Quinone-Thioether-Mediated Nephrotoxicity

References

• Glutathione Conjugation: Mechanisms and Biological Significance, H. Sies, B. Ketterer. Academic Press, San Diego, California 1988
   Google Scholar
• Glutathione Centennial. Molecular Perspectives and Clinical Implications, N. Taniguchi, T. Higashi, Y. Sakamoto, A. Meister. Academic Press, San Diego, California 1989
   Google Scholar
• Glutathione: Metabolism and Physiological Functions, J. Vina. CRC Press, Boca Raton, FL 1990
   Google Scholar
• Rushmore T. H., Pickett C. B., Lu A. Y. H. Regulation of expression of rat liver glutathione 5-transferases: Xenobiotic and antioxidant induction of the Ya subunit gene. Handbook of Experimental Pharmacology, Vol. 112: Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity, F. C. Kauffman. Springer-Verlag. 1994; 79–107
   Google Scholar
• Monks T. J., Lau S. S. Toxicology of quinone-thioethers. CRC Crit. Rev. Toxicol. 1992; 22: 243–270
   Google Scholar
• Monks T. J., Lau S. S. Glutathione conjugate mediated toxicities. Handbook of Experimental Pharmacology, Vol. 112: Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity, F. C. Kauffman. Springer-Verlag. 1994; 459–509
   Google Scholar
• Monks T. J., Lau S. S. Glutathione conjugation as a mechanism for the transport of reactive metabolites. Conjugation-Dependent Carcinogenicity and Toxicology of Foreign Compounds, M. W. Anders, W. Dekant. Academic Press. 1994; 185–212
   Google Scholar
• Smith M. T., Evans C. G., Thor H., Orrenius S. Quinone-in-duced oxidative injury to cells and tissues. Oxidative Stress, H. Sies. Academic Press, London 1985; 91–113
   Google Scholar
• Jocelyn P. C. Biochemistry of the SH Group. Academic Press, London 1972
   Google Scholar
• Finley K. T. The addition and substitution chemistry of quinones. The Chemistry of the Quinonoid Compounds, Part 2, S. Patai. Wiley and Sons, New York 1974; 877–1144
   Google Scholar
• Nickerson J. W., Falcone G., Strauss G. Studies on quinone-thioethers. I. Mechanism of formation of thiodone. Biochemistry 1962; 2: 537–543
   Web of Science ®Google Scholar
• Ito S., Novellino E., Chioccara F., Misuraca G., Prota G. Co-polymerization of dopa and cysteinyldopa in melanogenesis. in vitro, Experientia 1980; 36: 822–823
   PubMedGoogle Scholar
• Monks T. J., Lau S. S. Glutathione, γ-glutamyl transpeptidase and the mercapturic acid pathway as modulators of 2-bromohydro-quinone oxidation. Toxicol. Appl. Pharmacol. 1980; 103: 557–563
   Google Scholar
• Chung H., Harvey R. G., Armstrong R. N., Jarabak J. Poly-cyclic aromatic hydrocarbon quinones and glutathione thioethers as substrates and inhibitors of the human placental NADP-1 inked 15-hydroxyprostaglandin dehydrogenase. J. Biol. Chem. 1987; 12(262)448–12, 451
   Google Scholar
• van Ommen B., Besten C. Den, Rutten A. C. M., Ploemen J. H. T. M., Voo R. M. E., Muller M., van Bladeren P. J. Active site-directed irreversible inhibition of glutathione S-transferases by the glutathione conjugate of tetrachloro-l,4-benzoquinone. J. Biol. Chem. 1988; 263: 12, 939–12, 942
   Google Scholar
• Buffinton G. D., Ollinger K., Brunmark A., Cadenas E. DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates. Biochem. J. 1989; 257: 561–571
   PubMed Web of Science ®Google Scholar
• Wolff S. P., Spector A. Pro-oxidant activation of ocular reduc-tants. 2. Lens epithelial cell cytotoxicity of a dietary quinone is associated with a stable free radical formed with glutathione in vitro. Exp. Eye Res. 1987; 45: 791–801
   PubMed Web of Science ®Google Scholar
• Eyer P., Kiese M. Biotransformation of 4-dimethylaminophenol: Reaction with glutathione, and some properties of the reaction products. Chem.-Biol. Interact. 1976; 14: 165–178
   PubMed Web of Science ®Google Scholar
