메뉴 건너뛰기




Volumn 40, Issue 9, 2006, Pages 974-978

The reductive activation of the antitumor drug RH1 to its semiquinone free radical by NADPH cytochrome P450 reductase and by HCT116 human colon cancer cells

Author keywords

Cytochrome P450 reductase; EPR; Hydroxyl radical; Quinone; RH1; Semiquinone radical

Indexed keywords

2,5 DIAZIRIDINYL 3 (HYDROXYMETHYL) 6 METHYL 1,4 BENZOQUINONE; ALKYLATING AGENT; ANTINEOPLASTIC AGENT; CATALASE; DEFERASIROX; DOXORUBICIN; FREE RADICAL; HYDROGEN PEROXIDE; HYDROXYL RADICAL; IRON; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE) 1; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE FERRIHEMOPROTEIN REDUCTASE; RH 1; SEMIQUINONE; SUPEROXIDE; UNCLASSIFIED DRUG;

EID: 33749265694     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760600833077     Document Type: Article
Times cited : (16)

References (24)
  • 1
    • 0033785989 scopus 로고    scopus 로고
    • Establishment of an isogenic human colon tumor model for NQO1 gene expression: Application to investigate the role of DT-diaphorase in bioreductive drug activation in vitro and in vivo
    • Sharp, SY and Kelland, LR and Valenti, MR and Brunton, LA and Hobbs, S and Workman, P. (2000) Establishment of an isogenic human colon tumor model for NQO1 gene expression: Application to investigate the role of DT-diaphorase in bioreductive drug activation in vitro and in vivo Mol Pharmacol, 58, pp. 1146-1155.
    • (2000) Mol Pharmacol , vol.58 , pp. 1146-1155
    • Sharp, S.Y.1    Kelland, L.R.2    Valenti, M.R.3    Brunton, L.A.4    Hobbs, S.5    Workman, P.6
  • 2
    • 0032435478 scopus 로고    scopus 로고
    • A new screening system for NAD(P)H:Quinone oxidoreductase (NQO1)-directed antitumor quinones: Identification of a new aziridinylbenzoquinone, RH1, as a NQO1-directed antitumor agent
    • Winski, SL and Hargreaves, RH and Butler, J and Ross, D. (1998) A new screening system for NAD(P)H:Quinone oxidoreductase (NQO1)-directed antitumor quinones: Identification of a new aziridinylbenzoquinone, RH1, as a NQO1-directed antitumor agent Clin Cancer Res, 4, pp. 3083-3088.
    • (1998) Clin Cancer Res , vol.4 , pp. 3083-3088
    • Winski, S.L.1    Hargreaves, R.H.2    Butler, J.3    Ross, D.4
  • 3
    • 0344442219 scopus 로고    scopus 로고
    • Activity profile of the novel aziridinylbenzoquinones MeDZQ and RH1 in human tumour xenografts
    • Cummings, J and Ritchie, A and Butler, J and Ward, TH and Langdon, S. (2003) Activity profile of the novel aziridinylbenzoquinones MeDZQ and RH1 in human tumour xenografts Anticancer Res, 23, pp. 3979-3983.
    • (2003) Anticancer Res , vol.23 , pp. 3979-3983
    • Cummings, J.1    Ritchie, A.2    Butler, J.3    Ward, T.H.4    Langdon, S.5
  • 4
    • 0033981669 scopus 로고    scopus 로고
    • Pharmacological properties of a new aziridinylbenzoquinone, RH1 (2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone), in mice
    • Loadman, PM and Phillips, RM and Lim, LE and Bibby, MC. (2000) Pharmacological properties of a new aziridinylbenzoquinone, RH1 (2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone), in mice Biochem Pharmacol, 59, pp. 831-8377.
    • (2000) Biochem Pharmacol , vol.59 , pp. 831-8377
    • Loadman, P.M.1    Phillips, R.M.2    Lim, L.E.3    Bibby, M.C.4
  • 6
    • 0003820166 scopus 로고    scopus 로고
    • Allos Therapeutics Inc
    • Allos Therapeutics Inc. 2005, Annual Report. http://library.corporate-ir.net/library/12/125/125475/items/193964/ ALTH05AR.pdf. (Accessed May 13, 2006).
    • (2005) Annual Report
  • 7
    • 33749248446 scopus 로고    scopus 로고
    • Preparation of DT-Diaphorase directed anti-tumor agents
    • [USA patent US 6156744A]
    • Ross, D and Butler, J and Hargreaves, RHJ and Siegel, D and Beall, HD.[2000]. Preparation of DT-Diaphorase directed anti-tumor agents [USA patent US 6156744A].
