Antitumour polycyclic acridines. Part 4. Physico-chemical studies on the interactions between DNA and novel tetracyclic acridine derivatives

Anti-Cancer Drug Design

Volumn 13, Issue 5, 1998, Pages 431-451

  Giménez Arnau, Elena ^a,b   Missailidis, Sotiris ^a   Stevens, Malcolm F G ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY HOSPITAL OF STRASBOURG   (France)

Author keywords

Circular dichroism; DNA binding; Fluorescence quenching; Linear dichroism; Polycyclic acridine derivatives; Spectrophotometric analysis; Thermal denaturation; Topoisomerase II

Indexed keywords

ACRIDINE DERIVATIVE; AMSACRINE; ANTINEOPLASTIC AGENT; DNA; ETHIDIUM;

ARTICLE; BINDING AFFINITY; CIRCULAR DICHROISM; DENATURATION; DNA SEQUENCE; DRUG DNA INTERACTION; DRUG STRUCTURE; FLUORESCENCE; LINEAR DICHROISM; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON TRANSPORT; SPECTROPHOTOMETRY;

ACRIDINES; ALGORITHMS; ANTINEOPLASTIC AGENTS; BUFFERS; CHEMISTRY, PHYSICAL; CIRCULAR DICHROISM; DNA; ETHIDIUM; HEAT; KINETICS; NUCLEIC ACID DENATURATION; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0031857716     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. ALBERT, A. (1966). The Acridines, 2nd edn. Edward Arnold: London.
2. ALBERT, A (1973). In The Acridines: Their Preparation, Physical, Chemical and Biological Properties and Uses, 2nd edn. p. 159. Edward Arnold: London.
3. ARLIN, Z.A. (1989). A special role for amsacrine in the treatment of acute leukemia. Cancer Investigations, 7, 607.
4. BAGULEY, B.C. & LE BRET, M. (1984). Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron-transfer effect. Biochemistry, 23, 937.
5. BAILEY, M.L. (1973). Ultraviolet and visible absorption spectra. In Acridines, 2nd edn. p. 631. John Wiley & Sons Publishing Co.: New York.
6. BAILLY, C., POMMERY, N., HOUSSIN, R. & HENICHART, J-P. (1989). Design, synthesis, DNA binding, and biological activity of a series of DNA minor-groove binding intercalating drugs. Journal of Pharmaceutical Sciences, 78, 910.
7. BECKER, H.-C. & NORDÉN, B. (1997). DNA binding properties of 2,7-diazapyrene and its N-methylated cations studied by linear and circular dichroism spectroscopy and calorimetry. Journal of the American Chemical Society, 119, 5798.
8. BOYD, M.R. & PAULL, K.D. (1995). Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Development Research, 34, 91.
9. DENNY, W.A (1992). The role of medicinal chemistry in the discovery of DNA-active anticancer drugs: from random searching, through lead development. to de novo drug design. In The Search for New Anticancer Drugs, Waring, M.J. & Ponder, B.A.J. (eds), p. 19. Kluwer Academic Publishers: Dordrecht.
10. DENNY, W.A. & BAGULEY, B.C. (1994). New anticancer acridines. In Molecular Aspects of Anticancer Drug-DNA Interaction, 1st edn. Neidle, S. & Waring, M.J (eds), p. 270. Macmillan: London.
11. DENNY, W.A., ATWELL, G.J. & BAGULEY, B.C. (1983). Potential antitumor agents. 39. Anilino ring geometry of amsacrine and derivatives: relationship to DNA binding and antitumor activity. Journal of Medicinal Chemistry, 26, 1625.
12. DRAKE, F.H., HOFMANN, G.A., BARTUS, H.F, MATTERN, M.R., CROOKE, S.T. & MIRABELLI, C.K. (1989). Biochemical and pharmacological properties of p170 and p180 forms of topoisomerase II. Biochemistry, 28, 8154.
13. FINLAY, G.J., RIOU, J.-F. & BAGULEY B.C. (1996). From amsacrine to DACA (N-[2-dimethylamino)-ethyl]acridine-4-carboxamide): selectivity for topoisomerases I and II among acridine derivatives. European Journal of Cancer, 32A, 708.
14. GIMÉNEZ-ARNAU, E., MISSAILIDIS, S. &. STEVENS, M.F.G. (1998). Antitumour polycyclic acridines. Part 2. Physico-chemical studies on the interactions between DNA and novel polycyclic acridine derivatives. Anti-Cancer Drug Design, 13, 125.
15. HAGAN, D.J., GIMÉNEZ-ARNAU, E., SCHWALBE, C.H & STEVENS, M.E.G. (1997). Antitumour polycyclic acridines. Part 1. Synthesis of 7H-pyrido- and 8H-quino [4,3,2-kl]-acridines by Graebe-Ullmann thermolysis of 9-(l,2,3-triazol-1-yl)acridines: application of differential scanning calorimetry to predict optimum cyclisation conditions. Journal of the Chemical Society, Perkin Transactions I, 18, 2739.
