The hepatotoxicity of rhein involves impairment of mitochondrial functions

Chemico-Biological Interactions

Volumn 103, Issue 1, 1997, Pages 35-50

  Bironaite, Daiva ^a   Ollinger, Karin ^b  

^a LITHUANIAN ACADEMY OF SCIENCES   (Lithuania)

^b LINKÖPING UNIVERSITY   (Sweden)

Author keywords

Cytoplasmic free Ca2+; Hepatocytes; Lipid peroxidation; Mitochondrial inhibitors; Quinones; Redox cycling

Indexed keywords

2 OXO 4 THIAZOLIDINECARBOXYLIC ACID; BUTHIONINE SULFOXIMINE; CARMUSTINE; DITHIOTHREITOL; FREE RADICAL; GLUTATHIONE; MALONALDEHYDE; N,N' DIPHENYL 1,4 PHENYLENEDIAMINE; NIFEDIPINE; OXYGEN RADICAL; RHEIN;

ANIMAL CELL; ARTICLE; CALCIUM HOMEOSTASIS; CYTOTOXICITY; LIPID PEROXIDATION; LIVER TOXICITY; MALE; MEMBRANE POTENTIAL; MITOCHONDRIAL MEMBRANE; NONHUMAN; OXIDATION REDUCTION REACTION; PATHOLOGY; RAT;

ADENOSINE TRIPHOSPHATE; ANIMALS; ANTHRAQUINONES; ANTIOXIDANTS; CALCIUM; CELL DEATH; CELL MEMBRANE; CELLS, CULTURED; ENZYME INHIBITORS; GLUTATHIONE; HOMEOSTASIS; LIPID PEROXIDATION; LIVER; MALE; MEMBRANE POTENTIALS; MITOCHONDRIA; OXIDANTS; RATS; RATS, WISTAR;

ANIMALIA;

EID: 0031584706     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(96)03747-7     Document Type: Article

References (42)

