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Volumn 18, Issue 6, 2012, Pages 1684-1695

The 2-nitroimidazole EF5 is a biomarker for oxidoreductases that activate the bioreductive prodrug CEN-209 under hypoxia

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 NITRO 1H IMIDAZOL 1 YL) N (2,2,3,3,3 PENTAFLUOROPROPYL)ACETAMIDE; ANTINEOPLASTIC AGENT; CEN 209; DNA; GAMMA HISTONE H2AX; HISTONE H2AX; OXYGEN; PRODRUG; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE FERRIHEMOPROTEIN REDUCTASE; SN 30000; TIRAPAZAMINE; UNCLASSIFIED DRUG;

EID: 84863229621     PISSN: 10780432     EISSN: 15573265     Source Type: Journal    
DOI: 10.1158/1078-0432.CCR-11-2296     Document Type: Article
Times cited : (58)

References (51)
  • 1
    • 79957534572 scopus 로고    scopus 로고
    • Targeting hypoxia in cancer therapy
    • Wilson WR, Hay MP. Targeting hypoxia in cancer therapy. Nat Rev Cancer 2011;11:393-410.
    • (2011) Nat Rev Cancer , vol.11 , pp. 393-410
    • Wilson, W.R.1    Hay, M.P.2
  • 2
    • 79954582454 scopus 로고    scopus 로고
    • Hypoxia predicts aggressive growth and spontaneous metastasis formation from orthotopically grown primary xenografts of human pancreatic cancer
    • Chang Q, Jurisica I, Do T, Hedley DW. Hypoxia predicts aggressive growth and spontaneous metastasis formation from orthotopically grown primary xenografts of human pancreatic cancer. Cancer Res 2011;71:3110-20.
    • (2011) Cancer Res , vol.71 , pp. 3110-3120
    • Chang, Q.1    Jurisica, I.2    Do, T.3    Hedley, D.W.4
  • 4
    • 77949697909 scopus 로고    scopus 로고
    • Inhibition of vasculogenesis, but not angiogenesis, prevents the recurrence of glioblastoma after irradiation in mice
    • Kioi M, Vogel H, Schultz G, Hoffman RM, Harsh GR, Brown JM. Inhibition of vasculogenesis, but not angiogenesis, prevents the recurrence of glioblastoma after irradiation in mice. J Clin Invest 2010; 120:694-705.
    • (2010) J Clin Invest , vol.120 , pp. 694-705
    • Kioi, M.1    Vogel, H.2    Schultz, G.3    Hoffman, R.M.4    Harsh, G.R.5    Brown, J.M.6
  • 5
    • 0030025773 scopus 로고    scopus 로고
    • Hypoxia-mediated selection of cells with diminished apoptotic potential in solid tumours
    • DOI 10.1038/379088a0
    • Graeber TG, Osmanian C, Jacks T, Housman DE, Koch CJ, Lowe SW, et al. Hypoxia-mediated selection of cells with diminished apoptotic potential in solid tumours. Nature 1996;379:88-91. (Pubitemid 26008141)
    • (1996) Nature , vol.379 , Issue.6560 , pp. 88-91
    • Graeber, T.G.1    Osmanian, C.2    Jacks, T.3    Housman, D.E.4    Koch, C.J.5    Lowe, S.W.6    Giaccia, A.J.7
  • 7
    • 33846697957 scopus 로고    scopus 로고
    • Hypoxia-induced genetic instability - A calculated mechanism underlying tumor progression
    • DOI 10.1007/s00109-006-0133-6
    • Huang LE, Bindra RS, Glazer PM, Harris AL. Hypoxia-induced genetic instability-a calculated mechanism underlying tumor progression. J Mol Med 2007;85:139-48. (Pubitemid 46188219)
    • (2007) Journal of Molecular Medicine , vol.85 , Issue.2 , pp. 139-148
    • Huang, L.E.1    Bindra, R.S.2    Glazer, P.M.3    Harris, A.L.4
  • 8
    • 0027288316 scopus 로고
    • 4233 (tirapazamine): A new anticancer drug exploiting hypoxia in solid tumours
    • Brown JM. SR 4233 (tirapazamine): a new anticancer drug exploiting hypoxia in solid tumours. Br J Cancer 1993;67:1163-70.
    • (1993) Br J Cancer , vol.67 , pp. 1163-1170
    • Brown Sr., J.M.1
  • 9
    • 67649380881 scopus 로고    scopus 로고
    • Tirapazamine: A novel agent targeting hypoxic tumor cells
    • Reddy SB, Williamson SK. Tirapazamine: a novel agent targeting hypoxic tumor cells. Exp Opinion Invest Drugs 2009;18:77-87.
