The pH dependence of lipid peroxidation using water-soluble azo initiators

Free Radical Biology and Medicine

Volumn 23, Issue 5, 1997, Pages 712-719

  Hanlon, Mary C ^a   Seybert, David W ^a  

^a DUQUESNE UNIVERSITY   (United States)

Author keywords

Azo initiators; Free radicals; Lipid peroxidation; Methyl linoleate; Micelles; pH Dependence

Indexed keywords

2,2' AZOBIS(2 AMIDINOPROPANE); 2,2' AZOBIS[2 (2 IMIDAZOLIN 2 YL)PROPANE]; 4,4' AZOBIS(4 CYANOPENTANOIC ACID); LINOLEIC ACID; UNCLASSIFIED DRUG;

ARTICLE; KINETICS; LIPID PEROXIDATION; MICELLE; PH; PRIORITY JOURNAL; REACTION ANALYSIS;

AZO COMPOUNDS; BUFFERS; DETERGENTS; FREE RADICALS; HYDROGEN-ION CONCENTRATION; KINETICS; LINOLEIC ACIDS; LIPID PEROXIDATION; MICELLES; OCTOXYNOL; OXIDATION-REDUCTION; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 0030857729     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(97)00024-5     Document Type: Article

References (36)

1. Southorn P. A., Powis G. Free radicals in medicine. II. Involvement in human disease. Mayo Clin. Proc. 6:1988;390-408.
2. Esterbauer H., Gebicki J., Puhl G., Jurgens G. The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radic. Biol. Med. 3:1992;341-390.
3. Ito T., Nakano M., Yamamoto Y., Hiramitsu T., Mizuno Y. Hemoglobin-induced lipid peroxidation in the retina: A possible mechanism for macular degeneration. Arch. Biochem. Biophys. 316:1995;864-872.
4. Welsch C. W. Review of the effects of dietary fat on experimental mammary gland tumorigenesis: role of lipid peroxidation. Free Radic. Biol. Med. 18:1995;757-773.
5. Braughler J. M., Hall E. D. Central nervous system trauma and stroke. Biochemical considerations for oxygen radical formation and lipid peroxidation. Free Radic. Biol. Med. 6:1989;289-301.
6. Fukuzawa K., Seko T., Minami K., Terao J. Dynamics of iron-ascorbate-induced lipid peroxidation in charged and uncharged phospholipid vesicles. Lipids. 28:1993;497-503.
7. Goldstein S., Meyerstein D., Czapski G. The Fenton reagents. Free Radic. Biol. Med. 15:1993;435-445.
8. Minotti G., Aust S. D. Redox cycling of iron and lipid peroxidation. Lipids. 27:1992;219-225.
9. Kuzuya M., Yamada K., Hayashi T., Funkai C., Naito M., Asai K., Kuzuya F. Role of lipoprotein-copper complex in copper catalyzed peroxidation of low-density lipoprotein. Biochim. Biophys. Acta. 1123:1992;334-341.
10. Scaccini C., Jialal I. LDL modification by activated polymorphonuclear leukocytes: A cellular model of mild oxidative stress. Free Radic. Biol. Med. 16:1994;49-55.
11. Cathcart M. K., McNally A. K., Chisolm G. M. Lipoxygenase-mediated transformation of human low density lipoprotein to an oxidized and cytotoxic complex. J. Lipid Res. 32:1991;63-70.
12. Garner B., Dean R. T., Jessup W. Human macrophage-mediated oxidation of low-density lipoprotein is delayed and independent of superoxide production. Biochem. J. 301:1994;421-428.
13. Yamamoto Y., Niki E., Kamiya Y. Quantitative determination of the oxidation of methyl linoleate and methyl linolenate. Bull. Chem. Soc. Jpn. 55:1982;1548-1550.
14. Yamamoto Y., Haga S., Niki E., Kamiya Y. Oxidation of methyl linoleate in aqueous dispersion. Bull. Chem. Soc. Jpn. 57:1984;1260-1264.
15. Niki E., Saito M., Yoshikawa Y., Yamamoto Y., Kamiya Y. Inhibition of oxidation of soybean phosphatidylcholine and methyl linoleate in aqueous dispersions by uric acid. Bull. Chem. Soc. Jpn. 59:1986;471-477.
16. Barclay L. R. C., Locke S. J., MacNeil J. M., VanKessel J. Autoxidation of micelles and model membranes. Quantitative kinetic measurements can be made using either water-soluble or lipid-soluble initiators with water-soluble or lipid-soluble chain-breaking antioxidants. J. Am. Chem. Soc. 106:1984;2479-2481.
