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

被引：17
作者：
Dobrynin, Sergey A. [1 ]
Usatov, Mikhail S. [1 ,2 ]
Zhurko, Irina F. [1 ]
Morozov, Denis A. [1 ]
Polienko, Yuliya F. [1 ]
Glazachev, Yurii, I [3 ]
Parkhomenko, Dmitriy A. [1 ]
Tyumentsev, Mikhail A. [4 ]
Gatilov, Yuri, V [1 ]
Chernyak, Elena, I [1 ]
Bagryanskaya, Elena G. [1 ]
Kirilyuk, Igor A. [1 ]
机构：
[1] NN Vorozhtsov Novosibirsk Inst Organ Chem SB RAS, Lavrentiev Ave 9, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Pirogova Str 2, Novosibirsk 630090, Russia
[3] Voevodsky Inst Chem Kinet & Combust SB RAS, Inst Skaya 3, Novosibirsk 630090, Russia
[4] Inst Cytol & Genet SB RAS, Fed Res Ctr, Lavrentiev Ave 10, Novosibirsk 630090, Russia
来源：
MOLECULES | 2021年 / 26卷 / 19期
基金：
俄罗斯基础研究基金会;
关键词：
nitroxide; spin label; spin probe; ethynylmagnesium bromide; nitrone; pyrrolidine; IN-VIVO; PROTECTING GROUP; REDOX STATUS; NITROXIDE; MITOCHONDRIA; SITE; EPR; CYTOCHROME-P450; METABOLISM; MECHANISMS;
D O I：
10.3390/molecules26195761
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：
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.
引用
收藏
页数：18
相关论文
共 55 条
[1]  
ANDERSON ME, 1980, J BIOL CHEM, V255, P9530
[2]   Unexpected rapid aerobic transformation of 2,2,6,6-tetraethyl-4-oxo (piperidin-1-yloxyl) radical by cytochrome P450 in the presence of NADPH: Evidence against a simple reduction of the nitroxide moiety to the hydroxylamine [J].
Babic, Nikola ;
Orio, Maylis ;
Peyrot, Fabienne .
FREE RADICAL BIOLOGY AND MEDICINE, 2020, 156 :144-156
[3]   In vivo evaluation of different alterations of redox status by studying pharmacokinetics of nitroxides using magnetic resonance techniques [J].
Bacic, Goran ;
Pavicevic, Aleksandra ;
Peyrot, Fabienne .
REDOX BIOLOGY, 2016, 8 :226-242
[4]   Kinetic resolution of 1-oxyl-3-hydroxymethyl-2,2,5,5-tetramethylpyrrolidine derivatives by lipase-catalyzed enantiomer selective acylation [J].
Bálint, J ;
Kiss, V ;
Egri, G ;
Kálai, T ;
Demeter, A ;
Balog, M ;
Fogassy, E ;
Hideg, K .
TETRAHEDRON-ASYMMETRY, 2004, 15 (04) :671-679
[5]   Synthesis of new paramagnetic fatty acids and lipophilic spin labels [J].
Balog, Maria ;
Abe, Christoph ;
Kalai, Tamas ;
Steinhoff, Heinz-Juergen ;
Jeko, Jozsef ;
Hideg, Kalman .
SYNTHESIS-STUTTGART, 2007, 11 (11) :1663-1670
[6]  
Baracz N.M., 1996, SYNTHESIS, V1996, P204, DOI [10.1055/s-1996-4199, DOI 10.1055/S-1996-4199]
[7]   MALEIMIDE AND ISOMALEIMIDE PYRROLIDINE-NITROXIDE SPIN LABELS [J].
BARRATT, MD ;
DAVIES, AP ;
EVANS, MTA .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1971, 24 (02) :280-&
[8]  
Bleicken S, 2019, CHEMISTRYOPEN, V8, P1057, DOI [10.1002/open.201900232, 10.1002/open.201900119]
[9]   EPR and Quantum Chemical Studies of the pH-sensitive Imidazoline and Imidazolidine Nitroxides with Bulky Substituents [J].
Bobko, A. A. ;
Kirilyuk, I. A. ;
Gritsan, N. P. ;
Polovyanenko, D. N. ;
Grigor'ev, I. A. ;
Khramtsov, V. V. ;
Bagryanskaya, E. G. .
APPLIED MAGNETIC RESONANCE, 2010, 39 (04) :437-451
[10]   In-Cell EPR: Progress towards Structural Studies Inside Cells [J].
Bonucci, Alessio ;
Ouari, Olivier ;
Guigliarelli, Bruno ;
Belle, Valerie ;
Mileo, Elisabetta .
CHEMBIOCHEM, 2020, 21 (04) :451-460
123456