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

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 Full article

Journal

Molecules
, E-ISSN: 1420-3049

Output data

Year: 2021, Volume: 26, Number: 19, Article number : 5761, Pages count : DOI: 10.3390/molecules26195761

Tags

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

Authors

Dobrynin S.A. ¹ , Usatov M.S. ^1,2 , Zhurko I.F. ¹ , Morozov D.A. ¹ , Polienko Y.F. ¹ , Glazachev Y.I. ³ , Parkhomenko D.A. ¹ , Tyumentsev M.A. ⁴ , Gatilov Y.V. ¹ , Chernyak E.I. ¹ , Bagryanskaya E.G. ¹ , Kirilyuk I.A. ¹

Affiliations

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, 630090, Russian Federation
2	Novosibirsk State University, Pirogova Str. 2, Novosibirsk, 630090, Russian Federation
3	Voevodsky Institute of Chemical Kinetics and Combustion SB RAS, Institutskaya 3, Novosibirsk, 630090, Russian Federation
4	Federal Research Center Institute of Cytology and Genetics SB RAS, Lavrentiev Ave. 10, Novosibirsk, 630090, Russian Federation

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. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

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.
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. V.26. N19. 5761 . DOI: 10.3390/molecules26195761 WOS Scopus РИНЦ OpenAlex

Web of science:	WOS:000708317900001
Scopus:	2-s2.0-85115665294
Elibrary:	47104881
OpenAlex:	W3200653326

DB	Citing
Scopus	14
Elibrary	19
Web of science	16
OpenAlex	15