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Volumn 47, Issue 1, 2000, Pages 47-57

The role of side chains in the interaction of new antitumor pyrimidoacridinetriones with DNA: Molecular dynamics simulations

Author keywords

Molecular dynamics simulations; Pyrimidoacridinetrione antitumor agents; Role of side chain(s); Structure of intercalation complex

Indexed keywords

ACRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; DNA; PYRIMIDINE DERIVATIVE;

EID: 0033655687     PISSN: 0001527X     EISSN: None     Source Type: Journal    
DOI: 10.18388/abp.2000_4061     Document Type: Article
Times cited : (4)

References (34)
  • 1
    • 0020683314 scopus 로고
    • The design, synthesis, and development of a new class of potential antineoplastic anthraquinones
    • Ellis, G.P. & West, G.B., eds. and references cited therein, Elsevier, Amsterdam
    • Cheng, C.C. & Zee-Cheng, R.K.Y. (1983) The design, synthesis, and development of a new class of potential antineoplastic anthraquinones; in Progress in Medicinal Chemistry (Ellis, G.P. & West, G.B., eds.) pp. 83-118 and references cited therein, Elsevier, Amsterdam.
    • (1983) Progress in Medicinal Chemistry , pp. 83-118
    • Cheng, C.C.1    Zee-Cheng, R.K.Y.2
  • 2
    • 0018084754 scopus 로고
    • Antineoplastic agents. Structure-activity relationship study of bis(substituted aminoalkyloamino)anthraquinones
    • Zee-Cheng, R.K.Y. & Cheng, C.C. (1978) Antineoplastic agents. Structure-activity relationship study of bis(substituted aminoalkyloamino)anthraquinones. J. Med. Chem. 21, 291-294.
    • (1978) J. Med. Chem. , vol.21 , pp. 291-294
    • Zee-Cheng, R.K.Y.1    Cheng, C.C.2
  • 3
    • 0018680061 scopus 로고
    • Structural modification study of bis(substituted aminoalkyloamino)anthraquinones. An evaluation of the relationship of the [2-[(2-hydroxyethyl)amino]ethyl]amino side chain with antineoplastic activity
    • Zee-Cheng, R.K.Y., Podrebarac, E.G., Menon, C.S. & Cheng, C.C. (1979) Structural modification study of bis(substituted aminoalkyloamino)anthraquinones. An evaluation of the relationship of the [2-[(2-hydroxyethyl)amino]ethyl]amino side chain with antineoplastic activity. J. Med. Chem. 22, 501-505.
    • (1979) J. Med. Chem. , vol.22 , pp. 501-505
    • Zee-Cheng, R.K.Y.1    Podrebarac, E.G.2    Menon, C.S.3    Cheng, C.C.4
  • 5
    • 0008708573 scopus 로고
    • Biochemical pharmacology and tumor biology of mitoxantrone and ametantrone
    • Lown, J.W., ed. Elsevier, Amsterdam
    • Durr, F.E. (1988) Biochemical pharmacology and tumor biology of mitoxantrone and ametantrone; in Anthracycline and Anthracenedione-Based Anticancer Agents (Lown, J.W., ed.) pp. 401-445, Elsevier, Amsterdam.
    • (1988) Anthracycline and Anthracenedione-based Anticancer Agents , pp. 401-445
    • Durr, F.E.1
  • 6
    • 0016223489 scopus 로고
    • The experimental antitumor properties of three congeners of the acridinyl methanesulphonanilide (AMSA) series
    • Cain, B.F. & Atwell, G.J. (1974) The experimental antitumor properties of three congeners of the acridinyl methanesulphonanilide (AMSA) series. Eur. J. Cancer 10, 539-549.
    • (1974) Eur. J. Cancer , vol.10 , pp. 539-549
    • Cain, B.F.1    Atwell, G.J.2
  • 8
    • 0021338222 scopus 로고
    • 5-[(aminoalkyl)amino]-substituted anthra-[1,9-cd]-pyrazol-6(2H)-ones as novel anticancer agents. Synthesis and biological evaluation
    • Showalter, H.D.H., Johnson, J.L., Werbel, L.M., Leopold, W.R., Jackson, R.C. & Elslager, E.F. (1984) 5-[(Aminoalkyl)amino]-substituted anthra-[1,9-cd]-pyrazol-6(2H)-ones as novel anticancer agents. Synthesis and biological evaluation. J. Med. Chem. 27, 253-255.
    • (1984) J. Med. Chem. , vol.27 , pp. 253-255
    • Showalter, H.D.H.1    Johnson, J.L.2    Werbel, L.M.3    Leopold, W.R.4    Jackson, R.C.5    Elslager, E.F.6
  • 9
    • 0022349519 scopus 로고
    • Anthrapyrazoles. A new class of intercalating agents with high level, broad spectrum activity against murine tumors
    • Leopold, W.R., Nelson, J.M., Plowman, J. & Jackson, R.C. (1985) Anthrapyrazoles. A new class of intercalating agents with high level, broad spectrum activity against murine tumors. Cancer Res. 45, 5532-5539.
