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
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 s...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-09-01
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| Online Access: | https://www.mdpi.com/1420-3049/26/19/5761 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Sergey A. Dobrynin |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T06:54:56Z |
| format | Article |
| id | doaj.art-542f3f898ab04e9abcb6c47cd9269ec4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T06:54:56Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-542f3f898ab04e9abcb6c47cd9269ec42023-11-22T16:32:19ZengMDPI AGMolecules1420-30492021-09-012619576110.3390/molecules26195761A 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 SeriesSergey A. Dobrynin0Mikhail S. Usatov1Irina F. Zhurko2Denis A. Morozov3Yuliya F. Polienko4Yurii I. Glazachev5Dmitriy A. Parkhomenko6Mikhail A. Tyumentsev7Yuri V. Gatilov8Elena I. Chernyak9Elena G. Bagryanskaya10Igor A. Kirilyuk11N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaVoevodsky Institute of Chemical Kinetics and Combustion SB RAS, Institutskaya 3, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaFederal Research Center Institute of Cytology and Genetics SB RAS, Lavrentiev Ave. 10, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaStable 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.https://www.mdpi.com/1420-3049/26/19/5761nitroxidespin labelspin probeethynylmagnesium bromidenitronepyrrolidine |
| spellingShingle | 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 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 nitroxide spin label spin probe ethynylmagnesium bromide nitrone pyrrolidine |
| 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | nitroxide spin label spin probe ethynylmagnesium bromide nitrone pyrrolidine |
| url | https://www.mdpi.com/1420-3049/26/19/5761 |
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