Molecular origins of selectivity in the interaction of amsacrine-4-carboxamide with GC-rich sequences in DNA

Anti-Cancer Drug Design

Volumn 11, Issue 8, 1996, Pages 611-624

  Bailly, Christian ^a   Denny, William A ^b   Waring, Michael J ^c  

^a Institut de Recherche sur le Cancer de Lille   (France)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Amsacrine; DNA recognition; Footprinting; Guanine amino group

Indexed keywords

AMSACRINE 4 CARBOXAMIDE; AMSACRINE DERIVATIVE; ANTINEOPLASTIC AGENT; GUANINE; OLIGODEOXYNUCLEOTIDE; PURINE; UNCLASSIFIED DRUG;

ARTICLE; DNA FOOTPRINTING; DRUG DNA INTERACTION; MOLECULAR BIOLOGY; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL;

AMSACRINE; ANTINEOPLASTIC AGENTS; AUTORADIOGRAPHY; CYTIDINE; DNA; DNA FOOTPRINTING; ESCHERICHIA COLI; GUANINE; PLASMIDS;

EID: 0030472756     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. BAGULEY, B C (1991). DNA intercalating anti-tumour agents. Anti-Cancer Drug Design, 6, 1.
2. BAILLY, C & WARING, M J (1995a). Transferring the purine 2-amino group from guanines to adenines in DNA changes the sequence-specific binding of antibiotica Nucleic Acids Research, 23, 885.
3. BAILLY, C & WARING, M.J. (1995b). Comparison of different footprinting methodologies for detecting binding sites for a small ligand on DNA. Journal of Biomolecular Structure and Dynamics, 12, 869.
4. BAILLY, C , DENNY, W.A., MELLOR L , WAKELIN, L.P.G. & WARING, M J. (1992). Sequence-specificity of the binding of 9-aminoacridine- and amsacrine-4-carboxamides to DNA studied by DNase I footprinting. Biochemistry, 31, 3514.
5. BAILLY, C , MOLLEGAARD, N.E , NIELSEN, P E. & WARING, M J (1995a). The influence of the 2-amino group of guanine on DNA conformation. Uranyl and DNase I probing of inosine/diaminopurine substituted DNA. EMBO Journal, 14, 2121.
6. BAILLY, C., WARING, M.J. & TRAVERS, A.A. (1995b). Effects of base substitutions on the binding of a DNA-bending protein. Journal of Molecular Biology, 253, 1.
7. BAILLY, C. BRANA, M. & WARING, M.J. (1996a). Sequence-selective intercalation of antitumour bis-naphthalimides into DNA: evidence for an approach via the major groove. European Journal of Biochemistry, 240, 195.
8. BAILLY, C., HAMY, F. & WARING, M.J (1996b). Cooperativity in the binding of echinomycin to DNA fragments containing closely spaced CpG sites. Biochemistry, 35, 1150.
9. CAIN, B. F , ATWELL, GJ & DENNY, W.A. (1977). Potential antitumor agents. Part 23. 4′-(9-acridinyl-amino)alkanesulfonanilide congeners bearing hydrophilic functionality. Journal of Medicinal Chemistry, 20, 987.
10. CRENSHAW, J M , GRAVES, D.E & DENNY, W.A (1995). Interactions of acridine antitumor agents with DNA: binding energies and groove preferences. Biochemistry, 34, 13682.
11. DABROWIAK, J.C. & GOODDISMAN, J. (1989). Quantitative footprinting analysis of drug-DNA interactions. In Chemistry and Physics of DNA-Ligand Interactions. Kallenbach, N.R. (ed.), p. 143. Adenine Press.
12. DENNY, W. A. (1990). DNA-intercalating ligands as anti-cancer drugs: prospects for future design. Anti-Cancer Drug Design, 4, 241.
13. DENNY, W A & BAGULEY, B C (1994). Acridine-based anticancer drugs. In Molecular Aspects of Anticancer Drug-DNA Interactions. Neidle, S. & Waring, M.J. (eds), vol. 2, p. 270. Macmillan: London.
14. DENNY W.A. & WAKELIN, L.P.G. (1986). Kinetic and equilibrium studies of the interaction of amsacrine and anilino ring-substituted analogues with DNA. Cancer Research, 46, 1717.
15. DREW, H R., WEEKS, J.R. & TRAVERS, A.A (1985). Negative supercoiling induces unwinding of bacterial promoter. EMBO Journal, 4, 1025.
16. HARVEY, V.J., HARDY, J R., SMITH, S., GROVE, W. & BAGULEY, B C. (1991). Phase II study of the amsacrine analogue CI-921 (NSC 343499) in non-small cell lung cancer. European Journal of Cancer, 27, 1617.
17. JEHN, U. & HEINEMANN, V. (1991). New drugs in the treatment of acute leukemia, with some emphasis on m-AMSA. Anticancer Research, 11, 705.
18. JOHNSTON, R F , PICKETT, S C. & BARKER, D. L (1990). Autoradiography using storage phosphor technology. Electrophoresis, 11, 355.
19. MARCHAND, C. BAILLY, C., MCLEAN, M.J , MORONEY, S E. & WARING, M J. (1992). The 2-amino group of guanine is absolutely required for specific binding of the anti-cancer antibiotic echinomycin to DNA. Nucleic Acids Research, 20, 5601.
20. MILLER, L P., PYESMANY, A.F., WOLFF, L.J., ROGERS, P C J , SIEGEL, S E., WELLS, R J , BUCKLEY, J D & HAMMOND, G.D. (1991). Successful reinduction therapy with amsacrine and cyclocytidine in acute non-lymphoblastic leukemia in children - a report from the children's cancer study group. Cancer, 67, 2235.
21. SAYERS, E.W & WARING, M J (1993). Footprinting titration studies on the binding of echinomycin to DNA incapable of forming Hoogsteen base pairs. Biochemistry, 32, 9094.
22. WAKELIN, L P.G , CHETCUTI, P & DENNY, W A (1990). Kinetic and equilibrium binding studies of amsacrine-4-carboxamides: a class of asymmetrical DNA-intercalating agents which bind by threading through the DNA helix. Journal of Medicinal Chemistry, 33, 2039.
23. WILSON, W.D. & TANIOUS, F. A. (1994). Kinetic analysis of drug-nucleic acid binding modes: absolute rates and effects of salt concentrations. In Molecular Aspects of Anticancer Drug-DNA Interactions. Neidle, S. & Waring, M.J. (eds), vol. 2, p. 243. Macmillan: London.