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Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes. / Baranov, Denis S; Kashnik, Anna S; Atnyukova, Anastasiya N et al.

In: Molecules (Basel, Switzerland), Vol. 28, No. 16, 5991, 10.08.2023.

Research output: Contribution to journal › Article › peer-review

Harvard

Baranov, DS, Kashnik, AS, Atnyukova, AN & Dzuba, SA 2023, 'Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes', Molecules (Basel, Switzerland), vol. 28, no. 16, 5991. https://doi.org/10.3390/molecules28165991

APA

Baranov, D. S., Kashnik, A. S., Atnyukova, A. N., & Dzuba, S. A. (2023). Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes. Molecules (Basel, Switzerland), 28(16), [5991]. https://doi.org/10.3390/molecules28165991

Vancouver

Baranov DS, Kashnik AS, Atnyukova AN, Dzuba SA. Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes. Molecules (Basel, Switzerland). 2023 Aug 10;28(16):5991. doi: 10.3390/molecules28165991

Author

Baranov, Denis S ; Kashnik, Anna S ; Atnyukova, Anastasiya N et al. / Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes. In: Molecules (Basel, Switzerland). 2023 ; Vol. 28, No. 16.

BibTeX

@article{5c26390745b9473685e9c30829b89b9f,
title = "Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes",
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 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). 2H 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.",
keywords = "Diclofenac, Spin Labels, Anti-Inflammatory Agents, Non-Steroidal, Membranes, Glycerylphosphorylcholine",
author = "Baranov, {Denis S} and Kashnik, {Anna S} and Atnyukova, {Anastasiya N} and Dzuba, {Sergei A}",
note = "This work was supported by the Russian Science Foundation, project # 21-13-00025.",
year = "2023",
month = aug,
day = "10",
doi = "10.3390/molecules28165991",
language = "English",
volume = "28",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "16",

}

RIS

TY - JOUR

T1 - Spin-Labeled Diclofenac: Synthesis and Interaction with Lipid Membranes

AU - Baranov, Denis S

AU - Kashnik, Anna S

AU - Atnyukova, Anastasiya N

AU - Dzuba, Sergei A

N1 - This work was supported by the Russian Science Foundation, project # 21-13-00025.

PY - 2023/8/10

Y1 - 2023/8/10

N2 - 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). 2H 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.

AB - 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). 2H 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.

KW - Diclofenac

KW - Spin Labels

KW - Anti-Inflammatory Agents, Non-Steroidal

KW - Membranes

KW - Glycerylphosphorylcholine

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85168742685&origin=inward&txGid=3cd0f58291b4ae164a46f2d64631d0e4

U2 - 10.3390/molecules28165991

DO - 10.3390/molecules28165991

M3 - Article

C2 - 37630243

VL - 28

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 16

M1 - 5991

ER -

ID: 55287833