    • (2009) Exp Opinion Invest Drugs , vol.18 , pp. 77-87
    • Reddy, S.B.1    Williamson, S.K.2
  • 10
    • 70349921764 scopus 로고    scopus 로고
    • Spin trapping of radicals other than the*OH radical upon reduction of the anticancer agent tirapazamine by cytochrome P450 reductase
    • Shinde SS, Hay MP, Patterson AV, Denny WA, Anderson RF. Spin trapping of radicals other than the*OH radical upon reduction of the anticancer agent tirapazamine by cytochrome P450 reductase. J Am Chem Soc 2009;131:14220-1.
    • (2009) J Am Chem Soc , vol.131 , pp. 14220-14221
    • Shinde, S.S.1    Hay, M.P.2    Patterson, A.V.3    Denny, W.A.4    Anderson, R.F.5
  • 11
    • 0031306970 scopus 로고    scopus 로고
    • DNA damage from oxidants: Influence of lesion complexity and chromatin organization
    • Olive PL, Johnston PJ. DNA damage from oxidants: influence of lesion complexity and chromatin organization. Oncol Res 1997;9:287-94. (Pubitemid 127825982)
    • (1997) Oncology Research , vol.9 , Issue.6-7 , pp. 287-294
    • Olive, P.L.1    Johnston, P.J.2
  • 13
    • 0141507967 scopus 로고    scopus 로고
    • Multicellular resistance to tirapazamine is due to restricted extravascular transport: A pharmacokinetic/pharmacodynamic study in HT29 multicellular layer cultures
    • Hicks KO, Pruijn FB, Sturman JR, Denny WA, Wilson WR. Multicellular resistance to tirapazamine is due to restricted extravascular transport: a pharmacokinetic/pharmacodynamic study inHT29 multicellular layer cultures. Cancer Res 2003;63:5970-7. (Pubitemid 37187499)
    • (2003) Cancer Research , vol.63 , Issue.18 , pp. 5970-5977
    • Hicks, K.O.1    Pruijn, F.B.2    Sturman, J.R.3    Denny, W.A.4    Wilson, W.R.5
  • 15
    • 77958060317 scopus 로고    scopus 로고
    • Pharmacokinetic/pharmacodynamic modeling identifies SN30000 and SN29751 as tirapazamine analogues with improved tissue penetration and hypoxic cell killing in tumors
    • Hicks KO, Siim BG, Jaiswal JK, Pruijn FB, Fraser AM, Patel R, et al. Pharmacokinetic/pharmacodynamic modeling identifies SN30000 and SN29751 as tirapazamine analogues with improved tissue penetration and hypoxic cell killing in tumors. Clin Cancer Res 2010; 16:4946-57.
    • (2010) Clin Cancer Res , vol.16 , pp. 4946-4957
    • Hicks, K.O.1    Siim, B.G.2    Jaiswal, J.K.3    Pruijn, F.B.4    Fraser, A.M.5    Patel, R.6
  • 16
    • 34447506424 scopus 로고    scopus 로고
    • 2 histography
    • DOI 10.1089/ars.2007.1628
    • Vaupel P, Hockel M, Mayer A. Detection and characterization of tumor hypoxia using pO2 histography. Antioxid Redox Signal 2007;9: 1221-35. (Pubitemid 47080831)
    • (2007) Antioxidants and Redox Signaling , vol.9 , Issue.8 , pp. 1221-1235
    • Vaupel, P.1    Hockel, M.2    Mayer, A.3
  • 17
    • 77954600498 scopus 로고    scopus 로고
    • Tirapazamine, cisplatin, and radiation versus cisplatin and radiation for advanced squamous cell carcinoma of the head and neck (TROG 02.02, HeadSTART): A phase III trial of the Trans-Tasman Radiation Oncology Group
    • Rischin D, Peters LJ, O'Sullivan B, Giralt J, Fisher R, Yuen K, et al. Tirapazamine, cisplatin, and radiation versus cisplatin and radiation for advanced squamous cell carcinoma of the head and neck (TROG 02.02, HeadSTART): A phase III trial of the Trans-Tasman Radiation Oncology Group. J Clin Oncol 2010;28:2989-95.
