Thermal generation of stable spin trap adducts with super-hyperfine structure in their EPR spectra: An alternative EPR spin trapping assay for radical scavenging capacity determination in dimethylsulphoxide

References

• Fenton HJH. LXXIII—Oxidation of tartaric acid in presence of iron. J Chem Soc Perkin Trans 1894; 65: 899–910
   Google Scholar
• Fenton HJH, Jackson H. LVI—Crystalline glycollic aldehyde. J Chem Soc Perkin Trans 1899; 75: 575–579
   Google Scholar
• Clifton CL, Huie RE. Rate constants for hydrogen abstraction reactions of the sulfate radical, SO4• − alcohols. Int J Chem Kinet 1989; 21: 677–687
   Web of Science ®Google Scholar
• Huie RE, Clifton CL. Kinetics of the self-reaction of hydroxymethylperoxyl radicals. Chem Phys Lett 1993; 205: 163–167
   Web of Science ®Google Scholar
• Elbenberger H, Steenken S, O'Neill P, Schulte-Frohlinde D. Pulse radiolysis and electron spin resonance studies concerning the reaction of SO4• − with alcohols and ethers in aqueous solution [1]. J Phys Chem 1978; 82: 749–750
   Google Scholar
• Heckel E, Henglein A, Beck G. Pulsradiolytische Untersuschung des Radikalanions SO4• −. Ber Bunsenges Phys Chem 1966; 70: 149–154
   Google Scholar
• Stanbury DM. Reduction potentials involving inorganic free radicals in aqueous solution. Adv Inorg Chem 1989; 33: 69–138
   Google Scholar
• Davies, MJ, Gilbert, BC, Norman, ROC. Electron spin resonance. Part 67. Oxidation of aliphatic sulphides and sulphoxides by the sulphate radical anion (SO4• − ) and of aliphatic radicals by the peroxydisulphate anion (S2O82 − ). J Chem Soc Perkin Trans 2 1984;3:503–509.
   Google Scholar
• Davies, MJ, Gilbert, BC. Electron spin resonance studies. Part 68. Addition versus overall one-electron abstraction in the oxidation of alkenes and dienes by SO4• −, Cl2• −, and •OH in acidic aqueous solution. J Chem Soc Perkin Trans 2 1984;11:1809–1815.
   Google Scholar
• Davies, MJ, Gilbert, BC, Barry Thomas, C, Young, J. Electron spin resonance studies. Part 69. Oxidation of some aliphatic carboxylic acids, carboxylate anions, and related compounds by the sulphate radical anion (SO4• − ). J Chem Soc Perkin Trans 2 1985;8:1199–1204.
   Google Scholar
• Gilbert, BC, Scarratt, CJ, Thomas, CB, Young, J. Electron spin resonance studies. Part 71. Side-chain oxidation pathways in the reactions of •OH and SO4• − with some phenyl-substituted carboxylic acids, their anions, and some related compounds. J Chem Soc Perkin Trans 2 1987;3:371–380.
   Google Scholar
• Gilbert, BC, Lindsay Smith, JR, Taylor, P, Ward, S, Whitwood, AC. The interplay of electronic, steric and stereoelectronic effects in hydrogen-atom abstraction reactions of SO4• −, revealed by EPR spectroscopy. J Chem Soc Perkin Trans 2 1999;8:1631–1637.
   Google Scholar
• Steenken S. Purine bases, nucleosides, and nucleotides: Aqueous solution redox chemistry and transformation reactions of their radical cations and e− and OH adducts. Chem Rev 1989; 89: 503–520
   Web of Science ®Google Scholar
• Candeias LP, Steenken S. Structure and acid-base properties of one-electron-oxidized deoxyguanosine, guanosine, and 1-methylguanosine. J Am Chem Soc 1989; 111: 1094–1099
   Web of Science ®Google Scholar
• Schuchmann HP, Deeble DJ, Olbrich G, Von Sonntag C. The SO4• − induced chain reaction of 1,3-dimethyluracil with peroxodisulphate. Int J Radiat Biol 1987; 51: 441–453
   Web of Science ®Google Scholar
• Bothe E, Deeble DJ, Lemaire DGE, Rashid R, Schuchmann MN, Schuchmann HP, Schulte-Frohlinde D, Steenken S, Von Sonntag C. Pulse-radiolytic studies on the reactions of SO4• − with uracil derivatives. Radiat Phys Chem 1990; 36: 149–154
   Web of Science ®Google Scholar
• Hazra DK, Steenken S. Pattern of OH radical addition to cytosine and 1-, 3-, 5-, and 6-substituted cytosines. Electron transfer and dehydration reactions of the OH adducts. J Am Chem Soc 1983; 105: 4380–4386
   Web of Science ®Google Scholar
• Niehaus, H, Hildenbrand, K. Continuous-flow and spin-trapping EPR studies on the reactions of cytidine induced by the sulfate radical-anion in aqueous solution. Evidence for an intermediate radical-cation. J Chem Soc Perkin Trans 2 2000;5:947–952.
