In vitro free radical metabolism of phenolphthalein by peroxidases

Drug Metabolism and Disposition

Volumn 25, Issue 4, 1997, Pages 468-480

  Sipe Jr , Herbert J ^b   Corbett, Jean T ^c   Mason, Ronald P ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^b HAMPDEN SYDNEY COLLEGE   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ASCORBIC ACID; FREE RADICAL; GLUTATHIONE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; LACTOPEROXIDASE; LAXATIVE; PEROXIDASE; PHENOLPHTHALEIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; TRIPHENYLMETHANE DERIVATIVE;

ARTICLE; DRUG METABOLISM; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; OXYGEN CONSUMPTION; OXYGEN ELECTRODE; PRIORITY JOURNAL;

CATHARTICS; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; GLUTATHIONE; HORSERADISH PEROXIDASE; NAD; OXYGEN; PHENOLPHTHALEIN; PHENOLPHTHALEINS;

EID: 0343471415     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (50)

1. G. K. McEvoy: Cathartics and laxatives. In "AHFS Drug Information 95" (G. K. McEvoy, ed.) pp. 1986-1995. American Hospital Formulary Service (AHFS), American Society of Health System Pharmacists, Bethesda, MD, 1995.
2. American Medical Association: Laxatives and cathartics. In "AMA Drug Evaluations," 5th ed. pp. 1295-1309. American Medical Association, Chicago, IL, 1983.
3. American Society of Hospital Pharmacists: Diphenylmethane Laxatives. In "Drug Information 88," pp. 1628-1630. Am. Society of Hospital Pharmacists, Bethesda, MD, 1988.
4. L. L. Brunton: Agents affecting gastrointestinal water flux and motility, digestants, and bile acids. In "Goodman and Gillman's The Pharmacological Basis of Therapeutics," 8th ed. (A. G. Goodman, L. S. Goodman, and A. Gilman, eds.), pp. 914-924. MacMillan, New York, 1990.
5. J. K. Dunnick and J. R. Hailey: Phenolphthalein exposure causes multiple carcinogenic effects in experimental model systems. Cancer Res. 56, 4922-4926 (1996).
6. 1 mice. Fundam. Appl. Toxicol. 18, 48-58 (1992).
7. K. L. Witt, D. K. Gulati, P. Kaur, and M. D. Shelby: Phenolphthalein: induction of micronucleated erythrocytes in mice. Mutation Res. 341, 151-160 (1995).
8. R. B. Sund: Aspects of the pharmacology of diphenylmethane laxatives (bisacodyl, oxyphenisatin, and phenolphthalein derivatives). Nor. Pharm. Acta 45, 125-162 (1983).
9. F. Capasso, N. Mascolo, G. Autore, and M. R. Duraccio: Suppression of laxative action of phenolphthalein by orally-administered indomethacin or aspirin. J. Pharm. Pharmacol. 36, 132-133 (1984).
10. P. Millburn, R. L. Smith, and R. T. Williams: Biliary excretion of foreign compounds. Biochem. J. 105, 1275-1281 (1967).
11. J. H. Gustafson and L. Z. Benet: Biliary excretion kinetics of phenolphthalein glucuronide after intravenous and retrograde biliary administration. J. Pharm. Pharmacol. 26, 937-944 (1974).
12. Z. Gregus, J. B. Watkins, T. N. Thompson, and C. D. Klaassen: Depletion of hepatic uridine diphosphoglucuronic acid decreases the biliary excretion of drugs. J. Pharmacol. Exp. Ther. 225, 256-262 (1983).
13. C. R. Short, M. D. Maines, and B. A. Westfall: Postnatal development of drug-metabolizing enzyme activity in liver and extrahepatic tissues of swine. Biol. Neonate, 21, 54-68 (1972).
