Biotransformation and membrane transport in nephrotoxicity

Critical Reviews in Toxicology

Volumn 26, Issue 3, 1996, Pages 309-334

  Dekant, Wolfgang ^a   Vamvakas, Spiros ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

bioactivation; nephrotoxicity; organ specificity; renal transport

Indexed keywords

ALPHA 2 GLOBULIN; AMINOGLYCOSIDE ANTIBIOTIC AGENT; AMINOPHENOL DERIVATIVE; ANTIINFECTIVE AGENT; BETA LACTAM ANTIBIOTIC; CADMIUM; CEFALEXIN; CEFALOGLYCIN; CEFALORIDINE; CEFALOTIN; CEFTAZIDIME; CEPHALOSPORIN DERIVATIVE; CHLOROFORM; GAMMA GLUTAMYLTRANSFERASE; GENTAMICIN; GLUTATHIONE; HYDROQUINONE DERIVATIVE; KANAMYCIN; MERCURY; NEOMYCIN; NETILMICIN; PARACETAMOL; PENICILLIN DERIVATIVE; PHOSPHORIC ACID TRIS(2,3 DIBROMOPROPYL) ESTER; POLYHALO DERIVATIVE; STREPTOMYCIN; TOBRAMYCIN; UNINDEXED DRUG; XENOBIOTIC AGENT;

ARTICLE; BACTERIAL ENDOCARDITIS; CELL MEMBRANE TRANSPORT; DRUG ACCUMULATION; DRUG TRANSFORMATION; DRUG UPTAKE; HUMAN; NEPHROTOXICITY; NONHUMAN; RAT; SEPSIS; TOXICOKINETICS; XENOBIOTIC METABOLISM;

BACTERIA (MICROORGANISMS);

EID: 0029995533     PISSN: 10408444     EISSN: None     Source Type: Journal    
DOI: 10.3109/10408449609012526     Document Type: Article

References (203)

1. Anders, M. W., Metabolism of drugs by the kidney, Kidney Int., 18, 636, 1980.
2. Anders, M. W., Dekant, W., Henschler, D., Oberleithner, H., and Silbernagl, S., Eds., Renal Disposition and Nephrotoxicity of Xenobiotics, Academic Press, San Diego, 1993.
3. Hewitt, W. R., Goldstein, R. S., and Hook, J. B., Toxic responses of the kidney, in Casarett and Doull's Toxicology. The Basic Science of Poisons, Amdur, M. O., Doull, J., and Klaassen, C. D., Eds., Pergamon Press, New York, 1991, 354.
4. Lock, E. A., Mechanism of nephrotoxic action due to organohalogenated compounds, Toxicol. Lett., 46, 93, 1989.
5. Berndt, W. O., The nephrotoxicity of heavy metals, in Renal Disposition and Nephrotoxicity of Xenobiotics, Anders, M. W., Dekant, W., Henschler, D., Oberleithner, H., and Silbernagl, S., Eds., Academic Press, San Diego, 1993, 269.
6. Duggin, G. G., Analgesic induced kidney disease, Aust. J. Pharm. Sci., 6, 44, 1977.
7. Henschler, D. and Dekant, W., Nephrocarcinogenic xenobiotics, Toxicol. Lett., 53, 105, 1990.
8. Brenner, R. M. and Rector, F. C. J., The Kidney, W.B. Saunders, Philadephia, 1981.
9. Ullrich, K. J., Rumrich, G., Gemborys, M. W., and Dekant, W., Renal transport and nephrotoxicity, in Nephrotoxicity - Mechanisms, Early Diagnosis, and Therapeutic Management, Bach, P. H., Gregg, N. J., Wilks, M. F., and Delacruz, L., Eds., Marcel Dekker, New York, 1991, 1.
10. Grantham, J. J., Studies of organic anion and cation transport in isolated segments of the proximal tubule, Kidney Int., 22, 519, 1982.
11. Sokol, P. P. and McKinney, T. D., Mechanism of organic cation transport in rabbit renal basolateral membrane vesicles, Am. J. Physiol., 258, F1599, 1990.
12. McKinney, T. D., Heterogeneity of organic base secretion by proximal tubules, Am. J. Physiol., 243, F404, 1982.
13. Berndt, W. O., Nephrotoxicity of natural products. Mycotoxin-induced nephropathy, in Nephrotoxic Mechanisms of Drugs and Environmental Toxins, Porter, G. A., Ed., Plenum Publishing, New York, 1982, 241.
14. Anderson, M. E., Bridges, R. J., and Meister, A., Direct evidence for inter-organ transport of glutathione and that the non-filtration renal mechanism for glutathione utilization involves γ-glutamyl transpeptidase, Biochem. Biophys. Res. Commun., 96, 848, 1980.
15. Rankin, B. B. and Curthoys, N. P., Evidence for the renal paratubular transport of glutathione, FEBS Lett., 147, 193, 1982.
16. Lash, L. H. and Jones, D. P., Transport of glutathione by renal basal-lateral membrane vesicles, Biochem. Biophys. Res. Commun., 112, 55, 1983.
17. Lash, L. H. and Jones, D. P., Renal glutathione transport. Characteristics of the sodium-dependent system in the basal-lateral membrane, J. Biol. Chem., 259, 14508, 1984.
18. Elfarra, A. A. and Anders, M. W., Renal processing of glutathione conjugates. Role in nephrotoxicity, Biochem. Pharmacol., 33, 3729, 1984.
19. Monks, T. J. and Lau, S. S., Commentary: renal transport processes and glutathione conjugate-mediated nephrotoxicity, Drug Metab. Dispos., 15, 437, 1987.
20. Heuner, A., Schwegler, J. S., and Silbernagl, S., Renal tubular transport of glutathione in rat kidney, Pflügers Arch., 414, 551, 1989.
21. Monks, T. J., Anders, M. W., Dekant, W., Stevens, J. L., Lau, S. S., and van Bladeren, P. J., Glutathione conjugate mediated toxicities, Toxicol. Appl. Pharmacol., 106, 1, 1990.
