메뉴 건너뛰기




Volumn 336, Issue 1, 2005, Pages 332-338

Crystal structure of quinone reductase 2 in complex with cancer prodrug CB1954

Author keywords

CB1954; Menadione; QR1; QR2; Quinone reductase; Substrate specificity

Indexed keywords

5 (1 AZIRIDINYL) 2,4 DINITROBENZAMIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

EID: 24344493957     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2005.08.081     Document Type: Article
Times cited : (27)

References (32)
  • 1
    • 0000665443 scopus 로고
    • Enzymatic oxidation of some nonphosphorylated derivatives of dihydronicotinamide
    • S. Liao, and H.G. Williams-Ashmau Enzymatic oxidation of some nonphosphorylated derivatives of dihydronicotinamide Biochem. Biophys. Res. Commun. 4 1961 208 213
    • (1961) Biochem. Biophys. Res. Commun. , vol.4 , pp. 208-213
    • Liao, S.1    Williams-Ashmau, H.G.2
  • 2
    • 0033520090 scopus 로고    scopus 로고
    • Crystal structure of human quinone reductase type 2, a metalloflavoprotein
    • C.E. Foster, M.A. Bianchet, P. Talalay, Q. Zhao, and L.M. Amzel Crystal structure of human quinone reductase type 2, a metalloflavoprotein Biochemistry 38 1999 9881 9886
    • (1999) Biochemistry , vol.38 , pp. 9881-9886
    • Foster, C.E.1    Bianchet, M.A.2    Talalay, P.3    Zhao, Q.4    Amzel, L.M.5
  • 3
    • 0025018844 scopus 로고
    • Nucleotide and deduced amino acid sequence of a human cDNA (NQO2) corresponding to a second member of the NAD(P)H:quinone oxidoreductase gene family. Extensive polymorphism at the NQO2 gene locus on chromosome 6
    • A.K. Jaiswal, P. Burnett, M. Adesnik, and O.W. McBride Nucleotide and deduced amino acid sequence of a human cDNA (NQO2) corresponding to a second member of the NAD(P)H:quinone oxidoreductase gene family. Extensive polymorphism at the NQO2 gene locus on chromosome 6 Biochemistry 29 1990 1899 1906
    • (1990) Biochemistry , vol.29 , pp. 1899-1906
    • Jaiswal, A.K.1    Burnett, P.2    Adesnik, M.3    McBride, O.W.4
  • 4
    • 0035834571 scopus 로고    scopus 로고
    • An association between idiopathic Parkinson's disease and polymorphisms of phase II detoxification enzymes: Glutathione S-transferase M1 and quinone oxidoreductase 1 and 2
    • S. Harada, C. Fujii, A. Hayashi, and N. Ohkoshi An association between idiopathic Parkinson's disease and polymorphisms of phase II detoxification enzymes: glutathione S-transferase M1 and quinone oxidoreductase 1 and 2 Biochem. Biophys. Res. Commun. 288 2001 887 892
    • (2001) Biochem. Biophys. Res. Commun. , vol.288 , pp. 887-892
    • Harada, S.1    Fujii, C.2    Hayashi, A.3    Ohkoshi, N.4
  • 5
    • 0347592777 scopus 로고    scopus 로고
    • A possible association between an insertion/deletion polymorphism of the NQO2 gene and schizophrenia
    • S. Harada, H. Tachikawa, and Y. Kawanishi A possible association between an insertion/deletion polymorphism of the NQO2 gene and schizophrenia Psychiatr. Genet. 13 2003 205 209
    • (2003) Psychiatr. Genet. , vol.13 , pp. 205-209
    • Harada, S.1    Tachikawa, H.2    Kawanishi, Y.3
  • 6
    • 0043165082 scopus 로고    scopus 로고
    • Association analyses between polymorphisms of the phase II detoxification enzymes (GSTM1, NQO1, NQO2) and alcohol withdrawal symptoms
    • T. Okubo, S. Harada, S. Higuchi, and S. Matsushita Association analyses between polymorphisms of the phase II detoxification enzymes (GSTM1, NQO1, NQO2) and alcohol withdrawal symptoms Alcohol Clin. Exp. Res. 27 2003 68S 71S
