Quinone toxicity in DT-diaphorase-efficient and -deficient colon carcinoma cell lines

Biochemical Pharmacology

Volumn 57, Issue 1, 1999, Pages 27-37

  Karczewski, Jurgen M ^a   Peters, Janny G P ^a   Noordhoek, Jan ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

Caco 2; Colon carcinoma cell line; DT diaphorase; Glutathione; Menadione; Oxidative stress

Indexed keywords

1,4 BENZOQUINONE; 1,4 NAPHTHOQUINONE; 2,3 DIMETHOXY 1,4 NAPHTHOQUINONE; DISULFIDE; GLUTATHIONE; MENADIONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

ARTICLE; CANCER CELL CULTURE; COLON CARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; HUMAN; HUMAN CELL; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PRIORITY JOURNAL;

ADENOSINE TRIPHOSPHATE; CELL SURVIVAL; COLONIC NEOPLASMS; DICUMAROL; GLUTATHIONE; GLUTATHIONE DISULFIDE; HUMANS; KINETICS; NAD(P)H DEHYDROGENASE (QUINONE); NAPHTHOQUINONES; NEOPLASM PROTEINS; SULFHYDRYL COMPOUNDS; TUMOR CELLS, CULTURED; VITAMIN K;

EID: 0032896951     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(98)00288-3     Document Type: Article

References (68)

