Molecular mechanisms of SR 4233-induced hepatocyte toxicity under aerobic versus hypoxic conditions

British Journal of Cancer

Volumn 68, Issue 3, 1993, Pages 484-491

  Silva, J M ^a   O'Brien, P J ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMYCIN A1; ASCORBIC ACID; CATALASE; FRUCTOSE; GLUTATHIONE; GLUTATHIONE REDUCTASE; POTASSIUM CYANIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; TIRAPAZAMINE;

ANIMAL CELL; ARTICLE; CELL HYPOXIA; CELL VIABILITY; CYTOTOXICITY; DRUG DETOXIFICATION; DRUG POTENTIATION; ELECTRON SPIN RESONANCE; ENZYME INACTIVATION; LIVER CELL; LIVER TOXICITY; MALE; MITOCHONDRIAL RESPIRATION; NONHUMAN; PRIORITY JOURNAL; RAT; TUMOR CELL;

ANIMAL; ANTINEOPLASTIC AGENTS; CELL MEMBRANE; ELECTRON SPIN RESONANCE SPECTROSCOPY; GLUTATHIONE; LIVER; MALE; MICROSOMES, LIVER; MITOCHONDRIA; OXYGEN; OXYGEN CONSUMPTION; RATS; RATS, SPRAGUE-DAWLEY; TRIAZINES;

EID: 0027248915     PISSN: 00070920     EISSN: 15321827     Source Type: Journal    
DOI: 10.1038/bjc.1993.374     Document Type: Article

References (34)

