Secondary alkyl hydroperoxides as inhibitors and alternate substrates for lipoxygenase.

Secondary alkyl hydroperoxides as inhibitors and alternate substrates for lipoxygenase. Research Abstract Details 

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Secondary alkyl hydroperoxides as inhibitors and alternate substrates for lipoxygenase. Abstract Text:

Tiffany M Waller,Ilka Decker,Jonathan P Frisch,Robert M Kernstock,Yong-Wah Kim,Max O Funk,Tiffany M Waller,Ilka Decker,Jonathan P Frisch,Robert M Kernstock,Yong-Wah Kim,Max O Funk,

Lipoxygenase plays a central role in polyunsaturated fatty acid metabolism, inaugurating the biosynthesis of eicosanoids in animals and phytooxylipins in plants. Redox cycling of the non-heme iron cofactor represents a critical element of the catalytic mechanism. Paradoxically, the isolated enzyme contains Fe(II), but the catalytically active form contains Fe(III), and the natural oxidant for the iron is the hydroperoxide product of the catalyzed reaction. Controlling the redox state of lipoxygenase iron with small molecules, inhibitors or activators, could be a means to modulate the activity of the enzyme. The effects of secondary alkyl hydroperoxides and the corresponding alcohols on soybean lipoxygenase-1 reaction rates were investigated and found to be very different. Secondary alcohols were noncompetitive or linear mixed inhibitors with inhibition constants in the millimolar concentration range, with more hydrophobic compounds producing lower values. Secondary alkyl hydroperoxides were inhibitors of lipoxygenase-1 primarily at high substrate concentration. They were more effective inhibitors than the alcohols, with dissociation constants in the micromolar concentration range. The hydroperoxides bearing longer alkyl substituents were the more effective inhibitors. Oxidation of the iron in lipoxygenase-1 by 2-hydroperoxyalkanes was evident in electron paramagnetic resonance (EPR) measurements, but the enzyme was neither activated nor was it inactivated. Instead there was evidence for an entirely different reaction catalyzed by the enzyme, a homolytic dehydration of the hydroperoxide to produce the corresponding carbonyl compound.

Secondary alkyl hydroperoxides as inhibitors and alternate substrates for lipoxygenase. Publishing Authors By Initials

TM Waller,I Decker,JP Frisch,RM Kernstock,YW Kim,MO Funk,TM Waller,I Decker,JP Frisch,RM Kernstock,YW Kim,MO Funk,

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Secondary alkyl hydroperoxides as inhibitors and alternate substrates for lipoxygenase. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Biochemistry

VOLUME: 47

Page Numbers: 331-8

Journal Abbreviation: Biochemistry

ISSN: 0006-2960

DAY: 8

MONTH: 12

YEAR: 2007

Secondary alkyl hydroperoxides as inhibitors and alternate substrates for lipoxygenase. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Secondary alkyl hydroperoxides as inhibitors and alternate substrates for lipoxygenase.

AFFILIATION: Department of Chemistry, University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606.

Country: United States

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MEDLINETA: Biochemistry

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