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Lipid peroxidation-dependent chemiluminescence from the cyclization of alkylperoxyl radicals to dioxetane radical intermediates.

Abstract：

:This work reveals a novel mechanism for triplet carbonyl formation (and hence chemiluminescence) during lipid peroxidation, whose chemiluminescence has been attributed to both triplet carbonyls and singlet oxygen. As a model for polyunsaturated fatty acid hydroperoxides, we have synthesized 3-hydroperoxy-2,3-dimethyl-1-butene by photooxygenation of tetramethylethylene. One-electron oxidation of this hydroperoxide with heme proteins and peroxynitrite to the corresponding alkylperoxyl radical results in chemiluminescence, both direct and 9,10-dibromoanthracene-2-sulfonate-sensitized, the latter attributed to the formation of triplet acetone. It is postulated that triplet acetone results from the cyclization of the alkylperoxyl radical to a dioxetane radical intermediate followed by its thermolysis. This is supported by EPR spin-trapping experiments in which discrimination between carbon-centered radicals derived from the alkyloxyl and alkylperoxyl radicals is achieved through the use of one-electron oxidants and reductants, e.g., FeII- and TiIII.

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Tímmins GS,dos Santos RE,Whitwood AC,Catalani LH,Di Mascio P,Gilbert BC,Bechara EJ

doi

10.1021/tx970075p

subject

Has Abstract

pub_date

1997-10-01 00:00:00

pages

1090-6

issue

10

eissn

0893-228X

issn

1520-5010

pii

tx970075p

journal_volume

10

pub_type

杂志文章

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