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Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes
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, w...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10458756/ https://www.ncbi.nlm.nih.gov/pubmed/37630243 http://dx.doi.org/10.3390/molecules28165991 |
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author | Baranov, Denis S. Kashnik, Anna S. Atnyukova, Anastasiya N. Dzuba, Sergei A. |
author_facet | Baranov, Denis S. Kashnik, Anna S. Atnyukova, Anastasiya N. Dzuba, Sergei A. |
author_sort | Baranov, Denis S. |
collection | PubMed |
description | 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 a 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 a lipid membrane composed of palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). (2)H electron spin echo spectroscopy (ESEEM) was used to determine the position of the diclofenac-SL relative to the membrane surface. It was established that its average depth of immersion corresponds to the 5th position of the carbon atom in the lipid chain. |
format | Online Article Text |
id | pubmed-10458756 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-104587562023-08-27 Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes Baranov, Denis S. Kashnik, Anna S. Atnyukova, Anastasiya N. Dzuba, Sergei A. Molecules Article 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 a 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 a lipid membrane composed of palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). (2)H electron spin echo spectroscopy (ESEEM) was used to determine the position of the diclofenac-SL relative to the membrane surface. It was established that its average depth of immersion corresponds to the 5th position of the carbon atom in the lipid chain. MDPI 2023-08-10 /pmc/articles/PMC10458756/ /pubmed/37630243 http://dx.doi.org/10.3390/molecules28165991 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Baranov, Denis S. Kashnik, Anna S. Atnyukova, Anastasiya N. Dzuba, Sergei A. Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes |
title | Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes |
title_full | Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes |
title_fullStr | Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes |
title_full_unstemmed | Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes |
title_short | Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes |
title_sort | spin-labeled diclofenac: synthesis and interaction with lipid membranes |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10458756/ https://www.ncbi.nlm.nih.gov/pubmed/37630243 http://dx.doi.org/10.3390/molecules28165991 |
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