16. HAGAH, D.J., CHAN, D., SCHWALBE, C.H. & STEVENS, M.F.G. (1998). Antitumour polycyclic acridines. Part 3. A two-step conversion of 9-azidoacridine to 7H-pyrido-[4,3,2-kl]-acridines by Graebe-Ullmann thermolysis of substituted 9-(l,2,3-triazol-1-yl)acridines. Journal of the Chemical Society, Perkin Transactions I, 915.
17. HARVEY, VJ, 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.
18. JONES, G.B., DAVEY, C.L., JENKINS, T.C., KAMAL, A., KNEALE, G., NEIDLE, S., WEBSTER, G.D. & THURSTON, D.E. (1990). The non-covalent interaction of pyrrolo [2,1-c][1,4] benzodiazepine-5,11-diones with DNA. Anti- Cancer Drug Design, 5, 249.
19. KOHN, K.W. (1996). Beyond DNA cross-linking: history and prospects of DNA-targeted cancer treatment. Cancer Research, 56, 5533.
20. LYNG, R., RODGER, A. & NORDÉN, B. (1991). The CD of ligand-DNA systems. 1. Poly(dG-dC) B-DNA. Biopolymer, 31, 1709.
21. LYNG, R , RODGER, A. & NORDÉN, B. (1992). The CD of ligand-DNA systems. 2. Poly(dA-dT) B-DNA. Biopolymer, 32, 1201.
22. MCCONNAUGHIE, A.W. & JENKINS. T.C (1995). Novel acridine-triazenes as prototype combilexins: synthesis, DNA binding and biological activity. Journal of Medicinal Chemistry, 38, 3488.
23. MCDONALD, L.A., ELDREDGE, G.S., BARROWS, L.R & IRELAND, C.M. (1994). Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodites sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II. Journal of Medicinal Chemistry, 37, 3819.
24. 54) and its domains by circular dichroism. Molecular Microbiology, 24, 653.
25. MORGAN, A.R., LEE, J.S., PULLEYBLANK, D.E., MURRAY, N.L, & EVANS, D.H. (1979). Ethidium fluorescence assays. Part 1. Physicochemical studies. Nucleic Acids Research, 7, 547.
26. NORDÉN, B. & TJERNELD, F. (1982). Structure of methylene-blue-DNA complexes studied by linear and circular dichroism spectroscopy. Biopolymers, 21, 1713.
27. NORDÉN, B., KUBISTA, M. & KURUCSEV, T, (1992). The linear dichroism spectroscopy of nucleic acids. Quarterly Reviews of Biophysics, 25, 51.
28. PLOUVIER, B., HOUSSIN, R., HELBECQUE, N., COLSON, P., HOUSSIER, C., HENICHART, J.-P & BAILLY, C. (1995). Influence of the methyl substituents of a thiazoic-containing lexitropsin on the mode of binding to DNA. Anti-Cancer Drug Design, 10, 155.
29. SANDRI, M.I., HOCHHAUSER, D., AYTON, P., CAMPLEJOHN, R.C., WHITEHOUSE, R , TURLEY, H., GATTER, K., HICKSON, I.D. &. HARRIS, A.L (1996). Differential expression of the topoisomerase II-α and β-genes in human breast cancers. British Journal of Cancer, 73, 1518.
30. SCHIPPER, P.E. & NORDÉN, B. (1979). Spectroscopic investigation of magnetic dipole allowed transitions through the magnetic transition moment. Chemical Physical Letters, 67, 99.
31. VOSBERG, P.H. (1985). DNA topoisomerase: enzymes that control DNA conformation. Current Topics in Microbiology and Immunology, 114, 19.
32. WADA, A. (1964). Chain regularity and flow dichroism of deoxyribonucleic acids in solution. Biopolymers, 2, 361.
33. WADA, A. & KOZAWA, S. (1964). Instrument for studies of differential flow dichroism of polymer solutions. Journal of Polymer Science, Part A, 2, 853.
34. WANG, J.C. (1985). DNA topoisomerases. Annual Review of Biochemistry, 54, 665.
35. WANG, J.C. (1996). DNA topoisomerases. Annual Review of Biochemistry, 65, 635.
36. WEINSTEIN, J.N., MYERS, T.G., O'CONNOR, P.M., FRIEND, S.H., FORNACE, A.J., KOHN, K.W., FOJO, T., BATES, S.E., RUBINSTEIN, L.V., ANDERSON, N.L., BUOLAMWINI, J.K., VAN OSDOL, W.W., MONKS, A.P., SCUDIERO, D.A., SANSVILLE, E.A., ZAHAREVITZ, D.W., BUNOW, B., VISWANADHAN, V.N., JOHNSON, G.S., WITTES, R.E. & PAULL, K.D. (1997). An information intensive approach to the molecular pharmacology of cancer. Science, 275, 343.
37. WILSON, W.R., BAGULEY, B.C., WAKELIN, L.P.G. & WARIN̈G, M.J. (1981). Interaction of the antitumour drug m-AMSA (4'-(9-acridinylamino)methanesulphon-m-anisidide) and related acridines with nucleic acids. Molecular Pharmacology, 20, 404.
38. WIRTH, M., BUCHARDT, O., KOCH, T., NIELSEN, P.E., and NORDÉN, B. (1988). Interactions between DNA and mono-, bis-, tris-, tetrakis-, and hexakis(aminoacridines). A linear and circular dichroism, electric orientation relaxation, viscometry, and equilibrium study. Journal of the American Chemical Society, 110, 932.