    • (1985) Cancer Res. , vol.45 , pp. 5532-5539
    • Leopold, W.R.1    Nelson, J.M.2    Plowman, J.3    Jackson, R.C.4
  • 13
    • 0023251054 scopus 로고
    • Potential antitumor agents. 50. In vivo solid-tumor activity of derivatived of N-[2-(diethylamino)ethyl]acridine-4-carboxamide
    • Atwell, G.J., Rewcastle, G.W., Baguley, B.C. & Denny, W.A. (1987) Potential antitumor agents. 50. In vivo solid-tumor activity of derivatived of N-[2-(diethylamino)ethyl]acridine-4-carboxamide. J. Med. Chem. 30, 664-669.
    • (1987) J. Med. Chem. , vol.30 , pp. 664-669
    • Atwell, G.J.1    Rewcastle, G.W.2    Baguley, B.C.3    Denny, W.A.4
  • 14
    • 0023222336 scopus 로고
    • Relationship between DNA-binding kinetics and biological ac-tivity for the 9-aminoacridine-4-carboxamide class of antitumor agents
    • Wakelin, L.P.G., Atwell, G.J., Rewcastle, G.W. & Denny, W.A. (1987) Relationship between DNA-binding kinetics and biological ac-tivity for the 9-aminoacridine-4-carboxamide class of antitumor agents. J. Med. Chem. 30, 855-861.
    • (1987) J. Med. Chem. , vol.30 , pp. 855-861
    • Wakelin, L.P.G.1    Atwell, G.J.2    Rewcastle, G.W.3    Denny, W.A.4
  • 15
    • 0025165116 scopus 로고
    • 5-[(aminoalkyl)-amino]imidazo[4,5,1-de]acridin-6-ones as a novel class of antineoplastic agents. Synthesis and biological activity
    • Cholody, W.M., Martelli, S., Paradziej-Lukowicz, J. & Konopa, J. (1990) 5-[(Aminoalkyl)-amino]imidazo[4,5,1-de]acridin-6-ones as a novel class of antineoplastic agents. Synthesis and biological activity. J. Med. Chem. 33, 49-52.
    • (1990) J. Med. Chem. , vol.33 , pp. 49-52
    • Cholody, W.M.1    Martelli, S.2    Paradziej-Lukowicz, J.3    Konopa, J.4
  • 16
    • 0026602257 scopus 로고
    • Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias
    • Cholody, W.M., Martelli, S. & Konopa, J. (1992) Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias. J. Med. Chem. 35, 378-382.
    • (1992) J. Med. Chem. , vol.35 , pp. 378-382
    • Cholody, W.M.1    Martelli, S.2    Konopa, J.3
  • 17
    • 0001448070 scopus 로고
    • 8-substituted 5-[aminoalkylamino]-6h-triazolo[4,5,1-de]acridin-6-ones as potential antineoplastic agents. Synthesis and biological activity
    • Cholody, W.M., Martelli, S. & Konopa, J. (1990) 8-Substituted 5-[(aminoalkylamino]-6H-triazolo[4,5,1-de]acridin-6-ones as potential antineoplastic agents. Synthesis and biological activity. J. Med. Chem. 33, 2582-2586.
    • (1990) J. Med. Chem. , vol.33 , pp. 2582-2586
    • Cholody, W.M.1    Martelli, S.2    Konopa, J.3
  • 18
    • 84986432857 scopus 로고
    • The synthesis of a new polycyclic heterocyclic ring system: Pyrimido[5,6,1-de]acridine
    • Antonini, I. & Martelli, S. (1992) The synthesis of a new polycyclic heterocyclic ring system: Pyrimido[5,6,1-de]acridine. J. Heterocyclic Chem. 29, 471-473.
    • (1992) J. Heterocyclic Chem. , vol.29 , pp. 471-473
    • Antonini, I.1    Martelli, S.2
  • 20
    • 0029135131 scopus 로고
    • Synthesis and biological evaluation of dialkylaminoalkyl disubstituted pyrimidoacridinetriones, a novel group of antitumor, resistance reversing agents
    • Antonini, I., Cola, D., Polucci, P., Bontemps-Gracz, M., Borowski, E. & Martelli, S. (1995) Synthesis and biological evaluation of dialkylaminoalkyl disubstituted pyrimidoacridinetriones, a novel group of antitumor, resistance reversing agents. J. Med. Chem. 38, 3282-3286.
    • (1995) J. Med. Chem. , vol.38 , pp. 3282-3286
    • Antonini, I.1    Cola, D.2    Polucci, P.3    Bontemps-Gracz, M.4    Borowski, E.5    Martelli, S.6
  • 21
    • 0024805768 scopus 로고
    • DNA-intercalating ligands as anticancer drugs: Prospects for future design
    • Denny, W.A. (1989) DNA-Intercalating ligands as anticancer drugs: Prospects for future design. Anti-Cancer Drug Des. 4, 241-263.
    • (1989) Anti-cancer Drug Des. , vol.4 , pp. 241-263
    • Denny, W.A.1
  • 22
    • 0026026263 scopus 로고
    • DNA intercalating antitumor agents
    • Baguley, B.C. (1991) DNA Intercalating antitumor agents. Anti-Cancer Drug Des. 6, 1-35.
    • (1991) Anti-cancer Drug Des. , vol.6 , pp. 1-35