22. Waalkes, M. P. and Goering, P. L., Metallothionein and other cadmium-binding proteins: recent developments, Chem. Res. Toxicol., 3, 281, 1990.
23. 2u-Globulin nephropathy: review of the cellular and molecular mechanisms involved and their implications for human risk assessment, Environ. Health Perspect., 101, 39, 1993.
24. Squibb, K. S., Pritchard, J. B., and Fowler, B. A., Cadmium-metallothionein nephropathy: relationships between ultrastructural/biochemical alterations and intracellular cadmium binding, J. Pharmacol. Exp. Ther., 229, 311, 1984.
25. Zager, R. A., Gentamicin nephrotoxicity in the setting of acute renal hypoperfusion, Am. J. Physiol., 254, F574, 1989.
26. Sabatini, S., Koqqera, S., Manaligod, J., Arruda, J. A. L., and Kurtzman, N. A., Role of urinary concentrating ability in the generation of toxic papillary necrosis, Kidney Int., 23, 705, 1983.
27. Anders, M. W., Bioactivation mechanisms and hepatocellular damage, in The Liver: Biology and Pathology, 2nd ed., Arias, I. M., Jakoby, W. B., Popper, H., Schachter, D., and Shafritz, D. A., Eds., Raven Press, New York, 1988, 389.
28. Miller, E. C. and Miller, J. A., Searches for ultimate chemical carinogens and their reactions with cellular macromolecules, Cancer, 47, 2327, 1981.
29. Nelson, S. D. and Pearson, P. G., Covalent and noncovalent interactions in acute lethal cell injury caused by chemicals, Annu. Rev. Pharmacol. Toxicol., 30, 169, 1990.
30. Hinson, J. A. and Roberts, D. W., Role of covalent and noncovalent interactions in cell toxicity: effects on proteins, Annu. Rev. Pharmacol Toxicol., 32, 471, 1992.
31. Anders, M. W., Bioactivation of Foreign Compounds, Academic Press, Orlando, FL, 1985.
32. Guengerich, F. P. and Liebler, D. C., Enzymatic activation of chemicals to toxic metabolites, Crit. Rev. Toxicol., 14, 259, 1985.
33. Anders, M. W., Novel biotransformation and bioactivation reactions: carbamoyl glucuronide formation. Drug Metab. Newsl., 19, 1, 1989.
34. Rush, G. F., Smith, J. H., Newton, J. F., and Hook, J. B., Chemically induced nephrotoxicity: role of metabolic activation, Crit. Rev. Toxicol., 13, 99, 1984.
35. Wolf, C. R., Individuality in cytochrome P450 expression and its association with the nephrotoxic and carcinogenic effects of chemicals, IARC Sci. Publ., 115, 281, 1991.
36. Bell, D. R., Bars, R. G., and Elcombe, C. R., Differential tissue-specific expression and induction of cytochrome P450IVA1 and acyl-CoA oxidase, Eur. J. Biochem., 206, 979, 1992.
37. Henderson, C. J. and Wolf, C. R., Evidence that the androgen receptor mediates sexual differentiation of mouse renal cytochrome P450 expression, Biochem. J., 278, 499, 1991.
38. Imaoka, S., Yamazoe, Y., Kato, R., and Funae, Y., Hormonal regulation of rat renal cytochrome P450s by androgen and the pituitary, Arch. Biochem. Biophys., 299, 179, 1992.
39. Schuetz, E. G., Schuetz, J. D., Grogan, W. M., Naray-Fejes-Toth, A., Fejes-Toth, G., Raucy, J., Guzelian, P., Gionela, K., and Watlington, C. O., Expression of cytochrome P450 3A in amphibian, rat, and human kidney, Arch. Biochem. Biophys., 294, 206, 1992.
40. Guengerich, F. P., Kim, D.-H., and Iwasai, M., Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects, Chem. Res. Toxicol., 4, 168, 1991.
41. Hu, J. J., Rhoten, W. B., and Yang, C. S., Mouse renal cytochrome P450IIE1: immunochemical localization, sex-related difference and regulation by testosterone, Biochem. Pharmacol., 40, 2597, 1990.
42. Hong, J. Y., Pan, J., Ning, S. M., and Yang, C. S., Molecular basis for the sex-related difference in renal N-nitrosodimethylamine demethylase in C3H/HeJ mice, Cancer Res., 49, 2973, 1989.
43. Hu, J. J., Lee, M.-J., Vapiwala, M., Reuhl, K., Thomas, P. E., and Yang, C. S., Sex-related differences in mouse renal metabolism and toxicity of acetaminophen, Toxicol. Appl. Pharmacol., 122, 16, 1993.
44. Speerschneider, P. and Dekant, W., Renal tumorigenicity of 1,1-dichloroethene in mice: the role of male specific expression of cytochrome P450 2E1 in the renal bioactivation of 1,1-dichloroethene, Toxicol. Appl. Pharmacol., 130, 48, 1995.
45. Eling, T., Boyd, J., Reed, G., Mason, R., and Sivarajah, K., Xenobiotic metabolism by prostaglandin endoperoxide synthetase, Drug Metab. Rev., 14, 1023, 1983.
46. Krauss, R. S. and Eling, T. E., Arachidonic acid-dependent cooxidation. A potential pathway for the activation of chemical carcinogens in vivo, Biochem. Pharmacol., 33, 3319, 1984.
47. Eling, T. E., Thompson, D. C., Foureman, G. L., and Hughes, M. F., Prostaglandin H synthase and xenobiotic oxidation, Annu. Rev. Pharmacol. Toxicol., 30, 1, 1990.
48. Smith, W. L. and Marnett, L. J., Prostaglandin endoperoxide synthase: structure and catalysis, Biochim. Biophys. Acta, 1083, 1, 1991.
49. Zenser, T. V. and Davis, B. B., Enzyme systems involved in the formation of reactive metabolites in the renal medulla: cooxidation via prostaglandin H synthase, Fundam. Appl. Toxicol., 4, 922, 1984.
50. Smith, W. L. and Bell, T. G., Immunohistochemieal localisation of the prostaglandin-forming cyclooxygenase in renal cortex, Am. J. Physiol., 235, F451, 1978.
