Role of NADPH cytochrome P450 reductase in activation of RH1

Cancer Chemotherapy and Pharmacology

Volumn 60, Issue 5, 2007, Pages 713-723

  Begleiter, Asher ^a   Leith, Marsha K ^a   Patel, Daywin ^b   Hasinoff, Brian B ^b  

^a UNIVERSITY OF MANITOBA   (Canada)

^b UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Activation; NADPH cytochrome P450 reductase; Reduction; RH1

Indexed keywords

2,5 DIAZIRIDINYL 3 (HYDROXYMETHYL) 6 METHYL 1,4 BENZOQUINONE; ANTINEOPLASTIC AGENT; DICOUMAROL; DIPHENYLIODONIUM SALT; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE) OXIDOREDUCTASE 1; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; RH 1; RUFOCROMOMYCIN; TIRAPAZAMINE; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CANCER INHIBITION; CONTROLLED STUDY; DNA CROSS LINKING; DNA DAMAGE; DNA ISOLATION; DNA STRAND BREAKAGE; DRUG ACTIVATION; ELECTRON SPIN RESONANCE; ENZYME MECHANISM; ENZYME PURIFICATION; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; HYPOXIA; IC 50; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; REDUCTION KINETICS;

ANTINEOPLASTIC AGENTS; AZIRIDINES; BENZOQUINONES; BIPHENYL COMPOUNDS; CELL LINE, TUMOR; CELL PROLIFERATION; CROSS-LINKING REAGENTS; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; NAD(P)H DEHYDROGENASE (QUINONE); NADPH-FERRIHEMOPROTEIN REDUCTASE; ONIUM COMPOUNDS; OXIDATION-REDUCTION;

EID: 34547842362     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00280-007-0417-8     Document Type: Article

References (39)

