Overexpression of human NADPH:cytochrome c (P450) reductase confers enhanced sensitivity to both tirapazamine (SR 4233) and RSU 1069

British Journal of Cancer

Volumn 76, Issue 10, 1997, Pages 1338-1347

  Patterson, A V ^a,b,c   Saunders, M P ^a,b,c   Chinje, E C ^a,c   Talbot, D C ^b   Harris, A L ^b   Stratford, I J ^a,c  

^a MEDICAL RESEARCH COUNCIL   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Bioreductive drugs; Breast cancer; Hypoxia; P450 reductase; RSU 1069; Tirapazamine

Indexed keywords

1 AZIRIDINO 3 (2 NITRO 1 IMIDAZOLYL) 2 PROPANOL; COMPLEMENTARY DNA; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; TIRAPAZAMINE;

ARTICLE; BREAST CANCER; DRUG ACTIVATION; DRUG CYTOTOXICITY; DRUG METABOLISM; DRUG SENSITIVITY; ENZYME ACTIVITY; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; HYPOXIA; MOLECULAR CLONING; OXYGEN TENSION; PRIORITY JOURNAL; PROTEIN EXPRESSION; REDUCTION;

EID: 0030692717     PISSN: 00070920     EISSN: None     Source Type: Journal    
DOI: 10.1038/bjc.1997.558     Document Type: Article

References (51)

