메뉴 건너뛰기




Volumn 70, Issue 4, 2010, Pages 1573-1584

The bioreductive prodrug PR-104A is activated under aerobic conditions by human aldo-keto reductase 1C3

Author keywords

[No Author keywords available]

Indexed keywords

ALDO KETO REDUCTASE 1C3; DNA; NITROREDUCTASE; ORGANOPHOSPHATE; OXYGEN; PR 104A; PRODRUG; UNCLASSIFIED DRUG;

EID: 76749161362     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-09-3237     Document Type: Article
Times cited : (148)

References (44)
  • 1
    • 1242319559 scopus 로고    scopus 로고
    • NAD(P)H:quinone oxidoreductase 1 (NQO1, DTdiaphorase), functions and pharmacogenetics
    • Ross D, Siegel D. NAD(P)H:quinone oxidoreductase 1 (NQO1, DTdiaphorase), functions and pharmacogenetics. Methods Enzymol 2004;382:115-44.
    • (2004) Methods Enzymol , vol.382 , pp. 115-144
    • Ross, D.1    Siegel, D.2
  • 2
    • 1242319551 scopus 로고    scopus 로고
    • Quinone reductase-mediated nitro-reduction: Clinical applications
    • Knox RJ, Chen S. Quinone reductase-mediated nitro-reduction: clinical applications. Methods Enzymol 2004;382:194-221.
    • (2004) Methods Enzymol , vol.382 , pp. 194-221
    • Knox, R.J.1    Chen, S.2
  • 3
    • 58149389528 scopus 로고    scopus 로고
    • Imaging of tumor hypoxia to predict treatment sensitivity
    • Minn H, Gronroos TJ, Komar G, et al. Imaging of tumor hypoxia to predict treatment sensitivity. Curr Pharm Des 2008;14:2932-42.
    • (2008) Curr Pharm Des , vol.14 , pp. 2932-2942
    • Minn, H.1    Gronroos, T.J.2    Komar, G.3
  • 4
    • 58849153727 scopus 로고    scopus 로고
    • Design of anticancer prodrugs for reductive activation
    • Chen Y, Hu L. Design of anticancer prodrugs for reductive activation. Med Res Rev 2008;29:29-64.
    • (2008) Med Res Rev , vol.29 , pp. 29-64
    • Chen, Y.1    Hu, L.2
  • 5
    • 2942590732 scopus 로고    scopus 로고
    • Exploiting tumor hypoxia in cancer treatment
    • Brown JM, Wilson WR. Exploiting tumor hypoxia in cancer treatment. Nat Rev Cancer 2004;4:437-47.
    • (2004) Nat Rev Cancer , vol.4 , pp. 437-447
    • Brown, J.M.1    Wilson, W.R.2
  • 6
    • 34547121206 scopus 로고    scopus 로고
    • Hypoxia in cancer: Significance and impact on clinical outcome
    • Vaupel P, Mayer A. Hypoxia in cancer: significance and impact on clinical outcome. Cancer Metastasis Rev 2007;26:225-39.
    • (2007) Cancer Metastasis Rev , vol.26 , pp. 225-239
    • Vaupel, P.1    Mayer, A.2
  • 7
    • 34447122556 scopus 로고    scopus 로고
    • Mechanism of action and preclinical antitumor activity of the novel hypoxia-activated DNA crosslinking agent PR-104
    • Patterson AV, Ferry DM, Edmunds SJ, et al. Mechanism of action and preclinical antitumor activity of the novel hypoxia-activated DNA crosslinking agent PR-104. Clin Cancer Res 2007;13:3922-32.
    • (2007) Clin Cancer Res , vol.13 , pp. 3922-3932
    • Patterson, A.V.1    Ferry, D.M.2    Edmunds, S.J.3
  • 8
    • 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 A, Thiel A, et al. 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.
