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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.
Supplementary materials
Title
Supporting Information
Description
The Supporting Information contains Supplementary Figures S1‐S6, Supplementary Tables S1‐S8,
1H NMR spectra of the synthesized compounds 1a‐b, 4, 6a‐b, 7a‐b, 8a‐b, 9a‐b and glycerol
trioleate after 0 h, 24 h, and 120 h of incubation in the presence of ambient oxygen at 40 °C,
HRMS spectra of final compounds 1a‐b, and HPLC chromatograms of final compounds 1a‐b.
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