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Volumn 42, Issue 12, 1999, Pages 2245-2250

Cross-linking and sequence-specific alkylation of DNA by aziridinylquinones. 3. Effects of alkyl substituents

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIAZIRIDINYL 3 ETHYL 6 METHYL 1,4 BENZOQUINONE; 2,5 DIAZIRIDINYL 3 ISOPROPYL 6 METHYL 1,4 BENZOQUINONE; 2,5 DIAZIRIDINYL 3 METHYL 6 PROPYL 1,4 BENZOQUINONE; ALKYL GROUP; BENZOQUINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033577984     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991007y     Document Type: Article
Times cited : (14)

References (30)
  • 1
    • 0021347665 scopus 로고
    • Treatment of patients with recurrent primary brain tumours with AZQ
    • Schold, S. C.; Friedman, H. S.; Bjornsson, T. D.; Falleta, J. M. Treatment of patients with recurrent primary brain tumours with AZQ. Neurology 1984, 34, 615-619.
    • (1984) Neurology , vol.34 , pp. 615-619
    • Schold, S.C.1    Friedman, H.S.2    Bjornsson, T.D.3    Falleta, J.M.4
  • 3
    • 0018390104 scopus 로고
    • Trenimon: Biochemical, physiological and genetic effects on cells and organisms
    • Obe, G.; Beek, B. Trenimon: Biochemical, physiological and genetic effects on cells and organisms. Mutat. Res. 1979, 65, 21-70.
    • (1979) Mutat. Res. , vol.65 , pp. 21-70
    • Obe, G.1    Beek, B.2
  • 4
    • 0021205291 scopus 로고
    • Mechanisms of DNA strand breakage and interstrand cross-linking by diaziridinylbenzoquinone (Diaziquone) in isolated nuclei from human cells
    • Szmigiero, L.; Kohn, K. W. Mechanisms of DNA strand breakage and interstrand cross-linking by diaziridinylbenzoquinone (Diaziquone) in isolated nuclei from human cells. Cancer Res. 1984, 44, 4453-4457.
    • (1984) Cancer Res. , vol.44 , pp. 4453-4457
    • Szmigiero, L.1    Kohn, K.W.2
  • 5
    • 0025258497 scopus 로고
    • Metabolism of diaziquone by NAD(P)H:(qumone acceptor) oxireductase (DT-diaphorase); role in diaziquone-induced DNA damage and cytotoxicity in human colon carcinoma cells
    • Siegel, D.; Gibson, N. W.; Preusch, P. C.; Ross, D. Metabolism of diaziquone by NAD(P)H:(qumone acceptor) oxireductase (DT-diaphorase); role in diaziquone-induced DNA damage and cytotoxicity in human colon carcinoma cells. Cancer Res. 1990, 50, 7293-7300.
    • (1990) Cancer Res. , vol.50 , pp. 7293-7300
    • Siegel, D.1    Gibson, N.W.2    Preusch, P.C.3    Ross, D.4
  • 7
    • 0025237150 scopus 로고
    • A comparison of the structural and cytotoxic activity of novel AZQ analogues
    • Dzielendziak, A.; Butler, J.; Hoey, B. M.; Lea, J. S.; Ward, T. H. A comparison of the structural and cytotoxic activity of novel AZQ analogues. Cancer Res. 1990, 5, 2003-2007.
    • (1990) Cancer Res. , vol.5 , pp. 2003-2007
    • Dzielendziak, A.1    Butler, J.2    Hoey, B.M.3    Lea, J.S.4    Ward, T.H.5
  • 8
    • 0030025890 scopus 로고    scopus 로고
    • Cross-linking and sequence specific alkylation of DNA by diaziridinylquinones. 1. Quinone methides
    • Mayalarp, S. P.; Hargreaves, R. H. J.; Butler, J.; O'Hare, C. C.; Hartley, J. A. Cross-linking and sequence specific alkylation of DNA by diaziridinylquinones. 1. Quinone Methides. J. Med. Chem. 1996, 39, 531-537.
