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

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Oct 13

PMID 34641310

Citations 9

Authors

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

Affiliations

Soon will be listed here.

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.

Citing Articles

Contrast Agents Based on Human Serum Albumin and Nitroxides for H-MRI and Overhauser-Enhanced MRI.

Mitin D, Bullinger F, Dobrynin S, Engelmann J, Scheffler K, Kolokolov M Int J Mol Sci. 2024; 25(7).

PMID: 38612851 PMC: 11012161. DOI: 10.3390/ijms25074041.

Hydrophilic Reduction-Resistant Spin Labels of Pyrrolidine and Pyrroline Series from 3,4-Bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidine-1-oxyl.

Usatov M, Dobrynin S, Polienko Y, Morozov D, Glazachev Y, Ankov S Int J Mol Sci. 2024; 25(3).

PMID: 38338825 PMC: 10855552. DOI: 10.3390/ijms25031550.

2,5-Di-tert-butyl-2,5-diethylpyrrolidine-1-oxyls: Where Is a Reasonable Limit of Sterical Loading for Higher Resistance to Reduction?.

Zhurko I, Dobrynin S, Glazachev Y, Gatilov Y, Kirilyuk I Molecules. 2024; 29(3).

PMID: 38338344 PMC: 10856307. DOI: 10.3390/molecules29030599.

Origin of Long-Range Hyperfine Couplings in the EPR Spectra of 2,2,5,5-Tetraethylpyrrolidine-1-oxyls.

Polienko Y, Dobrynin S, Lomanovich K, Brovko A, Bagryanskaya E, Kirilyuk I ACS Omega. 2023; 8(41):38723-38732.

PMID: 37867656 PMC: 10586448. DOI: 10.1021/acsomega.3c06090.

Synthesis and Properties of (1(),5(),7(),8())-1,8-Bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl: Reduction-Resistant Spin Labels with High Spin Relaxation Times.

Khoroshunova Y, Morozov D, Kuznetsov D, Rybalova T, Glazachev Y, Bagryanskaya E Int J Mol Sci. 2023; 24(14).

PMID: 37511257 PMC: 10380268. DOI: 10.3390/ijms241411498.

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