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

被引：17

作者：

Dobrynin, Sergey A. ^{[1
]}

Usatov, Mikhail S. ^{[1
,2
]}

Zhurko, Irina F. ^{[1
]}

Morozov, Denis A. ^{[1
]}

Polienko, Yuliya F. ^{[1
]}

Glazachev, Yurii, I ^{[3
]}

Parkhomenko, Dmitriy A. ^{[1
]}

Tyumentsev, Mikhail A. ^{[4
]}

Gatilov, Yuri, V ^{[1
]}

Chernyak, Elena, I ^{[1
]}

Bagryanskaya, Elena G. ^{[1
]}

Kirilyuk, Igor A. ^{[1
]}

机构：

[1] NN Vorozhtsov Novosibirsk Inst Organ Chem SB RAS, Lavrentiev Ave 9, Novosibirsk 630090, Russia

[2] Novosibirsk State Univ, Pirogova Str 2, Novosibirsk 630090, Russia

[3] Voevodsky Inst Chem Kinet & Combust SB RAS, Inst Skaya 3, Novosibirsk 630090, Russia

[4] Inst Cytol & Genet SB RAS, Fed Res Ctr, Lavrentiev Ave 10, Novosibirsk 630090, Russia

来源：

MOLECULES | 2021年 / 26卷 / 19期

基金：

俄罗斯基础研究基金会;

关键词：

nitroxide; spin label; spin probe; ethynylmagnesium bromide; nitrone; pyrrolidine; IN-VIVO; PROTECTING GROUP; REDOX STATUS; NITROXIDE; MITOCHONDRIA; SITE; EPR; CYTOCHROME-P450; METABOLISM; MECHANISMS;

D O I：

10.3390/molecules26195761

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页数：18

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