1. BABSON, J. & REED, D. (1978). Inactivation of glutathione reductase by 2-chloroethylnitrosourea-derived isocyanates. Biochem. Res. Commun., 83, 754–762.
2. BAKER, M.A., ZEMAN, E M., HIRST, V.K. & BROWN, J.M. (1988). Metabolism of SR 4233 by Chinese hamster ovary cells: basis of selective hypoxic cytotoxicity. Cancer Res., 48, 5947–5952.
3. BRADFORD, M.M. (1976). A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein dye binding. Anal. Biochem., 72, 248–256.
4. CAIN, K. & SKILLETER, D.N. (1987). Preparation and use of mitochondria in toxicological research. In Biochemical Toxicology: A Practical Approach., Snell, K. & Mullock, B. (eds). Washington: IRL Press, pp. 217–223.
5. COSTA, A.K., BAKER, M.A., BROWN, J.M. & TRUDELL, J.R. (1989). In vitro hepatotoxicity of SR 4233 (3-amino-1,2,4-benzotriazine-dioxide), a hypoxic cytotoxin and potential antitumor agent. Cancer Res., 49, 925–929.
6. DOUSSIERE, J. & VIGNAIS, P.V. (1992). Diphenylene iodonium as an inhibitor of the NADPH oxidase complex. Eur. J. Biochem., 208, 61–71.
7. ERNSTER, L., LJUNGGREN, M. & DANIELSON, L. (1960). Purification and some properties of a highly dicumarol-sensitive liver diaphorase. Biochem. Biophys. Res. Comm., 2, 88–92.
8. ERNSTER, L., SUKEVITZ, P. & PALADE, G.E. (1962). Enzyme relationships in endoplasmic reticulum of rat liver. J. Cell Biol., 15, 541–562.
9. GORES, G.J., NIEMINEN, A., WRAY, B., HERMAN, B. & LEMASTERS, J. (1989). Intracellular pH during ‘chemical hypoxia’ in cultured rat hepatocytes. Protection by intracellular acidosis against the onset of cell death. J. Clin. Invest., 83, 386–396.
10. ILES, R.A., GRIFFITHS, JR., STEVENS, A., GADIAN, D.G. & PORTEOUS, R. (1980). Effects of fructose on the energy metabolism and acid-base status of the perfused starved rat-liver Biochem. J., 192, 191–202.
11. LADEROUTE, K., WARDMAN, P. & RAUTH, A.M. (1988). Molecular mechanisms for the hypoxic-dependent activation of 3-amino-benzotriazine-1,4-dioxide (SR 4233). Biochem. Pharmacol, 37, 1487–1495.
12. LLOYD, R.V., DULING, D R., RUMYANTSEVA, G.V., MASON, R.P. & BRIDSON, P.K. (1991). Microsomal reduction of 3-amino-1,2,4-benzotriazene 1,4-dioxide to a free radical. Mol. Pharmacol., 40, 440–445.
13. MASON, R.P. (1984). Assay of in situ radicals by electron spin resonance. Methods Enzymol., 105, 416–422.
14. MOLDEUS, P., HOGBERG, H. & ORRENIUS, S. (1978). Isolation and use of liver cells. Methods Enzymol., 52, 60–71.
15. MOULDER, J. & ROCKWELL, S. (1987). Tumour hypoxia: its impact on cancer therapy. In Cancer Metastasis Reviews, Vol. 5, Fidler, I.J. & Poste, G. (eds). Boston: Nijhoff Publishing, pp. 313–341.
16. NETTER, K.J. (1962). Drugs as inhibitors of drug metabolism. In Proceedings of the First International Pharmacology Meeting, vol. 6, B. Unvas (ed.) New York: Macmillan Co., pp. 213–228.
17. O’BRIEN, P.J. (1991). Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact., 80, 1–41.
18. PATEL, J.M., ORTIZ, E., KOLMSTETTER, C. & LEIBMAN, K.C. (1984). Selective inactivation of rat lung and liver microsomal NADPH-cytochrome c reductase by acrolein. Drug Metab. Dispos., 12, 460–463.
19. REED, D.J., BABSON, J R., BRODIE, A.E., ELLIS, W.W. & 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.
20. RILEY, R.J. & WORKMAN, P. (1992). Enzymology of the reduction of the benzotriazine-di-N-oxide hypoxic cell cytotoxin SR 4233 (WIN 59075) by NAD(P)H::(quinone acceptor) oxidoreductase (EC 1.6.99.2) purified from Walker 256 rat tumour cells. Biochem. Pharmacol., 43, 167–174.
21. ROSSI, L., SILVA, J.M., MCGIRR, L.G. & O’BRIEN, P.J. (1989). Nitrofurantoin-mediated oxidative stress in isolated rat hepatocytes. Biochem. Pharmacol., 37, 3109–3117.
22. RUSH, G.F. & ALBERTS, D. (1986). tert-Butyl hydroperoxide metabolism and stimulation of the pentose phosphate pathway in isolated rat hepatocytes. Toxicol. Appl. Pharmacol., 85, 324–331.
23. SEGLEN, P.O. (1974). Autoregulation of glycolysis, respiration, gluconeogenesis and glycogen synthesis in isolated parenchymal rat liver cells under aerobic and anaerobic conditions. Biochim. Biophys. Acta, 338, 317–336.
24. SIES, H. & NOACK, G. (1972). Proton movement accompanying monocarboxylate permeation in hemoglobin free perfused rat liver. FEBS Lett., 22, 193–196.
25. SILVA, J.M. & O’BRIEN, P.J. (1989). Diaziquone-induced cytotoxicity in isolated rat hepatocytes. Cancer Res., 49, 5550–5554.
26. STOCCHI, V., CUCCHIARINI, L., MAGNANI, M., CHIARANTINI, L., PALMA, P. & CRESCENTINI, G. (1984). Simultaneous extraction and reverse-phase high performance liquid chromatography determination of adenine and pyridine nucleotides in human red blood cells. Anal. Biochem., 146, 118–124.
27. WALTON, M.I. & WORKMAN, P. (1988). High-performance liquid chromatography assay for the benzotriazine di-N-oxide (SR 4233) and its reduced metabolites in biological materials. J. Chromatogr., 430, 4429–4437.
28. WALTON, M.I., WOLF, C.R. & WORKMAN, P. (1989). Molecular enzymology of the reductive bioactivation of hypoxic cell cytotoxins. Int. J. Radiat. Oncol. Biol. Phys., 16, 983–986.
29. WALTON, M.I. & WORKMAN, P. (1990). Enzymology of the reductive bioactivation of SR 4233. A novel benzotriazine di-N-oxide hypoxic cell cytotoxin. Biochem. Pharmacol., 39, 1735–1742.
30. WANG, J., BIEDERMANN, K.A. & BROWN, J.M. (1992). Repair of DNA and chromosome breaks in cells exposed to SR 4233 under hypoxia or to ionising radiation. Cancer Res., 52, 4473–4477.
31. WHITE, I.N., CAHILL, A., DAVIS, A. & CARTHEW, P. (1992). Acute lesions in rats caused by 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR 4233) or nitromin: a comparison with rates of reduction in microsomal systems from target organs. Arch. Toxicol., 66, 100–106.
32. WINTERBOURN, C.C. (1981). Cytochrome C reduction by semiquinone radicals can be directly inhibited by superoxide dismutase. Arch. Biochem. Biophys., 209, 159–167.
33. ZEMAN, E.M., BROWN, J.M., LEMMON, M.J., HIRST, B.K. & LEE, W.W. (1986). SR 4233: a new bioreductive agent with high selective toxicity for hypoxic mammalian cells. Int. J. Radiat. Oncol. Biol. Phys., 12, 1239–1942.
34. ZEMAN, E.M., BAKER, M.A., LEMMON, M.J., PEARSON, C.I., ADAMS, J.A., BROWN, J.M., LEE, W.W. & TRACY, M. (1989). Structure-activity relationships for benzotriazine di-N-oxides. Int. J. Radiat. Biol. Phys., 16, 977–981.