Large-scale synthesis of a persistent trityl radical for use in biomedical EPR applications and imaging

Ilirian Dhimitruka; Murugesan Velayutham; Andrey A. Bobko; Valery V. Khramtsov; Frederick A. Villamena; Christopher M. Hadad; Jay L. Zweier

doi:10.1016/j.bmcl.2007.10.030

Large-scale synthesis of a persistent trityl radical for use in biomedical EPR applications and imaging

Ilirian Dhimitruka, Murugesan Velayutham, Andrey A. Bobko, Valery V. Khramtsov, Frederick A. Villamena, Christopher M. Hadad, Jay L. Zweier

Research output: Contribution to journal › Article › peer-review

74 Scopus citations

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.

Original language	English (US)
Pages (from-to)	6801-6805
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	24
DOIs	https://doi.org/10.1016/j.bmcl.2007.10.030
State	Published - Dec 15 2007
Externally published	Yes

Keywords

EPR spectroscopy and imaging
TAM
Tetrathiatriarylmethyl
Trityl alcohol
Trityl radical

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Organic Chemistry
Drug Discovery
Pharmaceutical Science

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10.1016/j.bmcl.2007.10.030

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title = "Large-scale synthesis of a persistent trityl radical for use in biomedical EPR applications and imaging",

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, TAM, Tetrathiatriarylmethyl, Trityl alcohol, Trityl radical",

author = "Ilirian Dhimitruka and Murugesan Velayutham and Bobko, {Andrey A.} and Khramtsov, {Valery V.} and Villamena, {Frederick A.} and Hadad, {Christopher M.} and Zweier, {Jay L.}",

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doi = "10.1016/j.bmcl.2007.10.030",

language = "English (US)",

volume = "17",

pages = "6801--6805",

journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Large-scale synthesis of a persistent trityl radical for use in biomedical EPR applications and imaging

AU - Dhimitruka, Ilirian

AU - Velayutham, Murugesan

AU - Bobko, Andrey A.

AU - Khramtsov, Valery V.

AU - Villamena, Frederick A.

AU - Hadad, Christopher M.

AU - Zweier, Jay L.

PY - 2007/12/15

Y1 - 2007/12/15

N2 - 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.

AB - 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.

KW - EPR spectroscopy and imaging

KW - TAM

KW - Tetrathiatriarylmethyl

KW - Trityl alcohol

KW - Trityl radical

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DO - 10.1016/j.bmcl.2007.10.030

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 24

ER -

Large-scale synthesis of a persistent trityl radical for use in biomedical EPR applications and imaging

Abstract

Keywords

ASJC Scopus subject areas

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