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

被引：4

作者：

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
]}

机构：

[1] SB RAS, NN Vorozhtsov Inst Organ Chem, Acad Lavrentiev Av 9, Novosibirsk 630090, Russia

[2] Novosibirsk State Univ, Dept Phys, Pirogova Str 1, Novosibirsk 630090, Russia

[3] SB RAS, Voevodsky Inst Chem Kinet & Combust, Inst 3, Novosibirsk 630090, Russia

来源：

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES | 2023年 / 24卷 / 14期

基金：

俄罗斯科学基金会;

关键词：

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; EPR SPECTROSCOPY; NITROXIDES; PROTEIN; CYCLOADDITIONS; IMIDAZOLINE; TEMPERATURE; NITROXYLS; STABILITY; PYRROLINE; RADICALS;

D O I：

10.3390/ijms241411498

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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, T-m. (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 T-1 and T-m have been measured, and the kinetics of reduction with ascorbate have been studied.

引用

页数：24

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