Covalent binding of isoketals to ethanolamine phospholipids |
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Authors: | Bernoud-Hubac Nathalie Fay Laurent B Armarnath Venkataraman Guichardant Michel Bacot Sandrine Davies Sean S Roberts L Jackson Lagarde Michel |
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Institution: | INSERM U585, Physiopathologie des Lipides et Membranes, INSA-Lyon, 69621 Villeurbanne, France. Nathalie.Bernoud-Hubac@insa-lyon.fr |
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Abstract: | 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. |
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