1. Barnabé N, Zastre J, Venkataram S, Hasinoff BB (2002) Deferiprone protects against doxorubicin-induced myocyte cytotoxicity. Free Radic Biol Med 33:266-275
2. Begleiter A, Robotham E, Leith MK (1992) Role of NAD(P)H:(quinone acceptor) oxidoreductase (DT-diaphorase) in activation of mitomycin C under hypoxia. Mol Pharmacol 41:677-682
3. Benson AM, Hunkeler MJ, Talalay P (1980) Increase of NAD(P)H:quinone reductase by dietary antioxidants: possible role in protection against carcinogenesis and toxicity. Proc Natl Acad Sci USA 77:5216-5220
4. Berardini MD, Souhami RL, Lee CS, Gibson NW, Butler J, Hartley JA (1993) Two structurally related diaziridinylbenzoquinones preferentially cross-link DNA at different sites upon reduction with DT-diaphorase. Biochemistry 32:3306-3312
5. Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ (2000) Role of quinones in toxicology. Chem Res Toxicol 13:135-160
6. Cenas N, Anusevicius Z, Nivinskas H, Miseviciene L, Sarlauskas J (2004) Structure-activity relationships in two-electron reduction of quinones. Meth Enzymol 382:258-277
7. Cummings J, Ritchie A, Butler J, Ward TH, Langdon S (2003) Activity profile of the novel aziridinylbenzoquinones MeDZQ and RH1 in human tumor xenografts. Anticancer Res 23:3979-3984
8. Digby T, Leith MK, Thliveris JA, Begleiter A (2005) Effect of NQO1 induction on the antitumor activity of RH1 in human tumors in vitro and in vivo. Cancer Chemother Pharmacol 56:307-316
9. Fitzsimmons SA, Workman P, Grever M, Paull K, Camalier R, Lewis AD (1996) Reductase enzyme expression across the National Cancer Institute Tumor cell line panel: correlation with sensitivity to mitomycin C and EO9. J Natl Cancer Inst 88:259-269
10. Fourie J, Guziec Jr F, Guziec L, Monterrosa C, Fiterman DJ, Begleiter A (2004) Structure-activity study with bioreductive benzoquinone alkylating agents: effects on DT-diaphorase-mediated DNA crosslink and strand break formation in relation to mechanism of cytotoxicity. Cancer Chemother Pharmacol 53:191-203
11. Halliwell B, Gutteridge JMC (1999) Free radicals in biology and medicine. Clarendon, Oxford
12. Hasinoff BB, Wu X, Begleiter A, Guziec L, Guziec F, Giorgianni A, Yang S, Jiang Y, Yalowich JC (2006) Structure-activity study of the interaction of bioreductive benzoquinone alkylating agents with DNA topoisomerase II. Cancer Chemother Pharmacol 57:221-233
13. Hoban PR, Walton MI, Robson CN, Godden J, Stratford IJ, Workman P, Harris AL, Hickson ID (1990) Decreased NADPH:cytochrome P-450 reductase activity and impaired drug activation in a mammalian cell line resistant to mitomycin C under aerobic but not hypoxic conditions. Cancer Res 50:4692-4697
14. Johnston JB, Verburg L, Shore T, Williams M, Israels LG, Begleiter A (1994) Combination therapy with nucleoside analogs and alkylating agents. Leukemia 8(suppl):S140-S143
15. Kim JY, West CM, Valentine H, Ward TH, Patterson AV, Stratford IJ, Roberts SA, Hendry JH (2004) Cytotoxicity of the bioreductive agent RH1 and its lack of interaction with radiation. Radiother Oncol 70:311-317
16. Loadman PM, Phillips RM, Lim LE, Bibby MC (2000) Pharmacological properties of a new aziridinylbenzoquinone, RH1 (2,5-diaziridinyl-3- (hydroxymethyl)-6-methyl-1,4-benzoquinone), in mice. Biochem Pharmacol 59:831-837
17. Malkinson AM, Siegel D, Forrest GL, Gazdar AF, Oie HK, Chan DC, Bunn PA, Mabry M, Dykes DJ, Harrison SD Jr, Ross D (1992) 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 52:4752-4757
18. Marshall RS, Paterson MC, Rauth AM (1989) Deficient activation by a human cell strain leads to mitomycin resistance under aerobic but not hypoxic conditions. Br J Cancer 59:341-346
19. Monks TJ, Jones DC (2002) The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers. Curr Drug Metab 3:425-438
20. Nemeikaite-Ceniene A, Sarlauskas J, Anusevicius Z, Nivinskas H, Cenas N (2003) Cytotoxicity of RH1 and related aziridinylbenzoquinones: involvement of activation by NAD(P)H:quinone oxidoreductase (NQO1) and oxidative stress. Arch Biochem Biophys 416:110-118
21. O'Brien PJ (1991) Molecular mechanisms of quinone cytotoxicity. Chem Biol Interact 80:1-41
22. Ollinger K, Brunmark A (1991) Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes. J Biol Chem 266:21496-21503
23. Pan SS, Andrews PA, Blover CJ, Bachur NR (1984) Reductive activation of mitomycin C and mitomycin C metabolite catalyzed by NADPH-cytochrome P-450 reductase and xanthine oxidase. J Biol Chem 259:959-966
24. Patterson AV, Saunders MP, Chinje EC, Talbot DC, Harris AL, Stratford IJ (1997) Overexpression of human NADPH:cytochrome c (P450) reductase confers enhanced sensitivity to both tirapazamine (SR 4233) and RSU 1069. Br J Cancer 76:1338-1347
25. Phillips AH, Langdon RG (1962) Hepatic triphosphopyradine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies. J Biol Chem 237:2652-2660
26. Powis G (1989) Free radical formation by antitumor quinones. Free Radic Biol Med 6:63-101
27. Riley RJ, Workman P (1992) DT-diaphorase and cancer chemotherapy. Biochem Pharmacol 43:1657-1669
28. Rockwell S, Sartorelli AC, Tomasz M, Kennedy KA (1993) Cellular pharmacology of quinone bioreductive alkylating agents. Cancer Metastasis Rev 12:165-176
29. Ross D, Siegel D, Beall H, Prakash AS, Mulcahy RT, Gibson NW (1993) DT-diaphorase in activation and detoxification of quinones. Cancer Metastasis Rev 12:83-101
30. Seng F, Ley K (1972) Simple synthesis of 3-amino-1,2,4-benzotriazine 1,4-dioxide. Angew Chem Int Ed Eng 11:1009-1010
31. Sharp SY, Kelland LR, Valenti MR, Brunton LA, Hobbs S, Workman P (2000) Establishment of an isogenic human colon tumor model for NQO1 gene expression: application to investigate the role of DT-diaphorase in bioreductive drug activation in vitro and in vivo. Mol Pharmacol 58:1146-1155
32. Siegel D, Gibson NW, Preusch PC, Ross D (1990) Metabolism of mitomycin C by DT-diaphorase: role in mitomycin C-induced DNA damage and cytotoxicity in human colon carcinoma cells. Cancer Res 50:7483-7489
33. Strobel HW, Dignam JD (1978) Purification and properties of NADPH-cytochrome P-450 reductase. Meth Enzymol 52:89-96
34. Sun X, Ross D (1996) Quinone-induced apoptosis in human colon adenocarcinoma cells via DT-diaphorase mediated bioactivation. Chem-Biol Interac 100:267-276
35. Swallow AJ (1982) Physical chemistry of semiquinones. In: Trumpower BL (ed) Function of quinones in energy conserving systems. Academic, New York pp 59-72
36. Tudor G, Alley M, Nelson CM, Ruili, Covell DG, Gutierrez P, Sausville EA (2005) Cytotoxicity of RH1: NAD(P)H:quinone acceptor oxidoreductase (NQO1)-independent oxidative stress and apoptosis induction. Anti-Cancer Drugs 16:381-391
37. Winski SL, Hargreaves RHJ, Butler J, Ross D (1998) 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 4:3083-3088
38. Winski SL, Swann E, Hargreaves RHJ, Dehn DL, Butler J, Moody CJ, Ross D (2001) Relationship between NAD(P)H:quinone oxidoreductase 1 (NQO1) levels in a series of stably transfected cell lines and susceptibility to antitumor quinones. Biochem Pharmacol 61:1509-1516
39. Zhu BZ, Zhao HT, Kalyanaraman B, Frei B (2002) Metal-independent production of hydroxyl radicals by halogenated quinones and hydrogen peroxide: an ESR spin trapping study. Free Radic Biol Med 32:465-473