Protective role of aryl and alkyl diselenides on lipid peroxidation.
The concept that selenium-containing molecules may be better nucleophiles (and therefore antioxidants) than classical antioxidants has led to the design of synthetic organoselenium compounds. In the present study we appraised the antioxidant potential, thiol peroxidase activity, and rate of dithiotreitol and reduced glutathione oxidation of simple organodiselenide compounds in rats and mice. The present results demonstrate that alkyl and aryl diselenides are antioxidant compounds. We verified that the substitution on the aromatic moiety of diphenyl diselenide or the replacement of on aryl group by an alkyl substitute on diselenides changes their antioxidant and thiol peroxidase-like properties. The diaryl diselenides (PhSe)(2) and (p-ClPhSe)(2) presented higher thiol peroxidase activity and demonstrated better antioxidant potential than the other diselenides tested. In fact, the results revealed that alkyl diselenides, at low concentrations, were prooxidants and that aryl diselenides did not present this effect. Alkyl diselenides [(C(2)H(5)Se)(2) and (C(3)H(7)Se)(2)] demonstrated a higher potential for -SH group oxidation than aryl diselenides. In addition, this study demonstrated that diselenide protection against lipid peroxidation was different in mice and rats. The compounds tested acted more as antioxidants in the brains of mice than in the brains of rats.
Meotti
F C
FC
Departamento de Quimica, Centro de Ciencias Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria, RS, CEP 97105-900, Brazil.
Stangherlin
E C
EC
Zeni
G
G
Nogueira
C W
CW
Rocha
J B T
JB
D000818:Animals; D000975:Antioxidants / Q000378:metabolism*; D001921:Brain / Q000378:metabolism*; D004229:Dithiothreitol / Q000378:metabolism; D005978:Glutathione / Q000378:metabolism; D007700:Kinetics; D015227:Lipid Peroxidation / Q000502:physiology*; D008297:Male; D051379:Mice; D016566:Organoselenium Compounds / Q000378:metabolism*; D051381:Rats; D017208:Rats, Wistar; D013858:Thiobarbiturates
D000975:Antioxidants; D016566:Organoselenium Compounds; D013858:Thiobarbiturates; D005978:Glutathione; C029684:thiobarbituric acid; D004229:Dithiothreitol