    • (2010) J Clin Oncol , vol.28 , pp. 2989-2995
    • Rischin, D.1    Peters, L.J.2    O'Sullivan, B.3    Giralt, J.4    Fisher, R.5    Yuen, K.6
  • 18
    • 33646454133 scopus 로고    scopus 로고
    • 18F]-misonidazole positron emission tomography-detected tumor hypoxia in patients with advanced head and neck cancer randomly assigned to chemoradiation with or without tirapazamine: A substudy of Trans-Tasman Radiation Oncology Group study 98.02
    • DOI 10.1200/JCO.2005.05.2878
    • Rischin D, Hicks RJ, Fisher R, Binns D, Corry J, Porceddu S, et al. Prognostic significance of [18F]-misonidazole positron emission tomography-detected tumor hypoxia in patients with advanced head and neck cancer randomly assigned to chemoradiation with or without tirapazamine: a substudy of Trans-Tasman Radiation Oncology Group Study 98.02. J Clin Oncol 2006;24:2098-104. (Pubitemid 46622121)
    • (2006) Journal of Clinical Oncology , vol.24 , Issue.13 , pp. 2098-2104
    • Rischin, D.1    Hicks, R.J.2    Fisher, R.3    Binns, D.4    Corry, J.5    Porceddu, S.6    Peters, L.J.7
  • 19
    • 0025285228 scopus 로고
    • Characteristics of the binding of labeled fluoromisonidazole in cells in vitro
    • DOI 10.2307/3577760
    • Rasey JS, Nelson NJ, Chin L, Evans ML, Grunbaum Z. Characteristics of the binding of labeled fluoromisonidazole in cells in vitro. Radiat Res 1990;122:301-8. (Pubitemid 20214420)
    • (1990) Radiation Research , vol.122 , Issue.3 , pp. 301-308
    • Rasey, J.S.1    Nelson, N.J.2    Chin, L.3    Evans, M.L.4    Grunbaum, Z.5
  • 25
    • 77958466808 scopus 로고    scopus 로고
    • Biodistribution and dosimetry of (18)F-EF5 in cancer patients with preliminary comparison of (18)F-EF5 uptake versus EF5 binding in human glioblastoma
    • Koch CJ, Scheuermann JS, Divgi C, Judy KD, Kachur AV, Freifelder R, et al. Biodistribution and dosimetry of (18)F-EF5 in cancer patients with preliminary comparison of (18)F-EF5 uptake versus EF5 binding in human glioblastoma. Eur J Nucl Med Mol Imaging 2010;37:2048-59.
    • (2010) Eur J Nucl Med Mol Imaging , vol.37 , pp. 2048-2059
    • Koch, C.J.1    Scheuermann, J.S.2    Divgi, C.3    Judy, K.D.4    Kachur, A.V.5    Freifelder, R.6
  • 27
    • 44849127313 scopus 로고    scopus 로고
    • Importance of antibody concentration in the assessment of cellular hypoxia by flow cytometry: EF5 and pimonidazole
    • DOI 10.1667/RR1305.1
    • Koch CJ. Importance of antibody concentration in the assessment of cellular hypoxia by flow cytometry: EF5 and pimonidazole. Radiat Res 2008;169:677-88. (Pubitemid 351793457)
    • (2008) Radiation Research , vol.169 , Issue.6 , pp. 677-688
    • Koch, C.J.1
  • 29
    • 0026642263 scopus 로고
    • The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino-1,2,4-benzotriazine- 1,4-dioxide (SR 4233, WIN 59075) by mouse liver
    • Walton MI, Wolf CR, Workman P. The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino-1,2,4-benzotriazine- 1,4-dioxide (SR 4233, WIN 59075) by mouse liver. Biochem Pharmacol 1992;44:251-9.
    • (1992) Biochem Pharmacol , vol.44 , pp. 251-259
    • Walton, M.I.1    Wolf, C.R.2    Workman, P.3
  • 31
    • 34547653834 scopus 로고    scopus 로고
    • Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: A role for NADPH:cytochrome P450 oxidoreductase under hypoxia
    • DOI 10.1016/j.bcp.2007.06.014, PII S0006295207003759
    • Guise CP, Wang A, Thiel A, Bridewell D, Wilson WR, Patterson AV. Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: a role for NADPH:cytochrome P450 oxidoreductase under hypoxia. Biochem Pharmacol 2007;74:810-20. (Pubitemid 47212075)
    • (2007) Biochemical Pharmacology , vol.74 , Issue.6 , pp. 810-820
    • Guise, C.P.1    Wang, A.T.2    Theil, A.3    Bridewell, D.J.4    Wilson, W.R.5    Patterson, A.V.6
  • 33
    • 0028839715 scopus 로고
    • Oxygen dependence of cellular uptake of EF5 [2-(2-nitro-1H-imidazol-1-yl) -N-(2,2,3,3,3-pentafluoropropyl)a cet amide]: Analysis of drug adducts by fluorescent antibodies vs bound radioactivity
    • Koch CJ, Evans SM, Lord EM. Oxygen dependence of cellular uptake of EF5 [2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)a cet amide]: analysis of drug adducts by fluorescent antibodies vs bound radioactivity. Br J Cancer 1995;72:869-74.
