{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T19:51:08Z","timestamp":1790193068775,"version":"4.1.0"},"reference-count":33,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2007,8,2]],"date-time":"2007-08-02T00:00:00Z","timestamp":1186012800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Journal of Pineal Research"],"published-print":{"date-parts":[[2007,11]]},"abstract":"<jats:p><jats:bold>Abstract:\u2002<\/jats:bold> The different NO redox forms, NO<jats:sup>+<\/jats:sup>, <jats:sup>\u2022<\/jats:sup>NO and HNO (=\u2003protonated NO<jats:sup>\u2013<\/jats:sup>), were compared for their capabilities of interacting with the melatonin metabolite <jats:italic>N<\/jats:italic><jats:sup>1<\/jats:sup>\u2010acetyl\u20105\u2010methoxykynuramine (AMK), using NO<jats:sup>+<\/jats:sup>SbF<jats:sub>6<\/jats:sub><jats:sup>\u2013<\/jats:sup>, PAPA\u2010NONOate and Angeli\u2019s salt as donors of the respective NO species. Particular attention was paid to stability and possible interconversions of the redox forms. <jats:sup>\u2022<\/jats:sup>NO formation was followed by measuring the decolorization of 2\u2010(trimethylammonio\u2010phenyl)\u20104,4,5,5\u2010tetramethyl\u2010imidazoline\u20101\u2010oxyl\u20103\u2010oxide (TMA\u2010PTIO), at different pH values, at which NO<jats:sup>+<\/jats:sup> is, in aqueous solution, either highly unstable (pH 7.4) or relatively stable (pH 2.0). <jats:sup>\u2022<\/jats:sup>NO donation by PAPA\u2010NONOate, as indicated by TMA\u2010PTIO decolorization, was similar at either pH and 3\u2010acetamidomethyl\u20106\u2010methoxycinnolinone (AMMC) was formed as the major product from AMK, at pH 7.4 more efficiently than at pH 2.0. At pH 2.0, TMA\u2010PTIO decolorization by NO<jats:sup>+<\/jats:sup>SbF<jats:sub>6<\/jats:sub><jats:sup>\u2013<\/jats:sup> was much weaker than by PAPA\u2010NONOate, but AMMC was produced at substantial rates, whereas neither TMA\u2010PTIO decolorization nor AMMC formation was observed with the NO<jats:sup>+<\/jats:sup> donor at pH 7.4. As NO<jats:sup>+<\/jats:sup> is also stable in organic, especially aprotic solvents, NO<jats:sup>+<\/jats:sup>SbF<jats:sub>6<\/jats:sub><jats:sup>\u2013<\/jats:sup> was reacted with AMK in acetonitrile, ethanol, butanol, and ethyl acetate. In all these cases, AMMC was the only or major product. In ethyl acetate, <jats:italic>N<\/jats:italic><jats:sup>1<\/jats:sup>\u2010acetyl\u20105\u2010methoxy\u20103\u2010nitrokynuramine (AMNK) was also formed, presumably as a consequence of organic peroxides emerging in that solvent. Presence of <jats:italic>tert<\/jats:italic>\u2010butylhydroperoxide in an ethanolic solution of NO<jats:sup>+<\/jats:sup>SbF<jats:sub>6<\/jats:sub><jats:sup>\u2013<\/jats:sup> and AMK also resulted in AMNK formation, in addition to AMMC and two red\u2010fluoresecent, to date unknown products. However, hydrogen peroxide enhanced <jats:sup>\u2022<\/jats:sup>NO\u2010dependent AMMC production from AMK and also from <jats:italic>N<\/jats:italic><jats:sup>1<\/jats:sup>\u2010acetyl\u2010<jats:italic>N<\/jats:italic><jats:sup>2<\/jats:sup>\u2010formyl\u20105\u2010methoxykynuramine. HNO donation by Angeli\u2019s salt (Na<jats:sub>2<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>) also caused AMMC formation from AMK at pH 7.4, with a somewhat lower efficiency than PAPA\u2010NONOate, but no AMNK nor any other product was detected. Therefore, all three NO congeners are, in principle, capable of nitrosating AMK and forming AMMC, but in biological material the reaction with NO<jats:sup>+<\/jats:sup> is strongly limited by the extremely short life\u2010time of this redox form.<\/jats:p>","DOI":"10.1111\/j.1600-079x.2007.00489.x","type":"journal-article","created":{"date-parts":[[2007,8,2]],"date-time":"2007-08-02T18:58:33Z","timestamp":1186081113000},"page":"382-388","source":"Crossref","is-referenced-by-count":79,"title":["Reactions of the NO redox forms NO<sup>+<\/sup>, <sup>\u2022<\/sup>NO and HNO (protonated NO<sup>\u2013<\/sup>) with the melatonin metabolite <i>N<\/i><sup>1<\/sup>\u2010acetyl\u20105\u2010methoxykynuramine"],"prefix":"10.1111","volume":"43","author":[{"given":"R\u00fcdiger","family":"Hardeland","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudia","family":"Backhaus","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Azadeh","family":"Fadavi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2007,8,2]]},"reference":[{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1600-079X.2005.00242.x"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1600-079X.2007.00431.x"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0165-6147(00)88968-3"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.112202099"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.162095599"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M307572200"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1161\/01.RES.0000047529.26278.4D"},{"key":"e_1_2_5_9_2","doi-asserted-by":"crossref","first-page":"2315","DOI":"10.1242\/jcs.110.18.2315","article-title":"Differential 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