Relationship between NAD(P)H:quinone oxidoreductase 1 (NQO1) levels in a series of stably transfected cell lines and susceptibility to antitumor quinones

Biochemical Pharmacology

Volumn 61, Issue 12, 2001, Pages 1509-1516

  Winski, Shannon L ^a   Swann, Elizabeth ^b   Hargreaves, Robert H J ^c   Dehn, Donna L ^a   Butler, John ^c,d   Moody, Christopher J ^b   Ross, David ^a  

^a Sch Pharm Cancer Ctr Camp B   (United States)

^b UNIVERSITY OF EXETER   (United Kingdom)

^c CHRISTIE HOSPITAL   (United Kingdom)

^d UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

Antitumor quinones; Enzyme directed drug development; In vitro testing; NQO1; Preclinical research

Indexed keywords

2,5 DIAZIRIDINYL 3 (HYDROXYMETHYL) 6 METHYL 1,4 BENZOQUINONE; 3 (HYDROXYMETHYL) 1,2 DIMETHYL 5 (2 METHYLAZIRIDINYL YL)INDOLE 4,7 DIONE; 5 (1 AZIRIDINYL) 3 HYDROXYMETHYL 2 (3 HYDROXY 1 PROPENYL) 1 METHYL 4,7 INDOLEDIONE; 5 (AZIRIDIN 1 YL) 3 (HYDROXYMETHYL) 1,2 DIMETHYLINDOLE 4,7 DIONE; 5 METHOXY 1,2 DIMETHYL 3 [(4 NITROPHENOXY)METHYL]INDOLE 4,7 DIONE; 9 (HYDROXYMETHYL) 7 (2 METHYLAZIRIDIN 1 YL) 1,2 DIHYDRO 3H PYRROLO[1,2 A]INDOLE 5,8 DIONE; ANTINEOPLASTIC AGENT; DIAZIQUONE; ES 1352; ES 921; ES 923; ES 936; QUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); RUFOCROMOMYCIN; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARCINOMA CELL; CELL ACTIVITY; CELL LEVEL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA CROSS LINKING; DRUG ACTIVATION; DRUG CYTOTOXICITY; DRUG SENSITIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; GENETIC POLYMORPHISM; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; MAXIMUM ALLOWABLE CONCENTRATION; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANTIBIOTICS, ANTINEOPLASTIC; ANTINEOPLASTIC AGENTS; AZIRIDINES; BENZOQUINONES; BIOTRANSFORMATION; CELL DIVISION; DRUG INTERACTIONS; HUMANS; INHIBITORY CONCENTRATION 50; NAD(P)H DEHYDROGENASE (QUINONE); QUINONES; STREPTONIGRIN; TRANSFECTION; TUMOR CELLS, CULTURED;

EID: 0035877252     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(01)00631-1     Document Type: Article

References (47)

