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Vol. 284, Issue 3, 966-973, March 1998
Department of Pharmacology (M-H.W., E.B-S., B.A.Z., X.N., M.L.S.),
New York Medical College, Valhalla, New York, and Departments of
Biochemistry and Pharmacology (J.R.F., N.B.), University of Texas
Southwestern Medical Center, Dallas, Texas
We characterized the inhibitory activity of several acetylenic and
olefinic compounds on cytochrome P450 (CYP)-derived arachidonic acid
-hydroxylation and epoxidation using rat renal cortical microsomes
and recombinant CYP proteins. Among the acetylenic compounds,
6-(2-propargyloxyphenyl)hexanoic acid (PPOH) and
N-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide were found to be
potent and selective inhibitors of microsomal epoxidation with
IC50 values of 9 and 13 µM, respectively. On the other
hand, 17-octadecynoic acid inhibited both -hydroxylation and
epoxidation of arachidonic acid with IC50 values of 7 and 5 µM, respectively. The olefinic compounds
N-methylsulfonyl-12,12-dibromododec-11-enamide (DDMS) and
12,12-dibromododec-11-enoic acid (DBDD) exhibited a high degree of
selectivity inhibiting microsomal -hydroxylation with an
IC50 value of 2 µM, whereas the IC50 values
for epoxidation were 60 and 51 µM for DDMS and DBDD, respectively.
Studies using recombinant rat CYP4A isoforms showed that PPOH caused a
concentration-dependent inhibition of -hydroxylation and
11,12-epoxidation by CYP4A3 or CYP4A2 but had no effect on
CYP4A1-catalyzed -hydroxylase activity. On the other hand, DDMS
inhibited both CYP4A1- and CYP4A3- or CYP4A2-catalyzed arachidonic acid
oxidations. Inhibition of microsomal activity by PPOH, but not DDMS,
was time- and NADPH-dependent, a result characteristic of a
mechanism-based irreversible inhibitor. These studies provide
information useful for evaluating the role of the CYP-derived
arachidonic acid metabolites in the regulation of renal function and
blood pressure.
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