The 1′-substituent on the anilino ring of the antitumor drug amsacrine is a critical element for topoisomerase II inhibition and cytotoxicity

Molecular Pharmacology

Volumn 49, Issue 2, 1996, Pages 343-350

  Rene, Brigitte ^a   Fosse, Philippe ^a   Khelifa, Tayeb ^a   Jacquemin Sablon, Alain ^a   Bailly, Christian ^b  

^a INSTITUT GUSTAVE ROUSSY   (France)

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

Author keywords

[No Author keywords available]

Indexed keywords

AMSACRINE; DNA TOPOISOMERASE (ATP HYDROLYSING);

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CHO CELL; CYTOTOXICITY; DRUG STRUCTURE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AMSACRINE; ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE; CELL SURVIVAL; CRICETINAE; CRICETULUS; DNA TOPOISOMERASES, TYPE II; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; MOLECULAR STRUCTURE; PLASMIDS; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TRANSFECTION;

EID: 0030022599     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

1. Waring, M J. DNA modification and cancer. Annu. Rev Biochem. 50:159-192 (1981).
2. Hurley, L. H. DNA and associated targets for drug design. J. Med. Chem. 32:2027-2033 (1989).
3. Krugh, T. E. Drug-DNA interactions. Curr. Opin. Struct. Biol. 4:351-364 (1994).
4. Wang, J. C. DNA topoisomerases. Annu. Rev. Biochem. 54:665-697 (1985).
5. Chen, A. Y., and L. F. Liu. DNA topoisomerases: essential enzymes and lethal targets. Annu. Rev. Pharmacol. Toxicol. 34:191-218 (1994).
6. Ralph, R. K., W. Judd, Y. Pommier, and K. W. Kohn. DNA topoisomerases, in Molecular Aspects of Anticancer Drug-DNA Interactions (S. Neidle and M. J. Waring, eds.), Vol. 2. Macmillan, London, 1-95 (1994).
7. Kopka, M. L., and T. A. Larsen. Netropsin and the lexitropsins: the search for sequence-specific minor-groove-binding ligands, in Nucleic Acid Targeted Drug Design (C. L. Propst and T. J. Perun, eds.). Marcel Dekker, New York, 303-374 (1992).
8. Lown, J. W. DNA recognition by lexitropsins, minor groove binding agents. J. Mol. Recognit. 7:79-68 (1994).
9. Broggini, M., E. Erba, M. Ponti, D. Ballinari, C. Geroni, F. Spreafico, and M. D'Incalci. Selective DNA interaction of the novel distamycin derivative FCE 24517. Cancer Res. 51:199-204 (1991).
10. Fontana, M., M. Lestingi, C. Mondello, A. Braghetti, A. Montecucco, and G. Ciarrochi. DNA binding properties of FCE24517, an electrophilic distamycin analogue. Anti-Cancer Drug Des. 7:131-141 (1992).
11. Su, T.-L., T.-C. Chou, and K. A. Watanabe. DNA topoisomerase targeted anticancer agents: new trends and developments. Curr. Opin. Ther. Patents 1121-1139 (1992).
12. Pommier, Y., and A. Tanizawa. Mammalian DNA topoisomerase I, and its inhibitors, in Cancer Chemotherapy (J. A. Hickman and T. R. Tritton, eds.). Blackwell Scientific Publication, Oxford, 214-250 (1993).
13. Bailly, C., and J. P. Hénichart. DNA recognition by intercalator-minor groove binder hybrid molecules. Bioconjugate Chem. 2:379-393 (1991).
14. Bailly, C., and J. P. Hénichart. Molecular pharmacology of intercalator-minor groove binder hybrid molecules, in Molecular Aspects of Anticancer Drug-DNA Interactions (S. Neidle and M. J. Waring, eds.), Vol. 2. Macmillan, London, 162-196 (1994)
15. Bailly, C., C. Michaux, P. Colson, C. Houssier, J. S. Sun, T. Garestier, C. Hélène, J. P. Hénichart, C. Rivalle, E. Bisagni, and M. J. Waring. Reaction of a biscationic distamycin-ellipticine hybrid ligand with DNA: mode and sequence specificity of binding. Biochemistry 33:15348-15364 (1994).