1. Sartorelli A.C., Hodnick W.F., Belcourt M.F., Tomasz M., Haffty B., Fischer J.J., Rockwell S. Mitomycin C a prototype bioreductive agent . Oncol Res. 6:1994;501-508.
2. Crooke S.T., Bradner W.T. Mitomycin C a review . Cancer Treat Rev. 3:1976;121-139.
3. Spain R.C. The case for mitomycin in non-small cell lung cancer. Oncology. 50:(Suppl 1):1993;35-50.
4. Tomasz M., Palom Y. The mitomycin bioreductive antitumor agents cross-linking and alkylation of DNA as the molecular basis of their activity . Pharmacol Ther. 76:1997;73-87.
5. Ross D., Beall H.D., Siegel D., Traver R.D., Gustafson D.L. Enzymology of bioreductive drug activation. Br J Cancer. 74:1996;S1-S8.
6. Bligh H.F., Bartoszek A., Robson C.N., Hickson I.D., Kasper C.B., Beggs J.D., Wolf C.R. Activation of mitomycin C by NADPH cytochrome P-450 reductase . Cancer Res. 50:1990;7789-7792.
7. Kennedy K.A., Sligar S.G., Polomski L., Sartorelli A.C. Metabolic activation of mitomycin C by liver microsomes and nuclei. Biochem Pharmacol. 31:1982;2011-2016.
8. 5 reductase. Cancer Res. 53:1993;4907-4912.
9. Pan S.S., Andrews P.A., Glover C.J., Bachur N.R. Reductive activation of mitomycin C and mitomycin C metabolites catalyzed by NADPH-cytochrome P-450 reductase and xanthine oxidase. J Biol Chem. 259:1984;959-966.
10. Gustafson D.L., Pritsos C.A. Kinetics and mechanism of mitomycin C bioactivation by xanthine dehydrogenase under aerobic and hypoxic conditions. Cancer Res. 53:1993;5470-5474.
11. Siegel D., Beall H., Senekowitsch C., Kasai M., Arai H., Gibson N.W., Ross D. Bioreductive activation of mitomycin C by DT-diaphorase. Biochemistry. 31:1992;7879-7885.
12. Cummings J., Spanswick V.J., Smyth J.F. Re-evaluation of the molecular pharmacology of mitomycin C. Eur J Cancer. 31A:1995;1928-1933.
13. Schlager J.J., Powis G. Cytosolic NAD(P)H:(quinone-acceptor)oxidoreductase in human normal and tumor tissue effects of cigarette smoking and alcohol . Int J Cancer. 45:1990;403-409.
14. Jarrett C.M., Bibby M.C., Phillips R.M. Bioreductive enzymology of malignant and normal human tissues. Proc Am Assoc Cancer Res. 39:1998;429.
15. 1) gene in tumor cells compared to normal cells of the same origin. Biochem Pharmacol. 42:1991;1021-1027.
16. Malkinson A.M., Siegel D., Forrest G.L., Gazdar A.F., Oie H.K., Chan D.C., Bunn P.A., Mabry M., Dykes D.J., Harrison S.D. Jr, Ross D. Elevated DT-diaphorase activity and messenger RNA content in human non-small cell lung carcinoma relationship to the response of lung tumor xenografts to mitomycin C . Cancer Res. 52:1992;4752-4757.
17. Mikami K., Naito M., Ishiguro T., Yano H., Tomida A., Yamada T., Tanaka N., Shirakusa T., Tsuruo T. Immunological quantitation of DT-diaphorase in carcinoma cell lines and clinical colon cancers advanced tumors express greater levels of DT-diaphorase . Jpn J Cancer Res. 89:1998;910-915.
18. Smitskamp-Wilms E., Giaccone G., Pinedo H.M., van der Laan B.F., Peters G.J. DT-diaphorase activity in normal and neoplastic human tissues; an indicator for sensitivity to bioreductive agents? Br J Cancer. 72:1995;917-921.
19. Fitzsimmons S.A., Workman P., Grever M., Paull K., Camalier R., Lewis A.D. Reductase enzyme expression across the National Cancer Institute Tumor cell line panel correlation with sensitivity to mitomycin C and EO9 . J Natl Cancer Inst. 88:1996;259-269.
20. 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.
21. Traver R.D., Siegel D., Beall H.D., Phillips R.M., Gibson N.W., Franklin W.A., Ross D. Characterization of a polymorphism in NAD(P)H: quinone oxidoreductase (DT-diaphorase). Br J Cancer. 75:1997;69-75.
22. Winski S.L., Hargreaves R.H.J., Butler J., Ross D. A new screening system for NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor quinones identification of a new aziridinylbenzoquinone, RH1, as a NQO1-directed antitumor agent . Clin Cancer Res. 4:1998;3083-3088.
23. Beall H.D., Winski S., Swann E., Hudnott A.R., Cotterill A.S., O'Sullivan N., Green S.J., Bien R., Siegel D., Ross D., Moody C.J. Indolequinone antitumor agents correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity . J Med Chem. 41:1998;4755-4766.
24. Naylor M.A., Jaffar M., Nolan J., Stephens M.A., Butler S., Patel K.B., Everett S.A., Adams G.E., Stratford I.J. 2-Cyclopropylindoloquinones and their analogues as bioreductively activated antitumor agents structure-activity in vitro and efficacy in vivo . J Med Chem. 40:1997;2335-2346.
