PMID: 8968955Oct 1, 1996Paper

Haloenol lactones as inactivators and substrates of aldehyde dehydrogenase

Journal of Protein Chemistry
N MukerjeeR Pietruszko

Abstract

Human aldehyde dehydrogenase (EC 1.2.1.3) isozymes E1 and E2 were irreversibly inactivated by stoichiometric concentrations of the haloenol lactones 3-isopropyl-6(E)-bromomethylene tetrahydro-pyran-2-one and 3-phenyl-6(E)-bromomethylene tetrahydropyran-2-one. No inactivation occurred with the corresponding nonhalogenated enol lactones. Both the dehydrogenase and esterase activities were abolished. Activity was not regained on dialysis or treatment with 2-mercaptoethanol. The inactivation was subject to substrate protection: NAD afforded protection which increased in the presence of the aldehyde-substrate competitive inhibitor chloral. Saturation kinetics gave positive gamma-axis intercepts, allowing the determination of binding constants. Inactivation stiochiometry determined with 14C-labeled 3-(1-naphthyl)-6(E)-iodomethylene tetrahydropyran-2-one was found to correspond to the active-site number. The nonhalogenated lactone, 3-(1-naphthyl)-6(E)-methylene tetrahydropyran-1-one was shown to be a substrate for aldehyde dehydrogenase via its esterase function. Inactivation and enzymatic hydrolysis occurred within a similar time frame. Opening of the lactone ring to form enzyme-acyl intermediate with active site cysteine appears to ...Continue Reading

References

Jun 27, 1989·Biochemistry·W AmbroziakR Pietruszko
Sep 8, 1987·Biochemistry·D P AbriolaR Pietruszko
Mar 25, 1986·Biochemistry·S B Daniels, J A Katzenellenbogen
Jul 26, 1974·Science·R R Rando
Jan 1, 1982·Alcoholism, Clinical and Experimental Research·J D HempelR Pietruszko

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Citations

Oct 24, 2006·Trends in Cardiovascular Medicine·Zhiqiang Chen, Jonathan S Stamler
Dec 12, 2002·Chemical Reviews·James C PowersKaren Ellis James

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