From Amsacrine to DACA (N-[2-(Dimethylamino)ethyl]acridine-4-carboxamide): Selectivity for Topoisomerases I and II Among Acridine Derivatives

European Journal of Cancer

Volumn 32, Issue 4, 1996, Pages 708-714

  Finlay, G J ^a   Riou, J F ^b   Baguley, B C ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b SANOFI   (France)

Author keywords

Acridine; DNA intercalation; Multidrug resistance; Topoisomerase

Indexed keywords

AMSACRINE; AMSACRINE DERIVATIVE; DNA DIRECTED DNA POLYMERASE BETA; DNA POLYMERASE 2; N [(2 DEMETHYLAMINOETHYL)ETHYL]ACRIDINE 4 CARBOXAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; HUMAN; HUMAN CELL; LEUKEMIA CELL; MULTIDRUG RESISTANCE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ACRIDINES; AMSACRINE; ANTINEOPLASTIC AGENTS; DNA; DNA DAMAGE; DNA TOPOISOMERASES, TYPE I; DNA TOPOISOMERASES, TYPE II; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; HUMANS; LEUKEMIA; TUMOR CELLS, CULTURED;

EID: 0029893321     PISSN: 09598049     EISSN: None     Source Type: Journal    
DOI: 10.1016/0959-8049(95)00604-4     Document Type: Article

References (37)

