A carbamate analogue of amsacrine with activity against non-cycling cells stimulates topoisomerase II cleavage at DNA sites distinct from those of amsacrine

European Journal of Cancer Part A

Volumn 33, Issue 2, 1997, Pages 272-279

  Baguley, B C ^a   Leteurtre, F ^b,d   Riou, J F ^c   Finlay, G J ^a   Pommier, Y ^b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b NATIONAL CANCER INSTITUTE   (United States)

^c Lab de Pharmacologie Molec   (France)

^d SAINT LOUIS HOSPITAL   (France)

Author keywords

Acridine; Intercalation; Lewis lung; Topoisomerase

Indexed keywords

AMSACRINE; DNA; DNA TOPOISOMERASE (ATP HYDROLYSING); DOXORUBICIN; ETOPOSIDE; TRANEXAMIC ACID;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DNA CLEAVAGE; DRUG DNA BINDING; INTERCALATION COMPLEX; LEWIS CARCINOMA; MOUSE; NONHUMAN; PRIORITY JOURNAL;

AMSACRINE; ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA, LEWIS LUNG; DNA FRAGMENTATION; DNA TOPOISOMERASES, TYPE II; DNA, NEOPLASM; ELECTROPHORESIS, AGAR GEL; GENES, MYC; MICE; TRANEXAMIC ACID; TUMOR CELLS, CULTURED;

EID: 0030932881     PISSN: 09598049     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0959-8049(96)00410-8     Document Type: Article

References (40)

