Journal
CELLULAR AND MOLECULAR LIFE SCIENCES
Volume 59, Issue 5, Pages 808-820Publisher
SPRINGER BASEL AG
DOI: 10.1007/s00018-002-8469-8
Keywords
isoprostanes; lipid peroxidation; free radicals; protein adducts; isolevuglandins; mass spectrometry
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Funding
- NCI NIH HHS [CA68485, CA77839] Funding Source: Medline
- NIDDK NIH HHS [DK26657, DK48831] Funding Source: Medline
- NIGMS NIH HHS [GM15431, GM42056] Funding Source: Medline
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We previously reported the discovery of prostaglandin F-2-like compounds (F-2-isoprostanes) formed by nonenzymatic free-radical-induced peroxidation of arachidonic acid. Quantification of F-2-isoprostanes has proven to be a major advance in assessing oxidative stress status in vivo. Central in the pathway of formation of isoprostanes are prostaglandin H-2-like endoperoxides, which also undergo rearrangement in vivo to form E-ring, D-ring, and thromboxane-ring compounds. E-2- and D-2-isoprostanes also undergo dehydration in vivo to form reactive cyclopentenone A(2)- and J(2)-isoprostanes, which are susceptible to Michael addition reactions with thiols. Recently, we described the formation of highly reactive gamma-ketoaldehydes (now termed isoketals) as products of isoprostane endoperoxide rearrangement which readily adduct to lysine residues on proteins and induce cross-links at rates that far exceed other aldehyde products of lipid peroxidation. Isoprostane-like compounds (neuroprostanes) and isoketal-like compounds (neuroketals) are formed from oxidation of docosahexaenoic acid, which is enriched in the brain, and measurement of neuroprostanes may provide a unique marker of oxidative neuronal injury.
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