14. H. M. Mehendale: Assessment of hepatobiliary function with phenolphthalein and phenolphthalein glucuronide. Clin. Chem. Enzyme Comm. 2, 195-204 (1990).
15. R. J. Parker, P. C. Hirom, and P. Millburn: Enterohepatic recycling of phenolphthalein, morphine, lysergic acid diethylamide (LSD) and diphenylacetic acid in the rat: hydrolysis of glucuronic acid conjugates in the gut lumen. Xenobiotica, 10, 689-703 (1980).
16. T. Shiga and K. Imaizumi: Generation of phenoxy radicals by methemoglobin-hydrogen peroxide studied by electron paramagnetic resonance. Arch. Biochem. Biophys. 154, 540-547 (1973).
17. T. Shiga and K. Imaizumi: Electron spin resonance study on peroxidase-and oxidase-reactions of horse radish peroxidase and methemoglobin. Arch. Biochem. Biophys. 167, 469-479 (1975).
18. P. D. Josephy, T. E. Eling, and R. P. Mason: Oxidation of p-aminophenol catalyzed by horseradish peroxidase and prostaglandin synthase. Mol. Pharmacol. 23, 461-466 (1983).
19. P. R. West, L. S. Harman, and R. P. Mason: Acetaminophen: enzymatic formation of a transient phenoxyl free radical. Biochem. Pharmacol. 33, 2933-2936 (1984).
20. V. Fischer, L. S. Harman, P. R. West, and R. P. Mason: Direct electron spin resonance detection of free radical intermediates during the peroxidase catalyzed oxidation of phenacetin metabolites. Chem. Biol. Interact., 60, 115-127 (1986).
21. M. Valoti, H. J. Sipe, Jr., G. Sgaragli, and R. P. Mason: Free radical intermediates during peroxidase oxidation of 2-t-butyl-4-methoxyphenol, 2,6-di-t-butyl-4-methylphenol, and related phenol compounds. Arch. Biochem. Biophys. 269, 423-432 (1989).
22. H. J. Sipe, Jr., S. J. Jordan, P. M. Hanna, and R. P. Mason: The metabolism of 17β-estradiol by lactoperoxidase: a possible source of oxidative stress in breast cancer. Carcinogenesis, 15, 2637-2643 (1994).
23. D. N. R. Rao, W. D. Flitter, and R. P. Mason: The formation of free radical metabolites by mammalian peroxidases. In "Cellular Antioxidant Defense Mechanims" (C. K. Chow, ed.) vol. I, pp. 59-71, CRC Press, Boca Raton, FL, 1988.
24. R. P. Mason: Free radical metabolites of toxic chemicals and drugs as sources of oxidative stress. In "Biological Consequences of Oxidative Stress: Implications for Cardiovascular Disease and Carcinogenesis" (L. Spatz and A. D. Bloom, eds.), pp. 23-49. Oxford University Press, New York, 1992.
25. J. M. McCord and I. Fridovich: Superoxide dismutase: an enzymic function for erythrocuprein (hemocuprein). J. Biol. Chem. 244, 6049-6055 (1969).
26. R. P. Mason: Assay of in situ radicals by electron spin resonance. Methods Enzymol. 105, 416-422 (1984).
27. D. R. Duling: Simulation of multiple isotropic spin-trap ESR spectra. J. Magn. Reson. B, 104, 105-110 (1994).
28. L. S. Harman, D. K. Carver, J. Schreiber, and R. P. Mason: One-and two-electron oxidation of reduced glutathione by peroxidases. J. Biol. Chem. 261, 1642-1648 (1986).
29. C. Mottley, K. Toy, and R. P. Mason: Oxidation of thiol drugs and biochemicals by the lactoperoxidase/hydrogen peroxide system. Mol. Pharmacol. 31, 417-421 (1987).
30. G. R. Buettner and R. P. Mason: Spin-trapping methods for detecting Superoxide and hydroxyl free radicals in vitro and in vivo. Methods Enzymol. 186, 127-133 (1990).
