Structural Characterization of a 4-Hydroxy-2-alkenal-Derived Fluorophore That Contributes to Lipoperoxidation-Dependent Protein Cross-Linking in Aging and Degenerative Disease
- 26 March 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in Chemical Research in Toxicology
- Vol. 11 (4), 247-251
- https://doi.org/10.1021/tx980003d
Abstract
Modification of proteins by products of lipid peroxidation results in various fluorescent adducts associated with oxidative stress pathophysiology in degenerative disease. Using n-butylamine as a model for the lysine side chain, the structure of the probable major ex/em 360/430-nm fluorophore that arises from cross-linking of two protein-based lysines by one 4-hydroxy-2-alkenal is shown to be a 2-alkyl-2-hydroxy-1,2-dihydropyrrol-3-one iminium. That this fluorophore can be independently generated in higher yield from either 4-oxo-2-alkenals or 3,4-dioxoalkanals supports a proposed mechanistic pathway that involves two 2e oxidations following initial Schiff base formation.Keywords
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