Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes |
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| Authors: | Denis S. Baranov Anna S. Smorygina Sergei A. Dzuba |
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| Affiliation: | 1.V.V. Voevodsky Institute of Chemical Kinetics and Combustion, SB RAS, 630090 Novosibirsk, Russia;2.Department of Physics, Novosibirsk State University, 630090 Novosibirsk, Russia |
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| 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. |
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| Keywords: | non-steroidal anti-inflammatory drug NSAID lipid bilayer EPR 2H ESEEM |
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