메뉴 건너뛰기




Volumn 81, Issue 1, 2012, Pages 31-40

Diflavin oxidoreductases activate the bioreductive prodrug PR-104A under hypoxia

Author keywords

[No Author keywords available]

Indexed keywords

CARBONATE DEHYDRATASE IX; CYTOCHROME P450 REDUCTASE; DIFLAVIN OXIDOREDUCTASE; DIPHENYLIODONIUM SALT; FLAVOPROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INDUCIBLE NITRIC OXIDE SYNTHASE 2A; METHIONINE SYNTHASE REDUCTASE; NOVEL DIFLAVIN OXIDOREDUCTASE 1; OXIDOREDUCTASE; PR 104A; PRODRUG; UNCLASSIFIED DRUG;

EID: 84455170365     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.111.073759     Document Type: Article
Times cited : (56)

References (40)
  • 1
    • 0035882749 scopus 로고    scopus 로고
    • Involvement of NADPH:cytochrome P450 reductase in the activation of indoloquinone EO9 to free radical and DNA damaging species
    • Bailey SM, Lewis AD, Patterson LH, Fisher GR, Knox RJ, and Workman P (2001) Involvement of NADPH:cytochrome P450 reductase in the activation of indoloquinone EO9 to free radical and DNA damaging species. Biochem Pharmacol 62:461-468.
    • (2001) Biochem Pharmacol , vol.62 , pp. 461-468
    • Bailey, S.M.1    Lewis, A.D.2    Patterson, L.H.3    Fisher, G.R.4    Knox, R.J.5    Workman, P.6
  • 5
    • 58849153727 scopus 로고    scopus 로고
    • Design of anticancer prodrugs for reductive activation
    • Chen Y and Hu L (2009) Design of anticancer prodrugs for reductive activation. Med Res Rev 29:29-64.
    • (2009) Med Res Rev , vol.29 , pp. 29-64
    • Chen, Y.1    Hu, L.2
  • 6
    • 0038779269 scopus 로고    scopus 로고
    • Non-nuclear localized human NOSII enhances the bioactivation and toxicity of tirapazamine (SR4233) in vitro
    • DOI 10.1124/mol.63.6.1248
    • Chinje EC, Cowen RL, Feng J, Sharma SP, Wind NS, Harris AL, and Stratford IJ (2003) Non-nuclear localized human NOSII enhances the bioactivation and toxicity of tirapazamine (SR4233) in vitro. Mol Pharmacol 63:1248-1255. (Pubitemid 36627219)
    • (2003) Molecular Pharmacology , vol.63 , Issue.6 , pp. 1248-1255
    • Chinje, E.C.1    Cowen, R.L.2    Feng, J.3    Sharma, S.P.4    Wind, N.S.5    Harris, A.L.6    Stratford, I.J.7
  • 9
    • 33751089299 scopus 로고    scopus 로고
    • Oxygen levels in normal and previously irradiated human skin as assessed by EF5 binding
    • DOI 10.1038/sj.jid.5700451, PII 5700451
    • Evans SM, Schrlau AE, Chalian AA, Zhang P, and Koch CJ (2006) Oxygen levels in normal and previously irradiated human skin as assessed by EF5 binding. J Invest Dermatol 126:2596-2606. (Pubitemid 44764043)
    • (2006) Journal of Investigative Dermatology , vol.126 , Issue.12 , pp. 2596-2606
    • Evans, S.M.1    Schrlau, A.E.2    Chalian, A.A.3    Zhang, P.4    Koch, C.J.5
  • 10
    • 0029917028 scopus 로고    scopus 로고
    • Reductase enzyme expression across the National Cancer Institute Tumor Cell Line Panel: Correlation with sensitivity to mitomycin C and EO9
    • Fitzsimmons SA, Workman P, Grever M, Paull K, Camalier R, and 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.
    • (1996) J Natl Cancer Inst , vol.88 , pp. 259-269
    • Fitzsimmons, S.A.1    Workman, P.2    Grever, M.3    Paull, K.4    Camalier, R.5    Lewis, A.D.6
  • 11
    • 0034902347 scopus 로고    scopus 로고
    • Expression of DT-diaphorase and cytochrome P450 reductase correlates with mitomycin C activity in human bladder tumors