    • (2003) Alcohol Clin. Exp. Res. , vol.27
    • Okubo, T.1    Harada, S.2    Higuchi, S.3    Matsushita, S.4
  • 8
    • 0033805326 scopus 로고    scopus 로고
    • Persuasive evidence that quinone reductase type 1 (DT diaphorase) protects cells against the toxicity of electrophiles and reactive forms of oxygen
    • A.T. Dinkova-Kostova, and P. Talalay Persuasive evidence that quinone reductase type 1 (DT diaphorase) protects cells against the toxicity of electrophiles and reactive forms of oxygen Free Radic. Biol. Med. 29 2000 231 240
    • (2000) Free Radic. Biol. Med. , vol.29 , pp. 231-240
    • Dinkova-Kostova, A.T.1    Talalay, P.2
  • 9
    • 0033805383 scopus 로고    scopus 로고
    • Structure-function studies of DT-diaphorase (NQO1) and NRH: Quinone oxidoreductase (NQO2)
    • S. Chen, K. Wu, and R. Knox Structure-function studies of DT-diaphorase (NQO1) and NRH: quinone oxidoreductase (NQO2) Free Radic. Biol. Med. 29 2000 276 284
    • (2000) Free Radic. Biol. Med. , vol.29 , pp. 276-284
    • Chen, S.1    Wu, K.2    Knox, R.3
  • 11
    • 0033871181 scopus 로고    scopus 로고
    • Bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by human NAD(P)H quinone oxidoreductase 2: A novel co-substrate-mediated antitumor prodrug therapy
    • R.J. Knox, T.C. Jenkins, S.M. Hobbs, S. Chen, R.G. Melton, and P.J. Burke Bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by human NAD(P)H quinone oxidoreductase 2: a novel co-substrate-mediated antitumor prodrug therapy Cancer Res. 60 2000 4179 4186
    • (2000) Cancer Res. , vol.60 , pp. 4179-4186
    • Knox, R.J.1    Jenkins, T.C.2    Hobbs, S.M.3    Chen, S.4    Melton, R.G.5    Burke, P.J.6
  • 12
    • 12644302182 scopus 로고    scopus 로고
    • Unexpected genetic and structural relationships of a long-forgotten flavoenzyme to NAD(P)H:quinone reductase (DT-diaphorase)
    • Q. Zhao, X.L. Yang, W.D. Holtzclaw, and P. Talalay Unexpected genetic and structural relationships of a long-forgotten flavoenzyme to NAD(P)H:quinone reductase (DT-diaphorase) Proc. Natl. Acad. Sci. USA 94 1997 1669 1674
    • (1997) Proc. Natl. Acad. Sci. USA , vol.94 , pp. 1669-1674
    • Zhao, Q.1    Yang, X.L.2    Holtzclaw, W.D.3    Talalay, P.4
  • 15
    • 0037195924 scopus 로고    scopus 로고
    • Disruption of dihydronicotinamide riboside:quinone oxidoreductase 2 (NQO2) leads to myeloid hyperplasia of bone marrow and decreased sensitivity to menadione toxicity
    • D.J. Long 2nd, K. Iskander, A. Gaikwad, M. Arin, D.R. Roop, R. Knox, R. Barrios, and A.K. Jaiswal Disruption of dihydronicotinamide riboside:quinone oxidoreductase 2 (NQO2) leads to myeloid hyperplasia of bone marrow and decreased sensitivity to menadione toxicity J. Biol. Chem. 277 2002 46131 46139
    • (2002) J. Biol. Chem. , vol.277 , pp. 46131-46139
    • Long II, D.J.1    Iskander, K.2    Gaikwad, A.3    Arin, M.4    Roop, D.R.5    Knox, R.6    Barrios, R.7    Jaiswal, A.K.8
  • 16
    • 0036015563 scopus 로고    scopus 로고
    • Nitroreductase-based GDEPT
    • W.A. Denny Nitroreductase-based GDEPT Curr. Pharm. Des. 8 2002 1349 1361
    • (2002) Curr. Pharm. Des. , vol.8 , pp. 1349-1361
    • Denny, W.A.1
  • 17
    • 0027182862 scopus 로고
    • The bioactivation of CB 1954 and its use as a prodrug in antibody-directed enzyme prodrug therapy (ADEPT)