51. Mohandas, J., Duggin, G. G., Horvath, J. S., and Tiller, D. J., Metabolic oxidation of acetaminophen (paracetamol) mediated by cytochrome P-450 mixed function oxidase and prostaglandin endoperoxide synthetase in rabbit kidney, Toxicol. Appl. Pharmacol., 61, 252, 1981.
52. Spry, L. A., Zenser, T. V., and Davis, B. B., Bioactivation of xenobiotics by prostaglandin H synthase in the kidney: implications for therapy, Comments Toxicol., 1, 109, 1986.
53. Ziegler, D. M., Microsomal flavin-containing monooxygenase: oxygenation of nucleophilic nitrogen and sulfur compounds, in Enzymic Basis of Detoxification, Jacoby, W. B., Ed., Academic Press, New York, 1980, 201.
54. Hines, R. N., Cashman, J. R., Philpot, R. M., Williams, D. E., and Ziegler, D. M., The mammalian flavin-containing monooxygenases: molecular characterization and regulation of expression, Toxicol. Appl. Pharmacol., 125, 1, 1994.
55. Ziegler, D. M., Bioactivation of xenobiotics by flavin-containing monooxygenases, in Biological Reactive Intermediates, Witmer, C. M., Ed., Raven Press, New York, 1990, 41.
56. Tynes, R. E. and Philpot, R. M., Tissue- and species-dependent expression of multiple forms of mammalian microsomal flavin-containing monooxygenase, Mol. Pharmacol., 31, 569, 1991.
57. Hodgson, E. and Levi, P. E., Species, organ and cellular variation in the flavin-containing monooxygenase, Drug Metab. Dispos., 6, 219, 1988.
58. Sausen, P. J. and Elfarra, A. A., Cysteine conjugate S-oxidase. Characterization of a novel enzymatic activity in rat hepatic and renal microsomes, J. Biol. Chem., 265, 6139, 1990.
59. Sausen, P. J., Duescher, R. J., and Elfarra, A. A., Further characterization and purification of the flavin-dependent S-benzyl-L-cysteine S-oxidase activities of the rat liver and kidney microsomes, Mol. Pharmacol., 43, 388, 1993.
60. Mannervik, B. and Danielson, U. H., Glutathione transferases - structure and catalytic activity, Crit. Rev. Biochem., 23, 283, 1988.
61. Ketterer, B., Meyer, D. J., and Clark, A. G., Soluble glutathione transferase isoenzymes, in Glutathione Conjugation: Mechanisms and Biological Significance, Sies, H. and Ketterer, B., Eds., Academic Press, London, 1988, 73.
62. Hiley, C., Bell, J., Hume, R., and Strange, R., Differential expression of alpha and pi isoenzymes of glutathione S-transferase in the developing human kidney, Biochim. Biophys. Acta, 990, 321, 1989.
63. Mohandas, J., Marshall, J. J., Duggin, G. G., Horvath, J. S., and Tiller, D. J., Differential distribution of glutathione and glutathione-related enzymes in rabbit kidney. Possible implications in analgesic nephropathy, Biochem. Pharmacol., 33, 1801, 1984.
64. Guder, W. G. and Ross, B. D., Enzyme distribution along the nephron, Kidney Int., 26, 101, 1984.
65. Lau, S. S., Jones, T. W., Sioco, R., Hill, B. A., Pinon, R. K., and Monks, T. J., Species differences in renal γ-glutamyl transpeptidase activity do not correlate with susceptibility to 2-bromo-(digluthation-S-yl)-hydroquinone nephrotoxicity, Toxicology, 64, 291, 1990.
66. Elfarra, A. A., Jakobson, I., and Anders, M. W., Mechanism of S-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity, Biochem. Pharmacol., 35, 283, 1986.
67. Lash, L. H., Elfarra, A. A., and Anders, M. W., Renal cysteine conjugate β-lyase: bioactivation of nephrotoxic cysteine S-conjugates in mitochondrial outer membrane, J. Biol. Chem., 261, 5930, 1986.
68. Stevens, J. L. and Jakoby, W. B., Cysteine conjugate β-lyase, Mol. Pharmacol., 23, 761, 1983.
69. Stevens, J. L., Cysteine conjugate β-lyase activities in rat kidney cortex: subcellular localization and relationship to the hepatic enzyme, Biochem. Biophys. Res. Commun., 129, 499, 1985.
70. Dekant, W., Vamvakas, S., Berthold, K., Schmidt, S., Wild, D., and Henschler, D., Bacterial β-lyase mediated cleavage and mutagenicity of cysteine conjugates derived from the nephrocarcinogenic alkenes trichloroethylene, tetrachloroethylene and hexachlorobutadiene, Chem.-Biol. Interact., 60, 31, 1986.
71. MacFarlane, M., Foster, J. R., Gibson, G. G., King, L. J., and Lock, E. A., Cysteine conjugate β-lyase of rat kidney cytosol: characterization, immunocytochemical localization, and correlation with hexachlorobutadiene nephrotoxicity, Toxicol. Appl. Pharmacol., 98, 185, 1989.
72. Lash, L. H. and Tokarz, J. J., Oxidative stress in isolated rat renal proximal and distal tubular cells, Am. J. Physiol., 259, F338, 1990.
73. Lash, L. H. and Anders, M. W., Cytotoxicity of S-(1,2-dichlorovinyl)glutathione and S-(1,2-dichlorovinyl)-L-cysteine in isolated rat kidney cells, J. Biol. Chem., 261, 13076, 1986.
74. Webb, W. W., Elfarra, A. A., Webster, K. D., Thom, R. E., and Anders, M. W., Role for an episulfonium ion in S-(2-chloroethyl)-DL-cysteine-induced cytotoxicity and its reaction with glutathione, Biochemistry, 26, 3017, 1987.
75. Hall, S. H., Bushinsky, D. A., Wish, J. B., Cohen, J. J., and Harrington, J. T., Hospital acquired renal insufficiency: a prospective study, Am. J. Med., 74, 243, 1983.
