Synthesis and Characterization of Hydrophilic Trityl Radical TFO for Biomedical and Biophysical Applications
Autor: | Yuying Qu, Yangping Liu, Weixiang Zhai, Yingchun Li, Guifang Han, Xiaoli Tan, Jingli Hou, Guoquan Liu, Yuguang Song |
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Rok vydání: | 2019 |
Předmět: |
Aqueous solution
biology 010405 organic chemistry Chemistry Radical Organic Chemistry Phosphate buffered saline Patent literature General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences law.invention Partition coefficient law biology.protein Bovine serum albumin Electron paramagnetic resonance |
Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 25(33) |
ISSN: | 1521-3765 |
Popis: | Tetrathiatriarylmethyl (TAM, trityl) radicals have found wide applications as spin probes/labels for EPR spectroscopy and imaging, and as polarizing agents for dynamic nuclear polarization. The high hydrophilicity of TAM radicals is essential for their biomedical applications. However, the synthesis of hydrophilic TAM radicals (e.g., OX063) is extremely challenging and has only been reported in the patent literature, to date. Herein, an efficient synthesis of a highly water-soluble TAM radical bis(8-carboxyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dithiol-4-yl)-mono-(8-carboxyl-2,2,6,6-tetrakis(2-hydroxyethyl)benzo[1,2-d:4,5-d']bis([1,3]dithiol-4-yl)methyl (TFO), which contains four additional hydroxylethyl groups, relative to the Finland trityl radical CT-03, is reported. Similar to OX063, TFO exhibits excellent properties, including high water solubility in phosphate buffer, low log P, low pKa , long relaxation times, and negligible binding with bovine serum albumin. On the other hand, TFO has a sharper EPR line and higher O2 sensitivity than those of OX063. Therefore, in combination with its facile synthesis, TFO should find wide applications in magnetic resonance related fields and this synthetic approach would shed new light on the synthesis of other hydrophilic TAM radicals. |
Databáze: | OpenAIRE |
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