• Wong K. S., Dryhurst G. Tryptamine-4,5-dione: Properties and reaction with glutathione. Bioorg. Chem. 1990; 18: 253–264
   Web of Science ®Google Scholar
• Larsson R., Boutin J., Moldeus P. Peroxidase-catalysed metabolic activation of xenobiotics. Metabolism of Xenobiotics, J. W. Gorrod, H. Oelschlager, J. Caldwell. Taylor and Francis, New York 1988; 43–50
   Google Scholar
• Szinicz L. L., Weger N. Effects of 4-dimethylaminophenol in rat kidneys, isolated kidney tubules and hepatocytes. Xenobiotica 1980; 10: 611–620
   PubMed Web of Science ®Google Scholar
• Green C. R., Ham K. N., Tange J. D. Kidney lesions induced in rats by 4-aminophenol. Br. Med. J. 1969; 1: 162–164
   PubMed Web of Science ®Google Scholar
• Newton J. F., Kuo C. -H., Gemborys M. W., Mudge G. H., Hook J. B. Nephrotoxicity of 4-aminophenol, a metabolite of acetaminophen in the F344 rat. Toxicol. Appl. Pharmacol. 1982; 65: 336–344
   PubMed Web of Science ®Google Scholar
• Eckert K. -G., Eyer P., Sonnenbichler J., Zetl I. 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 1990; 20: 333–350
   PubMed Web of Science ®Google Scholar
• Gartland K. P. R., Bonner F. W., Timbrell J. A., Nicholson J. K. Biochemical characterization of 4-aminophenol-induced nephrotoxic lesions in the F344 rat. Arch. Toxicol. 1989; 63: 97–106
   PubMed Web of Science ®Google Scholar
• Fowler L. M., Moore R. D., Foster J. R., Lock E. A. Nephrotoxicity of 4-aminophenol glutathione conjugate. Human Exp. Toxicol. 1991; 10: 451–459
   PubMed Web of Science ®Google Scholar
• Klos C., Koob M., Kramer C., Dekant W. p-Aminophenol nephrotoxicity: Bio-synthesis of toxic glutathione conjugates, Toxicol. Appl. Pharmacol. 1992; 115: 98–106
   PubMed Web of Science ®Google Scholar
• Monks T. J., Lau S. S., Highet R. J., Gillette J. R. Glutathione conjugates of 2-bromohydroquinone are nephrotoxic. Drug Metab. Dispos. 1985; 13: 553–559
   PubMed Web of Science ®Google Scholar
• Monks T. J., Highet R. J., Lau S. S. 2-Bromo-(diglutathion-S-yl)hydroquinone nephrotoxicity: Physiological, biochemical and electrochemical determinants. Mol. Pharmacol. 1988; 34: 492–500
   PubMed Web of Science ®Google Scholar
• Lau S. S., Hill B. A., Highet R. J., Monks T. J. Sequential oxidation and glutathione addition to 1,4-benzoquinone: Correlation of toxicity with increased glutathione substitution. Mol. Pharmacol. 1988; 34: 829–836
   PubMed Web of Science ®Google Scholar
• Lau S. S., McMenamin M. G., Monks T. J. Differential uptake of isomeric-bromohydroquinone conjugates into kidney slices. Biochem. Biophys. Res. Commun. 1988; 152: 230–233
   Google Scholar
• Monks T. J., Highet R. J., Chu P. S., Lau S. S. Synthesis and nephrotoxicity of 6-bromo-2,5-dihydroxythiophenol. Mol. Pharmacol. 1988; 34: 15–22
   PubMed Web of Science ®Google Scholar
• Monks T. J., Jones T. W., Hill B. A., Lau S. S. Nephrotoxicity of 2-bromo-(cystein-S-yl)hydroquinone and 2-bromo-(N:-acetyl-cystein-S-yl)hydroquinone thioether. Toxicol. Appl. Pharmacol. 1991; 111: 279–298
   PubMed Web of Science ®Google Scholar
• Monks T. J., Highet R. J., Lau S. S. Oxidative cyclization, 1,4-benzothiazine form-ation and dimerization of 2-bromo-3-(glutathion-S-yl)hydroquinone. Mol. Pharmacol 1990; 38: 121–127
   PubMed Web of Science ®Google Scholar
• Lunte S. M., Kissinger P. T. Detection and identification of sulfhydryl conjugates of p-benzoquinone in microsomal incubations of benzene and phenol. Chem.-Biol. Interact. 1983; 47: 195–212
   PubMed Web of Science ®Google Scholar
• Tunek A., Piatt K. L., Pryzbylski M., Oesch F. Multi-step metabolic activation of benzene. Effect of superoxide dismutase on covalent binding to microsomal macromolecules, and identification of glutathione conjugates using high pressure liquid chromatography and field desorption mass spectrometry. Chem.-Biol. Interact. 1980; 33: 1–17
   PubMed Web of Science ®Google Scholar