    • R.J. Knox, F. Friedlos, and M.P. Boland The bioactivation of CB 1954 and its use as a prodrug in antibody-directed enzyme prodrug therapy (ADEPT) Cancer Metastasis Rev. 12 1993 195 212
    • (1993) Cancer Metastasis Rev. , vol.12 , pp. 195-212
    • Knox, R.J.1    Friedlos, F.2    Boland, M.P.3
  • 19
    • 0024205344 scopus 로고
    • The nitroreductase enzyme in Walker cells that activates 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) to 5-(aziridin-1-yl)-4- hydroxylamino-2-nitrobenzamide is a form of NAD(P)H dehydrogenase (quinone) (EC 1.6.99.2)
    • R.J. Knox, M.P. Boland, F. Friedlos, B. Coles, C. Southan, and J.J. Roberts The nitroreductase enzyme in Walker cells that activates 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) to 5-(aziridin-1-yl)-4- hydroxylamino-2-nitrobenzamide is a form of NAD(P)H dehydrogenase (quinone) (EC 1.6.99.2) Biochem. Pharmacol. 37 1988 4671 4677
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 4671-4677
    • Knox, R.J.1    Boland, M.P.2    Friedlos, F.3    Coles, B.4    Southan, C.5    Roberts, J.J.6
  • 20
    • 4544327822 scopus 로고    scopus 로고
    • Identification and purification of resveratrol targeting proteins using immobilized resveratrol affinity chromatography
    • Z. Wang, T.C. Hsieh, Z. Zhang, Y. Ma, and J.M. Wu Identification and purification of resveratrol targeting proteins using immobilized resveratrol affinity chromatography Biochem. Biophys. Res. Commun. 323 2004 743 749
    • (2004) Biochem. Biophys. Res. Commun. , vol.323 , pp. 743-749
    • Wang, Z.1    Hsieh, T.C.2    Zhang, Z.3    Ma, Y.4    Wu, J.M.5
  • 21
    • 0031059866 scopus 로고    scopus 로고
    • J.R.M.S.C.W. Carter Academic Press New York
    • Z. Otwinowski, and W. Minor J.R.M.S.C.W. Carter Methods in Enzymology 1997 Academic Press New York 307 326
    • (1997) Methods in Enzymology , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2
  • 23
    • 0031473847 scopus 로고    scopus 로고
    • SWISS-MODEL and the Swiss-PdbViewer: An environment for comparative protein modeling
    • N. Guex, and M.C. Peitsch SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling Electrophoresis 18 1997 2714 2723
    • (1997) Electrophoresis , vol.18 , pp. 2714-2723
    • Guex, N.1    Peitsch, M.C.2
  • 24
    • 0034903751 scopus 로고    scopus 로고
    • Molray-a web interface between O and the POV-Ray ray tracer
    • M. Harris, and T.A. Jones Molray-a web interface between O and the POV-Ray ray tracer Acta Crystallogr. D 57 2001 1201 1203
    • (2001) Acta Crystallogr. D , vol.57 , pp. 1201-1203
    • Harris, M.1    Jones, T.A.2
  • 25
    • 0026075733 scopus 로고
    • Bioactivation of CB 1954: Reaction of the active 4-hydroxylamino derivative with thioesters to form the ultimate DNA-DNA interstrand crosslinking species
    • R.J. Knox, F. Friedlos, T. Marchbank, and J.J. Roberts Bioactivation of CB 1954: reaction of the active 4-hydroxylamino derivative with thioesters to form the ultimate DNA-DNA interstrand crosslinking species Biochem. Pharmacol. 42 1991 1691 1697
    • (1991) Biochem. Pharmacol. , vol.42 , pp. 1691-1697
    • Knox, R.J.1    Friedlos, F.2    Marchbank, T.3    Roberts, J.J.4
  • 26
    • 0031573462 scopus 로고    scopus 로고
    • Catalytic properties of NAD(P)H:quinone oxidoreductase-2 (NQO2), a dihydronicotinamide riboside dependent oxidoreductase