1. Lai G.M., Moscow J.A., Alvarez M.G., Fojo A.T., Bates S.E. Contribution of glutathione and glutathione-dependent enzymes in the reversal of adriamycin resistance in colon carcinoma cell lines. Int J Cancer. 49:1991;688-695.
2. Peters W.H., Roelofs H.M. Biochemical characterization of resistance to mitoxantrone and adriamycin in Caco-2 human colon adenocarcinoma cells A possible role for glutathione S-transferases . Cancer Res. 52:1992;1886-1890.
3. Djuric Z., Corbett T.H., Valeriote F.A., Heilbrun L.K., Baker L.H. Detoxification ability and toxicity of quinones in mouse and human tumor cell lines used for anticancer drug screening. Cancer Chemother Pharmacol. 36:1995;20-26.
4. Alvarez M., Paull K., Monks A., Hose C., Lee J.S., Weinstein J., Grever M., Bates S., Fojo T. Generation of a drug resistance profile by quantitation of mdr-1/P-glycoprotein in the cell lines of the National Cancer Institute Anticancer Drug Screen. J Clin Invest. 95:1995;2205-2214.
5. Siegel D., Gibson N.W., Preusch P.C., Ross D. Metabolism of mitomycin C by DT-diaphorase Role in mitomycin C-induced DNA damage and cytotoxicity in human colon carcinoma cells . Cancer Res. 50:1990;7483-7489.
6. Traver R.D., Horikoshi T., Danenberg K.D., Stadlbauer T.H., Danenberg P.V., Ross D., Gibson N.W. NAD(P)H:quinone oxidoreductase gene expression in human colon carcinoma cells Characterization of a mutation which modulates DT-diaphorase activity and mitomycin sensitivity . Cancer Res. 52:1992;797-802.
7. Joseph P., Xie T., Xu Y., Jaiswal A.K. NAD(P)H:quinone oxidoreductase1 (DT-diaphorase) expression, regulation, and role in cancer . Oncol Res. 6:1994;525-532.
8. O'Brien P. Molecular mechanisms of quinone cytotoxicity. Chem-Biol Interact. 80:1991;1-41.
9. Ross D., Beall H., Traver R.D., Siegel D., Phillips R.M., Gibson N.W. Bioactivation of quinones by DT-diaphorase, molecular, biochemical, and chemical studies. Onco Res. 6:1994;493-500.
10. Thor H., Smith M.T., Hartzell P., Bellomo G., Jewell S.A., Orrenius S. The metabolism of menadione (2-methyl-1,4-naphthoquinone) by isolated hepatocytes. J Biol Chem. 257:1982;12419-12425.
11. Miller M., Rodgers A., Cohen G.M. Mechanisms of toxicity of naphthoquinones to isolated hepatocytes. Biochem Pharmacol. 35:1986;117-1184.
12. Toxopeus C., Holsteijn I., Thuring J.W., Blaauboer B.J., Noordhoek J. Cytotoxicity of menadione and related quinones in freshly isolated hepatocytes Effects on thiol homeostasis and energy charge . Arch Toxicol. 67:1993;674-679.
13. Gant T.W., Ramakrishna Rao D.N., Mason R.P., Cohen G.M. Redox cycling and sulphydryl arylation Their relative importance in the mechanism of quinone cytotoxicity to isolated hepatocytes . Chem-Biol Interact. 65:1988;157-173.
14. Lind C., Hochstein P., Ernster L. DT-diaphorase as a quinone reductase. A cellular control device against semiquinone and superoxide formation. Arch Biochem Biophys. 216:1982;178-185.
15. Akerboom T., Bultmann T., Sies H. Inhibition of biliary taurocholate excretion during menadione metabolism in perfused rat liver. Arch Biochem Biophys. 263:1988;10-18.
16. DiMonte D., Ross D., Bellomo G., Eklöw L., Orrenius S. Alterations in intracellular thiol homeostasis during the metabolism of menadione by isolated rat hepatocytes. Arch Biochem Biophys. 235:1984;334-342.
17. 2+ homeostasis. Arch Biochem Biophys. 235:1984;343-350.
18. Mirabelli F., Salis A., Perotti M., Taddei F., Bellomo G., Orrenius S. Alterations of surface morphology caused by the metabolism of menadione in mammalian cells are associated with the oxidation of critical sulphydryl groups in the cytoskeletal proteins. Biochem Pharmacol. 37:1988;3423-3427.
19. Mirabelli F., Salis A., Marinoni V., Finardi G., Bellomo G., Thor H., Orrenius S. Menadione-induced bleb formation in hepatocytes is associated with the oxidation of thiol groups in actin. Arch Biochem Biophys. 264:1988;261-269.
20. 2+-ATPase activity by menadione metabolism and its restoration by thiols. FEBS Lett. 181:1985;149-153.
21. Cantoni O., Fiorani M., Cattabeni F., Bellomo G. DNA breakage caused by hydrogen peroxide produced by the metabolism of 2-methyl-1,4-naphthoquinone (menadione) does not contribute to the toxicity of the cytotoxic action of the quinone. Biochem Pharmacol. 42:1991;S220-S222.