    • (2007) Biochem Pharmacol , vol.74 , pp. 810-820
    • Guise, C.P.1    Wang, A.2    Thiel, A.3
  • 9
    • 34548513083 scopus 로고    scopus 로고
    • Oxygen dependence and extravascular transport of hypoxia-activated prodrugs: Comparison of the dinitrobenzamide mustard PR-104A and tirapazamine
    • Hicks KO, Myint H, Patterson AV, et al. Oxygen dependence and extravascular transport of hypoxia-activated prodrugs: comparison of the dinitrobenzamide mustard PR-104A and tirapazamine. Int J Radiat Oncol Biol Phys 2007;69:560-71.
    • (2007) Int J Radiat Oncol Biol Phys , vol.69 , pp. 560-571
    • Hicks, K.O.1    Myint, H.2    Patterson, A.V.3
  • 10
    • 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
    • DOI: 10.1007/s00280-009-1188-1
    • Jameson MB, Rischin D, Pegram M, et al. 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 2010. DOI: 10.1007/s00280-009-1188-1.
    • (2010) Cancer Chemother Pharmacol
    • Jameson, M.B.1    Rischin, D.2    Pegram, M.3
  • 11
    • 65949102556 scopus 로고    scopus 로고
    • DNA crosslinks in human tumor cells exposed to the prodrug PR-104A: Relationships to hypoxia, bioreductive metabolism and cytotoxicity
    • SingletonRS, Guise CP, FerryDM, et al.DNA crosslinks in human tumor cells exposed to the prodrug PR-104A: relationships to hypoxia, bioreductive metabolism and cytotoxicity. Cancer Res 2009;69:3884-91.
    • (2009) Cancer Res , vol.69 , pp. 3884-3891
    • Singleton, R.S.1    Guise, C.P.2    Ferry, D.M.3
  • 12
    • 33847050801 scopus 로고    scopus 로고
    • Cell survival responses to environmental stresses via the Keap1-2-ARE pathway
    • Kensler TW, Wakabayashi N, Biswal S. Cell survival responses to environmental stresses via the Keap1-2-ARE pathway. Annu Rev Pharmacol Toxicol 2007;47:89-116.
    • (2007) Annu Rev Pharmacol Toxicol , vol.47 , pp. 89-116
    • Kensler, T.W.1    Wakabayashi, N.2    Biswal, S.3
  • 13
    • 34247594896 scopus 로고    scopus 로고
    • A genomic screen for activators of the antioxidant response element
    • Liu Y, Kern JT, Walker JR, et al. A genomic screen for activators of the antioxidant response element. Proc Natl Acad Sci U S A 2007; 104:5205-10.
    • (2007) Proc Natl Acad Sci U S A , vol.104 , pp. 5205-5210
    • Liu, Y.1    Kern, J.T.2    Walker, J.R.3
  • 14
    • 34547692874 scopus 로고    scopus 로고
    • Human aldo-keto reductases: Function, gene regulation, and single nucleotide polymorphisms
    • Penning TM, Drury JE. Human aldo-keto reductases: function, gene regulation, and single nucleotide polymorphisms. Arch Biochem Biophys 2007;464:241-50.
    • (2007) Arch Biochem Biophys , vol.464 , pp. 241-250
    • Penning, T.M.1    Drury, J.E.2
  • 15
    • 34248996204 scopus 로고    scopus 로고
    • Synthesis of asymmetric halomesylate mustards with aziridineethanol/alkali metal halides: Application to an improved synthesis of the hypoxia prodrug PR-104
    • Yang S, Atwell GJ, Denny WA. Synthesis of asymmetric halomesylate mustards with aziridineethanol/alkali metal halides: application to an improved synthesis of the hypoxia prodrug PR-104. Tetrahedron 2007;63:5470-6.
    • (2007) Tetrahedron , vol.63 , pp. 5470-5476
    • Yang, S.1    Atwell, G.J.2    Denny, W.A.3
  • 16
    • 33947403889 scopus 로고    scopus 로고
    • 2H4- labelled versions of the hypoxia-activated pre-prodrug 2-[(2-bromoethyl)-2,4- dinitro-6-[[[2-(phosphonooxy)ethyl]amino]carbonyl]anilino]ethyl methanesulfonate (PR-104)
    • 2H4- labelled versions of the hypoxia-activated pre-prodrug 2-[(2-bromoethyl)-2,4- dinitro-6-[[[2-(phosphonooxy)ethyl]amino]carbonyl]anilino]ethyl methanesulfonate (PR-104). J Labelled Comp Radiopharm 2007;50:7-12.