1. Baguley BC, Finlay GJ, Ching LM. Resistance mechanisms to topoisomerase poisons - the application of cell culture methods. Oncol Res 1992, 4, 267-274.
2. Ralph RK, Judd W, Pommier Y, Kohn KW. DNA topoisomerases. In Neidle S, Waring M, eds. Molecular Aspects of Anticancer Drug-DNA Interactions, 1st edn. Kent, Macmillan, 1994, Vol. 2, 1-95.
3. Endicott JA, Ling V. The biochemistry of P-glycoprotein-mediated multidrug resistance. Annu Rev Biochem 1989, 58, 351-375.
4. Cole SPC, Bhardwaj G, Gerlach JH, et al. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science 1992, 258, 1650-1654.
5. Beck WT, Cirtain MC, Danks MK, et al. Pharmacological, molecular, and cytogenetic analysis of 'atypical' multidrug-resistant human leukemic lines. Cancer Res 1987, 47, 5455-5460.
6. Takano H, Kohno K, Ono M, Uchida Y, Kuwano M. Increased phosphorylation of DNA topoisomerase II in etoposide-resistant mutants of human cancer KB cells. Cancer Res 1991, 51, 3951-3957.
7. Woessner RD, Mattern MR, Mirabelli CK, Johnson RK, Drake FH. Proliferation- and cell cycle-dependent differences in expression of the 170 kilodalton and 180 kilodalton forms of topoisomerase II in NIH-3T3 cells. Cell Growth Differ 1991, 2, 209-214.
8. Holdaway KM, Finlay GJ, Baguley BC. Relationship of cell cycle parameters to in vitro and in vivo chemosensitivity for a series of Lewis lung carcinoma lines. Eur J Cancer 1992, 28A, 1427-1431.
9. Finlay GJ, Holdaway KM, Baguley BC. Novel carbamate analogues of amsacrine with activity against non-cycling murine and human tumour cells. Cancer Chemother Pharmacol 1994, 34, 159-165.
10. Baguley BC, Holdaway KM, Fray LM. Design of DNA intercalators to overcome topoisomerase II-mediated multidrug resistance. J Natl Cancer Inst 1990, 82, 398-402.
11. 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.
12. Goldwater PN, Flynn KE, Gunn CS, Baguley BC. 9-Anilinoacridines: novel compounds active against herpes simplex virus. Chem-Biol Interact 1985, 54, 377-382.
13. Heck MM, Earnshaw WC. Topoisomerase II: specific marker for cell proliferation. J Cell Biol 1986, 103, 2569-2581.
14. Drake FH, Zimmerman JO, McCabe FL, et al. Purification of topoisomerase II from amsacrine-resistant P388 leukemia cells. Evidence for two forms of the enzyme. J Biol Chem 1987, 262, 16739-16747.
15. Holden JA, Rolfson DH, Witwer CT. The distribution of immunoreactive topoisomerase-II protein in human tissues and neoplasms. Oncol Res 1992, 4, 157-166.
16. Minford J, Pommier Y, Filipski J, et al. Isolation and intercalator-dependent protein-linked DNA strand cleavage activity from cell nuclei and identification as topoisomerase II. Biochemistry 1986, 25, 9-16.
17. 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.
18. Leteurtre F, Fesen M, Kohlhagen G, Kohn KW, Pommier Y. Specific interaction of camptothecin, a topoisomerase I inhibitor, with guanine residues of DNA detected by photoactivation at 365 nm. Biochemistry 1993, 32, 8955-8962.
19. Leteurtre F, Kohlhagen G, Fesen MR, Tanizawa A, Kohn KW, Pommier Y. Effects of DNA methylation on topoisomerase I and II cleavage activities. J Biol Chem 1994, 269, 7893-7900.
20. Riou J-F, Grondard L, Naudin A, Bailly C. Effects of two distamycin-ellipticine hybrid molecules on topoisomerase I and II mediated DNA cleavage: relation to cytotoxicity. Biochem Pharmacol 1995, 50, 424-428.
21. Leteurtre F, Madalengoitia J, Orr A, et al. Rational design and molecular effects of a new topoisomerase II inhibitor, azatoxin. Cancer Res 1992, 52, 4478-4483.
22. Baguley BC, Denny WA, Atwell GJ, Cain BF. Potential antitumor 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.
23. Baguley BC, Cain BF. Comparison of the in vivo and in vitro antileukemic activity of monosubstituted derivatives of 4′-(9-acridinylamino)methanesulphon-m-anisidide (m-AMSA). Mol Pharmacol 1982, 22, 486-492.
24. 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.
25. Baguley BC. The possible role of electron transfer complexes in the action of amsacrine analogues. Biophys Chem 1990, 23, 937-943.
26. Wilkoff LJ, Dulmadge E, Chopra DP. Viability of cultured Lewis lung cell populations exposed to β-retinoic acid (40753). Proc Soc Exp Biol Med 1980, 163, 233-236.
27. Fossé P, René B, Saucier JM, et al. Stimulation of site-specific topoisomerase II-mediated DNA cleavage by an N-methylpyrrolecarboxamide-anilinoacridine conjugate: relation to DNA binding. Biochemistry 1994, 33, 9865-9874.
28. Covey JM, Kohn KW, Kerrigan D, Tilchen EJ, Pommier Y. Topoisomerase II-mediated DNA damage produced by 4′-(9-acridinylammo)methanesulfon-m-anisidide and related acridines in L1210 cells and isolated nuclei: relation to toxicity. Cancer Res 1988, 48, 860-865.
29. Baguley BC. DNA intercalating anti-tumour agents. Anti-Cancer Drug Design 1991, 6, 1-35.
30. 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.
31. Granzen B, Graves DE, Baguley BC, Danks MK, Beck WT. Structure-activity studies of amsacrine analogs in drug resistant human leukemia cell lines expressing either altered DNA topoisomerase-II or P-glycoprotein. Oncol Res 1992, 4, 489-496.
32. Zini N, Santi S, Ognibene A, et al. Discrete localization of different DNA topoisomerases in HeLa and K562 cell nuclei and subnuclear fractions. Exp Cell Res 1994, 210, 336-348.
33. Harker WG, Slade DL, Drake FH, Parr RL. Mitoxantrone resistance in HL-60 leukemia cells: reduced nuclear topoisomerase-II catalytic activity and drug-induced DNA cleavage in association with reduced expression of the topoisomerase-II beta-isoform. Biochemistry 1991, 30, 9953-9961.
34. Brown GA, McPherson JP, Gu L, et al. Relationship of DNA topoisomerase II alpha and beta expression to cytotoxicity of antineoplastic agents in human acute lymphoblastic leukemia cell lines. Cancer Res 1995, 55, 78-82.
35. Per SK, Mattern MR, Mirabelli CK, Drake FH, Johnson RK. Characterization of a subline of P388 leukaemia resistant to amsacrine: evidence of altered topoisomerase II function. Mol Pharmacol 1987, 32, 17-25.
36. Ebert SN, Subramanian D, Shtrom SS, Chung IK, Parris DS, Muller MT. Association between the p170 form of human topoisomerase II and progeny viral DNA in cells infected with herpes simplex virus type 1. J Virology 1994, 68, 1010-1020.
37. Austin CA, Marsh KL, Wasserman RA, et al. Expression, domain structure, and enzymatic properties of an active recombinant human DNA topoisomerase II beta. J Biol Chem 1995, 270, 15739-15746.
38. Haldane A, Finlay GJ, Baguley BC. A comparison of the effects of aphidicolin and other inhibitors on topoisomerase II-directed cytotoxic drugs. Oncol Res 1993, 5, 133-138.
39. Chou RH, Churchill JR, Flubacher MM, Mapstone DE, Jones J. Identification of a nuclear matrix-associated region of the c-myc protooncogene and its recognition by a nuclear protein in the human leukemia HL-60 cell line. Cancer Res 1990, 50, 3199-3206.
40. Chou RH, Churchill JR, Mapstone DE, Flubacher MM. Sequence-specific binding of a c-myc nuclear-matrix-associated region shows increased nuclear matrix retention after leukemic cell (HL-60) differentiation. Am J Anat 1991, 191, 312-320.