Identification of Multi-S-Substituted Conjugates of Hydroquinone by HPLC-Coulometric Electrode Array Analysis and Mass Spectroscopy

Chemical Research in Toxicology

Volumn 6, Issue 4, 1993, Pages 459-469

  Hill, Barbara A ^a,b   Kleiner, Heather E ^a   Ryan, Elizabeth A ^c   Dulik, Deanne M ^d   Monks, Terrence J ^a   Lau, Serrine S ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

^c ESA Inc   (United States)

^d GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; CYTOCHROME P450; GLUTATHIONE; HYDROQUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFIDE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; BILE; CHEMICAL CARCINOGENESIS; CONTROLLED STUDY; COULOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KIDNEY TUBULE NECROSIS; LIVER MICROSOME; MALE; MASS SPECTROMETRY; NEPHROTOXICITY; NONHUMAN; OXIDATION REDUCTION POTENTIAL; OXIDATIVE STRESS; RAT; URINE;

ANIMAL; BILE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; ELECTROCHEMISTRY; GLUTATHIONE; HYDROQUINONES; IN VITRO; KIDNEY DISEASES; KIDNEY NEOPLASMS; MALE; MICROSOMES, LIVER; OXIDATION-REDUCTION; RATS; RATS, SPRAGUE-DAWLEY; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTRUM ANALYSIS, MASS; SULFHYDRYL COMPOUNDS; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0027297075     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00034a012     Document Type: Article

References (55)