    • (2000)
    • Ross, D.1    Butler, J.2    Hargreaves, R.H.J.3    Siegel, D.4    Beall, H.D.5
  • 8
    • 0035877252 scopus 로고    scopus 로고
    • Relationship between NAD(P)H:Quinone oxidoreductase 1 (NQO1) levels in a series of stably transfected cell lines and susceptibility to antitumor quinones
    • Winski, SL and Swann, E and Hargreaves, RH and Dehn, DL and Butler, J and Moody, CJ and Ross, D. (2001) Relationship between NAD(P)H:Quinone oxidoreductase 1 (NQO1) levels in a series of stably transfected cell lines and susceptibility to antitumor quinones Biochem Pharmacol, 61, pp. 1509-1516.
    • (2001) Biochem Pharmacol , vol.61 , pp. 1509-1516
    • Winski, S.L.1    Swann, E.2    Hargreaves, R.H.3    Dehn, D.L.4    Butler, J.5    Moody, C.J.6    Ross, D.7
  • 9
    • 18044364834 scopus 로고    scopus 로고
    • RH1 induces cellular damage in an NAD(P)H:Quinone oxidoreductase 1-dependent manner: Relationship between DNA cross-linking, cell cycle perturbations, and apoptosis
    • Dehn, DL and Inayat-Hussain, SH and Ross, D. (2005) RH1 induces cellular damage in an NAD(P)H:Quinone oxidoreductase 1-dependent manner: Relationship between DNA cross-linking, cell cycle perturbations, and apoptosis J Pharmacol Exp Ther, 313, pp. 771-779.
    • (2005) J Pharmacol Exp Ther , vol.313 , pp. 771-779
    • Dehn, D.L.1    Inayat-Hussain, S.H.2    Ross, D.3
  • 10
    • 0037676119 scopus 로고    scopus 로고
    • Cytotoxicity of RH1 and related aziridinylbenzoquinones: Involvement of activation by NAD(P)H:quinone oxidoreductase (NQO1) and oxidative stress
    • Nemeikaite-Ceniene, A and Sarlauskas, J and Anusevicius, Z and Nivinskas, H and Cenas, N. (2003) Cytotoxicity of RH1 and related aziridinylbenzoquinones: InvolveUent of activation by NAD(P)H:quinone oxidoreductase (NQO1) and oxidative stress Arch Biochem Biophys, 416, pp. 110-118.
    • (2003) Arch Biochem Biophys , vol.416 , pp. 110-118
    • Nemeikaite-Ceniene, A.1    Sarlauskas, J.2    Anusevicius, Z.3    Nivinskas, H.4    Cenas, N.5
  • 11
    • 15944374319 scopus 로고    scopus 로고
    • Cytotoxicity of RH1: NAD(P)H:Quinone acceptor oxidoreductase (NQO1)-independent oxidative stress and apoptosis induction
    • Tudor, G and Alley, M and Nelson, CM and Huang, R and Covell, DG and Gutierrez, P and Sausville, EA. (2005) Cytotoxicity of RH1: NAD(P)H:Quinone acceptor oxidoreductase (NQO1)-independent oxidative stress and apoptosis induction Anticancer Drugs, 16, pp. 381-391.
    • (2005) Anticancer Drugs , vol.16 , pp. 381-391
    • Tudor, G.1    Alley, M.2    Nelson, C.M.3    Huang, R.4    Covell, D.G.5    Gutierrez, P.6    Sausville, E.A.7
  • 12
    • 21744443424 scopus 로고    scopus 로고
    • Effect of NQO1 induction on the antitumor activity of RH1 in human tumors in vitro and in vivo
    • Digby, T and Leith, MK and Thliveris, JA and Begleiter, A. (2005) Effect of NQO1 induction on the antitumor activity of RH1 in human tumors in vitro and in vivo Cancer Chemother Pharmacol, 56, pp. 307-316.
    • (2005) Cancer Chemother Pharmacol , vol.56 , pp. 307-316
    • Digby, T.1    Leith, M.K.2    Thliveris, J.A.3    Begleiter, A.4
  • 14
    • 0033800627 scopus 로고    scopus 로고
    • The role of NAD(P)H oxidoreductase (DT-Diaphorase) in the bioactivation of quinone-containing antitumor agents: A review
    • Gutierrez, PL. (2000) The role of NAD(P)H oxidoreductase (DT-Diaphorase) in the bioactivation of quinone-containing antitumor agents: A review Free Radic Biol Med, 29, pp. 263-275.
    • (2000) Free Radic Biol Med , vol.29 , pp. 263-275
    • Gutierrez, P.L.1
  • 15
    • 0029730636 scopus 로고    scopus 로고
    • Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells
    • Qiu, X and Forman, HJ and Schonthal, AH and Cadenas, E. (1996) Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells J Biol Chem, 271, pp. 31915-31921.
