Baranov, D.S.; Kashnik, A.S.; Atnyukova, A.N.; Dzuba, S.A. Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes. Molecules2023, 28, 5991.
Baranov, D.S.; Kashnik, A.S.; Atnyukova, A.N.; Dzuba, S.A. Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes. Molecules 2023, 28, 5991.
Baranov, D.S.; Kashnik, A.S.; Atnyukova, A.N.; Dzuba, S.A. Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes. Molecules2023, 28, 5991.
Baranov, D.S.; Kashnik, A.S.; Atnyukova, A.N.; Dzuba, S.A. Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes. Molecules 2023, 28, 5991.
Abstract
Diclofenac is a non-steroidal anti-inflammatory drug (NSAID) from the group of phenylacetic acid derivatives, which has analgesic, anti-inflammatory and antipyretic properties. The interaction of non-steroidal anti-inflammatory drugs with cell membranes can affect their physicochemical properties, which, in turn, can cause a number of side effects in the use of these drugs. Electron paramagnetic resonance (EPR) spectroscopy could be used to study the interaction of diclofenac with the membrane, if its spin-labeled analogs existed. This paper describes the synthesis of spin-labeled diclofenac (diclofenac-SL), which consists of a simple sequence of transformations such as iodination, esterification, Sonogashira cross-coupling, oxidation and saponification. EPR spectra showed that diclofenac-SL binds to in a lipid membrane composed of palmito-yl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). 2H electron spin echo spectroscopy (ESEEM) was used to determine the position of the diclofenac-SL relative to the membrane surface. It has been established that the average its depth of immersion corresponds to the 5th position of the carbon atom in the lipid chain.
Chemistry and Materials Science, Physical Chemistry
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