Formation of S-Nitrosothiols from Regiospecific Reaction of Thiols with N-Nitrosotryptophan Derivatives

Abstract

S-nitrosothiols

Bioanalytical profile of the l-arginine/nitric oxide pathway and its evaluation by capillary electrophoresis

“…dinitrogen trioxide (N 2 O 3 ), is produced upon autooxidation of NO [137][138][139] (Eqs. 4 and 5).…”

“…It has been suggested that the majority of nitrosation occurs via a series of reactions between dinitrogen trioxide and thiols or aromatic moieties [137][138][139]. It was also proposed that a heterogeneous, NO-derived pool of higher nitrogen oxides (i.e., NO 2 , N 2 O 3 , and N 2 O 4 ) and intermediate organic NO derivatives may be responsible for a given profile of NO-dependent modifications in vivo [140].…”

“…may act as scavenger of RNS [135], NO donors [94] and/or NO transport vehicles [91,139,142]. For example, concentrations of thiols in the forms of albumin, cysteine, homocysteine, and glutathione in the human vascular system are 680 μM [143], ~10 μM [144], 5 up to 15 μM in healthy vs diseases subjects [145], and 7 μM [146], respectively.…”

“…The nitrosation of aromatic moieties may play important roles in buffering NO-RNS actions [139,140] conformational alteration of protein functions [168], and additional source providing NO and nitrosyl groups to thermodynamically favorable reactions (e.g. nitrosation of thiols [140]); however, a major effort has been made to understand the role of 3-nitrotyrosine [162][163][164][165][166], and to a lesser extent of N-nitrosotryptophan [138,139,[167][168][169], in pathological conditions and diseases.…”

“…nitrosation of thiols [140]); however, a major effort has been made to understand the role of 3-nitrotyrosine [162][163][164][165][166], and to a lesser extent of N-nitrosotryptophan [138,139,[167][168][169], in pathological conditions and diseases.…”