Singlet molecular oxygen generated from lipid hydroperoxides by the Russell Mechanism: Studies using 18O-labeled linoleic acid hydroperoxide and monomol light emission measurements

Journal of the American Chemical Society

Volumn 125, Issue 20, 2003, Pages 6172-6179

  Miyamoto, Sayuri ^a   Martinez, Glaucia R ^a   Medeiros, Marisa H G ^a   Di Mascio, Paolo ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

PEROXYL RADICALS;

BIOCHEMISTRY; MASS SPECTROMETRY; OXYGEN; PHOTOEMISSION; QUENCHING;

LIPIDS;

9,10 DIPHENYLANTHRACENE; ANTHRACENE DERIVATIVE; HYDROGEN PEROXIDE; LINOLEIC ACID; LIPID HYDROPEROXIDE; MOLYBDENUM; OXYGEN 18; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; DECOMPOSITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; LIPID PEROXIDATION; REACTION ANALYSIS; TANDEM MASS SPECTROMETRY;

CERIUM; CHEMILUMINESCENT MEASUREMENTS; FERROUS COMPOUNDS; LIGHT; LINOLEIC ACIDS; LIPID PEROXIDES; OXYGEN ISOTOPES; PHOTOCHEMISTRY; SINGLET OXYGEN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, NEAR-INFRARED;

EID: 0038288716     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029115o     Document Type: Article

References (50)

1. Esterbauer, H.; Gebicki, J.; Puhl, H.; Jurgens, G. Free Radic. Biol. Med. 1992, 13, 341-390.
2. Berliner, J. A.; Heinecke, J. W. Free Radic. Biol. Med. 1996, 20, 707-727.
3. Markesbery, W. R. Free Radic. Biol. Med. 1997, 23, 134-147.
4. Rowley, D.; Gutteridge, J. M. C.; Blake, D.; Farr, M.; Halliwell, B. Clin. Sci. 1984, 66, 691-695.
5. Baynes, J. W. Diabetes 1991, 40, 405-412.
6. Otamiri, T.; Sjodahl, R. Cancer 1989, 64, 422-425.
7. Esterbauer, H. Am. J. Clin. Nutr. 1993, 57, 779S-786S.
8. Girotti, A. W. J. Lipid Res. 1998, 39, 1529-1542.
9. Spiteller, G. Chem. Phys. Lipids 1998, 95, 105-162.
10. Terao, J.; Matsushita, S. J. Am. Oil Chem. Soc. 1977, 54, 234-238.
11. Frankel, E. N.; Neff, W. E.; Bressler, T. R. Lipids 1979, 14, 961-967.
12. Brash, A. R. J. Biol. Chem. 1999, 274, 23679-23682.
13. Hamberg, M.; Samuelsson, B. Biochim. Biophys. Acta 1980, 617, 545-547.
14. Gardner, H. W. Free Radic. Biol. Med. 1989, 7, 65-86.
15. Russell, G. A. J. Am. Chem. Soc. 1957, 79, 3871-3877.
16. Howard, J. A.; Ingold, K. U. J. Am. Chem. Soc. 1968, 90, 1057-1058.
17. King, M. M.; Lai, E. K.; McCay, P. B. J. Biol. Chem. 1975, 250, 6496.
18. Sugioka, K.; Nakano, M. Biochim. Biophys. Acta 1976, 423, 203-216.
19. Sies, H. Arch. Toxicol. 1987, 60, 138-143.
20. Hawco, F. J.; O'Brien, P. J. Biochem. Biophys. Res. Commun. 1976, 76, 354-361.
21. Kanofsky, J. R. J. Org. Chem. 1986, 51, 3386-3388.
22. Koga, S.; Nakano, M.; Uehara, K. Arch. Biochem. Biophys. 1991, 289, 223-229.
23. Niu, Q.; Mendenhall, G. D. J. Am. Chem. Soc. 1990. 112, 1656-1657.
24. Mendenhall, G. D.; Sheng, X. C. J. Am. Chem. Soc. 1991, 113, 8976-8977.
25. Cadet, J.; Douki, T.; Pouget, J. P.; Ravanat, J. L. Methods Enzymol. 2000, 319, 143-153.
26. Kang, P.; Foote, C. S. J. Am. Chem. Soc. 2002, 124, 4865-4873.
27. Klotz, L. O.; Briviba, K.; Sies, H. Methods Enzymol. 2000, 319, 130-143.
28. Ryter, S. W.; Tyrrell, R. M. Free Radic. Biol. Med. 1998, 24, 1520-1534.
29. Kühn, H.; Wiesner, R.; Lankin, V. Z.; Nekrasov, A.; Alder, L.; Schewe, T. Anal. Biochem. 1987, 160, 24-34.
30. Mulliez, E.; Leblanc, J. P.; Girerd, J. J.; Rigaud, M.; Chottard, J. C. Biochim. Biophys. Acta 1987, 916, 13-23.
31. Corey, E. J.; Taylor, W. C. J. Am. Chem. Soc. 1964, 86, 2909-2914.
32. Turro, N. J.; Chow, M. F.; Rigaudy, J. J. Am. Chem. Soc. 1981, 103, 7218-7224.
33. Cadenas, E.; Sies, H. Methods Enzymol. 1984, 105, 221-231.
34. Di Mascio, P.; Sies, H. J. Am. Chem. Soc. 1989, 111, 2909-2914.
35. Chan, H. W.-S.; Levett, G.; Matthew, J. A. Chem. Phys. Lipids 1979, 24, 245-256.
36. Jones, I. T. N.; Bayes, K. D. J. Chem. Phys. 1972, 2, 1003-1004.
37. Darmanyan, A. P.; Foote, C. S. J. Phys. Chem. 1993, 97, 4573-4576.
38. Loidl-Stahlhofen, A.; Hannemann, K.; Spiteller, G. Biochim. Biophys. Acta 1994, 1213, 140-148.
39. Bartlett, P. D.; Traylor, T. G. J. Am. Chem. Soc. 1963, 85, 2407-2410.
40. Traylor, T. G. J. Am. Chem. Soc. 1963, 85, 2411-2413.
41. Bennett, J. E.; Howard, J. A. J. Am. Chem. Soc. 1973, 95, 4008-4010.
42. Khan, A. U.; Kasha, M. J. Am. Chem. Soc. 1970, 92, 3293-3300.
43. Krasnovsky, A. A. Photochem. Photobiol. 1979, 29, 29-36.
44. Kasha, M.; Khan, A. U. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 6047.
45. Khan, A. U.; Kasha, M. J. Chem. Phys. 1963, 39, 2105.
46. Aubry, J.-M.; Cazin B. Inorg. Chem. 1988, 27, 2013.
47. Di Mascio, P.; Bechara, E. J. H.; Rubim, J. C. Appl. Spectrosc. 1992, 46, 236-239.
48. Briviba, K.; Saha-Möller, C. R.; Adam, W.; Sies, H. Biochem. Mol. Biol. Int. 1996, 38, 647-651.
49. Pierlot, C.; Aubry, J. M.; Briviba, K.; Sies, H.; Di Mascio, P. Methods Enzymol. 2000, 319, 3-20.
50. Pryor, W. A. In Free Radical in Molecular Biology, Aging, and Disease; Armstrong, D., Sohal, R. S., Cutler, R. G., Slater, T. F., Eds.; Raven Press: New York, 1984; pp 13-41.