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J. Biol. Chem., Vol. 265, Issue 11, 6139-6145, Apr, 1990
PJ Sausen and AA Elfarra
Cysteine conjugate S-oxidase activity, with S-benzyl-L-cysteine as
substrate, was found mostly in the microsomal fractions of rat liver and
kidney. In the presence of oxygen and NADPH, S-benzyl-L-cysteine is
converted to S-benzyl-L-cysteine sulfoxide; no S-benzyl-L-cysteine sulfone
was detected. The Vmax for S-benzyl-L-cysteine sulfoxide formation by
kidney microsomes was nearly 3-fold greater than the rate measured with
liver microsomes. Inclusion of catalase, superoxide dismutase, glutathione,
butylated hydroxyanisole, the peroxidase inhibitor, potassium cyanide, the
cytochrome P-450 inhibitors, 1- benzylimidazole and metyrapone, or a
monoclonal antibody to cytochrome P-450 reductase did not inhibit the
metabolic reaction. Flavin- containing monooxygenase alternate substrates,
N,N-dimethylaniline, n- octylamine, and methimazole inhibited the S-oxidase
activities. Analogues of S-benzyl-L-cysteine, S-methyl-L-cysteine, and
S-(1,2- dichlorovinyl)-L-cysteine inhibited the S-benzyl-L-cysteine
S-oxidase activities, whereas S-carboxymethyl-L-cysteine and
S-benzyl-L-cysteine methyl ester had no effect. These results provide clear
evidence against the involvement of reactive oxygen intermediates or
cytochrome P-450 in the sulfoxidation of S-benzyl-L-cysteine and indicate
that the S-oxidase activities may be associated with flavin-containing
monooxygenases which exhibit selectivity in the interaction with cysteine
S-conjugates.
Cysteine conjugate S-oxidase. Characterization of a novel enzymatic activity in rat hepatic and renal microsomes
Department of Comparative Biosciences and Environmental Toxicology Center, University of Wisconsin, Madison 53706.
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