    • (1996) J. Med. Chem. , vol.39 , pp. 531-537
    • Mayalarp, S.P.1    Hargreaves, R.H.J.2    Butler, J.3    O'Hare, C.C.4    Hartley, J.A.5
  • 9
    • 0031059420 scopus 로고    scopus 로고
    • Cross-linking and sequence specific alkylation of DNA by aziridinylquinones. 2. Structure requirements for sequence selectivity
    • Hargreaves, R. H. J.; Mayalarp, S. P.; Butler, J.; McAdam, S. R.; O'Hare, C. C.; Hartley, J. A. Cross-linking and sequence specific alkylation of DNA by aziridinylquinones. 2. Structure requirements for sequence selectivity. J. Med. Chem. 1997, 40, 357-362.
    • (1997) J. Med. Chem. , vol.40 , pp. 357-362
    • Hargreaves, R.H.J.1    Mayalarp, S.P.2    Butler, J.3    McAdam, S.R.4    O'Hare, C.C.5    Hartley, J.A.6
  • 10
    • 0027048768 scopus 로고
    • The relationship between DT-diaphorase mediated metabolism of a series of diaziridinylbenzoquinones and DNA damage and cytotoxicity
    • Gibson, N. W.; Hartley, J. A.; Butler, J.; Seigel, D.; Ross, D. The relationship between DT-diaphorase mediated metabolism of a series of diaziridinylbenzoquinones and DNA damage and cytotoxicity. Mol. Pharmacol. 1992, 42, 531-536.
    • (1992) Mol. Pharmacol. , vol.42 , pp. 531-536
    • Gibson, N.W.1    Hartley, J.A.2    Butler, J.3    Seigel, D.4    Ross, D.5
  • 11
    • 0029121481 scopus 로고
    • Nicotinamide adenine dinucleotide (phosphate): Quinone oxireductase (DT-diaphorase) as a target for bioreductive antitumor quinones: Quinone cytotoxicity and selectivity in human lung and breast cancer cell lines
    • Beall, H. D.; Murphy, A. M.; Siegel, D.; Hargreaves, R. H. J.; Butler, J.; Ross, D. Nicotinamide adenine dinucleotide (phosphate): Quinone oxireductase (DT-diaphorase) as a target for bioreductive antitumor quinones: Quinone cytotoxicity and selectivity in human lung and breast cancer cell lines. Mol. Pharmacol. 1995, 48, 499-504.
    • (1995) Mol. Pharmacol. , vol.48 , pp. 499-504
    • Beall, H.D.1    Murphy, A.M.2    Siegel, D.3    Hargreaves, R.H.J.4    Butler, J.5    Ross, D.6
  • 12
    • 0026348670 scopus 로고
    • DNA crosslinking and sequence selectivity of aziridinylbenzoquinones: A unique reaction at 5′-GC-3′ sequences with 2,5-diaziridinyl-1,4-benzoquinone upon reduction
    • Hartley, J. A.; Berardini, M.; Ponti, M.; Gibson, N. W.; Thompson, A. S.; Thurston, D. E.; Hoey, B. M.; Butler, J. DNA crosslinking and sequence selectivity of aziridinylbenzoquinones: A unique reaction at 5′-GC-3′ sequences with 2,5-diaziridinyl-1,4-benzoquinone upon reduction. Biochemistry 1991, 30, 11719-11724.
    • (1991) Biochemistry , vol.30 , pp. 11719-11724
    • Hartley, J.A.1    Berardini, M.2    Ponti, M.3    Gibson, N.W.4    Thompson, A.S.5    Thurston, D.E.6    Hoey, B.M.7    Butler, J.8
  • 13
    • 0027159001 scopus 로고
    • Two structurally related diaziridinyl-benzoquinones preferentially cross-link DNA at different sites upon reduction with DT-Diaphorase
    • Berardini, M. D.; Souhami, R. L.; Lee, C.-S.; Gibson, N. W.; Butler, J.; Hartley, J. A. Two structurally related diaziridinyl-benzoquinones preferentially cross-link DNA at different sites upon reduction with DT-Diaphorase. Biochemistry 1993, 32, 3306-3312.
