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

ABSTRACT: 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. Using ²H electron spin echo envelope modulation (ESEEM) spectroscopy, ibuprofen-SL was found to be embedded into the hydrophobic bilayer interior.

SUBMITTER: Baranov DS

PROVIDER: S-EPMC9268589 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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

Baranov Denis S DS Smorygina Anna S AS Dzuba Sergei A SA

Molecules (Basel, Switzerland) 20220627 13

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 result ...[more]

PMID: 35807376

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