25. Winski S.L., Siegel D., Zodrow J.M., Ross D. ES936, a novel indolequinone inhibitor of NAD(P)H:quinone oxidoreductase 1 (NQO1). Proc Am Assoc Cancer Res. 41:2000;4872.
26. Ernster L. DT-diaphorase. Methods Enzymol. 10:1967;309-317.
27. Benson A.M., Hunkeler M.J., Talalay P. Increase of NAD(P)H:quinone reductase by dietary antioxidants possible role in protection against carcinogenesis and toxicity . Proc Natl Acad Sci USA. 77:1980;5216-5220.
28. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the Folin phenol reagent. J Biol Chem. 193:1951;265-275.
29. Gustafson D.L., Beall H.D., Bolton E.M., Ross D., Waldren C.A. Expression of human NAD(P)H:quinone oxidoreductase (DT-diaphorase) in Chinese hamster ovary cells effect on the toxicity of antitumor quinones . Mol Pharmacol. 50:1996;728-735.
30. Mosmann T. Rapid colorimetric assay for cellular growth and survival application to proliferation and cytotoxicity assays . J Immunol Methods. 65:1983;55-63.
31. Ward T.H., Butler J., Shahbakhti H., Richards J.T. Comet assay studies on the activation of two diaziridinylbenzoquinones in K562 cells. Biochem Pharmacol. 53:1997;1115-1121.
32. Beall H.D., Hudnott A.R., Winski S., Siegel D., Swann E., Ross D., Moody C.J. Indolequinone antitumor agents relationship between quinone structure and rate of metabolism by recombinant human NQO1 . Bioorg Med Chem Lett. 8:1998;545-548.
33. Beall H.D., Murphy A.M., Siegel D., Hargreaves R.H.J., Butler J., Ross D. Nicotinamide adenine dinucleotide (phosphate):quinone oxidoreductase (DT-diaphorase) as a target for bioreductive antitumor quinones quinone cytotoxicity and selectivity in human lung and breast cancer cell lines . Mol Pharmacol. 48:1995;499-504.
34. Brown J.M. NCI's anticancer drug screening program may not be selecting for clinically active compounds. Oncol Res. 9:1997;213-215.
35. Ross D., Siegel D., Beall H., Prakash A.S., Mulcahy R.T., Gibson N.W. DT-diaphorase in activation and detoxification of quinones. Bioreductive activation of mitomycin C. Cancer Metastasis Rev. 12:1993;83-101.
36. Cummings J., Allan L., Willmott N., Riley R., Workman P., Smyth J.F. The enzymology of doxorubicin quinone reduction in tumour tissue. Biochem Pharmacol. 44:1992;2175-2183.
37. Gustafson D.L., Pritsos C.A. Enhancement of xanthine dehydrogenase mediated mitomycin C metabolism by dicumarol. Cancer Res. 52:1992;6936-6939.
38. Buffinton G.D., Ollinger K., Brunmark A., Cadenas E. DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates. Effect of substituents on autoxidation rates. Biochem J. 257:1989;561-571.
39. Gibson N.W., Hartley J.A., Butler J., Siegel D., Ross D. Relationship between DT-diaphorase-mediated metabolism of a series of aziridinylbenzoquinones and DNA damage and cytotoxicity. Mol Pharmacol. 42:1992;531-536.
40. Jaffar M., Naylor M.A., Robertson N., Lockyer S.D., Phillips R.M., Everett S.A., Adams G.E., Stratford I.J. 5-Substituted analogues of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) and their regioisomers as hypoxia-selective agents structure-cytotoxicity in vitro . Anticancer Drug Des. 13:1998;105-123.
41. Chou F., Khan A.H., Driscoll J.S. Potential central nervous system antitumor agents. Aziridinylbenzoquinones. J Med Chem. 19:1976;1302-1308.
42. Mikami K., Naito M., Tomida A., Yamada M., Sirakusa T., Tsuruo T. DT-diaphorase as a critical determinant of sensitivity to mitomycin C in human colon and gastric carcinoma cell lines. Cancer Res. 56:1996;2823-2826.
43. Cross J.V., Deak J.C., Rich E.A., Qian Y., Lewis M., Parrott L.A., Mochida K., Gustafson D., Vande Pol S., Templeton D.J. Quinone reductase inhibitors block SAPK/JNK and NFκB pathways and potentiate apoptosis. J Biol Chem. 274:1999;31150-31154.
44. Qiu X., Forman H.J., Schonthal A.H., Cadenas E. Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells. J Biol Chem. 271:1996;31915-31921.
45. Qiu X.B., Cadenas E. The role of NAD(P)H:quinone oxidoreductase in quinone-mediated p21 induction in human colon carcinoma cells. Arch Biochem Biophys. 346:1997;241-251.
46. Tudor G., Gutierrez P.L., Aguilera A., Sausville E.A. Correlation of quinones bioreductive activation with cytotoxicity and apoptotic modulation of Bad protein expression and cytochrome c release. Proc Am Assoc Cancer Res. 41:2000;4695.
47. Sun X., Ross D. Quinone-induced apoptosis in human colon adenocarcinoma cells via DT-diaphorase mediated bioactivation. Chem Biol Interact. 100:1996;267-276.