메뉴 건너뛰기




Volumn 40, Issue 3, 1997, Pages 357-361

Cross-linking and sequence specific alkylation of DNA by aziridinyl quinones. 2. Structure requirements for sequence selectivity

Author keywords

[No Author keywords available]

Indexed keywords

2,3,5,6 TETRAAZIRIDINYL 1,4 BENZOQUINONE; 2,5 DIAZIRIDINYL 3 (4 METHYLPHENYL) 1,4 BENZOQUINONE; 2,5 DIAZIRIDINYL 3 PHENYL 1,4 BENZOQUINONE; 2,5 DIAZIRIDINYL 3,6 DIMETHYL 1,4 BENZOQUINONE; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG;

EID: 0031059420     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960492j     Document Type: Article
Times cited : (18)

References (34)
  • 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. Mutation Res. 1979, 65, 21-70.
    • (1979) Mutation 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 diaziridinyibenzoquinone (Diaziquone) in isolated nuclei from human cells
    • Szmigiero, L.; Kohn, K. W. Mechanisms of DNA strand breakage and interstrand cross-linking by diaziridinyibenzoquinone (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:(quinone 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:(quinone 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
  • 6
    • 0025045577 scopus 로고
    • Contrasting cytotoxic mechanisms of similar antitumour diaziridinybenzoquinones
    • Butler, J.; Dzielendziak, A.; Lea, J. S.; Ward, T. H.; Hoey, B. M. Contrasting cytotoxic mechanisms of similar antitumour diaziridinybenzoquinones. Free Rad. Res. Commun. 1990, 8, 231-239.
    • (1990) Free Rad. Res. Commun. , vol.8 , pp. 231-239
    • Butler, J.1    Dzielendziak, A.2    Lea, J.S.3    Ward, T.H.4    Hoey, B.M.5
  • 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
    • 0026348670 scopus 로고
    • DNA cross-linking 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 cross-linking 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
  • 9
    • 0027159001 scopus 로고
    • Two structurally related diaziridinylbenzoquinones 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 diaziridinylbenzoquinones 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
  • 10
    • 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
  • 11
    • 0027989554 scopus 로고
    • DNA-DNA interstrand cross-linking by 2,5-bis(1-aziridinyl)-3,6-bis(carboethoxyamino)-1,4benzoquinone: Covalent structure of the dG-to-dG cross-links in calf thymus DNA and synthetic DNA duplex
    • Alley, S. C.; Hopkins, P. B. DNA-DNA interstrand cross-linking by 2,5-bis(1-aziridinyl)-3,6-bis(carboethoxyamino)-1,4benzoquinone: Covalent structure of the dG-to-dG cross-links in calf thymus DNA and synthetic DNA duplex. Chem. Res. Toxicol. 1994, 7, 666-672.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 666-672
    • Alley, S.C.1    Hopkins, P.B.2
  • 12
    • 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. 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.5
  • 14
    • 0003027545 scopus 로고
    • Redox Cycling drugs and DNA damage
    • Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: London
    • Butler, J.; Hoey, B. M. Redox Cycling drugs and DNA damage. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: London, 1993; pp 243-265.
    • (1993) DNA and Free Radicals , pp. 243-265
    • Butler, J.1    Hoey, B.M.2
  • 15
    • 0024592332 scopus 로고
    • Free radical formation by antitumour quinones
    • Powis, G. Free radical formation by antitumour quinones. Free Rad. Biol. Med. 1989, 6, 63-101.
    • (1989) Free Rad. Biol. Med. , vol.6 , pp. 63-101
    • Powis, G.1
  • 17
    • 0026461079 scopus 로고
    • 2: An Examination of propeller twist and minor-groove water structure at 2.2 Angstrom resolution
    • 2: An Examination of propeller twist and minor-groove water structure at 2.2 Angstrom resolution. J. Mol. Biol. 1992, 226, 1161-1173.
    • (1992) J. Mol. Biol. , vol.226 , pp. 1161-1173