76. Kahlmeter, G. and Dahlager, J. I., Aminoglycoside toxicity -a review of clinical studies published between 1975 and 1982, J. Antimicrob. Chem., 13, 9, 1984.
77. Goldstein, R. S., Biochemical heterogeneity and site-specific tubular injury, in Toxicology of the Kidney, Hook, J. B. and Goldstein, R. S., Eds., Raven Press, New York, 1993, 201.
78. Sande, M. A. and Mandell, G. L., Antimicrobial agents - the aminoglycosides, in The Pharmacological Basis of Therapeutics, Gilman, A. G., Rall, T. W., Nies, A. S., and Taylor, P., Eds., Pergamon Press, New York, 1991, 1098.
79. Kaloyanides, G. J., Aminoglycoside-induced functional and biochemical defects in the renal cortex, Fundam. Appl. Toxicol., 4, 930, 1984.
80. Humes, H. D. and O'Connor, R. P., Aminoglycoside nephrotoxicity, in Diseases of the Kidney, Schrier, R. W. and Gottschalk, C. W., Eds., Little, Brown, Boston, 1988, 1229.
81. Mingeot-Leclercq, M. P., Brasseur, R., and Schanck, A., Molecular parameters involved in aminoglycoside nephrotoxicity, J. Toxicol. Environ. Health, 44, 263, 1995.
82. Tune, B. M., The nephrotoxicity of cephalosporin antibiotics. Structure-activity relationships, Commun. Toxicol., 1, 145, 1993.
83. Tune, B. M., Relationship between transport and toxicity of cephalosporins in the kidney, J. Infect. Dis., 132, 189, 1975.
84. Williams, P. D., Hithchcock, M. J. M., and Hottendorf, G. H., Effect of cephalosporins on organic ion transport in renal membrane vesicles from rat and rabbit kidney cortex, Res. Commun. Chem. Pathol. Pharmacol., 47, 357, 1985.
85. Tune, B. M. and Hsu, C.-Y., Mechanisms of beta-lactam antibiotic nephrotoxicity, Toxicol. Lett., 53, 81, 1990.
86. Roels, H. A., Lauwerys, R. R., Buchet, J. P., Bernard, A. M., Vos, A., and Oversteyns, M., Health significance of cadmium induced renal dysfunction: a five year follow up, Br. J. Ind. Med., 46, 755, 1989.
87. Matsura, K., Takasugi, M., Kunifuji, Y., Horie, A., and Kuroiwa, A., Morphological effects of cadmium on proximal tubular cells in rats, Biol. Trace Element Res., 31, 171, 1991.
88. Newhook, R., Long, G., Meek, M. E., Liteplo, R. G., Chan, P., Argo, J., and Dormer, W., Cadmium and its compounds: evaluation of risks to health from environmental exposure in Canada, Environ. Carcinogenic Ecotoxicol. Rev., 12, 195, 1994.
89. Lauwerys, R. R., Bernard, A., Roels, H. A., Bachet, J. P., and Vian, C., Characterization of cadmium proteinuria in man and rat, Environ. Health Perspect., 28, 137, 1984.
90. Chubatsu, L. S. and Meneghini, R., Metallothionein protects DNA from oxidative damage, Biochem. J., 291, 193, 1993.
91. 109CdMT, Toxicol. Appl. Pharmacol., 114, 173, 1992.
92. Goyer, R. A., Mechanisms of lead and cadmium nephrotoxicity, Toxicol. Lett., 46, 153, 1989.
93. Alden, C. L., A review of the unique male rat hydrocarbon nephropathy, Toxicol. Pathol., 14, 109, 1986.
94. 2u-globulin in vitro - evaluating structure-activity relationships, Toxicol. Appl. Pharmacol., 107, 228, 1991.
95. 2u-globulin, Toxicol. Appl. Pharmacol., 91, 182, 1987.
96. 2u-globulin in 1,4-dichlorobenzene-induced nephrotoxicity, Toxicol. Appl. Pharmacol., 99, 122, 1989.
97. 2u-globulin-xenobiotic conjugates, Toxicol. Appl. Pharmacol., 103, 539, 1990.
98. Olson, M. J., Mancini, M. A., Garg, B. D., and Roy, A. K., Leupeptin-mediated alteration of renal phagolysosomes: similarity to hyaline droplet nephropathy of male rats exposed to unleaded gasoline, Toxicol. Lett., 41, 245, 1988.
99. 2u-globulin in F344 rats during chronic exposure to unleaded gasoline of 2,2,4-trimethylpentane, Toxicol. Appl. Pharmacol., 101, 414, 1989.
100. Bernard, A. M., Roels, H., Cardenas, H., and Lauwerys, R., Assessment of urinary protein I and transferrin as early markers of cadmium nephrotoxicity, Br. J. Ind. Med., 47, 559, 1990.
101. Hard, G. C., and Whysner, J., Risk assessment of d-limonene: an example of male rat-specific renal tumorigens, Crit. Rev. Toxicol., 24, 231, 1994.
102. Tanaka, T., Naganuma, A., and Imura, N., Role of γ-glutamyltranspeptidase in renal uptake and toxicity of inorganic mercury in mice, Toxicology, 60, 187, 1990.
103. Zalups, R. K., Organic anion transport and action of γ-glutamyl transpeptidase in kidney linked mechanistically to renal tubular uptake of inorganic mercury, Toxicol. Appl. Pharmacol., 132, 289, 1995.
104. Zalups, R. K. and Barfuss, D. W., Accumulation and handling of inorganic mercury in the kidney after coadministration with glutathione, J. Toxicol. Environ. Health, 44, 385, 1995.
105. Osterberg, R. E., Bierbower, G. W., and Hehir, R. M., Renal and testicular damage following dermal application of the flame retardant tris(2,3-dibromopropyl)phosphate, J. Toxicol. Environ. Health, 3, 979, 1977.
106. Elliot, W. C., Lynn, R. K., Hougton, D. C., Kennish, J. M., and Bennett, W. M., Nephrotoxicity of the flame retardant tris(2,3-dibromopropyl)phosphate, and its metabolites, Toxicol. Appl. Pharmacol., 63, 179, 1982.
