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

Sergey A. Dobrynin, Mikhail S. Usatov, Irina F. Zhurko, Denis A. Morozov, Yuliya F. Polienko, Yurii I. Glazachev, Dmitriy A. Parkhomenko, Mikhail A. Tyumentsev, Yuri V. Gatilov, Elena I. Chernyak, Elena G. Bagryanskaya, Igor A. Kirilyuk

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Article number5761
JournalMolecules
Volume26
Issue number19
DOIs
Publication statusPublished - 1 Oct 2021

Keywords

  • Ethynylmagnesium bromide
  • Nitrone
  • Nitroxide
  • Pyrrolidine
  • Spin label
  • Spin probe

OECD FOS+WOS

  • 1.04 CHEMICAL SCIENCES

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