Prooxidant activity and cytotoxic effects of indole-3-acetic acid derivative radicals

Chemical Research in Toxicology

Volumn 17, Issue 10, 2004, Pages 1350-1355

  Tafazoli, Shahrzad ^a   O'Brien, Peter J ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; ASCORBIC ACID; CATION; GLUTATHIONE; HYDROGEN PEROXIDE; INDOLEACETIC ACID DERIVATIVE; PEROXIDASE; PEROXY RADICAL; PRODRUG; RADICAL; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; SKATOLE; TUMOR ANTIGEN;

ANIMAL CELL; ANIMAL TISSUE; ANTIBODY SPECIFICITY; ARTICLE; CONJUGATION; CONTROLLED STUDY; CYTOTOXICITY; DECARBOXYLATION; LIPID PEROXIDATION; LIVER CELL; LIVER MICROSOME; MALE; NONHUMAN; OXIDATION; PH; PROOXIDANT ACTIVITY; RAT; TUMOR CELL;

ANIMALS; ANTIOXIDANTS; ASCORBIC ACID; CATALYSIS; FREE RADICALS; GLUTATHIONE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; HYDROGEN-ION CONCENTRATION; INDOLEACETIC ACIDS; MODELS, CHEMICAL; NAD; OXIDATION-REDUCTION; PEROXIDASE; RATS; RATS, SPRAGUE-DAWLEY;

ANIMALIA;

EID: 6344282628     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx034217t     Document Type: Article

References (21)

1. Folkes, L. K., and Wardman, P. (2001) Oxidative activation of indole-3-acetic acids to cytotoxic species-A potential new role for plant auxins in cancer therapy. Biochem. Pharmacol. 61, 129-136.
2. O'Brien, P. J. (1988) Radical formation during the peroxidase catalyzed metabolism of carcinogens and xenobiotics: the reactivity of these radicals with GSH, DNA, and unsaturated lipid. Free Radical Biol. Med. 4, 169-183.
3. Galati, G., Sabzevari, O., Wilson, J. X., and O'Brien, P. J. (2002) Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics. Toxicology 177, 91-104.
4. Job, D., and Dunford, H. B. (1976) Substituent effect on the oxidation of phenols and aromatic amines by horseradish peroxidase compound I. Eur. J. Biochem. 66, 607-614.
5. 2 system: Possible formation of indole acetate cation radical. Biochem. Biophys, Res. Commun. 93, 967-973.
6. Kobayashi, S., Sugioka, K., Nakano, H., Nakano, M., and Terokubota, S. (1984) Analysis of the stable end-products and intermediates of oxidative decarboxylation of indole-3-acetic acid by horseradish peroxidase. Biochemistry 23, 4589-4597.
7. Candeias, L. P., Wardman, P., and Mason, R. P. (1997) The reaction of oxygen with radicals from oxidation of tryptophan and indole-3-acetic acid. Biophys. Chem. 67, 229-237.
8. Folkes, L. K., Dennis, M. F., Stratford, M. R., Candeias, L. P., and Wardman, P. (1999) Peroxidase-catalyzed effects of indole-3-acetic acid and analogues on lipid membranes, DNA, and mammalian cells in vitro. Biochem. Pharmacol. 57, 375-382.
9. Candeias, L. P., Folkes, L. K., Porssa, M., Parrick, J., and Wardman, P. (1995) Enhancement of lipid peroxidation by indole-3-acetic acid and derivatives: Substituent effects. Free Radical Res. 23, 403-418.
10. Folkes, L. K., Rossiter, S., and Wardman, P. (2002) Reactivity toward thiols and cytotoxicity of 3-methylene-2-oxindoles, cytotoxins from indole-3-acetic acids, on activation by peroxidases. Chem. Res. Toxicol. 15, 877-882.
11. DeMaster, E. G., Redfern, B., Shirota, F. N., and Nagasawa, H. T. (1986) Differential inhibition of rat tissue catalase by cyanamide. Biochem. Pharmacol. 35, 2081-2085.
12. Dallner, G. (1978) Isolation of microsomal subfractions by use of density gradients. Methods Enzymol. 52, 71-82.
13. Joly, J. G., Doyon, C., and Peasant, Y. (1975) Cytochrome P-450 measurement in rat liver homogenate and microsomes. Its use for correction of microsomal losses incurred by differential centrifugation. Drug Metab. Dispos. 3, 577-586.
14. Moldeus, P., Hogberg, J., and Orrenius, S. (1978) Isolation and use of liver cells. Methods Enzymol. 52, 60-71.
15. Smith, M. T., Thor, H., Hartizell, P., and Orrenius, S. (1982) The measurement of lipid peroxidation in isolated hepatocytes. Biochem. Pharmacol. 31, 19-26.
16. Siraki, A. G., Pourahmad, J., Chan, T. S., Khan, S., and O'Brien, P. J. (2002) Endogenous and endobiotic induced reactive oxygen species formation by isolated hepatocytes. Free Radical Biol. Med. 32, 2-10.
17. Reed, D. J., Babson, J. R., Beatty, P. W., Brodie, A. E., Ellis, W. W., and Potter, D. W. (1980) High-performance liquid chromatography analysis of nanomole levels of glutathione, glutathione disulfide, and related thiols and disulfides. Anal. Biochem. 106, 55-62.
18. Galati, G., Tafazoli, S., Sabzevari, O., Chan, T. S., and O'Brien, P. J. (2002) Idiosyncratic NSAID drug induced oxidative stress. Chem.-Biol. Interact. 42, 25-41.
19. Metodiewa, D., de Melo, M. P., Escobar, J. A., Cilento, G., and Dunford, H. B. (1992) Horseradish peroxidase-catalyzed aerobic oxidation and peroxidation of indole-3-acetic acid. I. Optical spectra. Arch. Biochem. Biophys. 296, 27-33.
20. Candeias, L. P., Folkes, L. K., Porssa, M., Parrick, J., and Wardman, P. (1996) Rates of reaction of indoleacetic acids with horseradish peroxidase compound I and their dependence on the redox potentials. Biochemistry 35, 102-108.
21. Subrahmanyam, V. V., and O'Brien, P. J. (1985) Peroxidase catalyzed oxygen activation by arylamine carcinogens and phenol. Chem.-Biol. Interact. 56, 185-199.