107. Söderlund, E. J., Gordon, W. P., Nelson, S. D., Omichinski, J. G., and Dybing, E., Metabolism in vitro of tris(2,3-dibromopropyl)-phosphate: oxidative debromination and bis(2,3-dibromopropyl)phosphate formation as correlates of mutagenicity and covalent protein binding, Biochem. Pharmacol., 33, 4017, 1984.
108. Lynn, R. K., Garvie-Gould, C., Wong, K., and Kennish, J. M., Metabolism, distribution, and excretion of the flame retardant tris(2,3-dibromopropyl)-phosphate (Tris-BP) in the rat: identification of mutagenic and nephrotoxic metabolites, Toxicol. Appl. Pharmacol., 63, 105, 1982.
109. Inskeep, P. B. and Guengerich, F. P., Glutathione-mediated binding of dibromoalkanes to DNA: specificity of rat glutathione-S-transferases and dibromoalkane structure, Carcinogenesis, 5, 805, 1984.
110. Simula, T. P., Glancey, M. J., Söderlund, E. J., Dybing, E., and Wolf, C. R., Increased mutagenicity of 1,2-dibromo-3-chloropropane and tris(2,3-dibromopropyl)phosphate in Salmonella TA100 expressing human glutathione S-transferases, Carcinogenesis, 14, 2303, 1993.
111. Pearson, P. G., Omichinski, J. G., Holme, J. A., McClanahan, R. H., Brunborg, G., Soderlund, E. J., Dybing, E., and Nelson, S. D., Metabolic activation of tris(2,3-dibromopropyl)phosphate to reactive intermediates. II. Covalent binding, reactive metabolite formation, and differential metabolite-specific DNA damage in vivo, Toxicol. Appl. Pharmacol., 118, 186, 1993.
112. Söderlund, E. J., Brunborg, G., Dybing, E., Trygg, B., Nelson, S. D., and Holme, J. A., Organ-specific DNA damage of tris(2,3-dibromopropyl)-phosphate and its diester metabolite in the rat, Chem.-Biol. Interact., 82, 195, 1992.
113. Reichert, D., Ewald, D., and Henschler, D., Generation and inhalation toxicity of dichloroacetylene, Food Cosmet. Toxicol., 13, 511, 1975.
114. Potter, C. L., Gandolfi, A. J., Nagle, R., and Clayton, J. W., Effects of inhaled chlorotrifluoroethylene and hexafluoropropene on the rat kidney, Toxicol. Appl. Pharmacol., 59, 431, 1981.
115. Ishmael, J., Pratt, I., and Lock, E. A., Necrosis of the pars recta (S3 segment) of the rat kidney produced by hexachloro-1:3-butadiene, J. Pathol., 138, 99, 1982.
116. NCI, National Cancer Institute, Carcinogenesis bioassay of trichloroethylene, National Toxicology Program Technical Report, p. 311, 1986.
117. NCI, National Cancer Institute, Carcinogenesis bioassay of tetrachloroethylene, National Toxicology Program Technical Report, p. 232, 1986.
118. Kociba, R. J., Keyes, D. G., Jersey, G. C., Ballard, J. J., Dittenber, D. A., Quast, J. F., Wade, L. E., Humiston, C. G., and Schwetz, B. A., Results of a two year chronic toxicity study with hexachlorobutadiene in rats, Am. Ind. Hyg. Assoc. J., 38, 589, 1977.
119. Koob, M. and Dekant, W., Bioactivation of xenobiotics by formation of toxic glutathione conjugates, Chem.-Biol. Interact., 77, 107, 1991.
120. Anders, M. W., Dekant, W., and Vamvakas, S., Glutathione-dependent toxicity, Xenobiotica, 22, 1135, 1992.
121. Wolf, C. R., Berry, P. N., Nash, J. A., Green, T., and Lock, E. A., Role of microsomal and cytosolic glutathione S-transferases in the conjugation of hexachloro-1:3-butadiene and its possible relevance to toxicity, J. Pharmacol. Exp. Ther., 228, 202, 1984.
122. Dekant, W., Vamvakas, S., Henschler, D., and Anders, M. W., Enzymatic conjugation of hexachloro-1,3-butadiene with glutathione: formation of 1-(glutathion-S-yl)-1,2,3,4,4-pentachlorobuta-1,3-diene and 1,4-bis(glutathion-S-yl)-1,2,3,4- tetrachlorobuta-1,3-diene, Drug. Metab. Dispos., 16, 701, 1988.
123. Dekant, W., Martens, G., Vamvakas, S., Metzler, M., and Henschler, D., Bioactivation of tetrachloroethylene - role of glutathione S-transferase-catalyzed conjugation versus cytochrome P-450-dependent phospholipid alkylation, Drug Metab. Dispos., 15, 702, 1987.
124. Vamvakas, S., Herkenhoff, M., Dekant, W., and Henschler, D., Mutagenicity of tetrachloroethylene in the Ames-test - metabolic activation by conjugation with glutathione, J. Biochem. Toxicol., 4, 21, 1989.
125. Koob, M. and Dekant, W., Metabolism of hexafluoropropene - evidence for bioactivation by glutathione conjugate formation in the kidney, Drug. Metab. Dispos., 18, 911, 1990.
126. Kanhai, W., Dekant, W., and Henschler, D., Metabolism of the nephrotoxin dichloroacetylene by glutathione conjugation, Chem. Res. Toxicol., 2, 51, 1989.
127. 14C-dichloroethyne in rats, Xenobiotica, 21, 905, 1991.
128. 35S-(pentachlorobutadienyl)-L-cysteine in renal epithelial cells and mitochondria, Res. Commun. Chem. Pathol. Pharmacol., 66, 461, 1989.
129. Dekant, W., Metzler, M., and Henschler, D., Novel metabolites of trichloroethylene through dechlorination reactions in rats, mice and humans, Biochem. Pharmacol., 33, 2021, 1984.
130. Inoue, M., Okajima, K., and Morino, Y., Hepatorenal cooperation in biotransformation, membrane transport, and elimination of cysteine S-conjugates of xenobiotics, J. Biochem. (Tokyo), 95, 247, 1984.