22. Fischer-Nielsen A., Corcoran G.B., Poulsen H.E., Kamendulis L.M., Loft S. Menadione-induced DNA fragmentation without 8-oxo-2′deoxyguanosine formation in isolated rat hepatocytes. Biochem Pharmacol. 49:1995;1469-1474.
23. Morrison H., Jernström B., Nordenskjöld H., Thor H., Orrenius S. Induction of DNA damage by menadione (2-methyl-1,4-naphthoquinone) in primary cultures of rat hepatocytes. Biochem Pharmacol. 33:1984;1763-1769.
24. Martins E.A.L., Meneghini R. DNA damage and lethal effects of hydrogen peroxide and menadione in Chinese hamster cells Distinct mechanisms are involved . Free Radical Bio Med. 8:1990;433-440.
25. Morgan W.A., Harley J.A., Cohen G.M. Quinone-induced DNA single strand breaks in rat hepatocytes and human chronic myelogenous leukaemic K562 cells. Biochem Pharmacol. 44:1992;215-221.
26. Redegeld F.A.M., Moison R.M.W., Barentsen H.M., Koster A.S., Noordhoek J. Interaction with cellular ATP generating pathways mediates menadione-induced cytotoxicity in isolated rat hepatocytes. Arch Biochem Biophys. 280:1990;130-136.
27. Borenfreund E., Puerner J.A. Toxicity determined in vitro by morphological alterations and neutral red absorption. Toxicol Lett. 24:1985;119-124.
28. Fisher G.R., Gutierrez P.L. Free radical formation and DNA strand breakage during metabolism of diaziquone by NAD(P)H quinone-acceptor oxidoreductase (DT-diaphorase) and NADPH-cytochrome C reductase. Free Radical Bio Med. 10:1991;359-370.
29. Cotgreave I.A., Moldeus P. Methodologies for the application of monobromobimane to the simultaneous analysis of soluble and protein thiol component of biological systems. J Biochem Bioph Meth. 13:1986;231-249.
30. Ellman G. Tissue sulfhydryl groups. Arch Biochem Biophys. 82:1959;70-77.
31. Sedlak J., Lindsay R.H. Estimation of total, protein-bound, nonprotein sulfhydryl groups in tissue with Ellman's reagent. Anal Biochem. 25:1968;192-205.
32. Toxopeus C., Holsteijn I., De Winther M.P.J., Dobbelsteen D., Horbach J.G.J.M., Blaauboer B.J., Noordhoek J. Role of thiol homeostasis and adenine nucleotide metabolism in the protective effects of fructose in quinone-induced cytotoxicity in rat hepatocytes. Biochem Pharmacol. 48:1994;1683-1692.
33. Bradford M.M. A rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principal of protein-dye binding. Anal Biochem. 72:1976;248-254.
34. 2-mediated injury . J Biol Chem. 263:1988;1655-1675.
35. Tzeng W.F., Lee J.L., Chiou T.J. The role of lipid peroxidation in menadione-mediated toxicity in cardiomyocytes. J Mol Cell Cardiol. 27:1995;1999-2008.
36. Lash L.H., Hagen T.M., Jones D.P. Exogenous glutathione protects intestinal epithelial cells from oxidative injury. Proc Natl Acad Sci USA. 83:1986;4641-4645.
37. Finely K.T. The addition and substitution chemistry of quinones. Patai S., The Chemistry of Quinoniod Compounds. 1974;877-1144 John Wiley & Sons, London.
38. Wilson I., Wardman P., Lin T.S., Sartorelli A.C. Reactivity of thiols towards derivatives of 2-methyl and 6-methyl-1,4-naphthoquinone bioreductive alkylating agents. Chem-Biol Interact. 61:1987;229-240.
39. Buffinton G.D., Öllinger K., Brunmark A., Cadenas E. DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates. Biochem J. 257:1989;561-571.
40. Flowers Geary L., Harvey R.G., Penning T.M. Cytotoxicity of polycyclic aromatic hydrocarbon o-quinones in rat and human hepatoma cells. Chem Res Toxicol. 6:1993;252-260.
41. Beall H.D., Mulcahy R.T., Siegel D., Traver R.D., Gibson N.W., Ross D. Metabolism of bioreductive antitumor compounds by purified rat and human DT-diaphorases. Cancer Res. 54:1994;3196-3201.
42. Öllinger K., Buffington G.D., Ernster L., Cadenas E. Effect of superoxide dismutase on the autoxidation of substituted hydro- and semi-naphthoquinones. Chem-Biol Interact. 73:1990;53-76.
43. LLopis J., Ernster L., Cadenas E. Effect of glutathione on the redox transitions of naphthohydroquinone derivatives formed during DT-diaphorase catalysis. Free Rad Res Comm. 8:1990;271-285.
44. Cadenas E. Antioxidant and prooxidant functions of DT-diaphorase in quinone metabolism. Biochem Pharmacol. 49:1995;127-140.
45. Wong G.H.W., Goeddel D.V. Induction of manganous superoxide dismutase by tumor necrosis factor Possible protective mechanism . Science. 242:1988;941-944.