    • Baguley, B.C.1
  • 23
    • 0040792488 scopus 로고    scopus 로고
    • Binding free energy of selected anticancer compounds to DNA - Theoretical calculations
    • in press
    • Baginski, M., Polucci, P., Antonini, I., Borowski, E. & Martelli, S. (1999) Binding free energy of selected anticancer compounds to DNA - theoretical calculations. Biophys. Chem. (in press).
    • (1999) Biophys. Chem.
    • Baginski, M.1    Polucci, P.2    Antonini, I.3    Borowski, E.4    Martelli, S.5
  • 24
    • 0020262664 scopus 로고
    • Computer simulations of DNA double helix dynamics
    • Levitt, M. (1982) Computer simulations of DNA double helix dynamics. Cold Spring Harbor Symposia on Quant. Biol. XLVII, 251-262.
    • (1982) Cold Spring Harbor Symposia on Quant. Biol. , vol.47 , pp. 251-262
    • Levitt, M.1
  • 25
    • 0025308014 scopus 로고
    • Free energy calculations on base specificity of drug-DNA interactions: Application to daunomycin and acridine intercalation into DNA
    • Cieplak, P., Rao, S.N., Grootenhuis, P.D.J. & Kollman, P.A. (1990) Free energy calculations on base specificity of drug-DNA interactions: Application to daunomycin and acridine intercalation into DNA.Biopolymers 29, 717-727.
    • (1990) Biopolymers , vol.29 , pp. 717-727
    • Cieplak, P.1    Rao, S.N.2    Grootenhuis, P.D.J.3    Kollman, P.A.4
  • 27
    • 0025789088 scopus 로고
    • The dyneimicin-DNA intercalation complex. A model based on DNA affinity cleavage and molecular dynamics simulations
    • Langley, D.R., Doyle, T.W. & Beveridge, D.L. (1991) The dyneimicin-DNA intercalation complex. A model based on DNA affinity cleavage and molecular dynamics simulations. J. Am. Chem. Soc. 113, 4395-4403.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4395-4403
    • Langley, D.R.1    Doyle, T.W.2    Beveridge, D.L.3
  • 28
    • 0025816955 scopus 로고
    • Molecular dynamics investigation of the interaction between DNA and dystamycin
    • Boehncke, M., Nonella, M., Schulten, K. & Wang, A.H.-J. (1991) Molecular dynamics investigation of the interaction between DNA and dystamycin. Biochemistry 30, 5465-5474.
    • (1991) Biochemistry , vol.30 , pp. 5465-5474
    • Boehncke, M.1    Nonella, M.2    Schulten, K.3    Wang, A.H.-J.4
  • 30
    • 0031610288 scopus 로고    scopus 로고
    • The geometry of intercalation complex of antitumor mitoxantrone and ametantrone with DNA: Molecular dynamics simulations
    • Mazerski, J., Martelli, S. & Borowski, E. (1998) The geometry of intercalation complex of antitumor mitoxantrone and ametantrone with DNA: Molecular dynamics simulations. Acta Biochim. Polon. 45, 1-11.
    • (1998) Acta Biochim. Polon. , vol.45 , pp. 1-11
    • Mazerski, J.1    Martelli, S.2    Borowski, E.3
  • 31
    • 0033660582 scopus 로고    scopus 로고
    • The intercalation of imidazoacridinones into DNA induces conformational changes in their side chain
    • Mazerski, J. & Muchewicz, K. (1999) The intercalation of imidazoacridinones into DNA induces conformational changes in their side chain. Acta Biochim. Polon. 47, 65-78.
    • (1999) Acta Biochim. Polon. , vol.47 , pp. 65-78
    • Mazerski, J.1    Muchewicz, K.2
  • 33
    • 33646940952 scopus 로고
    • Numerical integration of the cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes
    • Ryckeart, J.P., Ciccotti, G. & Berendsen, J.H.C. (1977) Numerical integration of the cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes. J. Comput. Phys. 23, 327-341.
    • (1977) J. Comput. Phys. , vol.23 , pp. 327-341
    • Ryckeart, J.P.1    Ciccotti, G.2    Berendsen, J.H.C.3
  • 34
    • 0000930430 scopus 로고
    • Molecular dynamics of B-DNA including water and counterions. A 140-ps trajectory for d(CGCGAATTCGCG) based on the GROMOS force field
    • Subraminian, P.S., Ravishanker, G. & Beveridge, D.L. (1991) Molecular dynamics of B-DNA including water and counterions. A 140-ps trajectory for d(CGCGAATTCGCG) based on the GROMOS force field. J. Am. Chem. Soc. 113, 5027-5040.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5027-5040
    • Subraminian, P.S.1    Ravishanker, G.2    Beveridge, D.L.3


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