Reduction of phenoxyl radicals of the antitumour agent etoposide (VP-16) by glutathione and protein sulfhydryls in human leukaemia cells: Implications for cytotoxicity

Toxicology in Vitro

Volumn 10, Issue 1, 1996, Pages 59-68

  Yalowich, J C ^b,c,e   Tyurina, Y Y ^a,d   Tyurin, V A ^a,d   Allan, W P ^b   Kagan, V E ^a,c,e  

^a Dept of Environ and Occup Health ^*  (United States)

^b UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF PITTSBURGH CANCER INSTITUTE   (United States)

^d SECHENOV INSTITUTE OF EVOLUTIONARY PHYSIOLOGY AND BIOCHEMISTRY   (Russian Federation)

^e UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETOPOSIDE; FREE RADICAL; GLUTATHIONE; THIOL DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL FREE SYSTEM; CONTROLLED STUDY; CYTOTOXICITY; DNA DAMAGE; HUMAN; HUMAN CELL; LEUKEMIA CELL;

EID: 0029868988     PISSN: 08872333     EISSN: None     Source Type: Journal    
DOI: 10.1016/0887-2333(95)00106-9     Document Type: Article

References (45)

1. Asmus K. D. (1990) Sulfur-centered free radicals. Methods in Enzymology 186, 168-180.
2. Buettner G. R. and Jurkewiscz B. A. (1993) Ascorbate as a marker of oxidative stress: an EPR study. Free Radical Biology and Medicine 14, 49-55.
3. Chibatsu L. S. and Meneghini R. (1993) Metallothionein protects DNA from oxidative damage. Biochemical Journal 291, 193-198.
4. Corbett A. H. and Osheroff N. (1993) When good enzymes go bad: conversion of topoisomerase II to a cellular toxin by antineoplastic drugs. Chemical Research in Toxicology 6, 585-597.
5. Ellman G. L. (1959) Tissue sulfhydryl groups. Archives of Biochemistry and Biophysics 82, 70-77.
6. Freshney R. J. (1987) Culture of Animal Cells. A Manual of Basic Techniques. 397 pp. Wiley-Liss, New York.
7. Gantchev T. G., van Lier J. E., Stoyanovsky D. A., Yalowich J. C. and Kagan V. E. (1994) Interactions of phenoxyl radical of antitumor drug, etoposide, with reductants in solution and in cell and nuclear homogenates: electron spin resonance and high-performance liquid chromatography. Methods in Enzymology 234, 643-654.
8. Guyton K. L., Bhan P., Kuppusamy P., Lweier J. L., Trush M. A. and Kensler T. W. (1991) Free radical-derived quinone methide mediates skin tumor promotion by butylated hydroxytoluene hydroperoxide: expanded role for electrophiles in multistage carcinogenesis. Proceedings of the National Academy of Sciences of the U.S.A. 88, 946-950.
9. Guyton K. Z., Dolan P. M., Kensler T. W. (1994) Quinone methide mediates in vitro induction of ornithine decarboxylase by the tumor promoter butylated hydroxytoluene hydroperoxide. Carcinogenesis 15, 817-821.
10. Haim N., Nemec J., Roman J. and Sinha B. (1987) Peroxidase-catalyzed metabolism of etoposide (VP-16-213) and covalent binding of reactive intermediates to cellular macromolecules. Cancer Research 47, 5835-5840.
11. Haim N., Roman J., Nemec J. and Sinha B. K. (1986) Peroxidative free radical formation and O-demethylation of etoposide (VP-16) and teniposide (VM-26). Biochemical and Biophysical Research Communications 135, 215-220.
12. Kagan V. E., Serbinova E. A., Forte J., Scita G. and Packer L. (1992) Recycling of vitamin E in human low density lipoproteins. Journal of Lipid Research 33, 385-397.