46. Baker S.S., Baker R.D.J. Antioxidant enzymes in the differentiated Caco-2 cell line. In Vitro Cell Dev-An. 28A:1992;643-647.
47. Ciaccio P.J., Stuart J.E., Kenneth D.T. Overproduction of a 37.5-kDa cytosolic protein structurally related to prostagladin F synthase in ethacrynic acid-resistant human colon cells. Am Soc Pharmacol Exp Ther. 43:1993;845-853.
48. Schmiedlin-Ren P., Thummel K.E., Fisher J.M., Paine M.F., Lown K.S., Watkins P.B. Expression of enzymatically active CYP3A4 by Caco-2 cells grown on extracellular matrix-coated permeable supports in the presence of 1alpha,25-dihydroxyvitamin D3. Mol Pharmacol. 51:1997;741-754.
49. Rossi L., De Angelis I., Pedersen J.Z., Marchese E., Stammati A., Rotilio G., Zucco F.N. [5-nitro-2-furfurylidene]-3-amino-2-oxazolidinone activation by the human intestinal cell line Caco-2 monitored through noninvasive electron spin resonance spectroscopy. Mol Pharmacol. 49:1996;547-555.
50. Peters W.H., Roelofs H.M. Time-dependent activity and expression of glutathione S-transferases in the human colon adenocarcinoma cell line Caco-2. Biochem J. 264:1989;613-616.
51. Tew K.D., Bomber A.M., Hoffman S.J. Ethacrynic acid and piriprost as enhancers of cytotoxicity in drug-resistant and -sensitive cell lines. Cancer Res. 48:1988;3622-3925.
52. Lewis A.D., Forrester L.M., Hayes J.D., Wareing C.J., Carmichael J., Harris A.L., Mooghen M., Wolf C.R. Glutathione S-transferase isoenzymes in human tumours and tumour-derived cell lines. Br J Cancer. 60:1989;327-331.
53. Kuzmich S., Vanderveer L.A., Walsh E.S., LaCreta F.P., Tew K.D. Increased levels of glutathione S-transferase (pi) transcripts as a mechanism of resistance to ethacrynic acid. Biochem J. 281:1992;219-224.
54. Perry R.R., Kang Y., Greaves B. Biochemical characterization of a mitomycin C resistant colon cancer cell line variant. Biochem Pharmacol. 46:1993;1999-2005.
55. Bellomo G., Mirabelli F., DiMonte D., Richelmi P., Thor H., Orrenius C., Orrenius S. Formation and reduction of glutathione-protein mixed disulfides during oxidative stress. A study with isolated hepatocytes and menadione (2-methyl-1,4-naphthoquinone). Biochem Pharmacol. 36:1987;1313-1320.
56. Chai Y.C., Hendrich S., Thomas J.A. Protein S-thiolation in hepatocytes stimulated by t-butyl hydroperoxide, menadione, and neutrophils. Arch Biochem Biophys. 310:1994;264-272.
57. Birge R.B., Bartolone J.B., Cohen S.D., Khairallah E.A., Smolin L.A. A comparison of protein S-thiolated by glutathione or those arylated by acetaminophen. Biochem Pharmacol. 42:1991;S197-S207.
58. Meister A., Anderson M.E. Glutathione. Annu Rev Biochem. 52:1983;711-760.
59. Fernandez-Checa J.C., Ren C., Aw T.Y., Ookhtens M., Kaplowitz N. Effect of membrane potential and cellular ATP on glutathione efflux from isolated rat hepatocytes. Am J Physiol. 255:1988;G403-G408.
60. Griffiths J.C., Sies H., Meier P.J., Akerboom T.M.P. Inhibition of taurocholate efflux from rat hepatic canalicular membrane vesicles by glutathione disulfide. FEBS Lett. 213:1987;34-38.
61. Bilzer M., Krauth-Siegel R.L., Schirmer R.H., Akerboom T.P.M., Sies H., Schulz G.E. Interaction of a glutathione-S-conjugate with glutathione reductase. Kinetic and X-ray crystallographic studies. Eur J Biochem. 138:1984;373-378.
62. Lippold H.J. Quantitative succinic dehydrogenases histochemistry. Histochemistry. 76:1982;381-405.
63. Burdon R.H., Gill V., Rice-Evans C. Reduction of a tetrazolium salt and the superoxide generation in human tumor cell (HeLa). Free Rad Res Com. 18:1993;369-380.
64. Colpa-Boonstra J.P., Slater E.C. The possible role of vitamin K in the respiratory chain. Biochim Biophys Acta. 27:1958;122-133.
65. Berridge M.V., Tan A.S. Characterization of the cellular reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) Subcellular localization, substrate dependence, and the involvement of mitochondrial electron transport in MTT reduction . Arch Biochem Biophys. 303:1993;474-482.
66. Eggleston L.V., Krebs H.A. Regulation of the pentose phosphate cycle. Biochem J. 138:1974;425-435.
67. Burchell A., Burchell B. Stabilization of partially purified glucose-6-phosphatase by fluoride. Is enzyme inactivation caused by dephosphorylation? FEBS Lett. 118:1980;180-184.
68. Baker S., Baker R.D. Caco-2 cell metabolism of oxygen-derived radicals. Digest Dis Sci. 38:1993;2273-2280.