1. Adams GE and Stratford IJ (1986) Hypoxia-mediated nitro-heterocycle drugs in the radio chemotherapy of cancer: an overview. Biochem Pharmacol 35: 71-76
2. Adams GE and Stratford IJ (1994) Bioreductive drugs for cancer therapy: the search for tumour specificity. Int J Radiat Oncol Biol Phys 29: 231-238
3. Adams GE, Ahmed I. Sheldon PW and Stratford IJ (1984) Radiation sensitization and chemopotentiation: RSU 1069. a compound more efficient than misonidazole in vitro and in vivo. Br J Cancer 49: 571-577
4. Baker MA, Zeman EM, Hirst VK and Brown JM (1988) Metabolisim of SR 4233 by Chinese hamster ovary cells: basis of selective hypoxic cytotoxicity. Cancer Res 48: 5947-5952
5. 5 reductase in human tumour cells. Br J Cancer 74: 1188-1193
6. Belcourt MF, Hodnick WF, Rockwell S and Sartorelli AC (1996) Differential toxicity of mitomycin C and porfiromycin to aerobic and hypoxic Chinese hamster ovary cells overexpressing human NADPH:cytochrome c (P-450) reductase. Proc Natl Acad Sci USA 93: 456-460
7. Biedermann KA, Wang J, Graham RP and Brown JM (1991) SR 4233 cytotoxicity and metabolism in DNA repair-competent and repair-deficient cell cultures. r J Cancer 63: 358-362
8. Bradford M (1976) A rapid and sensitive method for quantification of microgram quantities of protein utilising the principle of protein dye binding. Anal Biochem 72: 248-254
9. Brown JM (1993) SR4233 (Tirapazamine): a new anticancer drug exploiting hypoxia in solid tumours. Br J Cancer 67: 1163-1170
10. Brown JM and Siim BG (1996) Hypoxia-specific cytotoxins in cancer therapy. Semin Radiat Oncol 6: 22-36
11. Cahill A, and White INH (1990) Reductive metabolism of 3-amino-1,2,4-benzotriazine-1,4-dixide (SR 4233) and the induction of unscheduled DNA synthesis in rat and human derived cell lines. Carcinogenesis 11: 1407-1411
12. Dachs GU, Patterson AV, Townsend S, Adams GE, Firth JD, Ratcliffe PJ, Harris AL and Stratford IJ (1995) Testing hypoxia responsive elements for their use in cancer therapy. Proc Am Assoc Cancer Res 36: 421
13. Denny WA, Wilson WR and Hay MP (1996) Recent developments in the design of bioreductive drugs. Br J Cancer 74 (suppl. 27): S32-38
14. Fitzsimmons SA, Lewis AD, Riley RJ and Workman P (1994) Reduction of 3-amino-1,2,4-benzotriazine-1,4-di-N-oxie (tripazamine, WIN 59075. SR 4233) to a DNA-damaging species: a direct role for NADPH:cytothrome P450 oxidoreductase. Carcinogenesis 15: 1503-1510
15. Griffith OW (1980) Determination of glutathione and glutathione disulfide using glutathione reductase and 2-vinylpyridine. Anal Biochem 106: 207-212
16. Hockel M, Schlenger K, Mitze M, Schaffer U and Vaupel P (1996) Hypoxia and radiation response in human tumors. Seminars in Radiation Oncology 6: 3-9, 1996
17. Houlbrook S, Kirk J, Stuart NSA. Stratford IJ, Harris AL, Pettit GR and Carmichael J (1994) Human tumour cell lines: a valuable model for evaluating new drugs and the mechanisms underlying cytotoxic drug resistance Oncol (Life Sci Adv) 13: 69-76
18. Kennedy KA (1987) Hypoxic cells as specific drug targets for chemotherapy. Anticancer Drug Res 2: 181-194
19. Keohane A, Godden J, Stratford IJ and Adams GE (1990) The effects of three bioreductive drugs (mitomycin C. RSU-1069 and SR 4233) on cell lines selected for their sensitivity to mitomycin C or ionising radiation. Br J Cancer 61: 722-726
20. Laderoute K, Wardman P and Rauth AM (1988) Molecular mechanisms for the hypoxia-dependent activation of 3-amino- 1,2,4-benzotriazine- 1,4-dioxide (SR 4233). Biochem Pharmacol 37: 1487-1495
21. Lloyd RV, Duling DR, Rumyantseva GV, Mason RP and Bridson PK (1991) Microsomal reduction of 3-amino-1,2,4-benzotriazine 1,4-dioxide to a free radical. Mol Pharmacol 40: 440-445
22. Mason RP and Holtzman JL (1975) The mechanism of microsomal and mitochodrial nitroreductase: ESR evidence for nitroaromatic free radical intermediates. Biochemistry 14: 1626-1632
23. Morgenstern P and Land H (1990) Advanced mammalian gene transfer: high titre retroviral vectors with multiple drug selection markers and a complementary helper-free packaging cell line. Nucl Acid Res 18: 3587-3596
24. Mossman T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65: 55-61
25. Noss MB, Panicuccir. McClelland RA and Rauth AM (1988) Preparation, toxicity and mutagenicity of 1-methyl-2-nitrosoimidazole, a toxic reduction product. Biochem Pharmacol 37: 2885-2593
26. O'Neill P, McNeil SS and Jenkins TC (1987) Induction of DNA crosslinks in vitro upon reduction of the nitroimidazole-aziridines RSU-1069 and RSU-1131. Biochem Pharmacol 36: 1787-1792
27. Osborne WR and Miler AD (1988) Design of vectors for efficient expression of human purine nucleoside phosphorylase in skin fibrohlasts from enzyme-deficient humans. Proc Natl Acad Sci USA 85: 6851-6855
