Thiol-Dependent Reduction of the Triester and Triamide Derivatives of Finland Trityl Radical Triggers O2-Dependent Superoxide Production
| Autor: | Frederick A. Villamena, Antal Rockenbauer, Yuguang Song, Li Chen, Yangping Liu, Xiaoli Tan, Jay L. Zweier |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Reducing agent Superoxide Radical General Medicine Glutathione 010402 general chemistry Toxicology Photochemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences law.invention chemistry.chemical_compound chemistry law Thiol Electron paramagnetic resonance Cysteine Carbanion |
| Zdroj: | Chemical Research in Toxicology. 30:1664-1672 |
| ISSN: | 1520-5010 0893-228X |
| Popis: | Tetrathiatriaylmethyl (trityl) radicals have found wide biomedical applications as magnetic resonance probes. Trityl radicals and their derivatives are generally stable toward biological reducing agents such as glutathione (GSH) and ascorbate. We demonstrate that the triester (ET-03) and triamide (AT-03) derivatives of the Finland trityl radical exhibit unique reduction by thiols such as GSH and cysteine (Cys) to generate the corresponding trityl carbanions as evidenced by the loss of EPR signal and appearance of characteristic UV–vis absorbance at 644 nm under anaerobic conditions. The trityl carbanions can be quickly converted back to the original trityl radicals by oxygen (O2) in air, thus rendering the reaction between the trityl derivative and biothiol undetectable under aerobic conditions. The reduction product of O2 by the trityl carbanions was shown to be superoxide radical (O2•–) by EPR spin-trapping. Kinetic studies showed that the reaction rate constants (k) depend on the types of both trityl r... |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|