    • (2007) J Labelled Comp Radiopharm , vol.50 , pp. 7-12
    • Atwell, G.J.1    Denny, W.A.2
  • 17
    • 33947621321 scopus 로고    scopus 로고
    • Bystander effects of bioreductive drugs: Potential for exploiting pathological tumor hypoxia with dinitrobenzamide mustards
    • Wilson WR, Hicks KO, Pullen SM, et al. Bystander effects of bioreductive drugs: potential for exploiting pathological tumor hypoxia with dinitrobenzamide mustards. Radiat Res 2007;167: 625-36.
    • (2007) Radiat Res , vol.167 , pp. 625-636
    • Wilson, W.R.1    Hicks, K.O.2    Pullen, S.M.3
  • 19
    • 0036012343 scopus 로고    scopus 로고
    • Replicated microarray data
    • Loennstedt I, Speed TP. Replicated microarray data. Stat Sin 2002; 12:31-46.
    • (2002) Stat Sin , vol.12 , pp. 31-46
    • Loennstedt, I.1    Speed, T.P.2
  • 20
    • 0032544921 scopus 로고    scopus 로고
    • Development of a bicistronic vector driven by the human polypeptide chain elongation factor 1á promoter for creation of stable mammalian cell lines that express very high levels of recombinant proteins
    • Hobbs S, Jitrapakdee S, Wallace JC. Development of a bicistronic vector driven by the human polypeptide chain elongation factor 1á promoter for creation of stable mammalian cell lines that express very high levels of recombinant proteins. Biochem Biophys Res Commun 1998;252:368-72.
    • (1998) Biochem Biophys Res Commun , vol.252 , pp. 368-372
    • Hobbs, S.1    Jitrapakdee, S.2    Wallace, J.C.3
  • 21
    • 33646497001 scopus 로고    scopus 로고
    • Radiolytic and cellular reduction of a novel hypoxia-activated cobalt(III) prodrug of a chloromethylbenzindoline DNA minor groove alkylator
    • Ahn GO, Botting KJ, Patterson AV, et al. Radiolytic and cellular reduction of a novel hypoxia-activated cobalt(III) prodrug of a chloromethylbenzindoline DNA minor groove alkylator. Biochem Pharmacol 2006;71:1683-94.
    • (2006) Biochem Pharmacol , vol.71 , pp. 1683-1694
    • Ahn, G.O.1    Botting, K.J.2    Patterson, A.V.3
  • 22
    • 54849441238 scopus 로고    scopus 로고
    • Imaging induction of cytoprotective enzymes in intact human cells: Coumberone, a metabolic reporter for human AKR1C enzymes reveals activation by panaxytriol, an active component of red ginseng
    • Halim M, Yee DJ, Sames D. Imaging induction of cytoprotective enzymes in intact human cells: coumberone, a metabolic reporter for human AKR1C enzymes reveals activation by panaxytriol, an active component of red ginseng. J Am Chem Soc 2008;130: 14123-8.
    • (2008) J Am Chem Soc , vol.130 , pp. 14123-14128
    • Halim, M.1    Yee, D.J.2    Sames, D.3
  • 23
    • 9944264069 scopus 로고    scopus 로고
    • Characterization of a monoclonal antibody for human aldo-keto reductase AKR1C3 (type 2 3α-hydroxysteroid dehydrogenase/type 5 17β-hydroxysteroid dehydrogenase); immunohistochemical detection in breast and prostate
    • Lin HK, Steckelbroeck S, Fung KM, Jones AN, Penning TM. Characterization of a monoclonal antibody for human aldo-keto reductase AKR1C3 (type 2 3α-hydroxysteroid dehydrogenase/type 5 17β-hydroxysteroid dehydrogenase); immunohistochemical detection in breast and prostate. Steroids 2004;69:795-801.