131. Okajima, K., Inoue, M., Itoh, K., Horiuchi, S., and Morino, Y., Interorgan cooperation in enzymic processing, in Glutathione: Storage, Transport and Turnover in Mammals, Sakamoto, Y., Higashi, T., and Tateishi, N., Eds., Japan Scientific Societies Press, Tokyo, 1983, 129.
132. Vore, M., Canalicular transport: discovery of ATP-dependent mechanisms, Toxicol. Appl. Pharmacol., 118, 2, 1993.
133. Vore, M., Phase III elimination: another two-edged sword, Environ. Health Perspect., 102, 422, 1994.
134. Awasthi, Y. C., Singh, S. V., Ahmad, H., Wronski, L. W., Srivastava, S. K., and Labelle, E. F., ATP dependent primary active transport of xenobiotic-glutathione conjugates by human erxthrocyte membrane, Cell Biochem., 91, 131, 1989.
135. Awasthi, Y. C., The interrelationship between p-glycoprotein and glutathione S-conjugate transporter(s), TIBS, 15, 376, 1990.
136. Inoue, M., Akerboom, T. P., Sies, H., Kinne, R., Thao, T., and Arias, I. M., Biliary transport of glutathione S-conjugate by rat liver canalicular membrane vesicles, J. Biol. Chem., 259, 4998, 1984.
137. Inoue, M., Kinne, R., Tran, T., and Arias, I. M., Glutathione transport across hepatocyte plasma membranes. Analysis using isolated rat-liver sinusoidal-membrane vesicles, Eur. J. Biochem., 138, 491, 1984.
138. Nash, J. A., King, L. J., Lock, E. A., and Green, T., The metabolism and disposition of hexachloro-1:3-butadiene in the rat and its relevance to nephrotoxicity, Toxicol. Appl. Pharmacol., 73, 124, 1984.
139. Gartland, K. P. R., Eason, C. T., Bonner, F. W., and Nicholson, J. K., Effects of biliary cannulation and buthionine sulphoximine pretreatment on the nephrotoxicity of para-aminophenol in the Fisher 334 rat, Arch. Toxicol., 64, 14, 1990.
140. Inoue, M., Kinne, R., Tran, T., Biempica, L., and Arias, I. M., Rat liver canalicular membrane vesicles - isolation and topological characterization, J. Biol. Chem., 258, 5183, 1983.
141. Meister, A., Glutathione metabolism and its selective modification, J. Biol. Chem., 263, 17205, 1988.
142. Dekant, W., Schrenk, D., Vamvakas, S., and Henschler, D., Metabolism of hexachloro-1,3-butadiene in mice: in vivo and in vitro evidence for activation by glutathione conjugation, Xenobiotica, 18, 803, 1988.
143. Duffel, M. W. and Jakoby, W. B., Cysteine S-conjugate N-acetyltransferase from rat kidney microsomes, Mol. Pharmacol., 21, 444, 1982.
144. Green, R. M. and Elce, J. S., Acetylation of S-substituted cysteines by rat liver and kidney microsomal N-acetyltransferase, Biochem. J., 147, 283, 1975.
145. Monks, T. J. and Lau, S. S., Sulphur conjugate-mediated toxicity, Rev. Biochem. Toxicol., 10, 41, 1989.
146. Anderson, M. E., Naganuma, A., and Meister, A., Protection against cisplatin toxicity by administration of glutathione ester, FASEB J., 4, 3251, 1990.
147. Guder, W. G. and Wirthensohn, G., Enzyme distribution and unique biochemical pathways in specific cells along the nephron, in Renal Heterogeneity and Target Cell Toxicity, Bach, P. H. and Lock, E. A., Eds., John Wiley & Sons, Chinchester, 1985, 195.
148. Hughey, R. P., Rankin, B. B., Elce, J. S., and Curthoys, N. P., Specificity of a participate rat renal peptidase and its localization along with other enzymes of mercapturic acid synthesis, Arch. Biochem. Biophys., 186, 211, 1978.
149. Schrenk, D., Dekant, W., and Henschler, D., Metabolism and excretion of S-conjugates derived from hexachlorobutadiene in the isolated perfused rat kidney, Mol. Pharmacol., 34, 407, 1988.
150. Jones, D. P., Moldeus, P., Stead, A. H., Ormstad, K., Joernvall, H., and Orrenius, S., Metabolism of glutathione and a glutathione conjugate by isolated kidney cells, J. Biol. Chem., 254, 2787, 1979.
151. Jones, D. P., Sundby, G.-B., Ormstad, K., and Orrenius, S., Use of isolated kidney cells for study of drug metabolism, Biochem. Pharmacol., 28, 929, 1979.
152. Moldeus, P., Jones, D. P., Ormstad, K., and Orrenius, S., Formation and metabolism of a glutathione-S-conjugate in isolated rat liver and kidney cells, Biochem. Biophys. Res. Commun., 83, 195, 1978.
153. Tsao, B. and Curthoys, N. P., The absolute asymetry of orientation of γ-glutamyltranspeptidase and aminopeptidase on the external surface of the rat renal brush border membrane, J. Biol. Chem., 255, 7708, 1980.
154. Kramer, R. A., Foureman, G., Greene, K. E., and Reed, D. J., Nephrotoxicity of S-(2-chloroethyl)-glutathione in the Fischer rat: evidence for γ-glutamyltranspeptidase-independent uptake by the kidney, J. Pharmacol. Exp. Ther., 242, 741, 1987.
155. Schaeffer, V. H. and Stevens, J. L., Mechanism of transport for toxic cysteine conjugates in rat kidney cortex membrane vesicles, Mol. Pharmacol., 32, 293, 1987.
156. Schaeffer, V. H. and Stevens, J. L., The transport of S-cysteine conjugates in LLC-PK1 cells and its role in toxicity, Mol. Pharmacol., 31, 506, 1987.
157. Lash, L. H. and Anders, M. W., Uptake of nephrotoxic S-conjugates by isolated rat renal proximal tubular cells, J. Pharmacol. Exp. Ther., 248, 531, 1989.
