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(Received for publication, September 10, 1996, and in revised form, November 19, 1996)
From the The objective of this study was to investigate
the mechanism of S-nitrosothiol formation under
physiological conditions. A mechanism is proposed by which nitric oxide
(·NO) reacts directly with reduced thiol to produce a radical
intermediate, R-S-N·-O-H. This intermediate reduces an electron
acceptor to produce S-nitrosothiol. Under aerobic
conditions O2 acts as the electron acceptor and is reduced
to produce superoxide (O
Volume 272, Number 5,
Issue of January 31, 1997
pp. 2841-2845
©1997 by The American Society for Biochemistry and Molecular Biology, Inc.
,§
and¶
Institute for Environmental Medicine, the
§ Departments of Physiology and Bioengineering, and the
¶ Department of Biochemistry and Biophysics, University of
Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104
2). The following experimental
evidence is provided in support of this mechanism. Cysteine accelerates
the consumption of ·NO by 2.5-fold under physiological
conditions. The consumption of O2 in the presence of
·NO and cysteine is increased by 2.4-fold. The reaction orders of ·NO and cysteine are second and first order, respectively.
The second order of reaction for ·NO may result from interaction
between ·NO and O2 to form peroxynitrite. In the
presence of Cu,Zn-superoxide dismutase, the reaction of ·NO with
cysteine generates hydrogen peroxide, indicating that the reaction
generates O2. Finally, the formation of
S-nitrosothiol is demonstrated in an anaerobic environment
and, as predicted by the mechanism, is dependent on the presence of an
electron acceptor. These results demonstrate that under physiological
conditions ·NO reacts directly with thiols to form
S-nitrosothiol in the presence of an electron acceptor.
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