N-nitrosomelatonin: synthesis, chemical properties, potential prodrug.
Melatonin is easily nitrosated via various mechanisms at the nitrogen atom of the indole ring to give N-nitrosomelatonin (NOMela). This mini-review provides a comprehensive view of this N-nitroso compound. With an improved procedure NOMela can now economically synthesized with low laboratory expenditure. The major chemical property of NOMela, i.e. the (formally) transfer of the NO+ function to its target nucleophile, is explained in detail and a variety of detection methods using this reaction are suggested. As the suspected carcinogenical potential of NOMela is clearly overruled it seems attractive to apply this nitroso compound for endogenous generation of S-nitrosothiols that act as nitric oxide donors in vivo.
Kirsch
Michael
M
Institut für Physiologische Chemie, Universitätsklinikum Essen, Essen, Germany. michael.kirsch@uni-duisburg-essen.de
de Groot
Herbert
H
D008550:Melatonin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009603:Nitroso Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*
C503522:N1-nitrosomelatonin; D009603:Nitroso Compounds; D011355:Prodrugs; D008550:Melatonin