1. [1] A.G.L. Kay, L.F. Griffiths, G.N. Volans and R. Grahame, Preliminary experience with diacethylrhein in the treatment of osteoarthritis, Curr. Med. Res. Opin., 6 (1990) 548-551.
2. [2] M. Neuman, Clinical, biological and gastric fibroscopic tolerance of a new non-steroidal anti-inflammatory analgetic, diacethylrhein (artrodar), Drugs Exp. Clin. Res., 6 (1980) 53-64.
3. [3] G. Powis, Free radical formation by antitumor quinones, Free Radical Biol. Med., 6 (1989) 63-101.
4. [4] K. Öllinger and A. Brunmark, Effect of hydroxy-substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes, J. Biol. Chem, 266 (1991) 21,496-21,503.
5. [5] P.J. O'Brien, Molecular mechanisms of quinone cytotoxicity, Chem.-Biol. Interact., 80 (1991) 1-41.
6. [6] A.R. Cross and O.T.G. James, Enzymatic mechanisms of superoxide production, Biochim. Biophys. Acta, 1057 (1991) 281-298.
7. [7] N. Cenas, Z. Anusevicius, D. Bironaite, G.I. Bachmanova, A.I. Archakov and K. Öllinger, The electron transfer reactions of NADPH:cytochrome P450 reductase with nonphysiological oxidants, Arch. Biochem. Biophys., 315 (1994) 400-406.
8. [8] D.A. Bironaite, N.K. Cenas and J.J. Kulys, The rotenone-insensitive reduction of quinones and nitrocompounds by mitochondrial NADH:ubiquinone reductase, Biochim. Biophys. Acta, 1060 (1991) 203-209.
9. [9] D.A. Bironaite, N.K. Cenas, Z.J. Anusevicius, A.G. Medentsev, V.K. Akimenko and S.A. Usanov, Fungal quinone pigments as oxidizers and inhibitors of NADH:ubiquinone reductase, Arch. Biochem. Biophys., 297 (1992) 253-257.
10. [10] E.A. Kean, M. Gutmann and T.P. Singer, Studies on respiratory chain-linked nicotinamide adenine dinucleotide dehydrogenase. XXII. Rhein, a competitive inhibitor of the dehydrogenase, J. Biol. Chem., 246 (1971) 2346-2353.
11. [11] G. Bellomo, F. Mirabelli, D. DiMonte et al., Formation and reduction of glutathione-protein disulfides during oxidative stress, Biochem. Pharmacol., 36 (1987) 1313-1320.
12. [12] D.A. Bironaite, N.K. Cenas, J.J. Kulys, A.G. Medentsev and V.K. Akimenko, The inhibition of glutathione reductase by quinones, Zeitschr. Naturforsch., 46c: 9-10 (1991) 966-968.
13. [13] E.A. Kean, M. Gutmann and T.R. Singer, Rhein, a selective inhibitor of the DPNH-Flavin step in mitochondrial electron transport, Biochem. Biophys. Res. Commun., 40 (1970) 1507-1513.
14. [14] A. Floridi, S. Castiglione and C. Bianchi, Sites of inhibition of mitochondrial electron transport by rhein, Biochem. Pharmacol., 38 (1989) 743-751.
15. [15] A. Floridi, S. Castiglione, C. Bianchi and A. Mancini, Effect of rhein on the glucose metabolism of Erlich ascites tumor cells, Biochem. Pharmacol., 40 (1990) 217-222.
16. [16] A. Floridi, F.P. Gentile, T. Bruno, S. Castiglione, M. Zeuli and M. Benassi, Growth inhibition by rhein and lonidamine of human glioma cells in vitro, Anticancer Res., 10 (1990) 1633-1636.
17. [17] A. Floridi, F.P. Gentile, T. Bruno et al., Cytotoxic effects of the association of BCNU with rhein or lonidamine on a liuman glioma cell line, Anticancer Res., 11 (1991) 789-792.
18. [18] F. Iosi, M.T. Santini and W. Malorni, Membrane and cytoskeleton are intracellular targets of rhein in A431 cells, Anticancer Res., 13 (1993) 545-554.
19. [19] H. Pertoft and B. Smedsrod, Separation and characterization of liver cells, in: T.G. Pretlow and T.B. Pretlow (Eds.), Cell Separation, Vol.4, Academic Press, New York, 1986, pp. 1-24.
20. [20] K. Öllinger and U.T. Brunk, Cellular injury induced by oxidative stress is mediated through lysosomal damage, Free Radical Biol. Med., 19 (1995) 565-574.
21. [21] C.G. Honegger, H. Langemann, W. Krenger and A. Kempf, Liquid chromatographic determination of common water-soluble antioxidants in biological samples, J. Chromatogr., 487 (1989) 463-468.
22. [22] O.H. Lowry, N.J. Rosebrough, A.L. Farr and R.J. Randall, Protein measurement with the Folin phenol reagent, J. Biol. Chem., 193 (1951) 265-275.
23. [23] C.R. Hackenbrock, Chemical and physical fixation isolated mitochondria in low-energy and high-energy states, Proc. Natl. Acad. Sci. USA, 61 (1968) 598-605.
24. [24] R.K. Emaus, R. Grunwald and J.J. Lemaster, Rhodamine 123 as a probe of transmembrane potential in isolated rat-liver mitochondria: spectral and metabolic properties, Biochim. Biophys. Acta, 850 (1986) 436-448.
25. [25] K. Abok, B-A. Fredriksson and U. Brunk, An experimental model system for leishmaniasis. An ultrastructural study on cultured macrophages exposed to Leishmania parasites and sodium stibogluconate, APMIS, 96 (1988) 589-595.
26. [26] M. Lindroth, B-A. Fredriksson and P.B. Bell, Cryosputtering - a combined freeze-drying and sputtering methods for high-resolution electron microscopy, J. Microsc., 161 (1991) 229-239.
27. [27] D.J. Worthington and M.A. Rosemeyer, Human glutathione reductase: purification of the crystaline enzyme from erythrocytes, Eur. J. Biochem., 48 (1974) 167-177.
28. [28] W.A. Günzler and L. Flohe, Glutathione peroxidase, in: R.A. Greenwald (Ed.), CRC Handbook of Methods for Oxygen Radical Research, CRC Press, Boca Raton, FL, 1985, pp. 285-290.
29. [29] A. Claiborne, Catalase activity, in: R.A. Greenwald (Ed.), CRC Handbook of Methods for Oxygen Radical Research, CRC Press, Boca Raton, FL, 1985, pp. 283-284.
30. [30] I. Fridovich, Cytochrome c, in: R.A. Greenwald (Ed.), CRC Handbook of Methods for Oxygen Radical Research, CRC Press, Boca Raton, FL, 1985, pp. 213-215.
31. [31] C.C Winterbourn, J.K. French and R.F.C. Claridge, Superoxide dismutase as an inhibitor of reactions of semiquinone radicals, FEBS Lett., 94 (1978) 269-272.
32. [32] L.V. Jonson, M.L. Walsh, B.J. Bockus and L.B. Chen, Monitoring of relative mitochondrial membrane potential in living cells by fluorescence microscopy, J. Cell Biol., 88 (1981) 526-535.
33. [33] H. Kappus, Overview of enzyme systems involved in bioreduction of drugs and in redox cycling, Biochem. Pharmacol., 35 (1986) 1-10.
34. [34] I.L. Sun, F.L. Crane, J.Y. Chou, H. Low and C. Grebing, Transformed liver cells have modified transplasma membrane redox activity which is sensitive to adriamycin, Biochem. Biophys. Res. Commun., 116 (1983) 210-216.
35. [35] F. Mirabelli, A. Salis, V. Marinoni et al., Menadione induced bleb formation in hepatocytes is associated with oxidation of critical thiol groups in actin, Arch. Biochem. Biophys., 270 (1989) 478-488.
36. [36] G. Pollakis, E. Goormaghtigh and J-M. Ruysschaert, Role of the quinone structure in the mitochondrial damage induced by antitumor anthracyclines, FEBS Lett., 155 (1983) 267-272.
37. [37] H.J. Forman and A. Boveris, Superoxide radical and hydrogen peroxide in mitochondria, in: W.A. Pryor (Ed.), Free Radicals in Biology, Vol.5, Academic Press, New York, 1982, pp. 65-90.
38. [38] S. Davis, M.J. Weiss, J.R. Wong, T.J. Lampidis and L.B. Chen, Mitochondrial and plasma membrane potentials cause unusual accumulation and retention of rhodamine 123 by human breast adenocarcinoma derived MCF-7 cells, J. Biol. Chem., 260 (1985) 13844-13850.
39. [39] S. Baumhuter and C. Richter, The hydroperoxide-induced release of mitochondrial calcium occurs via a distinct pathway and leaves mitochondria intact, FEBS Lett., 148 (1982) 271-275.
40. 2+ by liver mitochondria, J. Biol. Chem., 259 (1984) 1279-1287.
41. 2+ concentration, Arch. Biochem. Biophys., 269 (1989) 365-370.
42. [42] H.L. Yin, Gelsolin: calcium-and polyphosphoinositide-regulated actin modulating protein, Bio. Ess., 7 (1990) 176-179.