• Hill B. A., Kleiner H. K., Ryan E. A., Dulik D. M., Monks T. J., Lau S. S. In vivo identification of multi 5-substituted conjugates of hydroquinone by HPLC-coulometric electrode array analysis and mass spectroscopy. Chem. Res. Toxicol. 1993; 6: 459–469
   PubMed Web of Science ®Google Scholar
• Nerland D. E., Pierce W. M. Identification of N-acetyl-S-(2,5-dihydroxyphenyl)-.L-cysteine as a urinary metabolite of benzene, phenol, and hydroquinone. Drug Metab. Dispos. 1990; 18: 958–961
   PubMed Web of Science ®Google Scholar
• Kleiner H. E., Monks T. J., Lau S. S. N-acetylation/N-deacetyl-ation as a determinant of 2,3,5-(triglutathion-S-yl)-hydroquinone mediated nephrotoxicity. Toxicologist 1993; 13: 241
   Google Scholar
• Tate S. S. Enzymes of mercapturic acid formation. Enzymatic Basis of Detoxication, W. B. Jakoby. Academic Press, New York 1980; Vol. 2: 95–120
   Google Scholar
• Lau S. S., Jones T. W., Sioco R., Hill B. A., Pinon R. K., Monks T. J. Species differences in renal γ-glutamyl transpeptidase activity do not correlate with susceptibility to 2-bromo-(diglutathion-S-yl)hydroquinone mediated nephrotoxicity. Toxicology 1990; 64: 291–311
   PubMed Web of Science ®Google Scholar
• Kaissling B., Kriz W. Structural analysis of the rabbit kidney. Adv. Anat. Embryol. Cell Biol. 1982; 56: 1–123
   Google Scholar
• National Cancer Institute. Cancer Rates and Risks. NIH Publication No. 85–691 1985; 118–121
   Google Scholar
• National Cancer Institute. Cancer Statistics Review 1989; 1973–1986
   Google Scholar
• Paulson D. E., Perez C. A., Anderson T. Cancer of the kidney and ureter. Cancer: Principles and Practice of Oncology, V. T. DeVita, Jr., S. Hellman, S. A. Rosenberg. Lippincott, Philadelphia 1985; 895–1007
   Google Scholar
• Eker R., Mossige J., Johannessen J. V., Aars H. Hereditary renal adenomas and adenomas and adenocarcinomas in rats. Diagnostic Histopathology 1981; 4: 99–110
   PubMedGoogle Scholar
• Huff J. E., McConnell E. E., Hasemen J. K., et al. Carcinogenesis studies: Results of 398 experiments on 104 chemicals from the U.S. National Toxicology Program. Ann. NY Acad. Sci. 1988; 534: 1–30
   PubMed Web of Science ®Google Scholar
• Chu K. C., Cueto C., Jr., Ward J. M. Factors in the evaluation of 200 National Cancer Institute carcinogen bioassays. J. Toxicol Environ. Health 1981; 8: 251–280
   PubMed Web of Science ®Google Scholar
• Griesemer R. A., Cueto C., Jr. Toward a classification scheme for degrees of experimental evidence or the carcinogenicity of chemicals for animals. Molecular and Cellular Aspects of Carcinogenic Screening Tests, R. Montesano, B. L. Tomatis. IARC Scientific Publication 27, Lyon 1980; 259–281
   Google Scholar
• Chhabra R. S., Huff J. E., Schwetz B. S., Selkirk J. An overview of prechronic and chronic toxicity/carcinogenicity experimental study designs and criteria used by the National Toxicology Program. Environ. Health Perspect, in press
   Web of Science ®Google Scholar
• Haseman J. K., Huff J. E., Zeiger E., McConnell E. E. Comparative results of 327 chemical carcinogenicity studies. Environ. Health Perspect. 1987; 74: 229–235
   PubMed Web of Science ®Google Scholar
• Huff J. E., Eustis S. L., Haseman J. K. Occurrence and relevance of chemically induced benign neoplasma in long-term carcinogenicity studies. Cancer Metastasis Rev. 1989; 8: 1–21
   PubMed Web of Science ®Google Scholar
• Fowler L. M., Moore R. B., Foster J. R., Lock E. A. Nephrotoxicity of 4-aminophenol glutathione conjugate. Human Exp. Toxicol. 1991; 10: 451–459
   PubMed Web of Science ®Google Scholar
• Kari F. W. Toxicology and carcinogenesis studies of hydroquinoine in F344/N rats and B6C3F1 mice (gavage studies). National Toxicology Program Technical Report 366, U.S. Department of Health and Human Services, PHS, NIH 1989
