Covalent binding of isoketals to ethanolamine phospholipids.

Bernoud-Hubac N, Fay LB, Armarnath V, Guichardant M, Bacot S, Davies SS, Roberts LJ, Lagarde M
Free Radic Biol Med. 2004 37 (10): 1604-11

PMID: 15477011 · DOI:10.1016/j.freeradbiomed.2004.07.031

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.

MeSH Terms (8)

Aldehydes Arachidonic Acid Chromatography, Liquid Cross-Linking Reagents Free Radicals Mass Spectrometry Phosphatidylethanolamines Schiff Bases

Connections (3)

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