Journal
FREE RADICAL BIOLOGY AND MEDICINE
Volume 37, Issue 10, Pages 1604-1611Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.freeradbiomed.2004.07.031
Keywords
isoketals; aldehydes; lipid peroxidation; phosphatidylethanolamine; phospholipid adducts; free radicals
Funding
- NIGMS NIH HHS [GM42057] Funding Source: Medline
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Free radicals have been strongly implicated in the pathogenesis of many human diseases. We previously identified the formation of highly reactive gamma-ketoaldehydes, isoketals, in vivo as products of free radical-induced peroxidation of arachidonic acid. Isoketals react with lysine residues on proteins at a rate that far exceeds that of 4-hydroxynonenal and demonstrate a unique proclivity to crosslink proteins. Hydroxynonenal has been shown to react with aminophospholipids, particularly phosphatidylethanolamine. We explored whether isoketals also react with phosphatidylethanolamine. Using liquid chromatography/electrospray mass spectrometry, we found that isoketals form pyrrole and Schiff base adducts with phosphatidylethanolamine. In addition, the ability of isoketals to covalently modify phosphatidylethanolamine is greater than that of 4-hydroxynonenal. These studies identify in vitro novel isoketal adducts. This provides the basis to explore the formation of isoketal-aminophospholipid adducts in vivo and the biological consequences of the formation of these adducts. (C) 2004 Elsevier Inc. All rights reserved.
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