    • K. Wu, R. Knox, X.Z. Sun, P. Joseph, A.K. Jaiswal, D. Zhang, P.S. Deng, and S. Chen Catalytic properties of NAD(P)H:quinone oxidoreductase-2 (NQO2), a dihydronicotinamide riboside dependent oxidoreductase Arch. Biochem. Biophys. 347 1997 221 228
    • (1997) Arch. Biochem. Biophys. , vol.347 , pp. 221-228
    • Wu, K.1    Knox, R.2    Sun, X.Z.3    Joseph, P.4    Jaiswal, A.K.5    Zhang, D.6    Deng, P.S.7    Chen, S.8
  • 27
    • 0029068515 scopus 로고
    • The three-dimensional structure of NAD(P)H:quinone reductase, a flavoprotein involved in cancer chemoprotection and chemotherapy: Mechanism of the two-electron reduction
    • R. Li, M.A. Bianchet, P. Talalay, and L.M. Amzel The three-dimensional structure of NAD(P)H:quinone reductase, a flavoprotein involved in cancer chemoprotection and chemotherapy: mechanism of the two-electron reduction Proc. Natl. Acad. Sci. USA 92 1995 8846 8850
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 8846-8850
    • Li, R.1    Bianchet, M.A.2    Talalay, P.3    Amzel, L.M.4
  • 28
    • 0029609610 scopus 로고
    • Expression of the bacterial nitroreductase enzyme in mammalian cells renders them selectively sensitive to killing by the prodrug CB1954
    • J.A. Bridgewater, C.J. Springer, R.J. Knox, N.P. Minton, N.P. Michael, and M.K. Collins Expression of the bacterial nitroreductase enzyme in mammalian cells renders them selectively sensitive to killing by the prodrug CB1954 Eur. J. Cancer 31A 1995 2362 2370
    • (1995) Eur. J. Cancer , vol.31 , pp. 2362-2370
    • Bridgewater, J.A.1    Springer, C.J.2    Knox, R.J.3    Minton, N.P.4    Michael, N.P.5    Collins, M.K.6
  • 30
    • 0344118703 scopus 로고    scopus 로고
    • Synthesis and evaluation of nitroheterocyclic carbamate prodrugs for use with nitroreductase-mediated gene-directed enzyme prodrug therapy
    • M.P. Hay, R.F. Anderson, D.M. Ferry, W.R. Wilson, and W.A. Denny Synthesis and evaluation of nitroheterocyclic carbamate prodrugs for use with nitroreductase-mediated gene-directed enzyme prodrug therapy J. Med. Chem. 46 2003 5533 5545
    • (2003) J. Med. Chem. , vol.46 , pp. 5533-5545
    • Hay, M.P.1    Anderson, R.F.2    Ferry, D.M.3    Wilson, W.R.4    Denny, W.A.5
  • 31
    • 0038101357 scopus 로고    scopus 로고
    • Structure-activity relationships for 4-nitrobenzyl carbamates of 5-aminobenz[e]indoline minor groove alkylating agents as prodrugs for GDEPT in conjunction with E. coli nitroreductase
    • M.P. Hay, G.J. Atwell, W.R. Wilson, S.M. Pullen, and W.A. Denny Structure-activity relationships for 4-nitrobenzyl carbamates of 5-aminobenz[e]indoline minor groove alkylating agents as prodrugs for GDEPT in conjunction with E. coli nitroreductase J. Med. Chem. 46 2003 2456 2466
    • (2003) J. Med. Chem. , vol.46 , pp. 2456-2466
    • Hay, M.P.1    Atwell, G.J.2    Wilson, W.R.3    Pullen, S.M.4    Denny, W.A.5
  • 32
    • 1942424798 scopus 로고    scopus 로고
    • 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT
    • N.A. Helsby, D.M. Ferry, A.V. Patterson, S.M. Pullen, and W.R. Wilson 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT Br. J. Cancer 90 2004 1084 1092
    • (2004) Br. J. Cancer , vol.90 , pp. 1084-1092
    • Helsby, N.A.1    Ferry, D.M.2    Patterson, A.V.3    Pullen, S.M.4    Wilson, W.R.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.