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

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Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes. / Baranov, Denis S.; Smorygina, Anna S.; Dzuba, Sergei A.

In: Molecules, Vol. 27, No. 13, 4127, 01.07.2022.

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

Harvard

Baranov, DS, Smorygina, AS & Dzuba, SA 2022, 'Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes', Molecules, vol. 27, no. 13, 4127. https://doi.org/10.3390/molecules27134127

APA

Baranov, D. S., Smorygina, A. S., & Dzuba, S. A. (2022). Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes. Molecules, 27(13), [4127]. https://doi.org/10.3390/molecules27134127

Vancouver

Baranov DS, Smorygina AS, Dzuba SA. Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes. Molecules. 2022 Jul 1;27(13):4127. doi: 10.3390/molecules27134127

Author

Baranov, Denis S. ; Smorygina, Anna S. ; Dzuba, Sergei A. / Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes. In: Molecules. 2022 ; Vol. 27, No. 13.

BibTeX

@article{0c04ea713c274e0983f8453e1313db17,

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

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. Using2 H electron spin echo envelope modulation (ESEEM) spectroscopy, ibuprofen-SL was found to be embedded into the hydrophobic bilayer interior.",

keywords = "H ESEEM, EPR, lipid bilayer, non-steroidal anti-inflammatory drug, NSAID, Membranes, Lipid Bilayers/chemistry, Electron Spin Resonance Spectroscopy, Ibuprofen, Spin Labels",

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

note = "Funding Information: Funding: This work was supported by the Russian Science Foundation, project # 21-13-00025. Publisher Copyright: {\textcopyright} 2022 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2022",

month = jul,

day = "1",

doi = "10.3390/molecules27134127",

language = "English",

volume = "27",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "13",

}

RIS

TY - JOUR

T1 - Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes

AU - Baranov, Denis S.

AU - Smorygina, Anna S.

AU - Dzuba, Sergei A.

PY - 2022/7/1

Y1 - 2022/7/1

N2 - 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. Using2 H electron spin echo envelope modulation (ESEEM) spectroscopy, ibuprofen-SL was found to be embedded into the hydrophobic bilayer interior.

AB - 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. Using2 H electron spin echo envelope modulation (ESEEM) spectroscopy, ibuprofen-SL was found to be embedded into the hydrophobic bilayer interior.

KW - H ESEEM

KW - EPR

KW - lipid bilayer

KW - non-steroidal anti-inflammatory drug

KW - NSAID

KW - Membranes

KW - Lipid Bilayers/chemistry

KW - Electron Spin Resonance Spectroscopy

KW - Ibuprofen

KW - Spin Labels

UR - http://www.scopus.com/inward/record.url?scp=85133404355&partnerID=8YFLogxK

U2 - 10.3390/molecules27134127

DO - 10.3390/molecules27134127

M3 - Article

C2 - 35807376

AN - SCOPUS:85133404355

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 13

M1 - 4127

ER -

ID: 36571045