    • (1993) Biochemistry , vol.32 , pp. 3306-3312
    • Berardini, M.D.1    Souhami, R.L.2    Lee, C.-S.3    Gibson, N.W.4    Butler, J.5    Hartley, J.A.6
  • 14
    • 4243664295 scopus 로고
    • A survey of Hammett substituent constants and resonance and field parameters
    • Hansch, C.; Leo, A.; Taft, R. W. A survey of Hammett substituent constants and resonance and field parameters. Chem. Rev. 1991, 91, 165-195.
    • (1991) Chem. Rev. , vol.91 , pp. 165-195
    • Hansch, C.1    Leo, A.2    Taft, R.W.3
  • 15
    • 0027390265 scopus 로고
    • The one electron reduction potential of several substrates can be related to their reduction rates by cytochrome P450 reductase
    • Butler, J.; Hoey, B. M. The one electron reduction potential of several substrates can be related to their reduction rates by cytochrome P450 reductase. Biochim. Biophys Acta 1993, 1161, 73-77.
    • (1993) Biochim. Biophys Acta , vol.1161 , pp. 73-77
    • Butler, J.1    Hoey, B.M.2
  • 16
    • 0000955175 scopus 로고    scopus 로고
    • Redox cycling antitumour drugs
    • Halliwell, B., Aruoma, O. I., Eds.; OICA International: London
    • Butler, J.; Redox Cycling antitumour drugs. In DNA and Free Radicals: Techniques, Mechanisms and Applications; Halliwell, B., Aruoma, O. I., Eds.; OICA International: London, 1998; pp 131-154.
    • (1998) DNA and Free Radicals: Techniques, Mechanisms and Applications
    • Butler, J.1
  • 17
    • 0026537127 scopus 로고
    • Reactions of glutathione and glutathione radicals with benzoquinones
    • Butler, J.; Hoey, B. M. Reactions of glutathione and glutathione radicals with benzoquinones. Free Radical Biol. Med. 1992, 12, 337-345.
    • (1992) Free Radical Biol. Med. , vol.12 , pp. 337-345
    • Butler, J.1    Hoey, B.M.2
  • 19
    • 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
    • Li, R.; Bianchet, M. A.; Talalay, P.; Amzel, L. M. 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. U.S.A. 1995, 92, 8846-8850.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 8846-8850
    • Li, R.1    Bianchet, M.A.2    Talalay, P.3    Amzel, L.M.4
  • 20
    • 0031930369 scopus 로고    scopus 로고
    • 5-Substituted analogues of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) and their regioisomers as hypoxia-selective agents: Structure-cytotoxicity in vitro
    • Jaffar, M.; Naylor, M. A.; Robertson, N.; Lockyer, S. D.; Phillips, R. M.; Everett, S. A.; Adams, G. E.; Stratford, I. J. 5-Substituted analogues of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) and their regioisomers as hypoxia-selective agents: structure-cytotoxicity in vitro. Anticancer Drug Des. 1998, 13, 105-123.
    • (1998) Anticancer Drug Des. , vol.13 , pp. 105-123
    • Jaffar, M.1    Naylor, M.A.2    Robertson, N.3    Lockyer, S.D.4    Phillips, R.M.5    Everett, S.A.6    Adams, G.E.7    Stratford, I.J.8
  • 21
    • 0022656110 scopus 로고
    • Adriamycin and DT-diaphorase
    • Wallin, R. Adriamycin and DT-diaphorase. Cancer Lett. 1986, 30, 97-101.
    • (1986) Cancer Lett. , vol.30 , pp. 97-101
    • Wallin, R.1
  • 23
    • 37049116490 scopus 로고
    • Photochemical formation of benzoxazoline derivatives from aminated quinones
    • Cameron, D. W.; Giles, R. G. F. Photochemical formation of benzoxazoline derivatives from aminated quinones. J. Chem. Soc. C 1968, 1461-1464.
