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<p>Fenofibrate is a classical drug for treating hyperlipidemia and reducing high-density lipoprotein cholesterol levels. Electron paramagnetic resonance (EPR) spectroscopy can be used to study physicochemical properties of fenofibrate in the case of its spin-labeled analogues. A synthesis of spin-labeled fenofibrate (Feno-SL) was carried out, which included iodination, Sonogashira cross-coupling, and peroxidation steps. The EPR spectra showed that Feno-SL binds to the model lipid membrane composed of palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine. The degree of labeling determined by double electron-electron resonance (DEER) for Feno-SL in alcohol glass is close to 100%. As shown by <sup>2</sup>H electron spin echo envelope modulation (ESEEM) spectroscopy, when hydrating the membranes by heavy water (D<sub>2</sub>O) the average immersion depth of Feno-SL corresponds to position 5 of the carbon atom in the lipid chain.</p>

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Spin-labeled fenofibrate: synthesis and interaction with lipid membranes

  • 期刊论文

  • 发表日期：

    2026年2月1日

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  • D. S. Baranov,
  • A. N. Atnyukova,
  • S. V. Komlina,
  • A. S. Kashnik,
  • S. A. Dzuba

摘要

Fenofibrate is a classical drug for treating hyperlipidemia and reducing high-density lipoprotein cholesterol levels. Electron paramagnetic resonance (EPR) spectroscopy can be used to study physicochemical properties of fenofibrate in the case of its spin-labeled analogues. A synthesis of spin-labeled fenofibrate (Feno-SL) was carried out, which included iodination, Sonogashira cross-coupling, and peroxidation steps. The EPR spectra showed that Feno-SL binds to the model lipid membrane composed of palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine. The degree of labeling determined by double electron-electron resonance (DEER) for Feno-SL in alcohol glass is close to 100%. As shown by 2H electron spin echo envelope modulation (ESEEM) spectroscopy, when hydrating the membranes by heavy water (D2O) the average immersion depth of Feno-SL corresponds to position 5 of the carbon atom in the lipid chain.