    • (1995) Br J Cancer , vol.72 , pp. 869-874
    • Koch, C.J.1    Evans, S.M.2    Lord, E.M.3
  • 35
    • 76749161362 scopus 로고    scopus 로고
    • The bioreductive prodrug PR-104A is activated under aerobic conditions by human aldo-keto reductase 1C3
    • Guise CP, Abbattista M, Singleton RS, Holford SD, Connolly J, Dachs GU, et al. The bioreductive prodrug PR-104A is activated under aerobic conditions by human aldo-keto reductase 1C3. Cancer Res 2010;70:1573-84.
    • (2010) Cancer Res , vol.70 , pp. 1573-1584
    • Guise, C.P.1    Abbattista, M.2    Singleton, R.S.3    Holford, S.D.4    Connolly, J.5    Dachs, G.U.6
  • 37
    • 0032544921 scopus 로고    scopus 로고
    • Development of a bicistronic vector driven by the human polypeptide chain elongation factor 1alpha promoter for creation of stable mammalian cell lines that express very high levels of recombinant proteins
    • DOI 10.1006/bbrc.1998.9646
    • Hobbs S, Jitrapakdee S, Wallace JC. Development of a bicistronic vector driven by the human polypeptide chain elongation factor 1alpha promoter for creation of stable mammalian cell lines that express very high levels of recombinant proteins. Biochem Biophys Res Commun 1998;252:368-72. (Pubitemid 28542893)
    • (1998) Biochemical and Biophysical Research Communications , vol.252 , Issue.2 , pp. 368-372
    • Hobbs, S.1    Jitrapakdee, S.2    Wallace, J.C.3
  • 38
    • 0014714807 scopus 로고
    • Factors affecting the oxygen tension around cells growing in plastic petri dishes
    • Chapman JD, Sturrock J, Boag JW, Crookall JO. Factors affecting the oxygen tension around cells growing in plastic petri dishes. Int J Radiat Biol 1970;17:305-28.
    • (1970) Int J Radiat Biol , vol.17 , pp. 305-328
    • Chapman, J.D.1    Sturrock, J.2    Boag, J.W.3    Crookall, J.O.4
  • 39
    • 34548140058 scopus 로고    scopus 로고
    • Analysis of the hypoxia-activated dinitrobenzamide mustard phosphate pre-prodrug PR-104 and its alcohol metabolite PR-104A in plasma and tissues by liquid chromatography-mass spectrometry
    • DOI 10.1016/j.jchromb.2007.06.035, PII S1570023207004552
    • Patel K, Lewiston D, Gu Y, Hicks KO, Wilson WR. Analysis of the hypoxia-activated dinitrobenzamide mustard phosphate prodrug PR- 104 and its alcohol metabolite PR-104A in plasma and tissues by liquidchromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 2007;856:302-11. (Pubitemid 47302931)
    • (2007) Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences , vol.856 , Issue.1-2 , pp. 302-311
    • Patel, K.1    Lewiston, D.2    Gu, Y.3    Hicks, K.O.4    Wilson, W.R.5
  • 40
    • 0030692717 scopus 로고    scopus 로고
    • Overexpression of human NADPH:cytochrome c (P450) reductase confers enhanced sensitivity to both tirapazamine (SR 4233) and RSU 1069
    • Patterson AV, SaundersMP, Chinje EC, Talbot DC, Harris AL, Stratford IJ. Overexpression of human NADPH:cytochrome c (P450) reductase confers enhanced sensitivity to both tirapazamine (SR 4233) and RSU 1069. Br J Cancer 1997;76:1338-47. (Pubitemid 27474977)
    • (1997) British Journal of Cancer , vol.76 , Issue.10 , pp. 1338-1347
    • Patterson, A.V.1    Saunders, M.P.2    Chinje, E.C.3    Talbot, D.C.4    Harris, A.L.5    Stratford, I.J.6
  • 41
    • 0345835371 scopus 로고    scopus 로고
    • Expression of phosphorylated histone H2AX as a surrogate of cell killing by drugs that create DNA double-strand breaks
