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Volumn 16, Issue 4, 2003, Pages 469-478

Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the corresponding nitrogen mustard SN 23862: Distinct mechanisms of bioreductive activation

Author keywords

[No Author keywords available]

Indexed keywords

5 (1 AZIRIDINYL) 2,4 DINITROBENZAMIDE; AMINE; AZIRIDINE; CHLORMETHINE; HYDROXYLAMINE; NITRO DERIVATIVE; NITROREDUCTASE; PRODRUG; SN 23862;

EID: 0037399470     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025662b     Document Type: Article
Times cited : (55)

References (41)
  • 1
    • 0014525030 scopus 로고
    • 2,4-Dinitro-5-ethyleneiminobenzamide (CB 1954): A potent and selective inhibitor of the growth of the Walker carcinoma 256
    • Cobb, L. M., Connors, T. A., Elson, L. A., Khan, A. H., Mitchley, B. C. V., Ross, W. C. J., and Whisson, M. E. (1969) 2,4-dinitro-5-ethyleneiminobenzamide (CB 1954): A potent and selective inhibitor of the growth of the Walker carcinoma 256. Biochem. Pharmacol. 18, 1519-1527.
    • (1969) Biochem. Pharmacol. , vol.18 , pp. 1519-1527
    • Cobb, L.M.1    Connors, T.A.2    Elson, L.A.3    Khan, A.H.4    Mitchley, B.C.V.5    Ross, W.C.J.6    Whisson, M.E.7
  • 2
    • 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)
    • Knox, R. J., Boland, M. P., Friedlos, F., Coles, B., Southan, C., and Roberts, J. J. (1988) 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, 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
  • 3
    • 0026075733 scopus 로고
    • Bioactivation of CB 1954: Reaction of the active 4-hydroxylamino derivative with thioesters to form the ultimate DNA-DNA interstrand cross-linking species
    • Knox, R. J., Friedlos, F., Marchbank, T., and Roberts, J. J. (1991) Bioactivation of CB 1954: reaction of the active 4-hydroxylamino derivative with thioesters to form the ultimate DNA-DNA interstrand cross-linking species. Biochem. Pharmacol. 42, 1691-1697.
    • (1991) Biochem. Pharmacol. , vol.42 , pp. 1691-1697
    • Knox, R.J.1    Friedlos, F.2    Marchbank, T.3    Roberts, J.J.4
  • 4
    • 0026034848 scopus 로고
    • The differences in kinetics of rat and human DT diaphorase result in a differential sensitivity of derived cell lines to CB 1954 (5-(aziridin-1-yl)-2,4-dinitrobenzamide)
    • Boland, M. P., Knox, R. J., and Roberts, J. J. (1991) The differences in kinetics of rat and human DT diaphorase result in a differential sensitivity of derived cell lines to CB 1954 (5-(aziridin-1-yl)-2,4-dinitrobenzamide). Biochem. Pharmacol. 41, 867-875.
    • (1991) Biochem. Pharmacol. , vol.41 , pp. 867-875
    • Boland, M.P.1    Knox, R.J.2    Roberts, J.J.3
  • 5
    • 0026745562 scopus 로고
    • The bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954) - I. Purification and properties of a nitroreductase enzyme from Escherichia coli - A potential enzyme for antibody-directed enzyme prodrug therapy (ADEPT)
    • Anlezark, G. M., Melton, R. G., Sherwood, R. F., Coles, B., Friedlos, F., and Knox, R. J. (1992) The bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954)-I. Purification and properties of a nitroreductase enzyme from Escherichia coli- -a potential enzyme for antibody-directed enzyme prodrug therapy (ADEPT). Biochem. Pharmacol. 44, 2289-2295.
    • (1992) Biochem. Pharmacol. , vol.44 , pp. 2289-2295
    • Anlezark, G.M.1    Melton, R.G.2    Sherwood, R.F.3    Coles, B.4    Friedlos, F.5    Knox, R.J.6
  • 6
    • 0026677838 scopus 로고
    • The bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954) - II. A comparison of an Eschericia coli nitroreductase and Walker DT diaphorase
    • Knox, R. J., Friedlos, F., Sherwood, R. F., Melton, R. G., and Anlezark, G. M. (1992) The bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954)-II. A comparison of an Eschericia coli nitroreductase and Walker DT diaphorase. Biochem. Pharmacol. 44, 2297-2301.
