Melatonin nitrosation promoted by NO*2; comparison with the peroxynitrite reaction.

Abstract:

:N-nitroso species have recently been detected in animal tissues. Protein N-nitrosotryptophan is the best candidate for this N-nitroso pool. N-nitrosation of N-blocked trytophan derivatives like melatonin (MelH) by N2O3 or peroxynitrite (ONOOH/ONOO- ) has been observed under conditions of pH and reagent concentrations similar to in vivo conditions. We studied the reaction of NO*2 with MelH. When NO*2 was synthesized by gamma-irradiation of aqueous neutral solutions of nitrate under anaerobic conditions, detected oxidation and nitration of MelH were negligible. In the presence of additional nitrite, when NO* was also generated, formation of 1-nitrosomelatonin increased with nitrite concentration. Nitrosation is not due to N2O3 but could proceed via successive additions of NO*2 and NO*. For comparison, peroxynitrite was infused into a solution of MelH under air leading to the same products as those detected in irradiated solutions but in different proportions. In the presence of additional nitrite, the formation of nitroderivatives increased significantly while N-formylkynuramine and 1-nitrosomelatonin were maintained at similar levels. Mechanistic implications are discussed.

journal_name

Free Radic Res

journal_title

Free radical research

authors

Peyrot F,Houée-Levin C,Ducrocq C

doi

10.1080/10715760600693414

subject

Has Abstract

pub_date

2006-09-01 00:00:00

pages

910-20

issue

9

eissn

1071-5762

issn

1029-2470

pii

Q86HQ72468VV3552

journal_volume

40

pub_type

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