    • Banath JP, Olive PL. Expression of phosphorylated histone H2AX as a surrogate of cell killing by drugs that createDNAdouble-strand breaks. Cancer Res 2003;63:4347-50. (Pubitemid 36951002)
    • (2003) Cancer Research , vol.63 , Issue.15 , pp. 4347-4350
    • Banath, J.P.1    Olive, P.L.2
  • 42
    • 3442889371 scopus 로고    scopus 로고
    • Phosphorylated histone H2AX in spheroids, tumors, and tissues of mice exposed to etoposide and 3-amino-1,2,4-benzotriazine-1,3-dioxide
    • DOI 10.1158/0008-5472.CAN-04-0729
    • Olive PL, Banath JP, Sinnott LT. Phosphorylated histone H2AX in spheroids, tumors, and tissues of mice exposed to etoposide and 3- amino-1,2,4-benzotriazine-1,3-dioxide. Cancer Res 2004;64:5363-9. (Pubitemid 39006557)
    • (2004) Cancer Research , vol.64 , Issue.15 , pp. 5363-5369
    • Olive, P.L.1    Banath, J.P.2    Sinnott, L.T.3
  • 44
  • 45
    • 0028867912 scopus 로고
    • Importance of P450 reductase activity in determining sensitivity of breast tumour cells to the bioreductive drug, tirapazamine (SR 4233)
    • Patterson AV, Barham HM, Chinje EC, Adams GE, Harris AL, Stratford IJ. Importance of P450 reductase activity in determining sensitivity of breast tumour cells to the bioreductive drug, tirapazamine (SR 4233). Br J Cancer 1995;72:1144-50.
    • (1995) Br J Cancer , vol.72 , pp. 1144-1150
    • Patterson, A.V.1    Barham, H.M.2    Chinje, E.C.3    Adams, G.E.4    Harris, A.L.5    Stratford, I.J.6
  • 47
    • 0031661074 scopus 로고    scopus 로고
    • Bioreductive drugs into the next millennium
    • Stratford IJ, Workman P. Bioreductive drugs into the next millennium. Anticancer Drug Des 1998;13:519-28. (Pubitemid 28410146)
    • (1998) Anti-Cancer Drug Design , vol.13 , Issue.6 , pp. 519-528
    • Stratford, I.J.1    Workman, P.2
  • 48
    • 37549005208 scopus 로고    scopus 로고
    • Detection of reactive oxygen species via endogenous oxidative pentose phosphate cycle activity in response to oxygen concentration
    • Tuttle SW, Maity A, Oprysko PR, Kachur AV, Ayene IS, Biaglow JE, et al. Detection of reactive oxygen species via endogenous oxidative pentose phosphate cycle activity in response to oxygen concentration. J Biol Chem 2007;282:36790-6.
    • (2007) J Biol Chem , vol.282 , pp. 36790-36796
    • Tuttle, S.W.1    Maity, A.2    Oprysko, P.R.3    Kachur, A.V.4    Ayene, I.S.5    Biaglow, J.E.6
  • 49
    • 0030871773 scopus 로고    scopus 로고
    • Tirapazamine-induced cytotoxicity and DNA damage in transplanted tumors: Relationship to tumor hypoxia
    • Siim BG, Menke DR, Dorie MJ, Brown JM. Tirapazamine-induced cytotoxicity and DNA damage in transplanted tumors: relationship to tumor hypoxia. Cancer Res 1997;57:2922-8. (Pubitemid 27315040)
    • (1997) Cancer Research , vol.57 , Issue.14 , pp. 2922-2928
    • Siim, B.G.1    Menke, D.R.2    Dorie, M.J.3    Martin, B.J.4
  • 51
    • 84856111945 scopus 로고    scopus 로고
    • Homologous recombination repair cytotoxicity of the benzotriazine di-N-oxide CEN-209: Comparison with other hypoxia-activated prodrugs
    • in press; doi 10.1016/j.bcp. 2011.12.005
    • Hunter FW, Wang J, Patel R, Hsu H-L, Hickey AJR, Hay MP, et al. Homologous recombination repair cytotoxicity of the benzotriazine di-N-oxide CEN-209: comparison with other hypoxia-activated prodrugs. Biochem Pharmacol in press; doi 10.1016/j.bcp. 2011.12.005.
    • Biochem Pharmacol
    • Hunter, F.W.1    Wang, J.2    Patel, R.3    Hsu, H.-L.4    Hickey, A.J.R.5    Hay, M.P.6


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