Naphthalimide-Based Fluorescent Probe for Profiling of Aldehydes during Oxidation of Unsaturated Lipids

A lipophilic naphthalimide hydrazine fluorescent probe was successfully developed in this study for profiling aldehyde oxidation products. Dodecyl amine was applied to afford lipophilicity of the fluorescent probe for lipids. Investigation of fluorescence properties of the probe and condensation products with typical aldehydes including MDA and hexanal revealed significant enhancement of fluorescence intensity after condensation due to the inhibition of photo-induced electron transfer. MDA and hexanal could be differentiated by the probe through emission of different fluorescence colors (blue, MDA; green, hexanal). Eight major oxidation components including seven aldehydes were detected by the fluorescent probe coupled with high-performance liquid chromatography-mass spectrometry during aerobic oxidation of typical unsaturated lipids. Formation of these aldehyde oxidation products was rationalized through the radical oxidation mechanism. Detection of representative aldehyde products demonstrated the generality in the application of this fluorescent probe for profiling of aldehydes after lipid oxidation.