Publication Cover
Redox Report
Communications in Free Radical Research
Volume 3, 1997 - Issue 2
185
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

Use of isotopically labelled spin-traps to determine definitively the presence or absence of non-radical addition artefacts in EPR spin-trapping systems

, , , &
Pages 125-133 | Received 20 Dec 1996, Accepted 30 Jan 1997, Published online: 13 Jul 2016

REFERENCES

  • Janzen E G, Blackburn B J. Detection and identification of short-lived free radicals by an electron spin resonance trapping technique. J Am Chem Soc 1968; 90: 5909–5910.
  • Chalfont G R, Perkins M J, Horsfield A. A probe for homolytic reactions in solution. II. The polymerization of styrene. J Am Chem Soc 1968; 90: 7141–7142.
  • Janzen E G. A critical review of spin trapping in biological systems. In: Pryor W A, ed. Free Radicals in Biology, Vol. 4. New York: Academic Press, 1980: 115–154.
  • DeGray J A, Mason R P. Biological spin trapping. In: Atherton M, Davies M J, Gilbert B C, eds. Electron Spin Resonance, Vol. 14. Cambridge: The Royal Society of Chemistry, 1994: 246–294.
  • Perkins M J. Spin trapping. In: Gold V, Bethell D, eds. Advances in Physical Organic Chemistry, Vol 17, London: Academic Press, 1980: 1–64.
  • Davies M J, Timmins G S. EPR spectroscopy of biologically relevant free radicals in cellular, ex vitro and in vivo systems. In: Clark R J H, Hester R E, eds. Biomedical Applications of Spectroscopy, Vol. 25. Chichester: John Wiley, 1996: 217–266.
  • Burkitt M J, Mason R P. Direct evidence for in vivo hydroxyl-radical generation in experimental iron overload—An ESR spin-trapping investigation. Proc Natl Acad Sci USA 1991; 88: 8440–8444.
  • Knecht K T, Mason R P. In vivo spin-trapping of xenobiotic free-radical metabolites. Arch Biochem Biophys 1993; 303: 185–194.
  • Janzen E G, Stronks H J, DuBose C M et al. Chemistry and biology of spin-trapping radicals associated with halocarbon metabolism in vitro and in vivo. Env Health Persp 1985; 64: 151–170.
  • Eberson L. Inverted spin trapping—reactions between the radical cation of alpha-phenyl-N-tertbutylnitrone and ionic and neutral nucleophiles. J Chem Soc Perkin Trans 2 1992: 1807–1813.
  • Haire D L, Oehler U E, Krygsman P H, Janzen E G. Correlation of radical structure with EPR spin adduct parameters: utility of the 1H, 13C and 14N hyperfine splitting constants of aminoxyl adducts of PBN-nitronyl−13C for three-parameter plots. J Org Chem 1988; 53: 4535–4542.
  • Timmins G S, Wei X, Hawkins C L, Taylor R J K, Davies M J. The synthesis and use of a 15N and 2H isotopically-labelled derivative of the spin trap 3,5-dibromo-4-nitrosobenzenesulphonic acid. Redox Report 1996; 2: 407–410.
  • Janzen E G, Zhang Y K, Haire D L. Synthesis of a novel nitrone, 2-phenyl-5,5-dimethyl-1-pyrroline-N-oxide (nitronyl13C), for enhanced radical addend recognition and spin adduct persistence. J Am Chem Soc 1994; 116: 3738–3743.
  • Zhang Y K. First synthesis of C-phenyl-N-tertbutyl-[15N] nitrone (PBN-N-15) for the EPR spin-trapping methodology. Z Naturforsch Teil B 1996; 51: 139–143.
  • Pou S, Rosen G M, Wu Y X, Keana J F W. Synthesis of deuterium-containing and N-15-containing pyrroline-1-oxides—A spin trapping study. J Org Chem 1990; 55: 4438–4443.
  • Dimonte D, Ross D, Bellomo G, Eklow L, Orrenius S. Alterations in intracellular thiol homeostasis during the metabolism of menadione by isolated rat hepatocytes. Arch Biochem Biophys 1984; 235: 334–342.
  • Gunther M R, Kelman D J, Corbett J T, Mason R P. Self peroxidation of metmyoglobin results in formation of an oxygen-reactive tryptophan-centered radical. J Biol Chem 1995; 270: 16075–16081.
  • Hiramoto K, Hasegawa Y, Kikugawa K. Appearance of ESR signals by the reaction of 3,5-dibromo-4-nitrosobenzenesulfonate (DBNBS) and nonradical biological components. Free Radic Res 1994; 21: 341–349.
  • Keirs D, Moffat D, Overton K, Tomanek R. Assymetric syntheses of the naturally-occurring betaamino acids beta lysine, beta-leucine and beta-phenyl-beta-alanine via nitrone cycloaddition. J Chem Soc Perkin Trans 1 1991: 1041–1051.
  • Annunziata R, Cinquini M, Cozzi F, Giaroni P, Raimondi L. The diastereoselectivity of intermolecular nitrone cycloaddition to chiral allyl derivatives. Tet Letts 1991; 32: 1659–1662.
  • Kalyanaraman B, Karoui H, Singh R J, Felix C C. Detection of thiyl radical adducts formed during hydroxyl-radical-mediated and peroxynitrite-mediated oxidation of thiols—a high resolution ESR spin-trapping study at Q-band (35 GHz). Anal Biochem 996; 241: 75–81.
  • Jiang J J, Liu K J, Jordan S J, Swartz H M, Mason R P. Detection of free-radical metabolite formation using in vivo EPR spectroscopy—evidence of rat hemoglobin thiyl radical formation. Arch Biochem Biophys 1996; 330: 266–270.
  • Scrivens G, Gilbert B C, Lee TCP. EPR studies of the copper-catalyzed oxidation of thiols with peroxides. J Chem Soc Perkin Trans 2 1995: 955–963.
  • Zuman P, Shah B. Addition, reduction and oxidation reactions of nitrosobenzene. Chem Rev 1994; 94: 1621–1641.
  • Tuccio B, Lauricella R, Frejaville C, Bouteiller J C, Tordo P. Decay of the hydroperoxyl spin adduct of 5-diethoxyphosphoryl-5-methyl-1-pyrroline-N-oxide: an EPR kinetic study. J Chem Soc Perkin Trans 2 1995: 295–298.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.