31. A. S. W. Li, K. B. Cummings, H. P. Roethling, G. R. Buettner, and C. F. Chignell: A spin-trapping database implemented on the IBM PC/AT. J. Magn. Reson. 79, 140-142 (1988).
32. L. A. Marquez and H. B. Dunford: Transient and steady-state kinetics of the oxidation of scopoletin by horseradish peroxidase compounds I, II, and III in the presence of NADH. Eur. J. Biochem. 233, 364-371 (1995).
33. E. Finkelstein, G. M. Rosen, and E. J. Rauckman: Spin trapping. kinetics of the reaction of superoxide and hydroxyl radicals with nitrones. J. Am. Chem. Soc. 102, 4994-4999 (1980).
34. G. P. Laroff, R. W. Fessenden, and R. H. Schuler: The electron spin resonance spectra of radical intermediates in the oxidation of ascorbic acid and related substances. J. Am. Chem. Soc. 94, 9062-9073 (1972).
35. H. S. Mason: Mechanisms of oxygen metabolism. Adv. Enzymol. 19, 79 (1957).
36. T. J. Stone and W. A. Waters: Electron spin resonance spectra of transient aryloxyl and arylamino free radicals. Proc. Chem Soc. (Lond.), 253-254 (1962).
37. T. J. Stone and W. A. Waters: Aryloxy-radicals. Part I. Electron spin resonance spectra of radicals from some substituted monohydric phenols. J. Chem. Soc. 213-218 (1964).
38. M. D. Sevilla, M. Yan, and D. Becker: Thiol peroxyl radical formation from the reaction of cysteine thiyl radical with molecular oxygen: an ESR investigation. Biochem. Biophys. Res. Commun. 155, 405-410 (1988).
39. M. D. Sevilla, M. Yan, D. Becker, and S. Gillich: ESR investigations of the reactions of radiation-produced thiyl and DNA peroxyl radicals: formation of sulfoxyl radicals. Free Radical Res. Commun. 6, 99-102 (1989).
40. A. Nadezhdin and H. B. Dunford: Oxidation of nicotinamide adenine dinucleotide by hydroperoxyl radical: a flash photolysis study. J. Phys. Chem. 83, 1957-1961 (1979).
41. 2 system. Drug Metab. Disp. 19, 184-187 (1991).
42. J. F. Mouret, M. Polverelli, F. Sarrazini, and J. Cadet: Ionic and radical oxidations of DNA by hydrogen peroxide. Chem. Biol. Interact. 77, 187-201 (1991).
43. I. Gimenez-Conti, A. Viaje, J. Chesner, C. Conti, and T. J. Slaga: Induction of short-term markers of tumor promotion by organic peroxides. Carcinogenesis, 12, 563-569 (1991).
44. T. Kensler, K. Guyton, P. Egner, T. McCarthy, S. Lesko, and S. Akman: Role of reactive intermediates in tumor promotion and progression. Prog. Clin. Biol. Res. 391, 103-116 (1995).
45. U. Giri, S. D. Sharma, M. Abdulla, and M. Athar: Evidence that in situ generated reactive oxygen species act as a potent Stage I tumor promoter in mouse skin. Biochem. Biophys. Res. Commun. 209, 698-705 (1995).
46. E. Beubler and H. Juan: PGE-Mediated laxative effect of diphenolic laxatives. Nauyn-Schmiedeberg's Arch. Pharmacol. 305, 241-246 (1978).
47. E. Beubler and H. Juan: Is the effect of diphenolic laxatives mediated via release of prostaglandin E? Experientia 34, 386-387 (1978).
48. F. Capasso, I. E. Tavares, and A. Bennett: The production of arachidonate lipoxygenase products by rat intestine is increased by phenolphthalein. Eur. J. Pharmacol. 106, 419-422 (1985).
49. 2 and other agonists. Eur. J. Pharmacol. 145, 1-5 (1988).
50. C. M. Markey, A. Alward, P. E. Weller, and L. J. Marnett: Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. J. Biol. Chem. 262, 6266-6279 (1987).