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A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series. / Dobrynin, Sergey A.; Usatov, Mikhail S.; Zhurko, Irina F. et al.

In: Molecules, Vol. 26, No. 19, 5761, 01.10.2021.

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

Harvard

Dobrynin, SA, Usatov, MS, Zhurko, IF, Morozov, DA, Polienko, YF, Glazachev, YI, Parkhomenko, DA, Tyumentsev, MA, Gatilov, YV, Chernyak, EI, Bagryanskaya, EG & Kirilyuk, IA 2021, 'A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series', Molecules, vol. 26, no. 19, 5761. https://doi.org/10.3390/molecules26195761

APA

Dobrynin, S. A., Usatov, M. S., Zhurko, I. F., Morozov, D. A., Polienko, Y. F., Glazachev, Y. I., Parkhomenko, D. A., Tyumentsev, M. A., Gatilov, Y. V., Chernyak, E. I., Bagryanskaya, E. G., & Kirilyuk, I. A. (2021). A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series. Molecules, 26(19), [5761]. https://doi.org/10.3390/molecules26195761

Vancouver

Dobrynin SA, Usatov MS, Zhurko IF, Morozov DA, Polienko YF, Glazachev YI et al. A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series. Molecules. 2021 Oct 1;26(19):5761. doi: 10.3390/molecules26195761

Author

Dobrynin, Sergey A. ; Usatov, Mikhail S. ; Zhurko, Irina F. et al. / A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series. In: Molecules. 2021 ; Vol. 26, No. 19.

BibTeX

@article{4bb2b48f36694f43afdc4733bcf3e727,
title = "A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series",
abstract = "Stable free radicals are widely used as molecular probes and labels in various biophysical and biomedical research applications of magnetic resonance spectroscopy and imaging. Among these radicals, sterically shielded nitroxides of pyrrolidine series demonstrate the highest stability in biological systems. Here, we suggest new convenient procedure for preparation of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl, a reduction-resistant analog of widely used carboxy-Proxyl, from cheap commercially available reagents with the yield exceeding the most optimistic literature data. Several new spin labels and probes of 2,2,5,5-tetraethylpyrrolidine-1-oxyl series were prepared and reduction of these radicals in ascorbate solutions, mice blood and tissue homogenates was studied.",
keywords = "Ethynylmagnesium bromide, Nitrone, Nitroxide, Pyrrolidine, Spin label, Spin probe",
author = "Dobrynin, {Sergey A.} and Usatov, {Mikhail S.} and Zhurko, {Irina F.} and Morozov, {Denis A.} and Polienko, {Yuliya F.} and Glazachev, {Yurii I.} and Parkhomenko, {Dmitriy A.} and Tyumentsev, {Mikhail A.} and Gatilov, {Yuri V.} and Chernyak, {Elena I.} and Bagryanskaya, {Elena G.} and Kirilyuk, {Igor A.}",
note = "Funding Information: Funding: This work was supported by the Russian Foundation for Basic Research (18-53-76003 within the framework of the ERA.Net RUS+ project ST2017-382: NanoHyperRadicals) (Synthesis, spectra and kinetic measurements in model systems) and partly by the Ministry of Science and Higher Education of Russia (project number 14.W03.31.0034) (kinetics in blood and tissues). Funding Information: This work was supported by the Russian Foundation for Basic Research (18-53-76003 within the framework of the ERA.Net RUS+ project ST2017-382: NanoHyperRadicals) (Synthesis, spectra and kinetic measurements in model systems) and partly by the Ministry of Science and Higher Education of Russia (project number 14.W03.31.0034) (kinetics in blood and tissues).We thank the personnel of the Multi-Access Center of SB RAS for recording of IR, UV, NMR and HRMS spectra and for performing X-ray and elemental analyses. Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",
year = "2021",
month = oct,
day = "1",
doi = "10.3390/molecules26195761",
language = "English",
volume = "26",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "19",

}

RIS

TY - JOUR

T1 - A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series

AU - Dobrynin, Sergey A.

AU - Usatov, Mikhail S.

AU - Zhurko, Irina F.

AU - Morozov, Denis A.

AU - Polienko, Yuliya F.

AU - Glazachev, Yurii I.

AU - Parkhomenko, Dmitriy A.

AU - Tyumentsev, Mikhail A.

AU - Gatilov, Yuri V.

AU - Chernyak, Elena I.

AU - Bagryanskaya, Elena G.

AU - Kirilyuk, Igor A.

N1 - Funding Information: Funding: This work was supported by the Russian Foundation for Basic Research (18-53-76003 within the framework of the ERA.Net RUS+ project ST2017-382: NanoHyperRadicals) (Synthesis, spectra and kinetic measurements in model systems) and partly by the Ministry of Science and Higher Education of Russia (project number 14.W03.31.0034) (kinetics in blood and tissues). Funding Information: This work was supported by the Russian Foundation for Basic Research (18-53-76003 within the framework of the ERA.Net RUS+ project ST2017-382: NanoHyperRadicals) (Synthesis, spectra and kinetic measurements in model systems) and partly by the Ministry of Science and Higher Education of Russia (project number 14.W03.31.0034) (kinetics in blood and tissues).We thank the personnel of the Multi-Access Center of SB RAS for recording of IR, UV, NMR and HRMS spectra and for performing X-ray and elemental analyses. Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2021/10/1

Y1 - 2021/10/1

N2 - Stable free radicals are widely used as molecular probes and labels in various biophysical and biomedical research applications of magnetic resonance spectroscopy and imaging. Among these radicals, sterically shielded nitroxides of pyrrolidine series demonstrate the highest stability in biological systems. Here, we suggest new convenient procedure for preparation of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl, a reduction-resistant analog of widely used carboxy-Proxyl, from cheap commercially available reagents with the yield exceeding the most optimistic literature data. Several new spin labels and probes of 2,2,5,5-tetraethylpyrrolidine-1-oxyl series were prepared and reduction of these radicals in ascorbate solutions, mice blood and tissue homogenates was studied.

AB - Stable free radicals are widely used as molecular probes and labels in various biophysical and biomedical research applications of magnetic resonance spectroscopy and imaging. Among these radicals, sterically shielded nitroxides of pyrrolidine series demonstrate the highest stability in biological systems. Here, we suggest new convenient procedure for preparation of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl, a reduction-resistant analog of widely used carboxy-Proxyl, from cheap commercially available reagents with the yield exceeding the most optimistic literature data. Several new spin labels and probes of 2,2,5,5-tetraethylpyrrolidine-1-oxyl series were prepared and reduction of these radicals in ascorbate solutions, mice blood and tissue homogenates was studied.

KW - Ethynylmagnesium bromide

KW - Nitrone

KW - Nitroxide

KW - Pyrrolidine

KW - Spin label

KW - Spin probe

UR - http://www.scopus.com/inward/record.url?scp=85115665294&partnerID=8YFLogxK

U2 - 10.3390/molecules26195761

DO - 10.3390/molecules26195761

M3 - Article

C2 - 34641310

AN - SCOPUS:85115665294

VL - 26

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 19

M1 - 5761

ER -

ID: 34348700