17. Barclay L. R. C. Model biomembranes: Quantitative studies of peroxidation, antioxidant action, partitioning, and oxidative stress. Can. J. Chem. 71:1993;1-16.
18. Winterle J. S., Mill T. Free-radical dynamics in organized lipid bilayers. J. Am. Chem. Soc. 102:1980;6336-6338.
19. Miki M., Tamai H., Mino M., Yamamoto Y., Niki E. Free-radical chain oxidation of rat blood cells by molecular oxygen and its inhibition by α -tocopherol. Arch. Biochem. Biophys. 258:1987;373-380.
20. Matsura T., Yamada K., Kawasaki T. Difference in antioxidant activity between reduced coenzyme Q9 and reduced coenzyme Q10 in the cell: Studies with isolated rat and guinea pig hepatocytes treated with a water-soluble radical initiator. Biochim. Biophys. Acta. 1123:1992;309-315.
21. Ohlsson A. B., Berglund T., Komlos P., Rydstrom J. Plant defense metabolism is increased by the free radical-generating compound AAPH. Free Radic. Biol. Med. 19:1995;319-327.
22. Frei B., England L., Ames B. N. Ascorbate is an outstanding antioxidant in human blood plasma. Proc. Natl. Acad. Sci. USA. 86:1989;6377-6381.
23. Stocker R., Bowry W., Frei B. Ubiquinol protects human low density lipoprotein more efficiently against lipid peroxidation than does α -tocopherol. Proc. Natl. Acad. Sci. USA. 88:1991;1646-1650.
24. Thomas M. J., Thornburg T., Manning J., Hooper K., Rudell L. L. Fatty acid composition of low-density lipoprotein influences its susceptibility to autoxidation. Biochemistry. 33:1994;1828-1834.
25. Tamai H., Levin S., Gaginella T. S. Induction of colitis in rats by 2,2′-azobis(2-amidinopropane)hydrochloride. Inflammation. 16:1992;69-81.
26. Chan H. W.-S., Levett G., Matthew J. A. Thermal isomerisation of methyl linoleate hydroperoxides: Evidence of molecular oxygen as a leaving group in a radical rearrangement. J. Chem. Soc., Chem. Commun. 1978:1978;756-757.
27. Porter N. A., Lehman L. S., Weber B. A., Smith K. J. Unified mechanism for polyunsaturated fatty acid oxidation. Competition of peroxy radical hydrogen atom abstraction, β -scission, and cyclization. J. Am. Chem. Soc. 103:1981;6447-6455.
28. Maillard B., Ingold K. U., Scaiano J. C. Rate constants for the reactions of free radicals with oxygen in solution. J. Am. Chem. Soc. 105:1983;5095-5099.
29. Sykes P. A Guidebook to mechanism in organic chemistry. 6th ed. 1986;66-69 Longman, New York.
30. El-Saadani M., Esterbauer H., El-Sayed M., Goher M., Nassar A. Y., Jurgens G. A spectrophotometric assay for lipid hydroperoxides in serum lipoproteins using a commercially available reagent. J. Lipid Res. 30:1989;627-630.
31. Mortimer G. A new high-temperature free-radical source. J. Org. Chem. 30:1965;1632-1634.
32. McCoy-Messer J., Bateman R. C. Jr. Instability of the ABTS/peroxidase reaction product in biological buffers. BioTechniques. 15:1993;271-273.
33. Adamic K., Ingold K. U., Morton J. R. Electron spin resonance spectrum of oxygen-17 enriched t-alkylperoxyl radicals. J. Am. Chem. Soc. 92:1970;922-923.
34. Melamud E., Silver B. L. σ - φ Polarization parameters for oxygen-17 in organic and inorganic φ radicals. J. Phys. Chem. 77:1973;1896-1899.
35. Barclay L. R. C., Ingold K. U. Autoxidation of a model membrane. A comparison of the autoxidation of egg lecithin phosphatidylcholine in water and in chlorobenzene. J. Am. Chem. Soc. 102:1980;7792-7794.
36. Bordwell F. G., Cheng J.-P. Radical-cationacidities in solution and in the gas phase. J. Am. Chem. Soc. 111:1989;1792-1795.