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

Redox Report

Volumn 3, Issue 2, 1997, Pages 125-133

  Timmins, G S ^a   Barlow, G K ^a   Silvester, J A ^a   Wei, X ^a   Whitwood, A C ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIBROMO 4 NITROSOBENZENESULFONIC ACID; FREE RADICAL; GLUTATHIONE; N TERT BUTYL ALPHA PHENYLNITRONE; NITROXIDE; SULFONIC ACID DERIVATIVE; THIOL; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; ARTIFACT; ELECTRON SPIN RESONANCE; OXIDATION; PRIORITY JOURNAL; SPIN TRAPPING;

EID: 0030787970     PISSN: 13510002     EISSN: None     Source Type: Journal    
DOI: 10.1080/13510002.1997.11747099     Document Type: Article

References (25)

1. 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.
2. 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.
3. 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.
4. 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.
5. Perkins M J. Spin trapping. In: Gold V, Bethell D, eds. Advances in Physical Organic Chemistry, Vol 17, London: Academic Press, 1980: 1-64.
6. 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.
7. Burkitt M J, Mason R P. Direct evidence for in vivo hydroxyl-radical generation in experimental iron overload - An ESR spintrapping investigation. Proc Natl Acad Sci USA 1991; 88: 8440-8444.
8. Knecht K T, Mason R P. In vivo spin-trapping of xenobiotic free-radical metabolites. Arch Biochem Biophys 1993; 303: 185-194.
9. 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.
10. 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.
11. 13C for three-parameter plots. J Org Chem 1988; 53: 4535-4542.
12. 2H isotopically-labelled derivative of the spin trap 3,5-dibromo-4-nitrosobenzenesulphonic acid. Redox Report 1996; 2: 407-410.
13. 13C), for enhanced radical addend recognition and spin adduct persistence. J Am Chem Soc 1994; 116: 3738-3743.
14. 15N] nitrone (PBN-N-15) for the EPR spin-trapping methodology. Z Naturforsch Teil B 1996; 51: 139-143.
15. Pou S, Rosen G M, Wu Y X, Keana JFW. Synthesis of deuterium-containing and N-15-containing pyrroline-1-oxides - A spin trapping study. J Org Chem 1990; 55: 4438-4443.
16. 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.
17. 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.
18. 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
19. 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.
20. Annunziata R, Cinquini M, Cozzi F, Giarom P, Raimondi L. The diastereoselectivity of intermolecular nitrone cycloaddition to chiral allyl derivatives. Tet Letts 1991; 32: 1659-1662.
21. 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 1996; 241: 75-81.
22. 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.
23. Scrivens G, Gilbert B C, Lee T C P. EPR studies of the coppercatalyzed oxidation of thiols with peroxides. J Chem Soc Perkin Trans 2 1995: 955-963.
24. Zuman P, Shah B. Addition, reduction and oxidation reactions of nitrosobenzene. Chem Rev 1994; 94: 1621-1641.
25. 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.