    • (1992) Biochem. Pharmacol. , vol.44 , pp. 2297-2301
    • Knox, R.J.1    Friedlos, F.2    Sherwood, R.F.3    Melton, R.G.4    Anlezark, G.M.5
  • 9
    • 0024324086 scopus 로고
    • Molecular enzymology of the reductive bioactivation of hypoxic cell cytotoxins
    • Walton, M. I., Wolf, C. R., and Workman, P. (1989) Molecular enzymology of the reductive bioactivation of hypoxic cell cytotoxins. Int. J. Radiat. Oncol. Biol. Phys. 16, 983-986.
    • (1989) Int. J. Radiat. Oncol. Biol. Phys. , vol.16 , pp. 983-986
    • Walton, M.I.1    Wolf, C.R.2    Workman, P.3
  • 10
    • 0019834471 scopus 로고
    • Radiosensitizing and cytotoxicity studies with CB 1954 (2,4-dinitro-5-aziridinylbenzamide)
    • Stratford, I. J., Williamson, C., Hoe, S., and Adams, G. E. (1981) Radiosensitizing and cytotoxicity studies with CB 1954 (2,4-dinitro-5-aziridinylbenzamide). Radiat. Res. 88, 502-509.
    • (1981) Radiat. Res. , vol.88 , pp. 502-509
    • Stratford, I.J.1    Williamson, C.2    Hoe, S.3    Adams, G.E.4
  • 12
    • 0026698228 scopus 로고
    • Use of hypoxia-directed drugs in therapy of solid tumors
    • Rockwell, S. (1992) Use of hypoxia-directed drugs in therapy of solid tumors. Semin. Oncol. 19, 29-40.
    • (1992) Semin. Oncol. , vol.19 , pp. 29-40
    • Rockwell, S.1
  • 13
    • 0027328452 scopus 로고
    • The experimental development of bioreductive drugs and their role in cancer therapy
    • Workman, P., and Stratford, I. J. (1993) The experimental development of bioreductive drugs and their role in cancer therapy. Cancer Metastasis Rev. 12, 73-82.
    • (1993) Cancer Metastasis Rev. , vol.12 , pp. 73-82
    • Workman, P.1    Stratford, I.J.2
  • 14
    • 0029884764 scopus 로고    scopus 로고
    • Recent developments in the design of bioreductive drugs
    • Denny, W. A., Wilson, W. R., and Hay, M. P. (1996) Recent developments in the design of bioreductive drugs. Br. J. Cancer 27, S32-S38.
    • (1996) Br. J. Cancer , vol.27
    • Denny, W.A.1    Wilson, W.R.2    Hay, M.P.3
  • 15
    • 0030028884 scopus 로고    scopus 로고
    • Hypoxia-specific cytotoxins in cancer therapy
    • Brown, J. M., and Siim, B. G. (1996) Hypoxia-Specific Cytotoxins in Cancer Therapy. Semin. Radiat. Oncol. 6, 22-36.
    • (1996) Semin. Radiat. Oncol. , vol.6 , pp. 22-36
    • Brown, J.M.1    Siim, B.G.2
  • 16
    • 0035010504 scopus 로고    scopus 로고
    • Electron transfer and oxidative stress as key factors in the design of drugs selectively active in hypoxia
    • Wardman, P. (2001) Electron transfer and oxidative stress as key factors in the design of drugs selectively active in hypoxia. Curr. Med. Chem. 8, 739-761.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 739-761
    • Wardman, P.1
  • 17
    • 0022535929 scopus 로고
    • Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic tumor cells
    • Denny, W. A., and Wilson, W. R. (1986) Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic tumor cells. J. Med. Chem. 29, 879-887.
    • (1986) J. Med. Chem. , vol.29 , pp. 879-887
    • Denny, W.A.1    Wilson, W.R.2
  • 18
    • 0025021102 scopus 로고
    • Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N′-bis(2-chloroethyl)anilines
    • Palmer, B. D., Wilson, W. R., Pullen, S. M., and Denny, W. A. (1990) Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N′-bis(2-chloroethyl)anilines. J. Med. Chem. 33, 112-121.
    • (1990) J. Med. Chem. , vol.33 , pp. 112-121
    • Palmer, B.D.1    Wilson, W.R.2    Pullen, S.M.3    Denny, W.A.4
  • 19
    • 0031306972 scopus 로고    scopus 로고
    • Nitro reduction as an electronic switch for bioreductive drug activation
    • Siim, B. G., Denny, W. A., and Wilson, W. R. (1997) Nitro reduction as an electronic switch for bioreductive drug activation. Oncol. Res. 9, 357-369.
    • (1997) Oncol. Res. , vol.9 , pp. 357-369
    • Siim, B.G.1    Denny, W.A.2    Wilson, W.R.3
  • 20
    • 0026665360 scopus 로고
    • Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells
    • Palmer, B. D., Wilson, W. R., Cliffe, S., and Denny, W. A. (1992) Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells. J. Med. Chem. 35, 3214-3222.
    • (1992) J. Med. Chem. , vol.35 , pp. 3214-3222
    • Palmer, B.D.1    Wilson, W.R.2    Cliffe, S.3    Denny, W.A.4
  • 22
    • 0036494169 scopus 로고    scopus 로고
    • Quantitation of bystander effects in nitroreductase suicide gene therapy using three-dimensional cell cultures
    • Wilson, W. R., Pullen, S. M., Hogg, A., Helsby, N. A., Hicks, K. O., and Denny, W. A. (2002) Quantitation of bystander effects in nitroreductase suicide gene therapy using three-dimensional cell cultures. Cancer Res. 62, 1425-1432.
    • (2002) Cancer Res. , vol.62 , pp. 1425-1432
    • Wilson, W.R.1    Pullen, S.M.2    Hogg, A.3    Helsby, N.A.4    Hicks, K.O.5    Denny, W.A.6
  • 23
    • 0021824209 scopus 로고
    • Defective DNA cross-link removal in Chinese hamster cell mutants hypersensitive to bifunctional alkylating agents
    • Hoy, C. A., Thompson, L. H., Mooney, C. L., and Salazar, E. P. (1985) Defective DNA cross-link removal in Chinese hamster cell mutants hypersensitive to bifunctional alkylating agents. Cancer Res. 45, 1737-1743.
    • (1985) Cancer Res. , vol.45 , pp. 1737-1743
    • Hoy, C.A.1    Thompson, L.H.2    Mooney, C.L.3    Salazar, E.P.4
  • 25
    • 0017188582 scopus 로고
    • The metabolism of the anti-tumour agent 5-(1-aziridinyl)-2,4-dinitrobenzamide (CB 1954)
    • Jarman, M., Melzack, D. H., and Ross, W. C. J. (1976) The metabolism of the anti-tumour agent 5-(1-aziridinyl)-2,4-dinitrobenzamide (CB 1954). Biochem. Pharmacol. 25, 2475-2478.
    • (1976) Biochem. Pharmacol. , vol.25 , pp. 2475-2478
    • Jarman, M.1    Melzack, D.H.2    Ross, W.C.J.3
  • 26
    • 0028916689 scopus 로고
    • Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide
    • Palmer, B. D., van Zijl, P., Denny, W. A., and Wilson, W. R. (1995) Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide. J. Med. Chem. 38, 1229-1241.
    • (1995) J. Med. Chem. , vol.38 , pp. 1229-1241
    • Palmer, B.D.1    Van Zijl, P.2    Denny, W.A.3    Wilson, W.R.4
  • 28
    • 0033729429 scopus 로고    scopus 로고
    • Pharmacokinetics and metabolism of the nitrogen mustard bioreductive drug 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (SN 23862) and the corresponding aziridine (CB 1954) in KHT tumour-bearing mice
    • Kestell, P., Pruijn, F. B., Siim, B. G., Palmer, B. D., and Wilson, W. R. (2000) Pharmacokinetics and metabolism of the nitrogen mustard bioreductive drug 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (SN 23862) and the corresponding aziridine (CB 1954) in KHT tumour-bearing mice. Cancer Chemother. Pharmacol. 46, 365-374.
    • (2000) Cancer Chemother. Pharmacol. , vol.46 , pp. 365-374
    • Kestell, P.1    Pruijn, F.B.2    Siim, B.G.3    Palmer, B.D.4    Wilson, W.R.5
  • 30
    • 37049150114 scopus 로고
    • Aryl-2-halogenoalkylamines. Part I
    • Ross, W. C. (1949) Aryl-2-halogenoalkylamines. Part I. J. Chem. Soc. Perkin Trans. 1, 183-191.
    • (1949) J. Chem. Soc. Perkin Trans. 1 , pp. 183-191
    • Ross, W.C.1
  • 31
    • 0026069610 scopus 로고
    • Alkylation of nucleic acids by DNA-targeted 4-anilinoquinolinium aniline mustards: Kinetic studies
    • O'Connor, C. J., Denny, W. A., and Fan, J. Y. (1991) Alkylation of nucleic acids by DNA-targeted 4-anilinoquinolinium aniline mustards: kinetic studies. Chem.-Biol. Interact. 77, 223-241.
    • (1991) Chem.-Biol. Interact. , vol.77 , pp. 223-241
    • O'Connor, C.J.1    Denny, W.A.2    Fan, J.Y.3
  • 33
    • 0024466393 scopus 로고
    • Bioactivation of dapsone to a cytotoxic metabolite by human hepatic microsomal enzymes
    • Coleman, M. D., Breckenridge, A. M., and Park B. K. (1989) Bioactivation of dapsone to a cytotoxic metabolite by human hepatic microsomal enzymes. Br. J. Clin. Pharmacol. 28, 389-395.