158. Ullrich, K. J. and Rumrich, G., Contraluminal transport systems in the proximal renal tubule involved in secretion of organic anions, Am. J. Physiol, 254, 453, 462, 1988.
159. Ullrich, K. J., Rumrich, G., and Kloess, S., Contraluminal para-aminohippurate (PAH) transport in the proximal tubule of the rat kidney, Pflügers Arch., 413, 134, 1988.
160. Ullrich, K. J., Rumrich, G., and Klöss, S., Contraluminal organic anion and cation transport in the proximal renal tubule. V. Interaction with sulfamoyl- and phenoxy diuretics, and with β-lactam antibiotics, Kidney Int., 36, 78, 1989.
161. Ullrich, K. J., Rumrich, G., Wieland, T., and Dekant, W., Contraluminal para-aminohippurate (PAH) transport in the proximal tubule of the rat kidney, Eur. J. Physiol., 415, 342, 1989.
162. Heuner, A., Dekant, W., Schwegler, J. S., and Silbernagl, S., Localization and capacity of the last step of mercapturic acid biosynthesis and the reabsorption and acetylation of cysteine S-conjugates in the rat kidney, Eur. J. Physiol., 417, 523, 1991.
163. Lau, S. S., Monks, T. J., and Gillette, J. R., Identification of 2-bromohydroquinone as a metabolite of bromobenzene and o-bromophenol: implications for bromobenzene-induced nephrotoxicity, J. Pharmacol. Exp. Ther., 230, 360, 1984.
164. Lau, S. S., Monks, T. J., Greene, K. E., and Gillette, J. R., The role of ortho-bromophenol in the nephrotoxicity of bromobenzene in rats, Toxicol. Appl. Pharmacol., 72, 539, 1984.
165. Monks, T. J., Lau, S. S., Highet, R. J., and Gillette, J. R., Glutathione conjugates of 2-bromohydroquinone are nephrotoxic, Drug Metab. Dispos., 13, 553, 1985.
166. 14C]hydroquinone and the effect of γ-glutamyl transpeptidase inhibition, Toxicol. Appl. Pharmacol., 103, 121, 1990.
167. Lau, S. S., Hill, B. A., Highet, R. J., and Monks, T. J., Sequential oxidation and glutathione addition to 1,4-benzoquinone: correlation of toxicity with increased glutathione substitution, Mol. Pharmacol., 34, 829, 1988.
168. Hill, B. A., Kleiner, H. E., Ryan, E. A., Dulik, D. M., Monks, T. J., and Lau, S. S., Identification of multi-S-substituted conjugates of hydroquinones by HPLC-coulometric electrode array analysis and mass spectroscopy, Chem. Res. Toxicol., 6, 459, 1993.
169. Mertens, J. J., Temmink, J. H., Bladeren, P. J., Jones, T. W., Lo, H. H., Lau, S. S., and Monks, T. J., Inhibition of γ-glutamyl transpeptidase potentiates the nephrotoxicity of glutathione-conjugated chlorohydroquinones, Toxicol. Appl. Pharmacol., 110, 45, 1991.
170. Redegeld, F. A. M., Hofman, G. A., Loo, P. G. F., Koster, A. S., and Noordhoek, J., Nephrotoxicity of glutathione conjugate of menadione (2-methyl-1,4-naphthoquinone) in the isolated perfused rat kidney. Role of metabolism by γ-glutamyltranspeptidase and probenecid-sensitive transport, J. Pharmacol. Exp. Ther., 256, 665, 1991.
171. Hill, B. A., Monks, T. J., and Lau, S. S., The effects of 2,3,5-(triglutathion-S-yl)hydroquinone on renal mitochondrial respiratory function in vivo and in vitro: possible role in cytotoxicity, Toxicol. Appl. Pharmacol., 117, 165, 1992.
172. Gartland, K. P. R., Bonner, F. W., and Nicholson, J. K., Investigations into the biochemical effects of region-specific nephrotoxins, Mol. Pharmacol., 35, 242, 1989.
173. Gartland, K. P. R., Bonner, F. W., Timbrell, J. A., and Nicholson, J. K., Biochemical characterisation of para-aminophenol-induced nephrotoxic lesions in the F334 rat, Arch. Toxicol., 63, 97, 1989.
174. Eckert, K.-G. and Eyer, P., Formation and transport of xenobiotic glutathion-S-conjugates in red cells, Biochem. Pharmacol., 33, 2299, 1986.
175. Eckert, K.-G., Eyer, P., Sonnenbichler, J., and Zetl, I., Activation and detoxication of aminophenols. II. Synthesis and structural elucidation of various thiol addition products of 1,4-benzoquinoneimine and N-acetyl-1,4-benzoquinoneimine, Xenobiotica, 20, 333, 1990.
176. Eckert, K.-G., Eyer, P., Sonnenbichler, J., and Zetl, I., Activation and detoxication of aminophenols. III. Synthesis and structural elucidation of various glutathione addition products of 1,4-benzoquinoneimine, Xenobiotica, 20, 351, 1990.
177. Fowler, L. M., Moore, R. B., Foster, J. R., and Lock, E. A., Nephrotoxicity of 4-aminophenol glutathione conjugate, Hum. Exp. Toxicol., 10, 451, 1991.
178. Klos, C., Koob, M., Kramer, C., and Dekant, W., p-Aminophenol nephrotoxicity: biosynthesis of toxic glutathione conjugates, Toxicol. Appl. Pharmacol., 115, 98, 1992.
179. Kleiner, H. E., Hill, B. A., Monks, T. J., and Lau, S. S., In vivo and in vitro formation of several S-conjugates of hydroquinone, Toxicologist, 12, 1350, 1992.
180. Monks, T. J., Highet, R. J., and Lau, S. S., 2-Bromo-(diglutathion-S-yl)hydroquinone nephrotoxicity: physiological, biochemical, and electrochemical determinants, Mol. Pharmacol., 34, 492, 1988.
