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Large-scale synthesis of a persistent trityl radical for use in biomedical EPR applications and imaging |
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| Authors: | Dhimitruka Ilirian Velayutham Murugesan Bobko Andrey A Khramtsov Valery V Villamena Frederick A Hadad Christopher M Zweier Jay L |
| Affiliation: | aCenter for Biomedical EPR Spectroscopy and Imaging, The Davis Heart and Lung Research Institute, The Ohio State University, Columbus, OH 43210, USA bDivision of Cardiovascular Medicine, Department of Internal Medicine, The Ohio State University, Columbus, OH 43210, USA cDepartment of Pharmacology, College of Medicine, College of Medicine, The Ohio State University, Columbus, OH 43210, USA dDepartment of Chemistry, The Ohio State University, Columbus, OH 43210, USA |
| Abstract: | Tetrathiatriarylmethyl radicals are ideal spin probes for biological electron paramagnetic resonance (EPR) spectroscopy and imaging. The wide application of trityl radicals as biosensors of oxygen or other biological radicals was hampered by the lack of affordable large-scale syntheses. We report the large-scale synthesis of the Finland trityl radical using an improved addition protocol of the aryl lithium monomer to methylchloroformate. A new reaction for the formal one-electron reduction of trityl alcohols to trityl radicals using neat trifluoroacetic acid is reported as well. Initial applications show that the compound is very sensitive to molecular oxygen. It has already provided high-resolution EPR images on large aqueous samples and should be suitable for a broad range of in vivo applications. |
| Keywords: | EPR spectroscopy and imaging Trityl radical Trityl alcohol Tetrathiatriarylmethyl TAM |
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