    • (2004) Steroids , vol.69 , pp. 795-801
    • Lin, H.K.1    Steckelbroeck, S.2    Fung, K.M.3    Jones, A.N.4    Penning, T.M.5
  • 24
    • 33750885385 scopus 로고    scopus 로고
    • Dysfunctional KEAP1-2 interaction in non-small-cell lung cancer
    • Singh A, Misra V, Thimmulappa RK, et al. Dysfunctional KEAP1-2 interaction in non-small-cell lung cancer. PLoS Med 2006;3:e420.
    • (2006) PLoS Med , vol.3
    • Singh, A.1    Misra, V.2    Thimmulappa, R.K.3
  • 25
    • 41149155769 scopus 로고    scopus 로고
    • Redox cycling of 9,10-phenanthraquinone to cause oxidative stress is terminated through its monoglucuronide conjugation in human pulmonary epithelial A549 cells
    • Taguchi K, Shimada M, Fujii S, et al. Redox cycling of 9,10-phenanthraquinone to cause oxidative stress is terminated through its monoglucuronide conjugation in human pulmonary epithelial A549 cells. Free Radic Biol Med 2008;44:1645-55.
    • (2008) Free Radic Biol Med , vol.44 , pp. 1645-1655
    • Taguchi, K.1    Shimada, M.2    Fujii, S.3
  • 26
    • 33847021147 scopus 로고    scopus 로고
    • Aldo-keto reductases and bioactivation/detoxication
    • Jin Y, Penning TM. Aldo-keto reductases and bioactivation/detoxication. Annu Rev Pharmacol Toxicol 2007;47:263-92.
    • (2007) Annu Rev Pharmacol Toxicol , vol.47 , pp. 263-292
    • Jin, Y.1    Penning, T.M.2
  • 27
    • 70249138697 scopus 로고    scopus 로고
    • Characterization of the cancer chemopreventive NRF2-dependent gene battery in human keratinocytes: Demonstration that the KEAP1-2 pathway, and not the BACH1-2 pathway, controls cytoprotection against electrophiles as well as redox-cycling compounds
    • MacLeod AK, McMahon M, Plummer SM, et al. Characterization of the cancer chemopreventive NRF2-dependent gene battery in human keratinocytes: demonstration that the KEAP1-2 pathway, and not the BACH1-2 pathway, controls cytoprotection against electrophiles as well as redox-cycling compounds. Carcinogenesis 2009;30:1571-80.
    • (2009) Carcinogenesis , vol.30 , pp. 1571-1580
    • MacLeod, A.K.1    McMahon, M.2    Plummer, S.M.3
  • 28
    • 33344456501 scopus 로고    scopus 로고
    • Structural basis for defects of Keap1 activity provoked by its point mutations in lung cancer
    • Padmanabhan B, Tong KI, Ohta T, et al. Structural basis for defects of Keap1 activity provoked by its point mutations in lung cancer. Mol Cell 2006;21:689-700.
    • (2006) Mol Cell , vol.21 , pp. 689-700
    • Padmanabhan, B.1    Tong, K.I.2    Ohta, T.3
  • 29
    • 40449107193 scopus 로고    scopus 로고
    • Loss of Keap1 function activates Nrf2 and provides advantages for lung cancer cell growth
    • Ohta T, Iijima K, Miyamoto M, et al. Loss of Keap1 function activates Nrf2 and provides advantages for lung cancer cell growth. Cancer Res 2008;68:1303-9.
    • (2008) Cancer Res , vol.68 , pp. 1303-1309
    • Ohta, T.1    Iijima, K.2    Miyamoto, M.3
  • 30
    • 54249087596 scopus 로고    scopus 로고
    • RNAi-mediated silencing of nuclear factor erythroid-2-related factor 2 gene expression in non-small cell lung cancer inhibits tumor growth and increases efficacy of chemotherapy
    • Singh A, Boldin-Adamsky S, Thimmulappa RK, et al. RNAi-mediated silencing of nuclear factor erythroid-2-related factor 2 gene expression in non-small cell lung cancer inhibits tumor growth and increases efficacy of chemotherapy. Cancer Res 2008;68:7975.
