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Literature DB >> 17499990

Synthesis and characterization of a perchlorotriphenylmethyl (trityl) triester radical: a potential sensor for superoxide and oxygen in biological systems.

Vinh Dang¹, Jinhua Wang, Song Feng, Christophe Buron, Frederick A Villamena, Peng George Wang, Periannan Kuppusamy.

Abstract

Synthesis and characterization of an inert perchlorotriphenylmethyl triester radical, PTM-TE, are reported. PTM-TE was prepared by a facile 3-step synthesis using Friedel-Crafts reaction of tetrachlorobenzene with chloroform followed by ethoxycarbonylation and subsequent oxidation. PTM-TE is paramagnetic and exhibits a single sharp EPR spectrum. In solution, the EPR linewidth of PTM-TE is highly sensitive to the dissolved oxygen content, thus enabling accurate measurement of oxygen concentration (oximetry). In addition, the radical also shows high reactivity towards superoxide. The ester radical has the potential for use as a high-sensitive probe for determination of oxygen concentration and superoxide in biological systems.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17499990 PMCID： PMC3685182 DOI： 10.1016/j.bmcl.2007.04.070

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

8 in total

1. A highly sensitive biocompatible spin probe for imaging of oxygen concentration in tissues.

Authors: Anna Bratasz; Aditi C Kulkarni; Periannan Kuppusamy
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Review 2. Relationship between free radicals and vitamins: an overview.

Authors: H Sies
Journal: Int J Vitam Nutr Res Suppl Date: 1989

3. Metabolic imaging by hyperpolarized 13C magnetic resonance imaging for in vivo tumor diagnosis.

Authors: Klaes Golman; René In't Zandt; Mathilde Lerche; Rikard Pehrson; Jan Henrik Ardenkjaer-Larsen
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4. Application of a trityl-based radical probe for measuring superoxide.

Authors: Cëcile Rizzi; Alexandre Samouilov; Vijay Kumar Kutala; Narasimham L Parinandi; Jay L Zweier; Periannan Kuppusamy
Journal: Free Radic Biol Med Date: 2003-12-15 Impact factor: 7.376

5. Radical para-benzoic acid derivatives: transmission of ferromagnetic interactions through hydrogen bonds at long distances.

Authors: Daniel Maspoch; Laure Catala; Philippe Gerbier; Daniel Ruiz-Molina; José Vidal-Gancedo; Klaus Wurst; Concepció Rovira; Jaume Veciana
Journal: Chemistry Date: 2002-08-16 Impact factor: 5.236

6. Molecular imaging with endogenous substances.

Authors: Klaes Golman; Jan H Ardenkjaer-Larsen; J Stefan Petersson; Sven Mansson; Ib Leunbach
Journal: Proc Natl Acad Sci U S A Date: 2003-08-20 Impact factor: 11.205

7. Increase in signal-to-noise ratio of > 10,000 times in liquid-state NMR.

Authors: Jan H Ardenkjaer-Larsen; Björn Fridlund; Andreas Gram; Georg Hansson; Lennart Hansson; Mathilde H Lerche; Rolf Servin; Mikkel Thaning; Klaes Golman
Journal: Proc Natl Acad Sci U S A Date: 2003-08-20 Impact factor: 11.205

8. Reaction of superoxide with trityl radical: implications for the determination of superoxide by spectrophotometry.

Authors: Vijay Kumar Kutala; Narasimham L Parinandi; Jay L Zweier; Periannan Kuppusamy
Journal: Arch Biochem Biophys Date: 2004-04-01 Impact factor: 4.013

8 in total

7 in total

7. Perchlorinated Triarylmethyl Radical 99% Enriched ¹³C at the Central Carbon as EPR Spin Probe Highly Sensitive to Molecular Tumbling.

Authors: Justin L Huffman; Martin Poncelet; Whylder Moore; Sandra S Eaton; Gareth R Eaton; Benoit Driesschaert
Journal: J Phys Chem B Date: 2021-07-02 Impact factor: 3.466

7 in total

Synthesis and characterization of a perchlorotriphenylmethyl (trityl) triester radical: a potential sensor for superoxide and oxygen in biological systems.

1. A highly sensitive biocompatible spin probe for imaging of oxygen concentration in tissues.

Review 2. Relationship between free radicals and vitamins: an overview.

3. Metabolic imaging by hyperpolarized 13C magnetic resonance imaging for in vivo tumor diagnosis.

4. Application of a trityl-based radical probe for measuring superoxide.

5. Radical para-benzoic acid derivatives: transmission of ferromagnetic interactions through hydrogen bonds at long distances.

6. Molecular imaging with endogenous substances.

7. Increase in signal-to-noise ratio of > 10,000 times in liquid-state NMR.

8. Reaction of superoxide with trityl radical: implications for the determination of superoxide by spectrophotometry.

Review 1. Theory, instrumentation, and applications of electron paramagnetic resonance oximetry.

2. A radical containing injectable in-situ-oleogel and emulgel for prolonged in-vivo oxygen measurements with CW EPR.

3. A molecular paramagnetic spin-doped biopolymeric oxygen sensor.

4. Trityl radicals in perfluorocarbon emulsions as stable, sensitive, and biocompatible oximetry probes.

5. Perchlorotrityl radical-fluorophore conjugates as dual fluorescence and EPR probes for superoxide radical anion.

6. Esterified trityl radicals as intracellular oxygen probes.

7. Perchlorinated Triarylmethyl Radical 99% Enriched ¹³C at the Central Carbon as EPR Spin Probe Highly Sensitive to Molecular Tumbling.