    • Gan Y, Mo Y, Kalns JE, Lu J, Danenberg K, Danenberg P, Wientjes MG, and Au JL (2001) Expression of DT-diaphorase and cytochrome P450 reductase correlates with mitomycin C activity in human bladder tumors. Clin Cancer Res 7:1313-1319. (Pubitemid 32708686)
    • (2001) Clinical Cancer Research , vol.7 , Issue.5 , pp. 1313-1319
    • Gan, Y.1    Mo, Y.2    Kalns, J.E.3    Lu, J.4    Danenberg, K.5    Danenberg, P.6    Wientjes, M.G.7    Au, J.L.-S.8
  • 13
    • 67649354921 scopus 로고    scopus 로고
    • Roles of DNA repair and reductase activity in the cytotoxicity of the hypoxia-activated dinitrobenzamide mustard PR-104A
    • Gu Y, Patterson AV, Atwell GJ, Chernikova SB, Brown JM, Thompson LH, and Wilson WR (2009) Roles of DNA repair and reductase activity in the cytotoxicity of the hypoxia-activated dinitrobenzamide mustard PR-104A. Mol Cancer Ther 8:1714-1723.
    • (2009) Mol Cancer Ther , vol.8 , pp. 1714-1723
    • Gu, Y.1    Patterson, A.V.2    Atwell, G.J.3    Chernikova, S.B.4    Brown, J.M.5    Thompson, L.H.6    Wilson, W.R.7
  • 14
    • 79956220572 scopus 로고    scopus 로고
    • Glucuronidation of anticancer prodrug PR-104A: Species differences, identification of human UDP-glucuronosyltransferases, and implications for therapy
    • Gu Y, Tingle MD, and Wilson WR (2011b) Glucuronidation of anticancer prodrug PR-104A: species differences, identification of human UDP-glucuronosyltransferases, and implications for therapy. J Pharmacol Exp Ther 337:692-702.
    • (2011) J Pharmacol Exp Ther , vol.337 , pp. 692-702
    • Gu, Y.1    Tingle, M.D.2    Wilson, W.R.3
  • 16
    • 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
    • Guise CP, Wang AT, Theil A, Bridewell DJ, Wilson WR, and Patterson AV (2007) Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: a role for NADPH:cytochrome P450 oxidoreductase under hypoxia. Biochem Pharmacol 74:810-820.
    • (2007) Biochem Pharmacol , vol.74 , 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
  • 17
    • 0024519596 scopus 로고
    • Immunohistochemical localization of NADPH-cytochrome P450 reductase in human tissues
    • Hall PM, Stupans I, Burgess W, Birkett DJ, and McManus ME (1989) Immunohistochemical Localization of NADPH-Cytochrome P450 Reductase in Human Tissues. Carcinogenesis 10:521-530. (Pubitemid 19089919)
    • (1989) Carcinogenesis , vol.10 , Issue.3 , pp. 521-530
    • De La, H.M.P.1    Stupans, I.2    Burgess, W.3    Birkett, D.J.4    McManus, M.E.5
  • 18
    • 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, Hogg A, Liyanage HD, Dorie MJ, Brown JM, et al. (2010) Pharmacokinetic/pharmacodynamic modeling identifies SN30000 and SN29751 as tirapazamine analogues with improved tissue penetration and hypoxic cell killing in tumors. Clin Cancer Res 16:4946-4957.
    • (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    Hogg, A.7    Liyanage, H.D.8    Dorie, M.J.9    Brown, J.M.10
  • 20
    • 75749084473 scopus 로고    scopus 로고
    • A phase I trial of PR-104, a nitrogen mustard prodrug activated by both hypoxia and aldo-keto reductase 1C3, in patients with solid tumors
    • Jameson MB, Rischin D, Pegram M, Gutheil J, Patterson AV, Denny WA, and Wilson WR (2010) A phase I trial of PR-104, a nitrogen mustard prodrug activated by both hypoxia and aldo-keto reductase 1C3, in patients with solid tumors. Cancer Chemother Pharmacol 65:791-801.