    • (2008) Cancer Res , vol.68 , pp. 7975
    • Singh, A.1    Boldin-Adamsky, S.2    Thimmulappa, R.K.3
  • 31
    • 46949099638 scopus 로고    scopus 로고
    • Nrf2 enhances resistance of cancer cells to chemotherapeutic drugs, the dark side of Nrf2
    • Wang XJ, Sun Z, Villeneuve NF, et al. Nrf2 enhances resistance of cancer cells to chemotherapeutic drugs, the dark side of Nrf2. Carcinogenesis 2008;29:1235-43.
    • (2008) Carcinogenesis , vol.29 , pp. 1235-1243
    • Wang, X.J.1    Sun, Z.2    Villeneuve, N.F.3
  • 32
    • 66149168685 scopus 로고    scopus 로고
    • Nrf2 enhances cell proliferation and resistance to anticancer drugs in human lung cancer
    • Homma S, Ishii Y, Morishima Y, et al. Nrf2 enhances cell proliferation and resistance to anticancer drugs in human lung cancer. Clin Cancer Res 2009;15:3423-32.
    • (2009) Clin Cancer Res , vol.15 , pp. 3423-3432
    • Homma, S.1    Ishii, Y.2    Morishima, Y.3
  • 33
    • 0033057937 scopus 로고    scopus 로고
    • Immunocytochemical localization of type 5 17β-hydroxysteroid dehydrogenase in human reproductive tissues
    • Pelletier G, Luu-The V, Tetu B, Labrie F. Immunocytochemical localization of type 5 17β-hydroxysteroid dehydrogenase in human reproductive tissues. J Histochem Cytochem 1999;47:731-8.
    • (1999) J Histochem Cytochem , vol.47 , pp. 731-738
    • Pelletier, G.1    Luu-The, V.2    Tetu, B.3    Labrie, F.4
  • 34
    • 0034287545 scopus 로고    scopus 로고
    • Human 3α-hydroxysteroid dehydrogenase isoforms (AKR1C1-1C4) of the aldo-keto reductase superfamily: Functional plasticity and tissue distribution reveals roles in the inactivation and formation of male and female sex hormones
    • Penning TM, Burczynski ME, Jez JM, et al. Human 3α-hydroxysteroid dehydrogenase isoforms (AKR1C1-1C4) of the aldo-keto reductase superfamily: functional plasticity and tissue distribution reveals roles in the inactivation and formation of male and female sex hormones. Biochem J 2000;351:67-77.
    • (2000) Biochem J , vol.351 , pp. 67-77
    • Penning, T.M.1    Burczynski, M.E.2    Jez, J.M.3
  • 35
    • 49749125298 scopus 로고    scopus 로고
    • Tissue distribution of human AKR1C3 and rat homolog in the adult genitourinary system
    • Azzarello J, Fung KM, Lin HK. Tissue distribution of human AKR1C3 and rat homolog in the adult genitourinary system. J Histochem Cytochem 2008;56:853-61.
    • (2008) J Histochem Cytochem , vol.56 , pp. 853-861
    • Azzarello, J.1    Fung, K.M.2    Lin, H.K.3
  • 36
    • 60449106323 scopus 로고    scopus 로고
    • The aldo-keto reductase AKR1C3 contributes to 7,12-dimethylbenz(a)anthracene-3,4-dihydrodiol mediated oxidative DNA damage in myeloid cells: Implications for leukemogenesis
    • Birtwistle J, Hayden RE, Khanim FL, et al. The aldo-keto reductase AKR1C3 contributes to 7,12-dimethylbenz(a)anthracene-3,4-dihydrodiol mediated oxidative DNA damage in myeloid cells: Implications for leukemogenesis. Mutat Res 2009;662:67-74.
    • (2009) Mutat Res , vol.662 , pp. 67-74
    • Birtwistle, J.1    Hayden, R.E.2    Khanim, F.L.3
  • 37
    • 33745403240 scopus 로고    scopus 로고
    • Paracrine-stimulated gene expression profile favors estradiol production in breast tumors
    • Amin SA, Huang CC, Reierstad S, et al. Paracrine-stimulated gene expression profile favors estradiol production in breast tumors. Mol Cell Endocrinol 2006;253:44-55.
