Scavenging of Organic C-Centered Radicals by Nitroxides

Bagryanskaya, Elena G.; Marque, Sylvain R. A.

doi:10.1021/cr4000946

Cited by 101 publications

(101 citation statements)

References 241 publications

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“…This is because of the limitations of cell imaging techniques, including low selectivity and sensitivity, and the need for very complicated instrumentation. However, recent reports have described profluorescence nitroxides that rely on features of nitroxides, such as stable unpaired electrons, very efficient carbon-centered radical spin trapping 6 and the ability to function as fluorescence switching molecules 7 . Indeed, profluorescence nitroxides have been used to detect carbon-centered radicals generated by enzymatic and nonenzymatic processes 8,9 .…”

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confidence: 99%

Fluorescence probes to detect lipid-derived radicals

et al. 2016

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Lipids and their metabolites are easily oxidized in chain reactions initiated by lipid radicals, forming lipid peroxidation products that include the electrophiles 4-hydroxynonenal and malondialdehyde. These markers can bind cellular macromolecules, causing inflammation, apoptosis and other damage. Methods to detect and neutralize the initiating radicals would provide insights into disease mechanisms and new therapeutic approaches. We describe the first high-sensitivity, specific fluorescence probe for lipid radicals, 2,2,6-trimethyl-4-(4-nitrobenzo[1,2,5]oxadiazol-7-ylamino)-6-pentylpiperidine-1-oxyl (NBD-Pen). NBD-Pen directly detected lipid radicals in living cells by turn-on fluorescence. In a rat model of hepatic carcinoma induced by diethylnitrosamine (DEN), NBD-Pen detected lipid radical generation within 1 h of DEN administration. The lipid radical scavenging moiety of NBD-Pen decreased inflammation, apoptosis and oxidative stress markers at 24 h after DEN, and liver tumor development at 12 weeks. Thus, we have developed a novel fluorescence probe that provides imaging information about lipid radical generation and potential therapeutic benefits in vivo.

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confidence: 99%

Fluorescence probes to detect lipid-derived radicals

et al. 2016

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“…This result also indicated that the catalytic turnover might be suspended in the absence of TEMPO. TEMPO + ( 2 + ) lacked catalytic efficiency (Table , entry 7) …”

Section: Methodsmentioning

confidence: 99%

N‐Oxyl‐Radical‐Catalyzed Intermolecular Aminooxygenation of Styrenes and Inter/intramolecular Aminoalkoxylation of Homoallylic Alcohols

Weng

Zhang

2016

ChemCatChem

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By taking advantage of the redox cycle between the reductive N‐oxyl radical and its oxidative oxoammonium counterpart, the N‐oxyl‐radical‐catalyzed intermolecular aminohydroxylation of styrenes with N‐fluorobenzenesulfonimide was developed. Various vinyl arenes were aminohydroxylated in moderate to excellent yields with high regio‐ and diastereoselectivities by using environmentally benign H2O as the oxygen source. In addition, the sequential inter/intramolecular aminoalkoxylation of homoallylic alcohols was also achieved under anhydrous conditions, which allowed the exclusive synthesis of pharmaceutically useful 2‐aryl‐3‐amino‐disubstituted tetrahydrofurans.

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“…It has been proposed that the HAT event can be described by three different processes, which are not the topics of this review (Bagryanskaya & Marque, 2014).…”

Section: Kinetics Of Bioreductionmentioning

confidence: 99%