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J. Biol. Chem., Vol. 259, Issue 7, 4136-4141, Apr, 1984
PR Ortiz de Montellano and NO Reich
The terminal acetylenic analogue of lauric acid, 11-dodecynoic acid (11-
DDYA), specifically inactivates hepatic cytochrome P-450 enzymes that
catalyze omega- and omega-1-hydroxylation of lauric acid. The inactivation,
as required for a suicidal process, is NADPH- and time- dependent and
follows pseudo-first order kinetics. In contrast, 11-DDYA causes no
measurable change in the spectroscopically-measured concentration of
cytochrome P-450 or in the N-demethylation of benzphetamine or N-methyl
p-chloroaniline. 10-Undecynoic acid is as effective a suicide substrate for
fatty acid hydroxylases as 11-DDYA but 11-dodecenoic acid is much less
effective. 11-DDYA is able to completely inhibit omega-hydroxylation but
suppresses no more than 50% of omega-1-hydroxylation despite the fact that
both activities are completely inactivated by 1-aminobenzotriazole. At
least three hepatic cytochrome P-450 fatty acid hydroxylases, one
omega-hydroxylase and two omega-1-hydroxylases, are required by these
results. The construction of suicide substrates that specifically
inactivate cytochrome P-450 fatty acid hydroxylases provides a new
experimental probe of the physiological role of this process.
Specific inactivation of hepatic fatty acid hydroxylases by acetylenic fatty acids
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