    • (2006) Mol Cell Endocrinol , vol.253 , pp. 44-55
    • Amin, S.A.1    Huang, C.C.2    Reierstad, S.3
  • 38
    • 5644246147 scopus 로고    scopus 로고
    • 17β-Hydroxysteroid dehydrogenase type 1 is an independent prognostic marker in breast cancer
    • Oduwole OO, Li Y, Isomaa VV, et al. 17β-Hydroxysteroid dehydrogenase type 1 is an independent prognostic marker in breast cancer. Cancer Res 2004;64:7604-9.
    • (2004) Cancer Res , vol.64 , pp. 7604-7609
    • Oduwole, O.O.1    Li, Y.2    Isomaa, V.V.3
  • 39
    • 20144389477 scopus 로고    scopus 로고
    • In situ androgen producing enzymes in human prostate cancer
    • Nakamura Y, Suzuki T, Nakabayashi M, et al. In situ androgen producing enzymes in human prostate cancer. Endocr Relat Cancer 2005;12:101-7.
    • (2005) Endocr Relat Cancer , vol.12 , pp. 101-107
    • Nakamura, Y.1    Suzuki, T.2    Nakabayashi, M.3
  • 40
    • 42049098597 scopus 로고    scopus 로고
    • Expression of androgen receptor through androgen-converting enzymes is associated with biological aggressiveness in prostate cancer
    • Wako K, Kawasaki T, Yamana K, et al. Expression of androgen receptor through androgen-converting enzymes is associated with biological aggressiveness in prostate cancer. J Clin Pathol 2008; 61:448-54.
    • (2008) J Clin Pathol , vol.61 , pp. 448-454
    • Wako, K.1    Kawasaki, T.2    Yamana, K.3
  • 41
    • 33645056171 scopus 로고    scopus 로고
    • Increased expression of genes converting adrenal androgens to testosterone in androgenindependent prostate cancer
    • Stanbrough M, Bubley GJ, Ross K, et al. Increased expression of genes converting adrenal androgens to testosterone in androgenindependent prostate cancer. Cancer Res 2006;66:2815-25.
    • (2006) Cancer Res , vol.66 , pp. 2815-2825
    • Stanbrough, M.1    Bubley, G.J.2    Ross, K.3
  • 42
    • 33644909044 scopus 로고    scopus 로고
    • AKR1C1 and AKR1C3 may determine progesterone and estrogen ratios in endometrial cancer
    • Rizner TL, Smuc T, Rupreht R, Sinkovec J, Penning TM. AKR1C1 and AKR1C3 may determine progesterone and estrogen ratios in endometrial cancer. Mol Cell Endocrinol 2006;248:126-35.
    • (2006) Mol Cell Endocrinol , vol.248 , pp. 126-135
    • Rizner, T.L.1    Smuc, T.2    Rupreht, R.3    Sinkovec, J.4    Penning, T.M.5
  • 43
    • 33644891602 scopus 로고    scopus 로고
    • 17β-Hydroxysteroid dehydrogenases in human endometrium and its disorders
    • Ito K, Utsunomiya H, Suzuki T, et al. 17β-Hydroxysteroid dehydrogenases in human endometrium and its disorders. Mol Cell Endocrinol 2006;248:136-40.
    • (2006) Mol Cell Endocrinol , vol.248 , pp. 136-140
    • Ito, K.1    Utsunomiya, H.2    Suzuki, T.3
  • 44
    • 27544434868 scopus 로고    scopus 로고
    • Localization of cyclooxygenases-1 and -2, and prostaglandin F synthase in human kidney and renal cell carcinoma
    • Sakurai M, Oishi K, Watanabe K. Localization of cyclooxygenases-1 and -2, and prostaglandin F synthase in human kidney and renal cell carcinoma. Biochem Biophys Res Commun 2005; 338:82-6.
    • (2005) Biochem Biophys Res Commun , vol.338 , pp. 82-86
    • Sakurai, M.1    Oishi, K.2    Watanabe, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.