{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,27]],"date-time":"2026-10-27T06:44:03Z","timestamp":1793083443328,"version":"4.5.0"},"reference-count":43,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2002,12,9]],"date-time":"2002-12-09T00:00:00Z","timestamp":1039392000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["European Journal of Biochemistry"],"published-print":{"date-parts":[[2003,1]]},"abstract":"<jats:p>Nitric oxide (NO) is a potent intra\u2010 and intercellular messenger involved in the control of vascular tone, neuronal signalling and host response to infection. In mammals, NO is synthesized by oxidation of <jats:sc>l<\/jats:sc>\u2010arginine catalysed by hemeproteins called NO\u2010synthases with intermediate formation of <jats:italic>N<\/jats:italic><jats:sup>\u03c9<\/jats:sup>\u2010hydroxy\u2010<jats:sc>l<\/jats:sc>\u2010arginine (NOHA). NOHA and some hydroxyguanidines have been shown to be able to deliver nitrogen oxides including NO in the presence of various oxidative systems. In this study, NOHA and a model compound, <jats:italic>N<\/jats:italic>\u2010(4\u2010chlorophenyl)\u2010<jats:italic>N<\/jats:italic>\u2032\u2010hydroxyguanidine, were tested for their ability to generate NO in the presence of a haemprotein model, microperoxidase\u20038 (MP8), and hydrogen peroxide. Nitrite and nitrate production along with selective formation of 4\u2010chlorophenylcyanamide was observed from incubations of <jats:italic>N<\/jats:italic>\u2010(4\u2010chlorophenyl)\u2010<jats:italic>N<\/jats:italic>\u2032\u2010hydroxyguanidine in the presence of MP8 and hydrogen peroxide. In the case of NOHA, the corresponding cyanamide, <jats:italic>N<\/jats:italic><jats:sup>\u03b4<\/jats:sup>\u2010cyano\u2010L\u2010ornithine, was too unstable under the conditions used and <jats:sc>l<\/jats:sc>\u2010citrulline was the only product identified. A NO\u2010specific conversion of 2\u2010(4\u2010carboxyphenyl)\u20104,4,5,5\u2010tetramethylimidazoline\u20101\u2010oxyl 3\u2010oxide to 2\u2010(4\u2010carboxyphenyl)\u20104,4,5,5\u2010tetramethylimidazoline\u20101\u2010oxyl and formation of MP8\u2013Fe\u2013NO complexes were observed by EPR spectroscopy and low\u2010temperature UV\/visible spectroscopy, respectively. These results clearly demonstrate the formation of nitrogen oxides including NO from the oxidation of exogenous hydroxyguanidines by hydrogen peroxide in the presence of a minienzyme such as MP8. The importance of the bioactivation of endogenous (NOHA) or exogenous <jats:italic>N<\/jats:italic>\u2010hydroxyguanidines by peroxidases of physiological interest remains to be established <jats:italic>in vivo<\/jats:italic>.<\/jats:p>","DOI":"10.1046\/j.1432-1033.2003.03358.x","type":"journal-article","created":{"date-parts":[[2003,3,11]],"date-time":"2003-03-11T18:43:12Z","timestamp":1047408192000},"page":"47-55","source":"Crossref","is-referenced-by-count":19,"title":["Microperoxidase 8 catalysed nitrogen oxides formation from oxidation of <i>N<\/i>\u2010hydroxyguanidines by hydrogen peroxide"],"prefix":"10.1111","volume":"270","author":[{"given":"R\u00e9my","family":"Ricoux","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean\u2010Luc","family":"Boucher","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dominique","family":"Mandon","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yves\u2010Michel","family":"Frapart","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yann","family":"Henry","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel","family":"Mansuy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean\u2010Pierre","family":"Mahy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2002,12,9]]},"reference":[{"key":"e_1_2_14_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00022a001"},{"key":"e_1_2_14_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19990614)38:12<1714::AID-ANIE1714>3.0.CO;2-3"},{"key":"e_1_2_14_4_2","doi-asserted-by":"publisher","DOI":"10.1096\/fasebj.9.13.7557022"},{"key":"e_1_2_14_5_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.pharmtox.41.1.203"},{"key":"e_1_2_14_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(95)00181-6"},{"key":"e_1_2_14_7_2","doi-asserted-by":"crossref","first-page":"6259","DOI":"10.1016\/S0021-9258(18)38112-2","article-title":"N\n                  \u03c9\u2010hydroxy\u2010l\u2010arginine is an intermediate in the biosynthesis of nitric oxide from L\u2010arginine","volume":"296","author":"Stuehr D.J.","year":"1991","journal-title":"J. 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