16. Riou, J. F., L. Grondard, A. Naudin, and C. Bailly. Effects of two distamycin-ellipucine hybrid molecules on topoisomerase I and II-mediated DNA cleavage: relation to cytotoxicity. Biochem. Pharmacol. 50:424-428 (1995).
17. Fossé, P., B. René, J. M. Saucier, J. P. Hénichart, M. J. Waring, P. Colson, C. Houssier, and C. Bailly. Stimulation of site-specific topoisomerase II-mediated DNA cleavage by an N-methylpyrrolecarboxamide-anilinoacridine conjugate: relation to DNA binding. Biochemistry 33:9865-9874 (1994).
18. Bailly, C., N. Helbecque, J. P. Hénichart, P. Colson, C. Houssier, K. E. Rao, R. G. Shea, and J. W. Lown Molecular recognition between oligopeptides and nucleic acids: DNA sequence specificity and binding properties of an acridine-linked netropsin hybrid ligand. J. Mol. Recognit. 3:26-35 (1990).
19. Denny, W. A., and B. C. Baguley. Acridine-based anti-cancer drugs, in Molecular Aspects of Anticancer Drug-DNA Interactions (S. Neidle and M. J. Waring, eds.), Vol. 2. Macmillan, London, 270-311 (1994)
20. Nelson, E. M., K. M. Tewey, and L. F. Liu. Mechanism of antitumor drug action: poisoning of mammalian DNA topoisomerase II on DNA by 4′-(9-acridinylamino) methanesulfon-m-anisidide. Proc. Natl. Acad. Sci. USA 81:1361-1365 (1984).
21. Macdonald, T. L., E. K. Lehnert, J. T. Loper, K.-C. Chow, and W. E. Ross. , in DNA Topoisomerases in Cancer (M. Potmesil and K W. Kohn, eds.). Oxford University Press, New York, 199-214 (1991).
22. Zwelling, L. A., M. J. Mitchell, P. Satitpunwaycha, J. Mayes, E. Altschuler, M. Hinds, and B. Baguley. Relative activity of structural analogues of amsacrine against human leukemia cell lines containing amsacrine-sensitive or -resistant forms of topoisomerase II: use of a computer simulation in new drug development. Cancer Res. 52:209-217 (1992)
23. Capranico, G., M Palumbo, S. Tinelli, M. Mabilia, A. Pozzan, and F. Zunino. Conformational drug determinants of the sequence specificity of drug-stimulated topoisomerase II DNA cleavage. J. Mol. Biol. 235:1218-1230 (1994).
24. Baguley, B. C., K. M. Holdaway, and L. M. Fray. Design of DNA intercalators to overcome topoisomerase II-mediated multidrug resistance. J. Natl. Cancer Inst. 82:398-402 (1990).
25. Khélifa, T., M. R. Casabianca-Pignède, B René, and A. Jacquemin-Sablon. Expression of topoisomerase II α and β in Chinese hamster lung cells resistant to topoisomerase II inhibitors. Mol. Pharmacol. 46:323-328 (1994).
26. Bailly, C., N. Pommery, R. Houssin, and J. P. Hénichart. Design, synthesis, DNA-binding and biological activity of a series of DNA minor groove binding intercalating drugs. J. Pharm. Sci. 78:910-917 (1989).
27. Hénichart, J. P., J. L. Bernier, and J. P. Catteau. Interaction of 4́(9-acridinylamino)aniline and derivatives with DNA: influence of a lysyl glycyl side chain on the binding parameters. Hoppe-Seyler's Z. Physiol. Chem. 363:835-841 (1982).
28. Cain, B. F., G. J. Atwell, and W. A. Denny. Potential antitumor agents 4′-(aeridin-9-ylamino)methane-sulfon-anilides. J. Med. Chem. 18:1110-1117 (1975).
29. Miller, K. G., L. F. Liu, and P.T. England. A homogeneous type II DNA topoisomerase from HeLa cell nuclei. J. Biol. Chem. 256:9334-9339 (1981).
30. Halligan, B. D., K. A. Edwards, and L. F. Liu. Purification and characterization of a type II DNA topoisomerase from bovine calf thymus. J. Biol. Chem. 260:2475-2482 (1985).
31. Maniatis, T., E. F. Fritsch, and J. Sambrook. Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY (1982).
32. Fossé, P., B. René, M. Charra, C. Paoletti, and J. M. Saucier. Stimulation of topoisomerase II-mediated DNA cleavage by ellipticine derivatives: structure-activity relationship. Mol. Pharmacol. 42590-595 (1992).
