Oxidation of adrenaline and its derivatives by S-nitrosoglutathione.
An oxidizing effect of S-nitrosoglutathione toward adrenaline and its cyclic derivatives (adrenochrome and adrenolutin) is reported. The oxidation was monitored either spectrophotometrically or as oxygen uptake. Adrenaline was first oxidized to adrenochrome that, after isomerization to adrenolutin, was further oxidized to products monitored as fluorescence decrease. To occur to a significant extent, this oxidation requires copper ions that, in addition to a direct effect on the oxidation of the ortho-diphenol moiety, are also able to decompose nitrosothiols, giving rise to nitric oxide. The latter, after interaction with oxygen and superoxide, produces nitrogen oxides and peroxynitrite, respectively, that are important contributors to the oxidative process. In this context, catecholamines might act as regulatory factors toward nitric oxide and its derivatives.
Rigobello
M P
MP
Centro di Studio delle Biomembrane and Dipartmento di Chimica Biologica, Università di Padova, Padova, Italy.
Scutari
G
G
Boscolo
R
R
Bindoli
A
A
D000323:Adrenochrome / Q000378:metabolism*; D003300:Copper / Q000494:pharmacology; D004837:Epinephrine / Q000378:metabolism*; D005978:Glutathione / Q000031:analogs & derivatives* / Q000494:pharmacology*; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000378:metabolism*; D007536:Isomerism; D009566:Nitrates / Q000378:metabolism; D009569:Nitric Oxide / Q000378:metabolism*; D009603:Nitroso Compounds / Q000494:pharmacology*; D016877:Oxidants / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000378:metabolism; D026422:S-Nitrosoglutathione; D013053:Spectrophotometry; D013481:Superoxides / Q000378:metabolism
D007211:Indoles; D009566:Nitrates; D009603:Nitroso Compounds; D016877:Oxidants; C054791:adrenolutin; D013481:Superoxides; C039642:peroxynitric acid; D009569:Nitric Oxide; D026422:S-Nitrosoglutathione; D000323:Adrenochrome; D003300:Copper; D005978:Glutathione; D010100:Oxygen; D004837:Epinephrine