    • (1989) Br. J. Clin. Pharmacol. , vol.28 , pp. 389-395
    • Coleman, M.D.1    Breckenridge, A.M.2    Park, B.K.3
  • 34
    • 0027234856 scopus 로고
    • Identification, synthesis and properties of 5-(aziridin-1-yl)-2-nitro-4-nitrosobenzamide, a novel DNA cross-linking agent derived from CB1954
    • Knox, R. J., Friedlos, F., Biggs, P. J., Flitter, W. D., Gaskell, M., Goddard, P., Davies, L., and Jarman, M. (1993) Identification, synthesis and properties of 5-(aziridin-1-yl)-2-nitro-4-nitrosobenzamide, a novel DNA cross-linking agent derived from CB1954. Biochem. Pharmacol. 46, 797-803.
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 797-803
    • Knox, R.J.1    Friedlos, F.2    Biggs, P.J.3    Flitter, W.D.4    Gaskell, M.5    Goddard, P.6    Davies, L.7    Jarman, M.8
  • 36
    • 0017925519 scopus 로고
    • Structure-activity relationships in antitumor aniline mustards
    • Panthananickal, A., Hansch, C., and Leo, A. (1978) Structure-activity relationships in antitumor aniline mustards. J. Med. Chem. 21, 16-26.
    • (1978) J. Med. Chem. , vol.21 , pp. 16-26
    • Panthananickal, A.1    Hansch, C.2    Leo, A.3
  • 37
    • 0024556258 scopus 로고
    • Molecular orbital calculations on tumorinhibitory phenyl aziridines: QSARs
    • Lewis, D. F. V. (1989) Molecular orbital calculations on tumorinhibitory phenyl aziridines: QSARs. Xenobiotica 19, 341-356.
    • (1989) Xenobiotica , vol.19 , pp. 341-356
    • Lewis, D.F.V.1
  • 38
    • 12444296488 scopus 로고    scopus 로고
    • Extravascular transport of GDEPT prodrugs in multicellular layer cultures: Dinitrobenzamide mustard substrates for the E. coli nitroreductase NTR
    • Wilson, W. R., Ferry, D. M., Patterson, A. V., Pullen, S. M., Helsby, N. A., Pruijn, F. B., and Hicks, K. O. (2002) Extravascular transport of GDEPT prodrugs in multicellular layer cultures: Dinitrobenzamide mustard substrates for the E. coli nitroreductase NTR. Proc. Am. Assoc. Cancer Res. 43, 84-85.
    • (2002) Proc. Am. Assoc. Cancer Res. , vol.43 , pp. 84-85
    • Wilson, W.R.1    Ferry, D.M.2    Patterson, A.V.3    Pullen, S.M.4    Helsby, N.A.5    Pruijn, F.B.6    Hicks, K.O.7
  • 39
    • 0024209370 scopus 로고
    • A new cytotoxic, DNA interstrand cross-linking agent, 5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide, is formed from 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by a nitroreductase enzyme in Walker carcinoma cells
    • Knox, R. J., Friedlos, F., Jarman, M., and Roberts, J. J. (1988) A new cytotoxic, DNA interstrand cross-linking agent, 5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide, is formed from 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by a nitroreductase enzyme in Walker carcinoma cells. Biochem. Pharmacol. 37, 4661-4669.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 4661-4669
    • Knox, R.J.1    Friedlos, F.2    Jarman, M.3    Roberts, J.J.4
  • 40
    • 0015793816 scopus 로고
    • Biochemical formation and pharmacological, toxicological and pathological properties of hydroxylamines and hydroxamic acids
    • Weisburger, J. H., and Weisburger, K. W. (1973) Biochemical formation and pharmacological, toxicological and pathological properties of hydroxylamines and hydroxamic acids. Pharmacol. Rev. 25, 1-66.
    • (1973) Pharmacol. Rev. , vol.25 , pp. 1-66
    • Weisburger, J.H.1    Weisburger, K.W.2
  • 41
    • 0027219332 scopus 로고
    • Bioreducible mustards: A paradigm for hypoxia-selective prodrugs of diffusible cytotoxins (HPDCs)
    • Denny, W. A., and Wilson, W. R. (1993) Bioreducible mustards: a paradigm for hypoxia-selective prodrugs of diffusible cytotoxins (HPDCs). Cancer Metastasis Rev. 12, 135-151.
    • (1993) Cancer Metastasis Rev. , vol.12 , pp. 135-151
    • Denny, W.A.1    Wilson, W.R.2


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