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Article

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

by
Yulia V. Khoroshunova
1,2,
Denis A. Morozov
1,
Danil A. Kuznetsov
2,
Tatyana V. Rybalova
1,
Yurii I. Glazachev
3,
Elena G. Bagryanskaya
1 and
Igor A. Kirilyuk
1,*
1
N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, 630090 Novosibirsk, Russia
2
Department of Physics, Novosibirsk State University, Pirogova Str. 1, 630090 Novosibirsk, Russia
3
Voevodsky Institute of Chemical Kinetics and Combustion SB RAS, Institutskaya 3, 630090 Novosibirsk, Russia
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2023, 24(14), 11498; https://doi.org/10.3390/ijms241411498
Submission received: 22 June 2023 / Revised: 12 July 2023 / Accepted: 13 July 2023 / Published: 15 July 2023
(This article belongs to the Special Issue Small Molecules with Spiro-Conjugated Cycles: Advances in Synthesis and Applications)
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Abstract

Site-directed spin labeling followed by investigation using Electron Paramagnetic Resonance spectroscopy is a rapidly expanding powerful biophysical technique to study structure, local dynamics and functions of biomolecules using pulsed EPR techniques and nitroxides are the most widely used spin labels. Modern trends of this method include measurements directly inside a living cell, as well as measurements without deep freezing (below 70 K), which provide information that is more consistent with the behavior of the molecules under study in natural conditions. Such studies require nitroxides, which are resistant to the action of biogenic reductants and have high spin relaxation (dephasing) times, Tm. (1R(S),5R(S),7R(S),8R(S))-1,8-bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl is a unique nitroxide that combines these features. We have developed a convenient method for the synthesis of this radical and studied the ways of its functionalization. Promising spin labels have been obtained, the parameters of their spin relaxation T1 and Tm have been measured, and the kinetics of reduction with ascorbate have been studied.
Keywords: dispiro[pyrrolidine-2,1′-cyclopentane-5,1″-cyclopentane]; 6-azadispiro[4.1.4.2]tridecane; nitrones; 1,3-dipolar cycloaddition; pyrrolidine nitroxides; sterically shielded nitroxides; spin labels dispiro[pyrrolidine-2,1′-cyclopentane-5,1″-cyclopentane]; 6-azadispiro[4.1.4.2]tridecane; nitrones; 1,3-dipolar cycloaddition; pyrrolidine nitroxides; sterically shielded nitroxides; spin labels

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MDPI and ACS Style

Khoroshunova, Y.V.; Morozov, D.A.; Kuznetsov, D.A.; Rybalova, T.V.; Glazachev, Y.I.; Bagryanskaya, E.G.; Kirilyuk, I.A. Synthesis and Properties of (1R(S),5R(S),7R(S),8R(S))-1,8-Bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl: Reduction-Resistant Spin Labels with High Spin Relaxation Times. Int. J. Mol. Sci. 2023, 24, 11498. https://doi.org/10.3390/ijms241411498

AMA Style

Khoroshunova YV, Morozov DA, Kuznetsov DA, Rybalova TV, Glazachev YI, Bagryanskaya EG, Kirilyuk IA. Synthesis and Properties of (1R(S),5R(S),7R(S),8R(S))-1,8-Bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl: Reduction-Resistant Spin Labels with High Spin Relaxation Times. International Journal of Molecular Sciences. 2023; 24(14):11498. https://doi.org/10.3390/ijms241411498

Chicago/Turabian Style

Khoroshunova, Yulia V., Denis A. Morozov, Danil A. Kuznetsov, Tatyana V. Rybalova, Yurii I. Glazachev, Elena G. Bagryanskaya, and Igor A. Kirilyuk. 2023. "Synthesis and Properties of (1R(S),5R(S),7R(S),8R(S))-1,8-Bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl: Reduction-Resistant Spin Labels with High Spin Relaxation Times" International Journal of Molecular Sciences 24, no. 14: 11498. https://doi.org/10.3390/ijms241411498

APA Style

Khoroshunova, Y. V., Morozov, D. A., Kuznetsov, D. A., Rybalova, T. V., Glazachev, Y. I., Bagryanskaya, E. G., & Kirilyuk, I. A. (2023). Synthesis and Properties of (1R(S),5R(S),7R(S),8R(S))-1,8-Bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl: Reduction-Resistant Spin Labels with High Spin Relaxation Times. International Journal of Molecular Sciences, 24(14), 11498. https://doi.org/10.3390/ijms241411498

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