181. Monks, T. J. and Lau, S. S., Glutathione, γ-glutamyl transpeptidase, and the mercapturic acid pathway as modulators of 2-bromohydroquinone oxidation, Toxicol. Appl. Pharmacol., 103, 557, 1990.
182. Lau, S. S., McMenamin, M. G., and Monks, T. J., Differential uptake of isomeric 2-bromohydroquinone-glutathione conjugates into kidney slices, Biochem. Biophys. Res. Commun., 152, 223, 1988.
183. Adams, S. P. and Notides, A. C., Metabolism and irreversible binding of diethylstilbestrol in the kidney of the Syrian Golden Hamster, Biochem. Pharmacol., 35, 2171, 1986.
184. Goldstein, R. S., Smith, P. F., Tarloff, J. B., Contardi, L., Rush, G. F., and Hook, J. B., Biochemical mechanisms of cephaloridine nephrotoxicity, Life Sci., 42, 1809, 1988.
185. Smith, J. H., Maita, K., Sleight, S. D., and Hook, J. B., Effect of sex hormone status on chloroform nephrotoxicity and renal mixed function oxidases in mice, Toxicology, 30, 305, 1984.
186. Smith, J. H., Hewitt, W. R., and Hook, J. B., Role of intrarenal biotransformation in chloroform-induced nephrotoxicity in rats, Toxicol. Appl. Pharmacol., 79, 166, 1985.
187. Sausen, P. J. and Elfarra, A. A., Reactivity of cysteine S-conjugate sulfoxides: formation of S-(1-chloro-2-(S-glutathionyl)viny1)-L-cysteine sulfoxide by the reaction of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide with glutathione, Chem. Res. Toxicol., 4, 655, 1991.
188. Lash, L. H., Sausen, P. J., Duescher, A. J., and Elfarra, A. A., Roles of cysteine conjugate β-lyase and S-oxidase in nephrotoxicity: studies with S-(1,2-dichlorovinyl)-L-cysteine and S-(1,2-dichlorovinyl)-L-cysteine sulfoxide, J. Pharmacol. Exp. Ther., 269, 374, 1994.
189. Hashmi, M., Vamvakas, S., and Anders, M. W., Bioactivation mechanism of S-(3-oxopropyl)-N-acetyl-L-cysteine, the mercapturic acid of acrolein, Chem. Res. Toxicol., 5, 360, 1992.
190. Park, S. B., Osterloh, J. D., Vamvakas, S., Hashmi, M., Anders, M. W., and Cashman, J. R., Flavin-containing monooxygenase-dependent stereoselective S-oxygenation and cytotoxicity of cysteine S-conjugates and mercapturates, Chem. Res. Toxicol., 5, 193, 1992.
191. Bach, B. H. and Bridges, J. W., Chemically induced renal papillary necrosis and upper urothelial carcinoma. I, II, Crit. Rev. Toxicol., 15, 217, 1985.
192. Bach, P. H., Detection of chemically induced renal injury: the cascade of degenerative morphological and functional changes that follow the primary nephrotoxic insult and evaluation of these changes by in vitro methods, Toxicol. Lett., 46, 237, 1989.
193. Boyd, J. A. and Eling, T. E., Prostaglandin endoperoxide synthetase-dependent cooxidation of acetaminophen to intermediates which covalently bind in vitro to rabbit renal medullary microsomes, J. Pharmacol. Exp. Ther., 219, 659, 1981.
194. Mohandas, J., Duggin, G. G., Horvath, J. S., and Tiller, D. J., Regional differences in peroxidatic activation of paracetamol (acetaminophen) mediated by cytochrome P-450 mixed function oxidase and prostaglandin endoperoxide synthetase in rabbit kidney, Res. Commun. Chem. Pathol. Pharmacol., 34, 69, 1981.
195. Albano, E., Rundgren, M., Harvison, P. J., Nelson, S. D., and Moldeus, P., Mechanisms of N-acetyl-p-benzoquinone imine cytotoxicity, Mol. Pharmacol., 28, 306, 1985.
196. 2+, J. Biol. Chem., 260, 13035, 1985.
197. Torkelson, T. R., Sadek, S. E., Rowe, V. K., Kodama, I. K., Anderson, H. H., Loquvam, G. S., and Hine, C. H., Toxicological investigation of 1,2-dibromo-3-chloropropane, Toxicol. Appl. Pharmacol., 3, 545, 1961.
198. Jones, A. R., Fakhouri, G., and Gadiel, P., The metabolism of the soil fumigant 1,2-dibromo-3-chloropropane, Experientia, 35, 1432, 1979.
199. Pearson, P. G., Söderlund, E. J., Dybing, E., and Nelson, S. D., Metabolic activation of 1,2-dibromo-3-chloropropane: evidence for the formation of reactive episulfonium ion intermediates, Biochemistry, 29, 4971, 1990.
200. Lag, M., Omichinski, J. G., Söderlund, E. J., Brunborg, G., Holme, J. A., Dahl, J. E., Nelson, S. D., and Dybing, E., Role of P-450 activity and glutathione levels in 1,2-dibromo-3-chloropropane tissue distribution, renal necrosis and in vivo DNA damage, Toxicology, 56, 273, 1989.
201. Lag, M., Söderlund, E. J., Brunborg, G., Dahl, J. E., Holme, J. A., Omichinski, J. G., Nelson, S. D., and Dybing, E., Species differences in testicular necrosis and DNA damage, distribution and metabolism of 1,2-dibromo-3-chloropropane (DBCP), Toxicology, 58, 133, 1989.
202. Holme, J. A., Söderlund, E. J., Brunborg, G., Lag, M., Nelson, S. D., and Dybing, E., DNA damage and cell death induced by 1,2-dibromo-3-chloropropane (DBCP) and structural analogs in monolayer culture of rat hepatocytes: 3-aminobenzamide inhibits the toxicity of DBCP, Cell Biol. Toxicol., 7, 413, 1991.
203. Humphreys, W. G., Kim, D. H., and Guengerich, F. P., Isolation and characterization of N7-guanyl adducts derived from 1,2-dibromo-3-chloropropane, Chem. Res. Toxicol., 4, 445, 1991.