   Google Scholar
• Itahara, T, Ebihara, R, Seto, Y, Fujii, Y, Tada, M. Reaction of nucleic acids bases and their derivatives with peroxodisulfate ion. Nucleic Acids Symp Ser, 1985;16:61–64.
   PubMedGoogle Scholar
• Itahara, T, Ide, N, Nishino, A. Oxidation of pyrimidine bases and their derivatives by sodium peroxodisulfate. Nucleic Acids Symp Ser 1989;21:5–6.
   PubMedGoogle Scholar
• Itahara, T, Koga, S, Yoshitake, T. Oxidation of nucleosides and nucleotides by peroxosulfate ions. Nucleic Acids Symp Ser 1990;22:9–10.
   PubMedGoogle Scholar
• Hildenbrand, K. Spin-trapping studies of the reaction of the sulfate radical anion with N1-substituted pyrimidine bases. Comparison with continuous-flow electron paramagnetic resonance experiments. J Chem Soc Perkin Trans 2 1995;12:2153–2162.
   Google Scholar
• Staško A, Polovka M, Brezová V, Biskupič S, Malík F. Tokay wines as scavengers of free radicals (an EPR study). Food Chem 2006; 96: 185–196
   Web of Science ®Google Scholar
• Staško A, Liptáková M, Malík F, Mišík V. Free radical scavenging activities of white and red wines: an EPR spin trapping study. Appl Magn Reson 2002; 22: 101–113
   Web of Science ®Google Scholar
• Staško A, Brezová V, Liptáková M, Šavel J. Thermally initiated radical reactions of K2S2O8: EPR spin trapping investigations. Magn Reson Chem 2000; 38: 957–962
   Web of Science ®Google Scholar
• Davies, MJ, Gilbert, BC, Stell, JK, Whitwood, AC. Nucleophilic substitution reactions of spin adducts. Implications for the correct identification of reaction intermediates by EPR/spin trapping. J Chem Soc Perkin Trans 2 1992;3:333–335.
   Google Scholar
• Clément, JL, Gilbert, BC, Ho, WF, Jackson, ND, Newton, MS, Silvester, S, Timmins, GS, Tordo, P, Whitwood, AC. Use of a phosphorylated spin trap to discriminate between the hydroxyl radical and other oxidising species. J Chem Soc Perkin Trans 2 1998;8:1715–1717.
   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
• Rapta P, Polovka M, Zalibera M, Breierová E, Žitňanová I, Márová I, Čertík M. Scavenging and antioxidant properties of compounds synthesized by carotenogenic yeasts stressed by heavy metals—EPR spin trapping study. Biophys Chem 2005; 116: 1–9
   PubMed Web of Science ®Google Scholar
• Brindzová L, Čertík M, Rapta P, Zalibera M, Mikulajová A, Takácsová M. b Antioxidant activity, β-glucan and lipid contents of oat varieties. Czech J Food Sci 2008; 26: 163–173
   Web of Science ®Google Scholar
• Mikulajová A, Takácsová M, Rapta P, Brindzová L, Zalibera M, Nemeth K. Total phenolic contents and antioxidant capacities of cereal and pseudocereal genotypes. J Food Nutr Res 2007; 46: 150–157
   Web of Science ®Google Scholar
• Moore J, Yin JJ, Yu L. Novel fluorometric assay for hydroxyl radical scavenging capacity (HOSC) estimation. J Agric Food Chem 2006; 54: 617–626
   PubMed Web of Science ®Google Scholar
• Wardman P. Reduction potentials of one-electron couples involving free-radicals in aqueous-solution. J Phys Chem Ref Data 1989; 18: 1637–1755
   Web of Science ®Google Scholar
• Staško A, Brezová V, Biskupič S, Mišík V. The potential pitfalls of using 1,1-diphenyl-2-picrylhydrazyl to characterize antioxidants in mixed water solvents. Free Radic Res 2007; 41: 379–390
   PubMed Web of Science ®Google Scholar
• Duling DR. Simulation of multiple isotropic spin-trap EPR-spectra. J Magn Reson B 1994; 104: 105–110
   PubMedGoogle Scholar
• Eberson, L, Persson, O. Generation of acyloxyl spin adducts from N-tert-butyl-α-phenylnitrone (PBN) and 4,5-dihydro-5,5-dimethylpyrrole 1-oxide (DMPO) via nonconventional mechanisms. J Chem Soc Perkin Trans 2 1997;1689–1696.