28. Patterson AV, Robertson N, Houlbrook S, Stephens MA, Adams GE, Harris AL, Stratford IJ and Carmichael J (1994) The role of DT-diaphorase in determining the sensitivity of human tumour cells to tirapazamine (SR 4233). Int J Radiat Oncol Biol Phys 29: 369-372
29. Patterson AV, Barham HM, Chinje EC, Adams GE, Harris AL and Stratford IJ (1995) Importance of P450 reductase activity in determining sensitivity of breast tumour cells to the bioreductive drug, tirapazamine (SR4233). Br J Cancer 72: 1144-1150
30. Peterson AJ and Prough RA (1986) Cytochrome P450 reductase and cytochrome b5 in cytochrome P450 catalysis. In Cytochrome P450: Structure, Mechanism and Biochemistry. Oritz de Montellano RP. (ed.) pp. 89-119. Plenum Press: New York
31. Plumh JA, Gerritsen M and Workman (1994) DT-diaphorase protects cells from the hypoxic cytotoxicity of the indoloquinone EO9. Br J Cancer 70: 1136-1140
32. Riley JR and Workman P (1992) Enzymology of the reduction of the potent benzotriazene di-N-oxide hypoxic cell cytotoxin SR 4233 by NAD(P)H: (quinone acceptor) oxido-reductase (EC. 1.66.99.2) purified from Walker 256 rat tumour cells. Biochem Pharmacol 43: 167-174
33. Robertson N, Haigh A, Adams GE and Stratford IJ (1994) Factors affecting sensitivity to EO9 in rodent and human tumour cells in vitro: DT-diaphorase activity and hypoxia. Eur J Cancer 30A: 1013-1019
34. Seng F and Ley K (1972) Simple synthesis of 3-amino-1,2,4 benzotriazine 1,4-dioxide. Angew Chem Int XI, 1009-1010
35. Shephard EA, Palmer CN, Segall HJ and Phillips IR (1992) Quantification of cytochrome P450 reduclase gene expression in human tissues. Arch Biochcm Biophys 294: 168-172
36. Siim B, Van Zijl PL and Brown JM (1996) Tirapazamine-induced DNA damage measured using the comet assay correlates with cytotoxicity towards hypoxic tumour cells in vitro. Br J Cancer 73: 952-960
37. Silver AR and O'Neil P (1986) Interaction of the aziridine moiety of RSU-1069 with nucleotides and inorganic phosphate. Implications for alkylation of DNA. Biochem Pharmacol 35: 1107-1112
38. Stratford IJ and Stephens MA (1989) The differential hypoxic cytotoxicity of bioreductive agents determined in vitro by the MTT assay, Int J Radiat Oncol Biol Phys 16: 973-976
39. Stratford IJ. Walling JM and Silver ARJ (1986a) The differential cytotoxicity of RSU 1069: cell survival studies indicating interaction with DNA as a possible mode of action. Br J Cancer 53: 339-344
40. Stratford IJ. O'Neill P, Sheldon PW, Silver ARJ, Walling MJ and Adams GE (1986b) RSU 1069. a nitroimidazole containing an aziridine group. Bioreduction greatly increases cytotoxicity under hypoxic conditions. Biochem Pharmacol 35: 105-109
41. Van Den Hoff JB, Moorman FM and Lamers H (1992) Electroporation in 'intracellular' buffer increases cell survival. Nucl Acid Res 20: 2902
42. Walton MI and Workman P (1987) Nitroimidazole bioreductive metabolism. Quantitations and characterisation of mouse tissue benznidazole nitroreductases in vivo and in vitro. Biochem Pharmacol 36: 887-896
43. Walton MI and Workman P (1990) Enzymology of the reductive bioactivation of SR 4233: a novel benzotriazine di-N-oxide hypoxic cell cytotoxin. Biochem Pharmacol 39: 1735-1742
44. Walton MI, Wolf CR and Workman P(1989) Molecular enzymology of the reductive bioactivation of hypoxic cell cytotoxins. Int J Radiat Oncol Biol Phys 16: 983-986
45. Walton MI, Wolf CR and Workman P (1992) The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzoriazine Di-N-Oxide hypoxic cytotoxin 3-amino-1,2,4-henxotria/ine-1.4-dioxide (SR 4233. WIN 59075) by mouse liver. Biochem Pharmacol 44: 251-259
46. Wang J, Biedermann KA, Wolf CR and Crown JM (1993) Metabolism of the bioreductive cytotoxin SR 4233 by tumour cells: enzymatic studies. Br J Cancer 67: 321-325
47. Whitmore GF and Gulyas S (1986) Studies on the toxicity of RSU-1069. Int J Radiat Oncol Biol Phys 12: 1219-1222
48. Wilson JM, Johnston DE, Jefferson DM and Mulligan I (1988) Correction of the genetic defection hepatocytes from the Watanahe heritable hyperlipidemic rabbit. Proc Natl Acad Sci USA 85: 4421-4425
49. Workman P and Walton MI (1989) Enzyme-directed bioreductive drug development. In Selective activation of drugs by redox processes. Adams G, Breccia A, Fielden EM and Wardman P (eds) pp. 89-112. Plenum Press: New York
50. Workman P and Stratford IJ (1993) The experimental development of bioreductive drugs and their role in cancer therapy. Cancer Metastatis Rev 12: 73-82
51. Zeman EM, Brown JM, Lemmon MJ, Hirst VK and Lee WW (1986) SR4233: a new bioreductive agent with high selective toxicity for hypoxic mammalian cells. Int J Radiat Oncol Biol Phys 12: 1239-1242