    • (2010) Cancer Chemother Pharmacol , vol.65 , pp. 791-801
    • Jameson, M.B.1    Rischin, D.2    Pegram, M.3    Gutheil, J.4    Patterson, A.V.5    Denny, W.A.6    Wilson, W.R.7
  • 21
    • 62749124795 scopus 로고    scopus 로고
    • Transcriptional control of the tumor- And hypoxia-marker carbonic anhydrase 9: A one transcription factor (HIF-1) show?
    • Kaluz S, Kaluzová M, Liao SY, Lerman M, and Stanbridge EJ (2009) Transcriptional control of the tumor- and hypoxia-marker carbonic anhydrase 9: a one transcription factor (HIF-1) show? Biochim Biophys Acta 1795:162-172.
    • (2009) Biochim Biophys Acta , vol.1795 , pp. 162-172
    • Kaluz, S.1    Kaluzová, M.2    Liao, S.Y.3    Lerman, M.4    Stanbridge, E.J.5
  • 22
    • 33746886623 scopus 로고    scopus 로고
    • "Translating" tumor hypoxia: Unfolded protein response (UPR)-dependent and UPR-independent pathways
    • DOI 10.1158/1541-7786.MCR-06-0150
    • Koumenis C and Wouters BG (2006) "Translating" tumor hypoxia: unfolded protein response (UPR)-dependent and UPR-independent pathways. Mol Cancer Res 4:423-436. (Pubitemid 44197038)
    • (2006) Molecular Cancer Research , vol.4 , Issue.7 , pp. 423-436
    • Koumenis, C.1    Wouters, B.G.2
  • 23
    • 0344573107 scopus 로고    scopus 로고
    • Differential redox and electrontransfer properties of purified yeast, plant and human NADPH-cytochrome P-450 reductases highly modulate cytochrome P-450 activities
    • Louërat-Oriou B, Perret A, and Pompon D (1998) Differential redox and electrontransfer properties of purified yeast, plant and human NADPH-cytochrome P-450 reductases highly modulate cytochrome P-450 activities. Eur J Biochem 258:1040-1049.
    • (1998) Eur J Biochem , vol.258 , pp. 1040-1049
    • Louërat-Oriou, B.1    Perret, A.2    Pompon, D.3
  • 24
    • 0034857992 scopus 로고    scopus 로고
    • Diphenyleneiodonium inhibits NF- ≲καππα∀B activation and INOS expression induced by IL-1β: Involvement of reactive oxygen species
    • Mendes AF, Carvalho AP, Caramona MM, and Lopes MC (2001) Diphenyleneiodonium inhibits NF-≲καππα∀B activation and INOS expression induced by IL-1β: involvement of reactive oxygen species. Mediators Inflamm 10:209-215.
    • (2001) Mediators Inflamm , vol.10 , pp. 209-215
    • Mendes, A.F.1    Carvalho, A.P.2    Caramona, M.M.3    Lopes, M.C.4
  • 26
    • 0028104549 scopus 로고
    • Involvement of phenyl radicals in iodonium inhibition of flavoenzymes
    • O'Donnell VB, Smith GC, and Jones OT (1994) Involvement of phenyl radicals in iodonium inhibition of flavoenzymes. Mol Pharmacol 46:778-785.
    • (1994) Mol Pharmacol , vol.46 , pp. 778-785
    • O'Donnell, V.B.1    Smith, G.C.2    Jones, O.T.3
  • 27
    • 0141643321 scopus 로고    scopus 로고
    • Redundancy in the pathway for redox regulation of mammalian methionine synthase. Reductive activation by the dual flavoprotein, novel reductase 1
    • DOI 10.1074/jbc.M306282200
    • Olteanu H and Banerjee R (2003) Redundancy in the pathway for redox regulation of mammalian methionine synthase: reductive activation by the dual flavoprotein, novel reductase 1. J Biol Chem 278:38310-38314. (Pubitemid 37221722)
    • (2003) Journal of Biological Chemistry , vol.278 , Issue.40 , pp. 38310-38314
    • Olteanu, H.1    Banerjee, R.2
  • 28
    • 0345356572 scopus 로고    scopus 로고
    • Reductive Metabolism of the Nitroimidazole-Based Hypoxia-Selective Cytotoxin NLCQ-1 (NSC 709257)
