitric oxide Nitric Oxide - metabolism Thermodynamics Vertebrates: endocrinology |
| title | Nitrosation of melatonin by nitric oxide: a computational study |
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