1. Ishiguro, S., Saugawara, H., Kusama, M., Yano, S., Shimojima, N., and Sugawara, S. (1976) Glass capillary column gas chromatographic analysis of tobacco and cellulose cigarette smoke. I. Acidic fractions. Sci. Pap. Cent. Res. Inst. Jpn. Tob. Salt Public Corp. 118, 207–211.
2. Dean, B. J. (1978) Genetic toxicology of benzene, toluene, xylenes and phenols. Mutat. Res. 47, 75–97.
3. 14C] hydroquinone given orally to Sprague-Dawley rats. Toxicology 33, 9–18.
4. Nerland, D. E., and Pierce, W. M. (1990) Identification of N-acetyl-S-(2,5-dihydroxyphenyl)-L-cysteine as a urinary metabolite of benzene, phenol, and hydroquinone. Drug Metab. Dispos. 18, 958–961.
5. Sawahata, T., and Neal, R. A. (1983) Biotransformation of phenol to hydroquinone and catechol by rat liver microsomes. Mol. Pharmacol. 23, 453–460.
6. Tunek, A., Schelin, C., and Jergil, B. (1979) Microsomal target proteins of metabolically activated aromatic hydrocarbons. Chem.-Biol. Interact. 27, 133–144.
7. Lunte, S. M., and Kissinger, P. T. (1983) Detection and identification of sulfhydryl conjugates of p-benzoquinone in microsomal incubations of benzene and phenol. Chem.-Biol. Interact. 47, 195–212.
8. Kari, F. W. (1989) Toxicology and carcinogenesis studies of hydroquinone. National Toxicology Program; Technical Report Series 366, 1–86.
9. Shibata, M.-A., Hirose, M., Tanaka, H., Asakawa, E., Shirai, T., and Ito, N. (1991) Induction of renal cell tumors in rats and mice, and enhancement of hepatocellular tumor development in mice after long-term hydroquinone treatment. Jpn. J. Cancer Res. 82, 1211–1219.
10. Lau, S.S., Hill, B. A., Highet, R. J., and Monks, T. J. (1988) Sequential oxidation and glutathione addition to 1,4-benzoquinone: Correlation of toxicity with increased glutathione substitution. Mol. Pharmacol. 34, 829–836.
11. Spence, J. T., Cotton, J. W., Underwood, B. J., and Duncan, C. P., Eds. (1983) Elementary Statistics, Prentice-Hall, Englewood Cliffs.
12. Matson, W. R., Langlais, P., Volicer, L., Gamache, P. H., Bird, E., and Mark, K. A. (1984) n-Electrode three-dimensional liquid chromatography with electrochemical detection for determination of neurotransmitters. Clin. Chem. 30, 1477–1488.
13. Matson, W. R., Gamache, P. H., Beal, M. F., and Bird, E. (1987) EC array sensor concepts and data. Life Sci. 41, 905–908.
14. Hinson, J. A., Nelson, S. D., and Mitchell, J. R. (1977) Studies on the microsomal formation of arylating metabolites of acetaminophen and phenacetin. Mol. Pharmacol. 13, 625–633.
15. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. (1951) Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265–275.
16. Monks, T. J., Lau, S. S., Highet, R. J., and Gillette, J. R. (1985) Glutathione conjugates of 2-bromohydroquinone are nephrotoxic. Drug Metab. Dispos. 13, 553–559.
17. 14C]-hydroquinone and the effect of γ-glutamyl transpeptidase inhibition. Toxicol. Appl. Pharmacol. 103, 121–132.
18. Elce, J. S. (1972) Metabolism of a glutathione conjugate of 2-hydroxyoestradiol-17β in the adult male rat. Biochem. J. 126, 067–1071.
19. Weisz, J. (1990) Metabolism of estrogens by target cells; diversification and amplification of hormone action and the catecholestrogen hypothesis. In The New Biology of Steroid Hormones (Hochberg, R. B., and Naftolin, F., Eds.) Serono Symposia, pp 101–112, Raven Press, New York.
20. Tajima, K., Hashizaki, M., Yamamoto, K., and Mizutani, T. (1991) Identification and structure characterization of S-containing metabolites of 3-tert-butyl-4-hydroxyanisole in rat urine and liver microsomes. Drug Metab. Dispos. 19, 1028–1033.
21. Tsuda, H., Fukushima, S., Imaida, K., Sakata, T., and Ito, N., (1984) Modification of carcinogenesis by antioxidants and other compounds, Acta. Pharmacol. Toxicol. 55 (Suppl. 2), 125–143.
22. Szinicz, L. L., and Weger, N. (1980) Effects of 4-dimethylaminophenol in rat kidneys, isolated kidney tubules and hepatocytes. Xenobiotica 10, 611–620.
23. Green, C. R., Ham, K. N., and Tange, J. D. (1969) Kidney lesions induced in rats by 4-aminophenol. Br. Med. J. 1, 162–164.
24. Newton, J. F., Kuo C.-H., Gemborys, M. W., Mudge, G. H., and Hook, J. B. (1982) Nephrotoxicity of 4-aminophenol, a metabolite of acetaminophen in the F344 rat. Toxicol. Appl. Pharmacol. 65, 336–344.
25. Eckert, K.-G., Eyer, P., Sonnenbichler, J., and Zetl, I. (1990) Activation and detoxication of aminophenols. II. Synthesis and structural elucidation of various thiol addition products of 1,4-benzoquinoneimine and N-acetyl-l,4-benzoquinoneimine. Xenobiotica 20, 333–350.
26. Gartland, K. P. R., Bonner, F. W., Timbrell, J. A., and Nicholson, J. K. (1989) Biochemical characterization of 4-aminophenol-induced nephrotoxic lesions in the F344 rat. Arch. Toxicol. 63, 97–106.
27. Fowler, L. M., Moore, R. D., Foster, J. R., and Lock, E. A. (1991) Nephrotoxicity of 4-aminophenol glutathione conjugate. Hum. Exp. Toxicol. 10, 451–459.
28. Klos, C., Koob, M., Kramer, C., and Dekant, W. (1992) p-Aminophenol nephrotoxicity: Bio-synthesis of toxic glutathione conjugates. Toxicol. Appl. Pharmacol. 115, 98–106.
29. Monks, T. J., and Lau, S. S. (1992) Toxicology of quinone-thioethers. CRC Crit. Rev. Toxicol. 22, 243–270.
