Open Access

Molecules

, volume 27 , issue 13 , pages 4127

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

D. S. Baranov ¹

Anna S Smorygina ¹

Sergei A. Dzuba ^{1, 2}

Hide authors affiliations Show authors affiliations: 2 affiliations

V.V. Voevodsky Institute of Chemical Kinetics and Combustion, SB RAS, 630090 Novosibirsk, Russia |

Department of Physics, Novosibirsk State University, 630090 Novosibirsk, Russia |

Publication type: Journal Article

Publication date: 2022-06-27

MDPI

Molecules

scimago Q1

wos Q2

SJR: 0.865

CiteScore: 8.6

Impact factor: 4.6

ISSN: 14203049

DOI: 10.3390/molecules27134127

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PubMed ID: 35807376

Organic Chemistry

Drug Discovery

Physical and Theoretical Chemistry

Pharmaceutical Science

Molecular Medicine

Analytical Chemistry

Chemistry (miscellaneous)

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.

Found

1 citation

Selyutina Olga

🥼 🤝

PhD in Physics and Mathematics

47 publications, 984 citations

h-index: 16

Voevodsky Institute of Chemical Kinetics and Combustion of the Siberian Branch of the Russian Academy of Sciences

Research interests

Biophysics

Chemical polarization of nuclei (CPA)

Lipid membranes

Molecular dynamics

NMR spectroscopy

Photodynamic Therapy (PDT)

The structure of proteins

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GOST Copy

Baranov D. et al. Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes // Molecules. 2022. Vol. 27. No. 13. p. 4127.

GOST all authors (up to 50) Copy

Baranov D., Smorygina A. S., Dzuba S. A. Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes // Molecules. 2022. Vol. 27. No. 13. p. 4127.

RIS |

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RIS Copy

TY - JOUR

DO - 10.3390/molecules27134127

UR - https://doi.org/10.3390/molecules27134127

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

T2 - Molecules

AU - Baranov, D. S.

AU - Smorygina, Anna S

AU - Dzuba, Sergei A.

PY - 2022

DA - 2022/06/27

PB - MDPI

SP - 4127

IS - 13

VL - 27

PMID - 35807376

SN - 1420-3049

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2022_Baranov,

author = {D. S. Baranov and Anna S Smorygina and Sergei A. Dzuba},

title = {Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes},

journal = {Molecules},

year = {2022},

volume = {27},

publisher = {MDPI},

month = {jun},

url = {https://doi.org/10.3390/molecules27134127},

number = {13},

pages = {4127},

doi = {10.3390/molecules27134127}

}

MLA

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MLA Copy

Baranov, D. S., et al. “Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes.” Molecules, vol. 27, no. 13, Jun. 2022, p. 4127. https://doi.org/10.3390/molecules27134127.

Publisher

MDPI

Journal

Molecules

scimago Q1

wos Q2

SJR

0.865

CiteScore

8.6

Impact factor

4.6

ISSN

14203049 (Print, Electronic)