13. Kagan V. E., Yalowich J. C., Day B. W., Goldman R. and Stoyanovsky D. A. (1994) Ascorbate in the primary reductant of the phenoxyl radical of etoposide (VP-16) in the presence of thiols both in cell homogenates and in model system. Biochemistry 33, 52561-52567.
14. Kalyanaraman B., Nemec J. and Sinha B. K. (1989) Characterization of free radicals produced during oxidation of Etoposide (VP-16) and its catechol and quinone derivatives. An ESR study. Biochemistry 28, 4839-4346.
15. Kaufmann S. H. and Shaper J. H. (1991) Association of topoisomerase II with hepatoma cell nuclear matrix: the role of intermolecular disulfide bond formation. Experimental Cell Research 192, 511-523.
16. Ketterer N. S., Coles B. and Meyer D. J. (1983) The role of glutathione in detoxication. Environmental Health Perspectives 49, 59-69.
17. Kohn K. W., Erickson L. C., Ewig R. A. G. and Friedman C. A. (1976) Fractionation of DNA from mammalian cells by alkaline elution. Biochemistry 14, 4629-4637.
18. Kosower N. S. and Kosower E. M. (1978) The glutathione status of cells. International Review of Cytology 54, 109-160.
19. Li W., Kagan H. M. and Chou I. N. (1994) Alterations in cytoskeletal organization and homeostasis of cellular thiols in cadmium-resistant cells. Toxicology and Applied Pharmacology 126, 114-123.
20. Li W., Zhao Y. and Chou I. N. (1993) Alterations in cytoskeletal protein sulfhydryls and cellular glutathione in cultured cells exposed to cadmium and nickel ions. Toxicology 77, 65-79.
21. Lin F., Thomas J. P. and Girotti A. W. (1993) Hyperexpression of catalase in selenium-derived murine L1210 cells. Archives of Biochemistry and Biophysics 305, 176-185.
22. Loike J. D. and Horwitz S. B. (1976) Effect of VP-16-213 on the intracellular degradation of DNA in HeLa cells. Biochemistry 15, 5443-5448.
23. Long B. H., Musial S. F. and Brattain M. G. (1984) Comparison of cytotoxicity and DNA breakage activity of congeners of podophyllotoxin including VP-16-213 and VM-26: a quantitative structure-activity relationship. Biochemistry 23, 1183-1188.
24. Mans D. R. A., Lafleur M. V., Westmijze E. J., Horn I. R., Bets D., Schuurhuis G. J., Lankelma J. and Retel J. (1992a) Reactions of glutathione with the catechol, the ortho-quinone and the semi-quinone free radical of etoposide. Consequences for DNA inactivation. Biochemical Pharmacology 43, 1761-1768.
25. Mans D. R., Schuurhuis G. J., Treskes M., Lafleur M. V., Retel J., Pinedo H. M. and Lankelma J. (1992b) Modulation by D,L-buthionine-S,R-sulphoximine of etoposide cytotoxicity on human non-small cell lung, ovarian and breast carcinoma cell lines. European Journal of Cancer 28A, 1447-1452.
26. Meister A. (1994) Glutathione-ascorbic acid antioxidant system in animals. Journal of Biological Chemistry 269, 9397-9400.
27. Mukai K., Nishimura M. and Kikuchi S. (1991) Stopped-flow investigation of the reaction of vitamin C with tocopheroxyl radical in aqueous Triton X-100 micellar solution. Journal of Biological Chemistry 266, 274-278.
28. Orrenius S. and Moldeus P. (1984) The multiple role of glutathione in drug metabolism. Trends in Pharmacological Sciences 5, 432-435.
29. Packer J. E., Slater T. F. and Willson R. L. (1979) Direct observation of a free radical interaction between vitamin E and vitamin C. Nature 278, 737-738.
30. Reed D. J. (1985) Cellular defense mechanisms against reactive metabolites. In Bioactivation of Foreign Compounds. Edited by M. W. Anders, pp. 71-108. Academic Press, New York.