30. Nickerson, J. W., Falcone, G., and Strauss, G. (1962) Studies on quinone-thioethers. I. Mechanism of formation of thiodone. Biochemistry 2, 537–543.
31. Brown, E. R., Finley, K. T., and Reeves, R.L. (1971). Steric effects of vicinal substituents on redox equilibria in quininoid compounds. J. Org. Chem. 36, 2849–2853.
32. Ito, S., Novellino, E., Chioccara, F., Misuraca, G., and Prota, G. (1980) Co-polymerization of dopa and cysteinyldopa in melanogenesis in vitro. Experientia 36, 822–823.
33. Hansson, C., Rorsman, H., and Rosengren, E. (1980) 5-S-Cysteinyldopa as a substrate for tyrosinase. Acta Derm.-Venereol. 60, 399–402.
34. Wefers, H., and Sies, H. (1983) Hepatic low-level chemiluminescence during redox cycling of menadione and the menadione–glutathione conjugate: Relation to glutathione and NAD (P) H:quinone reductase (DT-diaphorase) activity. Arch. Biochem. Biophys. 224, 568–578.
35. Wilson, I. Wardman, P., Lin, T., and Sartorelli, A. C. (1986) One-electron reduction of 2- and 6-methyl-l,4-naphthoquinone biore-ductive alkylating agents. J. Med. Chem. 29, 1381–1384.
36. Miyata, N., Miyahara, M., and Kamiya, S. (1988) Chemical studies related to the mechanism of action of 3-tert-butyl-4-hydroxyanisole. Proc. 4th Bienn. Meet. Soc. Free Radical Res., 214.
37. Monks, T. J., and Lau, S. S. (1990) Glutathione, γ,-glutamyl transpeptidase and the mercapturic acid pathway as modulators of 2-bromohydroquinone oxidation. Toxicol. Appl. Pharmacol. 103, 557–563.
38. Eckert, K.-G., Eyer, P., Sonnenbichler, J., and Zetl, I. (1990) Activation and detoxication of aminophenols. III. Synthesis and structural elucidation of various glutathione addition products to 1,4-benzoquinone. Xenobiotica 20, 351–361.
39. Chung, H., Harvey, R. G., Armstrong, R. N., and Jarabak, J. (1987) Polycyclic aromatic hydrocarbon quinones and glutathione thioethere as substrates and inhibitors of the human placental NADP-linked 15-hydroxyprostaglandin dehydrogenase. J. Biol. Chem. 262, 12448–12451.
40. van Ommen, B., Den Besten, C., Rutten, A. C. M., Ploemen, J. H. T. M., Voo, R. M. E., Muller, M., and van Bladeren, P. J. (1988) Active site-directed irreversible inhibition of glutathione S-transferases by the glutathione conjugate of tetrachloro-1,4-benzoquinone. J. Biol. Chem. 263, 12939–12942.
41. Buffinton, G. D., Ollinger, K., Brunmark, A., and Cadenas, E. (1989) DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl–quinone conjugates. Biochem. J. 257, 561–571.
42. Monks, T. J., Highet, R. J., and Lau, S. S. (1988) 2-Bromo-(diglutathion-S-yl)hydroquinone nephrotoxicity: Physiological, biochemical and electrochemical determinants. Mol. Pharmacol. 34, 492–500.
43. Wolff, S. P., and Spector, A. (1987) Pro-oxidant activation of ocular reductants. 2. Lens epithelial cell cytotoxicity of a dietary quinone is associated with a stable free radical formed with glutathione in vitro. Exp. Eye Res. 45, 791–801.
44. Eyer, P., and Kiese, M. (1976) Biotransformation of 4-dimethylaminophenol: reaction with glutathione, and some properties of the reaction products. Chem.-Biol. Interact. 14, 165–178.
45. Wong, K. S., and Dryhurst, G. (1990) Tryptamine-4,5-dione: properties and reaction with glutathione. Bioorg. Chem. 18, 253–264.
46. Larsson, R., Boutin, J., and Moldeus, P. (1988) Peroxidase-catalysed metabolic activation of xenobiotica. In Metabolism of Xenobiotics (Gorrod, J. W., Oelschlager, H., and Caldwell, J., Eds.) pp 43–50, Taylor and Francis, New York.
47. Netter, K. J. (1980) Inhibition of oxidative drug metabolism in microsomes. Pharmacol Ther. 10, 515–535.
48. Wilkinson, C. F., Hetnarski, K., and Hicks, L. J. (1974) Substituted imidazoles as inhibitors of microsomal oxidation and insecticide synergists. Pestic. Biochem. Physiol. 4, 299–312.
49. Ortiz de Montellano, P. R., and Mathews, J. M. (1981) Autocatalytic alkylation of the cytochrome P450 prosthetic haem group by 1-aminobenzotriazole. Biochem. J. 195, 761–764.
50. Ziegler, D. M. (1988) Flavin-containing monooxygenases: Catalytic mechanism and substrate specificities. Drug Metab. Rev. 19, 1–32.
51. Klapper, M. H., and Hackett, D. P. (1963) The oxidatic activity of horseradish peroxidase. I. Oxidation of hydro- and naphthohydroquinones. J. Biol. Chem. 238, 3736–3742.
52. Smith, M. T., Yager, J. W., Steinmetz, K. L., and Eastmond, D. A. (1990) Peroxidase-dependent mechanism of benzene's phenolic metabolites and its potential role in benzene toxicity and carcinogenicity. Environ. Health Perspect. 82, 23–29.
53. Kettle, A. J., and Winterbourne, C. C. (1992) Oxidation of hydroquinone by myeloperoxidase. Mechanism of stimulation by benzoquinone. J. Biol. Chem. 267, 8319–8324.
54. Puckett-Vaughn, D. L., Stenken, J. A., Scott, D. O., Lunte, S. M., and Lunte, C. E. (1993) Enzymatic formation and electrochemical characterization of multiply substituted glutathione conjugates of hydroquinone. Life Sci. 53, 1239–1247.
55. Ortiz de Montellano, P. R., David, S. K., Ator, M. A., and Tew, D. (1988) Mechanism-based inactivation of horseradish peroxidase by sodium azide. Formation of meso-azidoprotoporphyrin DC. Biochemistry 27, 5470–5476.