Nitric oxide ((*)NO) may act as either a pro-oxidant or an antioxidant in biological systems. Although (*)NO and nitroxide radicals react slowly with most molecules, they react at near diffusion-controlled rates with other radicals and may therefore be efficient protective agents. This study assessed the ability of (*)NO and nitroxides to intercept specific protein-derived radicals and compared the efficacy of these species. Three protein radical systems were investigated as follows: BSA-derived radicals generated via radical transfer from H(2)O(2)-activated horseradish peroxidase, radicals formed on myoglobin via reaction with H(2)O(2), and carbon-centered radicals formed from amino acid hydroperoxides on exposure to Fe(2+)-EDTA. In each case, radicals were generated in the absence or presence of (*)NO or nitroxides of different size and charge. Concentration-dependent loss of the protein radicals was detected by electron paramagnetic resonance with both (*)NO and nitroxides and time-dependent consumption of (*)NO using an (*)NO electrode. The protein oxidation product dityrosine was significantly reduced by (*)NO and nitroxides, and 3,4-dihydroxyphenylalanine levels were reduced by nitroxides but not (*)NO. Overall, these studies demonstrate that (*)NO and nitroxides are efficient near-stoichiometric scavengers of protein radicals and, hence, are potential protective agents against protein oxidation reactions and resulting damage. These reactions show little dependence on nitroxide structure or charge.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/tx800183t | DOI Listing |
Molecules
October 2024
Institute of Organic Chemistry, University of Regensburg, Universitaetstrasse 31, 93053 Regensburg, Germany.
This study examines experimental data on the influence of the surrounding medium and non-covalent interactions on the isotropic hyperfine coupling constant, A(N), of the stable nitroxide radical 2,2,6,6-Tetramethylpiperidin-1-yl)oxyl (TEMPO) in solution. The data were used to identify a density functional theory functional/basis set combination that accurately reproduces the experimental A(N) values. The variations in A(N) due to external factors are two orders of magnitude greater than the accuracy of its experimental measurements, making A(N) a highly sensitive experimental probe for quantifying these effects.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Engineering Science, The University of Electro-Communications, Chofu, Tokyo 182-8585, Japan.
The title compound was synthesized, and ESR and magnetic analysis revealed diamagnetic properties below 400 K. The crystal structure analysis clarified that the molecule possesses an approximate symmetry with a head-to-tail (N-O) four-membered ring. The N···O distances are 2.
View Article and Find Full Text PDFChemphyschem
December 2024
College of Engineering, Peking University, Beijing, 10087, China.
The study investigated the impact of protonation and hydration on the geometry of nitroxide radicals using B3LYP and M06-2X methods. Results indicated that TEMPO exhibited the highest proton affinity in comparison to TEMPOL and TEMPONE. Two pathways contribute to hydrated protonated molecules.
View Article and Find Full Text PDFMolecules
June 2024
Department of Pharmacology and Toxicology, Medical University of Lodz, ul. Zeligowskiego 7/9, 90-752 Lodz, Poland.
Nitroxides are stable radicals consisting of a nitroxyl group, >N-O, which carries an unpaired electron. This group is responsible for the paramagnetic and antioxidant properties of these compounds. A recent study evaluated the effects of pyrrolidine and pyrroline derivatives of nitroxides on the antioxidant system of human red blood cells (RBCs).
View Article and Find Full Text PDFSci Rep
April 2024
Department of Chemistry, Faculty of Science, Suez University, P.O. Box: 43221, Suez, Egypt.
The study investigates the molecular structure of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and its derivatives in the gas phase using B3LYP and M06-2X functional methods. Intermolecular interactions are analyzed using natural bond orbital (NBO) and atoms in molecules (AIM) techniques. NO-substituted TEMPO displays high reactivity, less stability, and softer properties.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!