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J Biol Chem, Vol. 274, Issue 31, 21695-21700, July 30, 1999
From the Hydroperoxide-induced tyrosyl radicals are
putative intermediates in cyclooxygenase catalysis by prostaglandin H
synthase (PGHS)-1 and -2. Rapid-freeze EPR and stopped-flow were used
to characterize tyrosyl radical kinetics in PGHS-1 and -2 reacted with
ethyl hydrogen peroxide. In PGHS-1, a wide doublet tyrosyl radical
(34-35 G) was formed by 4 ms, followed by transition to a wide singlet
(33-34 G); changes in total radical intensity paralleled those of
Intermediate II absorbance during both formation and decay phases. In
PGHS-2, some wide doublet (30 G) was present at early time points, but
transition to wide singlet (29 G) was complete by 50 ms. In contrast to
PGHS-1, only the formation kinetics of the PGHS-2 tyrosyl radical
matched the Intermediate II absorbance kinetics. Indomethacin-treated
PGHS-1 and nimesulide-treated PGHS-2 rapidly formed narrow singlet EPR
(25-26 G in PGHS-1; 21 G in PGHS-2), and the same line shapes
persisted throughout the reactions. Radical intensity paralleled
Intermediate II absorbance throughout the indomethacin-treated PGHS-1
reaction. For nimesulide-treated PGHS-2, radical formed in concert with
Intermediate II, but later persisted while Intermediate II relaxed.
These results substantiate the kinetic competence of a tyrosyl radical
as the catalytic intermediate for both PGHS isoforms and also indicate
that the heme redox state becomes uncoupled from the tyrosyl radical in
PGHS-2.
Rapid Kinetics of Tyrosyl Radical Formation and Heme Redox
State Changes in Prostaglandin H Synthase-1 and -2
,,,
,, and
Division of Hematology, Department of
Internal Medicine, University of Texas Health Science Center,
Houston, Texas 77030, the ¶ Department of Biochemistry and Cell
Biology, Rice University, Houston, Texas 77005, and the
Arthritis Research Department, Novartis Pharmaceuticals, Summit,
New Jersey 07901
Copyright © 1999 by The American Society for Biochemistry and Molecular Biology, Inc.
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