New fluorogenic triacylglycerols as sensors for dynamic measurement of lipid oxidation

Abstract

Lipids are major constituents of food but are also highly relevant substructures of drugs and are increasingly applied for the development of lipid-based drug delivery systems. Lipids are prone to oxidative degradation, thus affecting the quality of food or medicines. Therefore, analytical methods or tools that enable to assess the degree of lipid oxidation are of utmost importance to guarantee food and drug safety. Herein, we report the design, synthesis, and application of the first-in-class fluorogenic triacylglycerols that enable a dynamic monitoring of lipid oxidation via straightforward fluorescence readout. Our fluorogenic triacylglycerols can be used both in an aqueous and lipid-based environment. Further, we showed that the sensitivity of our fluorescent tracers towards oxidation can be tuned by incorporating either saturated or unsaturated acyl chains in their triacylglycerol core structure. With this, we provide a first proof-of-principle for the applicability of fluorescently labelled triacylglycerols as tracers to monitor the dynamics of lipid oxidation, thus paving the way for novel discoveries in the area of lipid analytics.