33. Fossé, P., B. René, J. M. Saucier, C. H. Nguyen, E. Bisagni and C. Paoletti. Stimulation by γ-carboline derivatives (simplified analogues of antitumor ellipticines) of site specific DNA cleavage by calf thymus DNA topoisomerase II. Biochem. Pharmacol. 3:669-676 (1990).
34. Fossé, P., B. René, M. Le Bret, C. Paoletti, and J. M. Saucier. Sequence requirements for mammalian topoisomerase II mediated DNA cleavage stimulated by an ellipticine derivative. Nucleic Acids Res. 19:2861-2868 (1991).
35. Markovits, J., C. Linassier, P. Fossé, J. Couprie, J. Pierre, A. Jaequemin-Sablon, J. M. Saucier, J. B. Le Pecq, and A. K. Larsen. Inhibitory effects of the tyrosine kinase inhibitor genistein on mammalian DNA topoisomerase II. Cancer Res. 49:5111-5117 (1989).
36. Salles, B., J. Y. Charcosset, and A. Jacquemin-Sablon. Isolation and properties of Chinese hamster lung cells resistant to ellipticine derivatives. Cancer Treat. Rep. 66:327-338 (1982).
37. Charcosset, J. Y., J. P. Bendirdjian, M. F. Lantieri, and A. Jacquemin-Sablon. Effects of 9-OH-ellipticine on cell survival, macromolecular syntheses, and cell cycle progression in sensitive and resistant Chinese hamster lung cells. Cancer Bes. 45:4229-4236 (1985).
38. Charcosset, J. Y., J. M. Saucier, and A. Jacquemin-Sablon. Reduced topoisomerase II activity and drug-stimulated DNA cleavage in 9-hydroxy-ellipticine resistant cells. Biochem. Pharmacol. 37:2145-2149 (1988).
39. Khélifa, T., B. René, J. Markovits, H. Jacquemin-Sablon, and A. Jacquemin-Sablon. Expression of human topoisomerase II α in 9-OH-ellipticine resistant Chinese hamster fibroblasts does not reverse the resistance to 9-OH-ellipticine but restores partial sensitivity to some other topoisomerase II inhibitors. J. Biol. Chem., in press.
40. Jacquemin-Sablon, A., K. Bojanowski, M. R. Casabianca-Pignède, S. Crémier, C. Delaporte, T. Khélifa, B. René, J. M. Saucier, and A. K. Larsen. Phenotypic properties of Chinese hamster lung cells resistant to DNA topoisomerase II inhibitors, in Molecular Biology of DNA Topoisomerases and Its Application to Chemotherapy (T. Andoh, H. Ikeda, and M. Oguro, eds.). CRC Press, Boea Raton, FL, 265-273 (1993).
41. Pommier, Y., R. E. Schwartz, L. A. Zwelling, D. Kerrigan, M. R. Mattern, J. Y. Charcosset, A. Jacquemin-Sablon, and K. W. Kohn. Reduced formation of protein-associated DNA strand breaks in Chinese hamster cells resistant to topoisomerase II inhibitors. Cancer Res. 46:611-616 (1986).
42. Pommier Y., D. Kerrigan, J. M. Covey, C. S. Kao-Shan, and J. Whang-Peng. Sister chromatid exchanges, chromosomal aberrations, and cytotoxicity produced by antitumor topoisomerase II inhibitors in sensitive (DC-3F) and resistant (DC-3F/9-OH-E) Chinese hamster cells. Cancer Res. 48:512-516 (1988).
43. Drake, F. H., G. A. Hofmann, H. F. Bartus, M. R. Mattern, S. T. Crooke, and C. K. Mirabelli. Biochemical and pharmacological properties of p170 and p180 forms of topoisomerase II. Biochemistry 28:8154-8160 (1989).
44. Danks, M. K, J. Qiu, C. V. Catapano, C A. Schmidt, W. T. Beck, and D. J. Fernandes Subcellular distribution of the α and β topoisomerase II-DNA complexes stabilized by VM-26. Biochem. Pharmacol. 48:1785-1795 (1994).
45. Austin, C. A., K. L. Marsch, R. A. Wasserman, E. Willmore, P. J. Sayer, J. C. Wang, and L. M. Fisher. Expression, domain structure, and enzymatic properties of an active recombinant human DNA topoisomerase II β. J. Biol. Chem. 270:15739-15746 (1995).
46. Bailly, C., and J. P. Hénichart. Subcellular distribution of a nitroxide spin-labeled netropsin-acridine hybrid in living KB cells. Biochem. Biophys. Res Commun 167:798-806 (1990).