31. Ritke M. K., Allan W. P., Gunduz N., Fattman C. and Yalowich J. C. (1994a) Reduced phosphorylation of topoisomerase II in etoposide-resistant human leukemia K562 cells. Molecular Pharmacology 46, 58-66.
32. Ritke M. K., Roberts D., Alla W. P., Raymond J., Bergottz V. V. and Yalowich J. C. (1994b) Altered stability of etoposide-induced topoisomerase II-DNA complexes in resistant human leukemia K562 cells. British Journal of Cancer 69, 687-697.
33. 2+-ATPaSe in skeletal muscle sarcoplasmic reticulum membranes. Archives of Biochemistry and Biophysics 321, 140-152.
34. Sato M. and Bremner I. (1993) Oxygen free radicals and metallothionein. Free Radical Biology and Medicine 14, 325-337.
35. Scarpa M., Rigo A., Maiorino M., Ursini F. and Gregolim C. (1984) Formation of alpha-tocopherol radical and recycling of alpha-tocopherol by ascorbate during peroxidation of phosphatidylcholine liposomes. Biochimica et Biophysica Acta 801, 215-219.
36. Schwarz M. A., Lazo J. S., Yalowich J. C., Reynolds I., Kagan V. E., Tyurin V. A., Kim Y. M., Watkins S. and Pitt B. (1994) Cytoplasmic metallothionein overexpression protects NIH 3T3 cells from tert-butyl hydroperoxide toxicity. Journal of Biological Chemistry 269, 15238-15243.
37. Sinha B. K., Antholine W. M., Kalyanaraman B. and Eliot H. M. (1990) Copper ion-dependent oxyradical mediated DNA damage from dihydroxy derivative of etoposide. Biochimica et Biophysica Acta 1096, 81-83.
38. Sinha B. and Trush M. (1983) Free radical metabolism of VP-16 and inhibition of anthracycline-induced lipid peroxidation. Biochemical Pharmacology 32, 3495-3498.
39. Slevin M. L. (1991) The clinical pharmacology of Etoposide. Cancer 67, 319-329.
40. Tyurina Y. Y., Tyurin V. A., Yalowich J. C., Quinn P. J., Claycamp H. G., Schor N., Pitt B. R. and Kagan V. E. (1995) Phenoxyl radical of etoposide (VP-16) can directly oxidize intracellular thiols: protective versus damaging effects of phenolic antioxidants. Toxicology and Applied Pharmacology 131, 277-288.
41. Usui N. and Sinha B. K. (1990) Tyrosinase-induced free radical formation from VP-16-213: relationship to cytotoxicity. Free Radical Research Communications 10, 287-293.
42. Van Maanen J. M. S., De Ruiter C., de Vries J., Kootstra P. R., Gobass F. and Pinedo H. M. (1985) The role of metabolic activation by cytochrome P-450 in covalent binding of VP-16-213 to rat liver and HeLa cell microsomal proteins. European Journal of Clinical Oncology 21, 1099-1106.
43. Van Maanen J. M. S., Retel J., de Vries J. and Pinedo H. M. (1988) Mechanism of action of antitumor drug etoposide: a review. Journal of the National Cancer Institute 80, 1526-1533.
44. Yalowich J. C., Claycamp H. G., Stoyanovsky D. A., Allan W. P., Gantchev T. G., Day B. W. and Kagan V. E. (1993a) Two faces of the phenolic antitumor drug Etoposide (VP-16): free radical enhancement and protection against free radical-induced damage. Free Radical Biology and Medicine 15, 493.
45. Yalowich J. C., Stoyanovsky D. A., Allan W. P., Day B. W. and Kagan V. E. (1993b) Potentiation of etoposide (VP-16)-induced activity in the presence of the free radical initiator, 2,2′-azobis(2,4-dimethyl-valeronitrile), in human leukemia K562 cells. Proceedings of the American Association for Cancer Research 34, 1797.