    • (1968) J. Chem. Soc. C , pp. 1461-1464
    • Cameron, D.W.1    Giles, R.G.F.2
  • 24
    • 0001593008 scopus 로고
    • Synthesis of simple quinone derivatives with fungicidal, bacteriostatic and cytostatic properties
    • Petersen, S.; Gauss, W.; Urbschat, E. Synthesis of simple quinone derivatives with fungicidal, bacteriostatic and cytostatic properties. Angew. Chem. 1955, 67, 217-231.
    • (1955) Angew. Chem. , vol.67 , pp. 217-231
    • Petersen, S.1    Gauss, W.2    Urbschat, E.3
  • 25
    • 0017103769 scopus 로고
    • Phenyalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-2,5-dimethoxy-4-methylphenyl-butane
    • Standridge, R. T.; Howell, H. G.; Gylys, J. A.; Partyka, R. A.; Shulgin, A. T. Phenyalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-(2,5-dimethoxy-4-methylphenyl-butane. J. Med. Chem. 1976, 19, 1400-1404.
    • (1976) J. Med. Chem. , vol.19 , pp. 1400-1404
    • Standridge, R.T.1    Howell, H.G.2    Gylys, J.A.3    Partyka, R.A.4    Shulgin, A.T.5
  • 26
    • 85010165175 scopus 로고
    • Antileukemic agents. II. New 2,5-Bis(1-aziridinyl)-p-benzoquinone derivatives
    • Nakao, H.; Arakawa, M.; Nakamura, T.; Fukushima, M. Antileukemic agents. II. New 2,5-Bis(1-aziridinyl)-p-benzoquinone derivatives. Chem. Pharm. Bull. 1972, 20, 1968-1979.
    • (1972) Chem. Pharm. Bull. , vol.20 , pp. 1968-1979
    • Nakao, H.1    Arakawa, M.2    Nakamura, T.3    Fukushima, M.4
  • 28
    • 0023130372 scopus 로고
    • Evaluation of tetrazolium-based semiautomatic colorimetric assay; assessment of chemosensitivity testing
    • Carmichael, J.; DeGraff, W. G.; Gazdar, A. F.; Minna, J. D.; Michael, J. B. Evaluation of tetrazolium-based semiautomatic colorimetric assay; assessment of chemosensitivity testing. Cancer Res. 1987, 47, 936-942.
    • (1987) Cancer Res. , vol.47 , pp. 936-942
    • Carmichael, J.1    DeGraff, W.G.2    Gazdar, A.F.3    Minna, J.D.4    Michael, J.B.5
  • 29
    • 0028243181 scopus 로고
    • Metabolism of bioreductive antitumor compounds by purified rat and human DT-diaphorase
    • Beall, H. D.; Mulcahy, R. T.; Siegel, D.; Traver, R. D.; Gibson, N. W.; Ross, D. Metabolism of bioreductive antitumor compounds by purified rat and human DT-diaphorase. Cancer Res. 1994, 54, 3196-3201.
    • (1994) Cancer Res. , vol.54 , pp. 3196-3201
    • Beall, H.D.1    Mulcahy, R.T.2    Siegel, D.3    Traver, R.D.4    Gibson, N.W.5    Ross, D.6
  • 30
    • 0026099406 scopus 로고
    • An agarose gel method for the determination of DNA interstrand cross-linking applicable to the measurement of total and second-arm cross-link reactions
    • Hartley, J. A.; Berardini, M.; Souhami, R. L. An agarose gel method for the determination of DNA interstrand cross-linking applicable to the measurement of total and second-arm cross-link reactions. Anal. Biochem. 1991, 193, 131-134.
    • (1991) Anal. Biochem. , vol.193 , pp. 131-134
    • Hartley, J.A.1    Berardini, M.2    Souhami, R.L.3


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