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

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 Full article

Journal

International Journal of Molecular Sciences
ISSN: 1661-6596

Output data

Year: 2023, Volume: 24, Number: 14, Pages: 11498 Pages count : 24 DOI: 10.3390/ijms241411498

Tags

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

Authors

Khoroshunova Yulia V. ^1,2 , Morozov Denis A. ¹ , Kuznetsov Danil A. ² , Rybalova Tatyana V. ¹ , Glazachev Yurii I. ³ , Bagryanskaya Elena G. ¹ , Kirilyuk Igor A. ¹

Affiliations

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

Funding (1)

Российский Научный Фонд

23-23-00617

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.

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
International Journal of Molecular Sciences. 2023. V.24. N14. P.11498. DOI: 10.3390/ijms241411498 WOS Scopus РИНЦ

Submitted:	Jun 22, 2023
Accepted:	Jul 13, 2023
Published online:	Jul 15, 2023

Web of science	WOS:001039458400001
Scopus	2-s2.0-85166009639
Elibrary	61970194
OpenAlex	W4384525949