    • (1996) J Biol Chem , vol.271 , pp. 31915-31921
    • Qiu, X.1    Forman, H.J.2    Schonthal, A.H.3    Cadenas, E.4
  • 16
    • 0028966862 scopus 로고
    • Enzymic- and thiol-mediated activation of halogen-substituted diaziridinylbenzoquinones: Redox transitions of the semiquinone and semiquinone-thioether species
    • Goin, J and Giulivi, C and Butler, J and Cadenas, E. (1995) Enzymic- and thiol-mediated activation of halogen-substituted diaziridinylbenzoquinones: Redox transitions of the semiquinone and semiquinone-thioether species Free Radic Biol Med, 18, pp. 525-536.
    • (1995) Free Radic Biol Med , vol.18 , pp. 525-536
    • Goin, J.1    Giulivi, C.2    Butler, J.3    Cadenas, E.4
  • 17
    • 0037098878 scopus 로고    scopus 로고
    • Deferiprone protects against doxorubicin-induced myocyte cytotoxicity
    • Barnabé, N and Zastre, J and Venkataram, S and Hasinoff, BB. (2002) Deferiprone protects against doxorubicin-induced myocyte cytotoxicity Free Radic Biol Med, 33, pp. 266-275.
    • (2002) Free Radic Biol Med , vol.33 , pp. 266-275
    • Barnabé, N.1    Zastre, J.2    Venkataram, S.3    Hasinoff, B.B.4
  • 18
    • 0018992113 scopus 로고
    • Spin trapping of superoxide and hydroxyl radical: Practical aspects
    • Finkelstein, E and Rosen, GM and Rauckman, EJ. (1980) Spin trapping of superoxide and hydroxyl radical: Practical aspects Arch Biochem Biophys, 200, pp. 1-16.
    • (1980) Arch Biochem Biophys , vol.200 , pp. 1-16
    • Finkelstein, E.1    Rosen, G.M.2    Rauckman, E.J.3
  • 19
    • 0023505008 scopus 로고
    • Spin trapping: ESR parameters of spin adducts
    • Buettner, GR. (1987) Spin trapping: ESR parameters of spin adducts Free Radic Biol Med, 3, pp. 259-303.
    • (1987) Free Radic Biol Med , vol.3 , pp. 259-303
    • Buettner, G.R.1
  • 20
    • 0033520468 scopus 로고    scopus 로고
    • [3,5-Bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-benzoic acid: A novel efficient and selective iron(III) complexing agent
    • Heinz, U and Hegetschweiler, K and Acklin, P and Faller, B and Lattmann, R and Schnebli, HP. (1999) [3,5-Bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]-benzoic acid: A novel efficient and selective iron(III) complexing agent Angew Chem Int Ed Engl, 38, pp. 2568-2570.
    • (1999) Angew Chem Int Ed Engl , vol.38 , pp. 2568-2570
    • Heinz, U.1    Hegetschweiler, K.2    Acklin, P.3    Faller, B.4    Lattmann, R.5    Schnebli, H.P.6
  • 21
    • 0345306160 scopus 로고    scopus 로고
    • The oral iron chelator ICL670A (deferasirox) does not protect myocytes against doxorubicin
    • Hasinoff, BB and Patel, D and Wu, X. (2003) The oral iron chelator ICL670A (deferasirox) does not protect myocytes against doxorubicin Free Radic Biol Med, 35, pp. 1469-1479.
    • (2003) Free Radic Biol Med , vol.35 , pp. 1469-1479
    • Hasinoff, B.B.1    Patel, D.2    Wu, X.3
  • 22
    • 0036489193 scopus 로고    scopus 로고
    • Metal-independent production of hydroxyl radicals by halogenated quinones and hydrogen peroxide: An ESR spin trapping study
    • Zhu, BZ and Zhao, HT and Kalyanaraman, B and Frei, B. (2002) Metal-independent production of hydroxyl radicals by halogenated quinones and hydrogen peroxide: An ESR spin trapping study Free Radic Biol Med, 32, pp. 465-473.
    • (2002) Free Radic Biol Med , vol.32 , pp. 465-473
    • Zhu, B.Z.1    Zhao, H.T.2    Kalyanaraman, B.3    Frei, B.4
  • 23
    • 0029892535 scopus 로고    scopus 로고
    • Inhibition of anthracycline semiquinone formation by ICRF-187 (dexrazoxane) in cells
    • Malisza, KL and Hasinoff, BB. (1996) Inhibition of anthracycline semiquinone formation by ICRF-187 (dexrazoxane) in cells Free Radic Biol Med, 20, pp. 905-914.
    • (1996) Free Radic Biol Med , vol.20 , pp. 905-914
    • Malisza, K.L.1    Hasinoff, B.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.