Formation of artifactual DMPO-OH spin adduct in acid solutions containing nitrite ions

References

• Janzen EG. Spin trapping. Acc Chem Res 1971;4(1):31–40.
   Web of Science ®Google Scholar
• Finkelstein E, Rosen GM, Rauckman EJ. Spin trapping of superoxide and hydroxyl radical: practical aspects. Arch Biochem Biophys 1980;200:1–16.
   PubMed Web of Science ®Google Scholar
• Frejaville C, Karoui H, Tuccio B, Le Moigne F, Culcasi M, Pietri S, et al. 5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide: a new efficient phosphorylated nitrone for the in vitro and in vivo spin trapping of oxygen-centered radicals. J Med Chem 1995;38:258–265.
   PubMed Web of Science ®Google Scholar
• Liu KJ, Miyake M, Panz T, Swartz H. Evaluation of DEPMPO as a spin trapping agent in biological systems. Free Radic Biol Med 1999;26:714–721.
   PubMed Web of Science ®Google Scholar
• Olive G, Mercier A, Le Moigne F, Rockenbauer A, Tordo P. 2-Ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide: evaluation of the spin trapping properties. Free Radic Biol Med 2000;28:403–408.
   PubMed Web of Science ®Google Scholar
• Eberson L. ‘Inverted spin trapping’ Reactions between the radical cation of α-phenyl-N-tert-butylnitrone and ionic and neutral nucleophiles. J Chem Soc Perkin Trans 2 1992;0:1807–1813.
   Google Scholar
• Bhattacharjee S, Khan MN, Chandra H, Symons MCR. Radical cations from nitrone spin-traps: reaction with water to give OH adducts. J Chem Soc Perkin Trans 2 1996;0:2631–2634.
   Google Scholar
• Chandra H, Symons MCR. Hydration of spin-trap cations as a source of hydroxyl adducts. J Chem Soc Chem Commun 1986;0:1301–1302.
   Google Scholar
• Eberson L. Inverted spin trapping part III Further studies on the chemical and photochemical oxidation of spin traps in the presence of nucleophiles. J Chem Soc Perkin Trans 2 1994;0:171–176.
   Google Scholar
• Forrester AR, Hepburn SP. Spin traps. A cautionary note. J Chem Soc C 1971;0:701–703.
   Google Scholar
• Timmins GS, Liu KJ, Bechara EJH, Kotake Y, Swartz HM. Trapping of free radicals with direct in vivo EPR detection: a comparison of 5,5-dimethyl-1-pyrroline-N-oxide and 5-diethoxyphosphoryl-5-methyl-1-pyrroline-N-oxide as spin traps for HO* and SO4*-. Free Radic Biol Med 1999;27:329–333.
   PubMed Web of Science ®Google Scholar
• Ranguelova K, Mason RP. The fidelity of spin trapping with DMPO in biological systems. Magn Reson Chem 2011;49:152–158.
   PubMed Web of Science ®Google Scholar
• Leinisch F, Jiang J, DeRose EF, Khramtsov VV, Mason RP. Investigation of spin-trapping artifacts formed by the Forrester–Hepburn mechanism. Free Radic Biol Med 2013;65:1497–1505.
   PubMed Web of Science ®Google Scholar
• Makino K, Hagiwara T, Hagi A, Nishi M, Murakami A. Cautionary note for DMPO spin trapping in the presence of iron ion. Biochem Biophys Res Commun 1990;172:1073–1080.
   PubMed Web of Science ®Google Scholar
• Makino K, Hagi A, Ide H, Murakami A, Nishi M. Mechanistic studies on the formation of aminoxyl radicals from 5,5-dimethyl-1-pyrroline-N-oxide in Fenton systems. Characterization of key precursors giving rise to background ESR signals. Can J Chem 1992;70:2818–2827.
   Web of Science ®Google Scholar
• Hanna PM, Chamulitrat W, Mason RP. When are metal ion-dependent hydroxyl and alkoxyl radical adducts of 5,5-dimethyl-1-pyrroline N-oxide artifacts? Arch Biochem Biophys 1992;296:640–644.
   PubMed Web of Science ®Google Scholar
• Hanna PM, Mason RP. Direct evidence for inhibition of free radical formation from Cu(I) and hydrogen peroxide by glutathione and other potential ligands using the EPR spin-trapping technique. Arch Biochem Biophys 1992;295:205–213.
   PubMed Web of Science ®Google Scholar
• Verstraeten SV, Lucangioli S, Galleano M. ESR characterization of thallium(III)-mediated nitrones oxidation. Inorg Chim Acta 2009;362:2305–2310.
   Web of Science ®Google Scholar
• Nakajima A, Ueda Y, Endoh N, Tajima K, Makino K. Electron spin resonance analysis of the oxidation reactions of nitrone type spin traps with gold(III) ion. Can J Chem 2005;83:1178–1184.
   Web of Science ®Google Scholar
• Miura Y, Ueda J, Ozawa T. Formation of the DMPO-OH adduct from Ti(IV) and DMPO in aqueous solution – the first ESR evidence. Inorg Chim Acta 1995;234:169–171.
   Web of Science ®Google Scholar
• Martínez MC, Andriantsitohaina R. Reactive nitrogen species: molecular mechanisms and potential significance in health and disease. Antioxid Redox Signal 2009;11:669–702.
   PubMed Web of Science ®Google Scholar
• Patel RP, McAndrew J, Sellak H, White CR, Jo H, Freeman BA, Darley-Usmar VM. Biological aspects of reactive nitrogen species. Biochim Biophys Acta 1999;1411:385–400.
