ArticleThe Journal of organic chemistry2010
Synthesis of 14N- and 15N-labeled trityl-nitroxide biradicals with strong spin-spin interaction and improved sensitivity to redox status and oxygen.
Article in The Journal of organic chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 59 citations in OpenAlex.
- Synthesis and Characterization of Pyridine-Containing Tetrathiatriarylmethyl (TAM) Stable Radicals for Biomedical Magnetic Resonance Applications.The Journal of organic chemistry · 2026Article
- Frequency-Chirped Magic Angle Spinning Dynamic Nuclear Polarization Combined with Electron Decoupling.The journal of physical chemistry letters · 2024Article
- Sensitive simultaneous measurements of oxygenation and extracellular pH by EPR using a stable monophosphonated trityl radical and lithium phthalocyanine.Free radical biology & medicine · 2024Article
- An EPR Study on Highly Stable Nitroxyl-Nitroxyl Biradicals for Dynamic Nuclear Polarization Applications at High Magnetic Fields.Molecules (Basel, Switzerland) · 2023Article
- Highly bioresistant, hydrophilic and rigidly linked trityl-nitroxide biradicals for cellular high-field dynamic nuclear polarization.Chemical science · 2022Article
- Synthesis and characterization of a Cu(ii) coordination-containing TAM radical as a nitroxyl probe.RSC advances · 2022Article
- Imaging analysis for multiple paramagnetic agents using OMRI and electrophoresis.Journal of clinical biochemistry and nutrition · 2022Article
- Spin-spin interaction and relaxation in two trityl-nitroxide diradicals.Journal of magnetic resonance (San Diego, Calif. : 1997) · 2021Article
- Large-scale synthesis of a monophosphonated tetrathiatriarylmethyl spin probe for concurrentRSC advances · 2021Article
- Injectable, thermosensitive, fast gelation, bioeliminable, and oxygen sensitive hydrogels.Materials science & engineering. C, Materials for biological applications · 2019Article
- Diastereoisomers of l-proline-linked trityl-nitroxide biradicals: synthesis and effect of chiral configurations on exchange interactions.Chemical science · 2018Article
- Efficient cross-effect dynamic nuclear polarization without depolarization in high-resolution MAS NMR.Chemical science · 2017Article
- Triarylmethyl Radicals: EPR Study ofZeitschrift fur physikalische Chemie (Frankfurt am Main, Germany) · 2017Article
- EPR Imaging Spin Probe Trityl Radical OX063: A Method for Its Isolation from Animal Effluent, Redox Chemistry of Its Quinone Methide Oxidation Product, and in Vivo Application in a Mouse.Chemical research in toxicology · 2016Article
- Trityl-based alkoxyamines as NMP controllers and spin-labels.Polymer chemistry · 2016Article
- In vivo EPR oximetry using an isotopically-substituted nitroxide: Potential for quantitative measurement of tissue oxygen.Journal of magnetic resonance (San Diego, Calif. : 1997) · 2016Article
- Poly-arginine conjugated triarylmethyl radical as intracellular spin label.Bioorganic & medicinal chemistry letters · 2016Article
- Facile and High-Yielding Synthesis of TAM Biradicals and Monofunctional TAM Radicals.Synlett : accounts and rapid communications in synthetic organic chemistry · 2016Article
- Supramolecular host-guest interaction of trityl-nitroxide biradicals with cyclodextrins: modulation of spin-spin interaction and redox sensitivity.Organic & biomolecular chemistry · 2016Article
- Efficient Dynamic Nuclear Polarization at 800 MHz/527 GHz with Trityl-Nitroxide Biradicals.Angewandte Chemie (International ed. in English) · 2015Article
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
Simultaneous evaluation of redox status and oxygenation in biological systems is of great importance for the understanding of biological functions. Electron paramagnetic resonance (EPR) spectroscopy coupled with the use of the nitroxide radicals have been an indispensable technique for this application but are still limited by low oxygen sensitivity and low EPR resolution in part due to the moderately broad EPR triplet and spin quenching through bioreduction. In this study, we showed that these drawbacks can be overcome through the use of trityl-nitroxide biradicals allowing for the simultaneous measurement of redox status and oxygenation. A new trityl-nitroxide biradical TNN14 composed of a pyrrolidinyl-nitroxide and a trityl and its isotopically labeled (15)N analogue TNN15 were synthesized and characterized. Both biradicals exhibited much stronger spin-spin interaction with J > 400 G compared with that of the previous synthesized trityl-nitroxide biradicals TN1 (∼160 G) and TN2 (∼52 G) with longer linker chain length. The enhanced stability of TNN14 was evaluated using ascorbate as reductant, and the effect of different types of cyclodextrins on its stability in the presence of ascorbate was also investigated. Both biradicals are sensitive to redox status, and their corresponding trityl-hydroxylamines resulting from the reduction of the biradicals by ascorbate share the same oxygen sensitivity. Of note is that the (15)N-labeled TNN15-H with an EPR doublet exhibits improved EPR signal amplitude as compared with that of TNN14-H with an EPR triplet. In addition, cyclic voltammetric studies verify the characteristic electrochemical behaviors of the trityl-nitroxide biradicals.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.