ArticleJournal of the American Chemical Society2007
Reactivity of superoxide radical anion with cyclic nitrones: role of intramolecular H-bond and electrostatic effects.
Article in Journal of the American Chemical Society, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Spin trap-mediated conversion of singlet oxygen to hydroxyl radical in photosensitization: mechanistic insights and the role of biological reductants.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2026Article
- Nitric Oxide-Releasing Nanoscale Metal-Organic Layer Overcomes Hypoxia and Reactive Oxygen Species Diffusion Barriers to Enhance Cancer Radiotherapy.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- A magnetic-void-porous MnFeEnvironmental science and ecotechnology · 2021Article
- Article
- Physicochemical properties of polysaccharides from Dendrobium officinale by fractional precipitation and their preliminary antioxidant and anti-HepG2 cells activities in vitro.Chemistry Central journal · 2018Article
- European contribution to the study of ROS: A summary of the findings and prospects for the future from the COST action BM1203 (EU-ROS).Redox biology · 2017Review
- Reactivities of substituted α-phenyl-N-tert-butyl nitrones.The Journal of organic chemistry · 2014Article
- Investigation of spin-trapping artifacts formed by the Forrester-Hepburn mechanism.Free radical biology & medicine · 2013Article
- Theoretical and experimental studies of the spin trapping of inorganic radicals by 5,5-dimethyl-1-pyrroline N-oxide (DMPO). 3. Sulfur dioxide, sulfite, and sulfate radical anions.The journal of physical chemistry. A · 2012Article
- Potential implication of the chemical properties and bioactivity of nitrone spin traps for therapeutics.Future medicinal chemistry · 2012Review
- Reactivities of superoxide and hydroperoxyl radicals with disubstituted cyclic nitrones: a DFT study.The journal of physical chemistry. A · 2012Article
- Evaluation of the Forrester-Hepburn mechanism as an artifact source in ESR spin-trapping.Chemical research in toxicology · 2011Article
- Environmentally persistent free radicals (EPFRs). 1. Generation of reactive oxygen species in aqueous solutions.Environmental science & technology · 2011Article
- Fast reactivity of a cyclic nitrone-calix[4]pyrrole conjugate with superoxide radical anion: theoretical and experimental studies.Journal of the American Chemical Society · 2010Article
- Spin trapping and cytoprotective properties of fluorinated amphiphilic carrier conjugates of cyclic versus linear nitrones.Chemical research in toxicology · 2009Article
- Lipophilic beta-cyclodextrin cyclic-nitrone conjugate: synthesis and spin trapping studies.The Journal of organic chemistry · 2009Article
- Superoxide-mediated formation of tyrosine hydroperoxides and methionine sulfoxide in peptides through radical addition and intramolecular oxygen transfer.The Journal of biological chemistry · 2009Article
- Dimethyl cis-2-methyl-3-p-tolyl-isoxazolidine-4,5-dicarboxyl-ate.Acta crystallographica. Section E, Structure reports online · 2009Article
- Superoxide radical anion adduct of 5,5-dimethyl-1-pyrroline N-oxide. 4. Conformational effects on the EPR hyperfine splitting constants.The journal of physical chemistry. A · 2008Article
- Theoretical and experimental studies of tyrosyl hydroperoxide formation in the presence of H-bond donors.Chemical research in toxicology · 2008Article
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Authors and funding
7 authors.
Funding
Abstract
Limitations exist among the commonly used cyclic nitrone spin traps for biological free radical detection using electron paramagnetic resonance (EPR) spectroscopy. The design of new spin traps for biological free radical detection and identification using EPR spectroscopy has been a major challenge due to the lack of systematic and rational approaches to their design. In this work, density functional theory (DFT) calculations and stopped-flow kinetics were employed to predict the reactivity of functionalized spin traps with superoxide radical anion (O2*-). Functional groups provide versatility and can potentially improve spin-trap reactivity, adduct stability, and target specificity. The effect of functional group substitution at the C-5 position of pyrroline N-oxides on spin-trap reactivity toward O2*- was computationally rationalized at the PCM/B3LYP/6-31+G(d,p)//B3LYP/6-31G(d) and PCM/mPW1K/6-31+G(d,p) levels of theory. Calculated free energies and rate constants for the reactivity of O2*- with model nitrones were found to correlate with the experimentally obtained rate constants using stopped-flow and EPR spectroscopic methods. New insights into the nucleophilic nature of O2*- addition to nitrones as well as the role of intramolecular hydrogen bonding of O2*- in facilitating this reaction are discussed. This study shows that using an N-monoalkylsubstituted amide or an ester as attached groups on the nitrone can be ideal in molecular tethering for improved spin-trapping properties and could pave the way for improved in vivo radical detection at the site of superoxide formation.
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