   PubMed Web of Science ®Google Scholar
• Nash KM, Rockenbauer A, Villamena FA. Reactive nitrogen species reactivities with nitrones: theoretical and experimental studies. Chem Res Toxicol 2012;25:1581–1597.
   PubMed Web of Science ®Google Scholar
• Tomasi J, Mennucci B, Cammi R. Quantum mechanical continuum solvation models. Chem Rev 2005;105:2999–3093.
   PubMed Web of Science ®Google Scholar
• Borowski P. An evaluation of scaling factors for multiparameter scaling procedures based on DFT force fields. J Phys Chem A 2012;116:3866–3880.
   PubMed Web of Science ®Google Scholar
• Fu Y, Liu L, Yu HZ, Wang YM, Guo OX. Quantum-chemical predictions of absolute standard redox potentials of diverse organic molecules and free radicals in acetonitrile. J Am Chem Soc 2005;127:7227–7234.
   PubMed Web of Science ®Google Scholar
• Trasatti S. The absolute electrode potential: an explanatory note. Pure Appl Chem 1986;58:955–966.
   Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 09. Revision D. Wallingford, CT: Gaussian Inc; 2016. p. 01.
   Google Scholar
• Available from: https://winmostar.com.
   Google Scholar
• Buettner GR. Spin Trapping: ESR parameters of spin adducts. Free Radic Biol Med 1987;3:259–303.
   PubMed Web of Science ®Google Scholar
• Mason RP, Hanna PM, Burkitt MJ, Kadiiska MB. Detection of oxygen-derived radicals in biological systems using electron spin resonance. Environ Health Perspect 1994;102:33–36.
   PubMed Web of Science ®Google Scholar
• Eberson L. Formation of hydroxyl spin adducts via nucleophilic addition – oxidation to 5,5-dimethyI-1-pyrroline N-oxide. Acta Chem Scand 1999;53:584–593.
   Google Scholar
• Burkitt MJ, Tsang SY, Tam SC, Bremner I. Generation of 5,5-dimethyl-1-pyrroline N-oxide hydroxyl and scavenger radical adducts from copper/H2O2 mixtures: effects of metal ion chelation and the search for high-valent metal–oxygen intermediates. Arch Biochem Biophys 1995;323:63–70.
   PubMed Web of Science ®Google Scholar
• Overend R, Paraskevopoulos G. Rates of hydroxyl radical reactions. 4. Reactions with methanol, ethanol, 1-propanol, and 2-propanol at 296 K. J Phys Chem 1978;82:1329–1333.
   Web of Science ®Google Scholar
• Riordan E, Minogue N, Healy D, O’Driscoll P, Sodeau JR. Spectroscopic and optimization modeling study of nitrous acid in aqueous solution. J Phys Chem A 2005;109:779–786.
   PubMed Web of Science ®Google Scholar
• Burgett RA, Bao X, Villamena FA. Superoxide radical anion adduct of 5, 5-dimethyl-1-pyrroline N-oxide (DMPO). 3. Effect of mildly acidic pH on the thermodynamics and kinetics of adduct formation. J Phys Chem A 2008;112:2447–2455.
   PubMed Web of Science ®Google Scholar
• Francisco JS. Protonated nitrous acid (H2ONO+): molecular structure, vibrational frequencies, and proton affinity. J Chem Phys 2001;115:2117–2122.
   Web of Science ®Google Scholar
• Wu H, Glaser R. The heterolytic dissociation of neutral and protonated nitrous acid. J Phys Chem A 2003;107:11112–11119.
   Web of Science ®Google Scholar
• Crugeiras J, Ríos A, Maskill H. DFT and AIM study of the protonation of nitrous acid and the pKa of nitrous acidium ion. J Phys Chem A 2011;115:12357–12363.
   PubMed Web of Science ®Google Scholar
• Varma R, Curl RF. Study of the dinitrogen trioxide-water-nitrous acid equilibrium by intensity measurements in microwave spectroscopy. J Phys Chem 1976;80:402–409.
   Web of Science ®Google Scholar
• Rienstra-Kiracofe JC, Tschumper GS, Schaefer HF, Nandi S, Ellison GB. Atomic and molecular electron affinities: photoelectron experiments and theoretical computations. Chem Rev 2002;102:231–282.
   PubMed Web of Science ®Google Scholar
• Stanbury DM. Reduction potentials involving inorganic free radicals in aqueous solution. Adv Inorg Chem 1989;33:69–138.
   Google Scholar
• Benderskii VA, Krivenko AG, Ponomarev EA. Homogeneous and electrode reactions of NO2− ions. Sov Electrochem 1989;25:154–161.
   Web of Science ®Google Scholar
• Koppenol WH, Liebman JF. The oxidizing nature of the hydroxyl radical. A comparison with the ferryl ion (FeO2+). J Phys Chem 1984;88:99–101.
   Web of Science ®Google Scholar
• Ram MS, Stanbury DM. Kinetics and equilibria for reactions of the hexachloroiridate redox couple in nitrous acid. Inorg Chem 1985;24:2954–2962.
   Web of Science ®Google Scholar
• Tresp H, Hammer MU, Winter J, Weltmann K-D, Reuter S. Quantitative detection of plasma-generated radicals in liquids by electron paramagnetic resonance spectroscopy. J Phys D: Appl Phys 2013;46:435401.
   Web of Science ®Google Scholar