   Google Scholar
• Shibata M. -A., Hirose M., Tanaka H., Asakawa E., Shirai T., Ito N. 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. 1991; 82: 1211–1219
   PubMedGoogle Scholar
• Canales P. L., Kleiner H. E., Monks T. J., Lau S. S. Formation of 8-hydroxydeoxyguanosine by quinol-thioethers,. Toxicologist 1993; 13: 202
   Google Scholar
• Rehwoldt R. Tracking the use of antioxidants through industry surveys. Food Chem. Toxicol. 1986; 24: 1039–1041
   PubMed Web of Science ®Google Scholar
• Clayson D. B., Iverson F., Nera E. A., Lok E. The significance of induced forestomach tumors. Ann. Rev. Toxicol. 1990; 30: 441–446
   PubMed Web of Science ®Google Scholar
• Tsuda H., Fukushima S., Imaida K., Sakata T., Ito N. Modification of carcino-genesis by antioxidants and other compounds. Acta. Pharmacol. Toxicol. 1984; 55: 125–143
   PubMedGoogle Scholar
• Verhagen H., Schilderman P. A. E. L., Kleinjans J. C. S. Butylated hydroxyanisole in perspective. Chem.-Biol. Interact. 1991; 80: 109–134
   PubMed Web of Science ®Google Scholar
• Tajima K., Hashizaki M., Yamamoto K., Mizutani T. Identification and structure characterization of ^-containing metabolites of 3-fm-butyl-4-hydroxyanisole in rat urine and liver microsomes. Drug Metab. Dispos. 1991; 19: 1028–1033
   PubMed Web of Science ®Google Scholar
• Lau S. S., Peters M. M., Meussen E., Rivera M. I., Jones T. W., van Ommen B., van Bladeren P. J., Monks T. J. Nephrotoxicity of 2-tert-butyl-hydroquinone glutathione conjugates,. Toxicolo-gist 1994; 14: 180
   Google Scholar
• Jang J. J., Takahashi M., Hasegawa R., Furukawa F., Toyoda K., Sato H., Miyakawa Y., Hayashi Y. Mammary and renal tumor induction by low doses of adriamycin in Sprague-Dawley rats. Carcinogenesis 1987; 8: 1149–1153
   PubMed Web of Science ®Google Scholar
• Rivera M. I., Jones T. W., Lau S. S., Monks T. J. Early morphological and biochemical changes during 2-Br-(di-glutathion-5-yl)hydroquinone-induced nephrotoxicity. Toxicol. Appl. Pharmacol. 1994; 128: 139–250
   Google Scholar
• Schnellman R. G., Ewell F. P. Q., Sgambati M., Mandel L. J. Mitochondrial toxicity of 2-bromohydroquinone in rabbit renal proximal tubules. Toxicol. Appl. Pharmacol. 1987; 90: 420–426
   PubMed Web of Science ®Google Scholar
• Schnellman R. G., Monks T. J., Mandel L. J., Lau L. J.S.S. 2-Bromohydroquinone-induced toxicity to rabbit renal proximal tubules: the role of biotransformation, glutathione, and covalent binding. Toxicol. Appl. Pharmacol. 1989; 99: 19–27
   PubMed Web of Science ®Google Scholar
• Hill B. A., Monks T. J., Lau S. S. The effects of 2,3,5-(tri-glutathion-5-yl)hydroquinone on renal mitochondrial respiratory function in vivo and in vitro: Possible role in cytotoxicity. Toxicol. Appl. Pharmacol. 1992; 117: 165–171
   PubMed Web of Science ®Google Scholar
• Lau S. S., Monks T. J. The in vivo disposition of 2-bromo[14C] hydroquinone and the effect of γ-glutamyl frans-peptidase inhibition. Toxicol. Appl. Pharmacol. 1990; 103: 121–132
   PubMed Web of Science ®Google Scholar
• Rivera M. I., Jones T. W., Lau S. S., Monks T. J. Early morphological and biochemical changes during 2-Br-(di-glutathion-S-yl)hydroquinone-induced nephrotoxicity,. Toxicologist 1993; 13: 131
   Google Scholar
• Lau S. S., Monks T. J., Gibson N. W. Quinone-thioether induced DNA single-strand breaks in LLC-PK, cells,. Toxicologist 1993; 13: 242
   Google Scholar
• Mertens J. J. W. M., Lau S. S., Monks T. J. Hydroxyl radical mediated cytotoxicity of 2-bromohydroquinone-glutathione conjugates in LLC-PK1 cells,. Toxicologist 1993; 13: 243
   Google Scholar
• Leanderson P., Tagesson C. Cigarette smoke-induced DNA damage in cultured human lung cells: Role of hydroxyl radicals and endonuclease activation. Chem.-Biol. Interact. 1992; 81: 197–208
   PubMed Web of Science ®Google Scholar