1. D'Arpa P, Liu LF. Topoisomerase-targeting antitumor drugs. Biochim Biophys Acta 1989, 989, 163-177.
2. Trask DK, Muller MT. Stabilization of type I topoisomerase - DNA covalent complexes by actinomycin D. Proc Natl Acad Sci USA 1988, 85, 1417-1421.
3. Yamashita Y, Kawada S, Fujii N, Nakano H. Induction of mammalian DNA topoisomerase I and II mediated DNA cleavage by saintopin, a new antitumor agent from fungus. Biochemistry 1991, 30, 5838-5845.
4. Riou JF, Fosse P, Nguyen CH, et al. Intoplicine (RP-60475) and its derivatives, a new class of antitumor agents inhibiting both topoisomerase-I and topoisomerase-II activities. Cancer Res 1993, 53, 5987-5993.
5. Riou JF, Helissey P, Grondard L, Giorgi-Renault S. Inhibition of eukaryotic DNA topoisomerase-I and topoisomerase-II activities by indoloquinolinedione derivatives. Mol Pharmacol 1991, 40, 699-706.
6. Janin YL, Croisy A, Riou J-F, Bisagni E. Synthesis and evaluation of new 6-amino-substituted benzo[c]phenanthridine derivatives. J Med Chem 1993, 36, 3686-3692.
7. Crow RT, Crothers DM. Inhibition of topoisomerase I by anthracycline antibiotics: evidence for general inhibition of topoisomerase I by DNA-binding agents. J Med Chem 1994, 37, 3191-3194.
8. Sorensen BS, Jensen PB, Sehested M, et al. Antagonistic effect of aclarubicin on camptothecin induced cytotoxicity: role of topoisomerase I. Biochem Pharmacol 1994, 47, 2105-2110.
9. Baguley BC. DNA intercalating anti-tumour agents. Anticancer Drug Des 1991, 6, 1-35.
10. Denny WA, Baguley BC. New anticancer acridines. In Neidle S, Waring MJ, eds. Molecular Aspects of Anticancer Drug-DNA Interaction, 1st edn. London, Macmillan, 1994, 270-311.
11. Arlin ZA. A special role for amsacrine in the treatment of acute leukemia. Cancer Invest 1989, 7, 607-609.
12. Harvey VJ, Hardy JR, Smith S, Grove W, Baguley BC. Phase II study of the amsacrine analogue CI-921 (NSC 343499) in non-small-cell lung cancer. Eur J Cancer 1991, 27, 1617-1620.
13. Atwell GJ, Rewcastle GW, Baguley BC, Denny WA. Potential antitumor agents. 50. In vivo solid tumor activity of derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide. J Med Chem 1987, 30, 664-669.
14. Baguley BC, Zhuang L, Marshall E. Experimental solid tumour activity of N-[2-(dimethylamino)ethyl]-acridine-4-carboxamide. Cancer Chemother Pharmacol 1995, 36, 244-248.
15. Finlay GJ, Baguley BC. Selectivity of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide towards Lewis lung carcinoma and human tumour cell lines in vitro. Clin Oncol, Eur J Cancer 1989, 25, 271-277.
16. Haldane A, Finlay GJ, Gavin JB, Baguley BC. Unusual dynamics of killing of cultured Lewis lung cells by the DNA-intercalating antitumour agent N-[2-(dimethylamino)ethyl]acridine-4-carboxamide. Cancer Chemother Pharmacol 1992, 29, 475-479.
17. Finlay GJ, Marshall ES, Matthews JHL, Paull KD, Baguley BC. In vitro assessment of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide, a DNA-intercalating antitumour drug with reduced sensitivity to multidrug resistance. Cancer Chemother Pharmacol 1993, 31, 401-406.
18. Baguley BC, Denny WA, Atwell GJ, Cain BF. Potential anti-tumor agents. Part 35. Quantitative relationships between anti-tumor (L1210) potency and DNA binding for 4′-(9-acridinylamino)methanesulphon-m-anisidide analogues. J Med Chem 1981, 24, 520-525.
19. Rewcastle GW, Atwell GJ, Chambers D, Baguley BC, Denny WA. Potential antitumor agents. 46. Structure-activity relationships for acridine mono-substituted derivatives of the antitumor agent N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide. J Med Chem 1986, 29, 472-477.
20. Denny WA, Atwell GJ, Rewcastle GW, Baguley BC. Potential antitumor agents. 49. 5-substituted derivatives of N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide with in vivo solid tumor activity. J Med Chem 1987, 30, 658-663.
21. Wakelin LPG, Denny WA. Kinetic and equilibrium binding studies of a series of intercalating agents that bind by threading a sidechain through the DNA helix. In Pullman B, Jortner J, eds. Molecular Basis of Specificity in Nucleic Acid-Drug Interactions. Dordrecht, Kluwer Academic, 1990, 191-206.
22. Larsen AK, Grondard L, Couprie J, et al. The antileukemic alkaloid fagaronine is an inhibitor of DNA topoisomerase-I and topoisomerase-II. Biochem Pharmacol 1993, 46, 1403-1412.
23. Baguley BC, Denny WA, Atwell GJ, Cain BF. Potential anti-tumor agents. Part 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring. J Med Chem 1981, 24, 170-177.
24. Baguley BC, Cain BF. Comparison of the in vivo and in vitro antileukaemic activity of monosubstituted derivatives of 4′-(9-acridinylamino)methanesulphon-m-anisidide (m-AMSA). Mol Pharmacol 1982, 22, 486-492.
25. Baguley BC, Falkenhaug E-M. The interaction of ethidium with synthetic double-stranded polynucleotides at low ionic strength. Nucleic Acids Res 1978,5, 161-171.
26. Baguley BC. The possible role of electron transfer complexes in the action of amsacrine analogues. Biophys Chem 1990, 23, 937-943.
27. Riou J-F, Gabillot M, Philippe M, Schrevel J, Riou G. Purification and characterization of Plasmodium bergei DNA topoisomerases I and II. Drug action, inhibition of decatenation and relaxation, and stimulation of DNA cleavage. Biochemistry 1986, 25, 1471-1479.
28. Snow K, Judd W. Characterisation of adriamycin-resistant and amsacrine-resistant human leukaemic T-cell lines. Br J Cancer 1991, 63, 17-28.
29. Finlay GJ, Baguley BC, Snow K, Judd W. Multiple patterns of resistance of human leukemia cell sublines to amsacrine analogues. J Natl Cancer Inst 1990, 82, 662-667.
30. Skehan P, Storeng R, Scudiero D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990, 82, 1107-1112.
31. Wilson WR, Baguley BC, Wakelin LPG, Waring MJ. Interaction of the antitumour drug m-AMSA (4′-(9-acridinylamino)methanesulphon-m-anisidide) and related acridines with nucleic acids. Mol Pharmacol 1981, 20, 404-414.
32. Nabiev I, Chourpa I, Riou JF, Nguyen CH, Lavelle F, Manfait M. Molecular interactions of DNA-topoisomerase I and II inhibitor with DNA and topoisomerases and in ternary complexes: binding modes and biological effects for intoplicine derivatives. Biochemistry 1994, 33, 9013-9023.
33. Zwelling LA, Mitchell MJ, Satitpunwaycha P, et al. Relative activity of structural analogues of amsacrine against human leukemia cell lines containing amsacrine-sensitive or amsacrine-resistant forms of topoisomerase-II - use of computer simulations in new drug development. Cancer Res 1992, 52, 209-217.
34. Denny WA, Roos IAG, Wakelin LPG. Inter-relationship between antitumour activity, DNA breakage and DNA binding kinetics for 9-aminoacridinecarboxamide antitumour agents. Anticancer Drug Des 1986, 1, 141-147.
35. Baguley BC, Kernohan AR, Wilson WR. Divergent activity of derivatives of amsacrine (m-AMSA) towards Lewis lung carcinoma and P388 leukaemia in mice. Clin Oncol, Eur J Cancer 1983, 19, 1607-1613.
36. Baguley BC, Denny WA, Atwell GJ, et al. Synthesis, antitumor activity, and DNA binding properties of a new derivative of amsacrine, N-5-dimethyl-9-[2-methoxy-4-methysulfonylamino)-phenylamino]-4- acridinecarboxamide. Cancer Res 1984, 44, 3245-3251.
37. Endicott JA, Ling V. The biochemistry of P-glycoprotein-mediated multidrug resistance. Annu Rev Biochem 1989, 58, 351-375.