    • Edwards, K.J.1    Brown, D.G.2    Spink, N.3    Skelly, J.V.4    Neidle, S.5
  • 18
    • 0025966606 scopus 로고
    • Analysis of local geometry in three B-DNA decamers and eight dodecamers
    • Yanagi, K.; Privé, G. G.; Dickerson, R. E. Analysis of local geometry in three B-DNA decamers and eight dodecamers. J. Mol. Biol. 1991, 217, 201-214.
    • (1991) J. Mol. Biol. , vol.217 , pp. 201-214
    • Yanagi, K.1    Privé, G.G.2    Dickerson, R.E.3
  • 19
    • 0026702486 scopus 로고
    • DNA structure from A to Z
    • Dickerson, R. E. DNA structure from A to Z. Methods Enzymol. 1992, 211, 67-111.
    • (1992) Methods Enzymol. , vol.211 , pp. 67-111
    • Dickerson, R.E.1
  • 21
    • 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
  • 22
    • 84912674252 scopus 로고
    • Über die umsetzung einiger alkoxy-p-benzochinone mit äthylenimine
    • Gauss, W. Über die umsetzung einiger alkoxy-p-benzochinone mit äthylenimine. Chem. Ber. 1958, 91, 2216-2222.
    • (1958) Chem. Ber. , vol.91 , pp. 2216-2222
    • Gauss, W.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
    • 0017181413 scopus 로고
    • Potential central nervous system antitumor agents. Aziridinylquinones. 2
    • Chou, F.; Khan, A. H.; Driscoll, J. S. Potential central nervous system antitumor agents. Aziridinylquinones. 2. J. Med. Chem. 1976, 19, 1302-1308.
    • (1976) J. Med. Chem. , vol.19 , pp. 1302-1308
    • Chou, F.1    Khan, A.H.2    Driscoll, J.S.3
  • 25
    • 0342473385 scopus 로고
    • 1,4-Benzoquinones: Improved methods of synthesis and new Diaziridinyl analogues
    • Dzielendziak, A.; Butler, J. 1,4-Benzoquinones: Improved methods of synthesis and new Diaziridinyl analogues. Synthesis 1989, 643-643.
    • (1989) Synthesis , pp. 643-643
    • Dzielendziak, A.1    Butler, J.2
  • 26
    • 85010165175 scopus 로고
    • Anti-leukemic agents II. New 2,5-Bis(1-Aziridinyl)-p-benzoquinone derivatives
    • Nakao, H.; Arakawa, M.; Nakamura, T.; Fukushima, M. Anti-leukemic 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
  • 27
    • 15144361396 scopus 로고
    • Stellaquinones, a new class of dark coloured compounds
    • Wallenfels, K.; Draber, W. Stellaquinones, a new class of dark coloured compounds. Angew. Chem. 1958, 70, 318.
    • (1958) Angew. Chem. , vol.70 , pp. 318
    • Wallenfels, K.1    Draber, W.2
  • 28
    • 0001657448 scopus 로고
    • An optical method for the study of reversible organic oxidation-reduction systems. IV. Arylquinones
    • Kvalnes, D. E. An optical method for the study of reversible organic oxidation-reduction systems. IV. Arylquinones. J. Am. Chem. Soc. 1934, 56, 2478-2481.
    • (1934) J. Am. Chem. Soc. , vol.56 , pp. 2478-2481
    • Kvalnes, D.E.1
  • 29
    • 0012128972 scopus 로고
    • Chemistry of fluorinated quinones. Part II. Proton and fluorine NMR spectra
    • Hudlicky, M.; Bell, H. M. Chemistry of fluorinated quinones. Part II. Proton and fluorine NMR spectra. J. Fluorine Chem. 1975, 6, 201-212.
    • (1975) J. Fluorine Chem. , vol.6 , pp. 201-212
    • Hudlicky, M.1    Bell, H.M.2
  • 31
    • 0018846636 scopus 로고
    • Sequencing end-labelled DNA with base specific chemical cleavages
    • Maxam, A. M.; Gilbert, W. Sequencing end-labelled DNA with base specific chemical cleavages. Methods Enzymol. 1980, 65, 499-560.
    • (1980) Methods Enzymol. , vol.65 , pp. 499-560
    • Maxam, A.M.1    Gilbert, W.2
  • 33
    • 0022521735 scopus 로고
    • Mechanism of DNA strand breakage by piperidine at sites of N7-alkyl guanine
    • Mattes, W. B.; Hartley, J. A.; Kohn, K. W. Mechanism of DNA strand breakage by piperidine at sites of N7-alkyl guanine. Biochim. Biophys. Acta 1986, 868, 71-76.
    • (1986) Biochim. Biophys. Acta , vol.868 , pp. 71-76
    • Mattes, W.B.1    Hartley, J.A.2    Kohn, K.W.3
  • 34
    • 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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.