3-羧基-2,2,5,5-四乙基吡咯烷-1-氧自由基的简便合成方法及吡咯烷系列抗还原型自旋标记物和探针的制备。

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.

机构信息

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, Russia.

Novosibirsk State University, Pirogova Str. 2, Novosibirsk 630090, Russia.

出版信息

Molecules. 2021 Sep 23;26(19):5761. doi: 10.3390/molecules26195761.

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.

稳定自由基广泛用作磁共振波谱和成像等各种生物物理和生物医学研究应用中的分子探针和标记物。在这些自由基中，具有吡咯烷系列的空间位阻氮氧自由基在生物系统中表现出最高的稳定性。在这里，我们建议了一种新的简便方法，可从廉价的商业上可获得的试剂中制备 3-羧基-2,2,5,5-四乙基吡咯烷-1-氧自由基，这是广泛使用的羧基-普罗布醇的还原抗性类似物，其产率超过了最乐观的文献数据。还制备了几种新的 2,2,5,5-四乙基吡咯烷-1-氧自由基系列的自旋标记物和探针，并研究了这些自由基在抗坏血酸溶液、小鼠血液和组织匀浆中的还原情况。