   Google Scholar
• Rosen GM, Beselman A, Tsai P, Pou S, Mailer C, Ichikawa K, Robinson BH, Nielsen R, Halpern HJ, MacKerell AD. Influence of conformation on the EPR spectrum of 5,5-dimethyl-1-hydroperoxy-1-pyrrolidinyloxyl: a spin trapped adduct of superoxide. J Org Chem 2004; 69: 1321–1330
   PubMed Web of Science ®Google Scholar
• Clement JL, Ferre N, Siri D, Karoui H, Rockenbauer A, Tordo P. Assignment of the EPR spectrum of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) superoxide spin adduct. J Org Chem 2005; 70: 1198–1203
   PubMed Web of Science ®Google Scholar
• Dikalov S, Jiang JJ, Mason RP. Characterization of the high-resolution ESR spectra of superoxide radical adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) and 5,5-dimethyl-1-pyrroline N-oxide (DMPO). Analysis of conformational exchange. Free Radic Res 2005; 39: 825–836
   PubMed Web of Science ®Google Scholar
• Rockenbauer A, Clement JL, Culcasi M, Mercier A, Tordo P, Pietri S. Combined ESR and thermodynamic studies of the superoxide adduct of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO): hindered rotation around the O-O bond evidenced by two-dimensional simulation of temperature-dependent spectra. J Phys Chem A 2007; 111: 4950–4957
   PubMed Web of Science ®Google Scholar
• Padmaja S, Alfassi ZB, Neta P, Huie RE. Rate constants for reactions of SO4• − radicals in acetonitrile. Int J Chem Kinet 1993; 25: 193–197
   Web of Science ®Google Scholar
• Wu G, Yosuke Katsumura Y, Chub G. Photolytic and radiolytic studies of SO4• − in neat organic solvents. Phys Chem Chem Phys 2000; 2: 5602–5605
   Web of Science ®Google Scholar
• Ivanov KL, Glebov EM, Plyusnin VF, Ivanov YuV, Grivin VP, Bazhin NM. Laser flash photolysis of sodium persulfate in aqueous solution with additions of dimethylformamide. J Photochem Photobiol A 2000; 133: 99–104
   Web of Science ®Google Scholar
• Davies MJ. Recent developments in EPR spin-trapping. Electron paramagnetic resonance. Volume 18, Electron paramagnetic resonance, specialist periodical reports, BC Gilbert, JM Davies, DM Murphy, KA McLauchlan. Royal Chemical Society, Cambridge 2002; 47–73
   Google Scholar
• Tordo P. Spin-trapping: recent developments and applications. Electron paramagnetic resonance. Volume 16, Electron paramagnetic resonance, specialist periodical reports, NM Atherton, BC Gilbert, JM Davies. Royal Chemical Society, Cambridge 1998; 116–144
   Google Scholar
• Culcasi M, Rockenbauer A, Mercier A, Clément JL, Pietri S. The line asymmetry of electron spin resonance spectra as a tool to determine the cis:trans ratio for spin-trapping adducts of chiral pyrrolines N-oxides: the mechanism of formation of hydroxyl radical adducts of EMPO, DEPMPO, and DIPPMPO in the ischemic-reperfused rat liver. Free Radic Biol Med 2006; 40: 1524–1538
   PubMed Web of Science ®Google Scholar
• Roginsky V, Lissi EA. Review of methods to determine chain-breaking antioxidant activity in food. Food Chem 2005; 92: 235–254
   Web of Science ®Google Scholar
• Antolovich M, Prenzler PD, Patsalides E, McDonald S, Robards K. Methods for testing antioxidant activity. Analyst 2002; 127: 183–198
   PubMed Web of Science ®Google Scholar
• Zang LY, Cosma G, Gardner H, Castranova V, Vallyathan V. Effect of chlorogenic acid on hydroxyl radical. Mol Cell Biochem 2003; 247: 205–210
   PubMed Web of Science ®Google Scholar
• Brezová, V, Šlebodová, A, Staško, A. Coffee as a source of antioxidants: an EPR study Food Chem. 2009;114:859–868. doi:10.1016/j.foodchem.2008.10.025.
   Google Scholar
• Rice-Evans CA, Miller NJ, Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 1996; 20: 933–956
   PubMed Web of Science ®Google Scholar