    • Papadopoulou MV, Ji M, Rao MK, and Bloomer WD (2003) Reductive metabolism of the nitroimidazole-based hypoxia-selective cytotoxin NLCQ-1 (NSC 709257). Oncol Res 14:21-29. (Pubitemid 38166341)
    • (2003) Oncology Research , vol.14 , Issue.1 , pp. 21-29
    • Papadopoulou, M.V.1    Ji, M.2    Rao, M.K.3    Bloomer, W.D.4
  • 31
    • 0034543132 scopus 로고    scopus 로고
    • AQ4N: A new approach to hypoxia-activated cancer chemotherapy
    • DOI 10.1054/bjoc.2000.1564
    • Patterson LH and McKeown SR (2000) AQ4N: a new approach to hypoxia-activated cancer chemotherapy. Br J Cancer 83:1589-1593. (Pubitemid 32001698)
    • (2000) British Journal of Cancer , vol.83 , Issue.12 , pp. 1589-1593
    • Patterson, L.H.1    McKeown, S.R.2
  • 33
    • 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, Trotti A, Bernier J, Bourhis J, Ringash J, et al. (2010) 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 28:2989-2995.
    • (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    Trotti, A.7    Bernier, J.8    Bourhis, J.9    Ringash, J.10
  • 34
    • 65949102556 scopus 로고    scopus 로고
    • DNA cross-links in human tumor cells exposed to the prodrug PR-104A: Relationships to hypoxia, bioreductive metabolism, and cytotoxicity
    • Singleton RS, Guise CP, Ferry DM, Pullen SM, Dorie MJ, Brown JM, Patterson AV, and Wilson WR (2009) DNA cross-links in human tumor cells exposed to the prodrug PR-104A: relationships to hypoxia, bioreductive metabolism, and cytotoxicity. Cancer Res 69:3884-3891.
    • (2009) Cancer Res , vol.69 , pp. 3884-3891
    • Singleton, R.S.1    Guise, C.P.2    Ferry, D.M.3    Pullen, S.M.4    Dorie, M.J.5    Brown, J.M.6    Patterson, A.V.7    Wilson, W.R.8
  • 35
    • 33947713013 scopus 로고    scopus 로고
    • Pregnancy-promoting actions of HCG in human myometrium and fetal membranes
    • Ticconi C, Zicari A, Belmonte A, Realacci M, Rao ChV, and Piccione E (2007) Pregnancy-promoting actions of HCG in human myometrium and fetal membranes. Placenta 28 (Suppl A):S137-S143.
    • (2007) Placenta , vol.28 , Issue.SUPPL. A
    • Ticconi, C.1    Zicari, A.2    Belmonte, A.3    Realacci, M.4    Rao, C.5    Piccione, E.6
  • 37
    • 34547121206 scopus 로고    scopus 로고
    • Hypoxia in cancer: Significance and impact on clinical outcome
    • DOI 10.1007/s10555-007-9055-1, Special issue on Hypoxia and Cancer, Guest Editor: Gregg L. Semenza
    • Vaupel P and Mayer A (2007) Hypoxia in cancer: significance and impact on clinical outcome. Cancer Metastasis Rev 26:225-239. (Pubitemid 47101660)
    • (2007) Cancer and Metastasis Reviews , vol.26 , Issue.2 , pp. 225-239
    • Vaupel, P.1    Mayer, A.2
  • 39
    • 79957534572 scopus 로고    scopus 로고
    • Targeting hypoxia in cancer therapy
    • Wilson WR and Hay MP (2011) Targeting hypoxia in cancer therapy. Nat Rev Cancer 11:393-410.
    • (2011) Nat Rev Cancer , vol.11 , pp. 393-410
    • Wilson, W.R.1    Hay, M.P.2
  • 40
    • 0027328452 scopus 로고
    • The experimental development of bioreductive drugs and their role in cancer therapy
    • Workman P and Stratford IJ (1993) The experimental development of bioreductive drugs and their role in cancer therapy. Cancer Metastasis Rev 12:73-82. (Pubitemid 23220673)
    • (1993) Cancer and Metastasis Reviews , vol.12 , Issue.2 , pp. 73-82
    • Workman, P.1    Stratford, I.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.