Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes

Denis S. Baranov, Anna S. Smorygina, Sergei A. Dzuba

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

Аннотация

Ibuprofen is a non-steroidal anti-inflammatory drug possessing analgesic and antipyretic activity. Electron paramagnetic resonance (EPR) spectroscopy could be applied to study its interaction with biological membranes and proteins if its spin-labeled analogs were synthesized. Here, a simple sequence of ibuprofen transformations—nitration, esterification, reduction, Sandmeyer reaction, Sonogashira cross-coupling, oxidation and saponification—was developed to attain this goal. The synthesis resulted in spin-labeled ibuprofen (ibuprofen-SL) in which the spin label TEMPOL is attached to the benzene ring. EPR spectra confirmed interaction of ibuprofen-SL with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) bilayers. Using2 H electron spin echo envelope modulation (ESEEM) spectroscopy, ibuprofen-SL was found to be embedded into the hydrophobic bilayer interior.

Язык оригиналаанглийский
Номер статьи4127
ЖурналMolecules
Том27
Номер выпуска13
DOI
СостояниеОпубликовано - 1 июл 2022

Предметные области OECD FOS+WOS

  • 1.04 ХИМИЧЕСКИЕ НАУКИ

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