Design and synthesis of modified quinolones as antitumoral acridones

Journal of Medicinal Chemistry

Volumn 42, Issue 12, 1999, Pages 2136-2144

  Tabarrini, Oriana ^a   Cecchetti, Violetta ^a   Fravolini, Arnaldo ^a   Nocentini, Giuseppe ^a   Barzi, A ^a   Sabatini, Stefano ^a   Miao, Hua ^a   Sissi, Claudia ^b  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDONE DERIVATIVE; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE INHIBITOR; GYRASE INHIBITOR; QUINOLONE;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL PROLIFERATION; CYTOTOXICITY; DRUG DESIGN; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; FEMALE; MOUSE; NONHUMAN; TARGET CELL;

ACRIDINES; ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; CRICETINAE; DNA TOPOISOMERASES, TYPE II; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; FEMALE; HUMANS; MICE; QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0033578031     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980324m     Document Type: Article

References (63)

1. This work was previously presented in part: Tabarrini, O.; Cecchetti, V.; Fravolini, A.; Lorenzini, M. C.; Siena, T.; Pagella, P. G.; Barzi, A.; Nocentini, G. Acridone Derivatives as Antitumoral Agents by Quinolone Moiety Modifications. XIIIth International Symposium on Medicinal Chemistry, Paris, France, September 1994; P241.
2. (a) Gellert, M. DNA Topoisomerases. Annu. Rev. Biochem. 1981, 50, 879-910.
3. (b) Drlica, K. Biology of Bacterial Deoxyribonucleic Acid Topoisomerases. Microbiol. Rev. 1984, 48, 273-289.
4. (c) Wang, J. C. DNA Topoisomerases. Annu. Rev. Biochem. 1985, 54, 665-697.
5. (d) Maxwell, A.; Gellert, M. Mechanistic Aspects of DNA Topoisomerases. Adv. Protein Chem. 1986, 38, 69-107.
6. (e) Sutcliffe, J. A.; Gootz, T. D.; Barret, J. F. Biochemical Characteristics and Physiological Significance of Major DNA Topoisomerases. Antimicrob. Agents Chemother. 1989, 33, 2027-2033.
7. (f) Wang, J. C. DNA Topoisomerases. Annu. Rev. Biochem. 1996, 65, 635-692.
8. Morrison, A.; Cozzarelli, N. R. Contacts between DNA Gyrase and its Binding Site on DNA: Features of Symmetry and Asymmetry Revealed by Protection from Nucleases. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 1416-1420.
9. (a) Huff, A. C.; Kreuzer, K. N. Evidence for a Common Mechanism of Action for Antitumor and Antibacterial Agents That Inhibit Type II DNA Topoisomerases. J. Biol. Chem. 1990, 265, 20496-20505.
10. (b) Insaf, S. S.; Danks, M. K.; Witiak, D. T. A Structure-Function Analyses of DNA Topoisomerase II Inhibitors. Curr. Med. Chem. 1996, 3, 437-466.
11. (a) Gellert, M.; Mizuuchi, K.; O'Dea, M. H.; Itoh, T.; Tomizawa, J. I. Nalidixic Acid Resistance: A Second Genetic Character Involved in DNA Gyrase Activity. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 4772-4776.
12. (b) Sugino, A.; Peebles, C. L.; Cozzarelli, N. R.; Kreuzer, K. N. Mechanism of Action of Nalidixic Acid: Purification of Escherichia coli nalA Gene Prodrug and its Relationship to DNA Gyrase and a Novel Nicking-closing Enzyme. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 4767-4771.
13. (c) Quinolone Antimicrobial Agents, 2nd ed.; Wolfson, J. S., Hooper, D. C., Eds.; American Society for Microbiology: Washington, DC, 1989.
14. (d) Shen, L. L.; Chu, D. T. W. Type II DNA Topoisomerases as Antibacterial Targets. Curr. Pharm. Des. 1996, 2, 195-208.
15. (a) Lock, R. B.; Ross, W. E. DNA Topoisomerases in Cancer Therapy. Anti-Cancer Drug Des. 1987, 2, 151-154.
16. (b) Liu, L. F. DNA Topoisomerases Poisons as Antitumor Drugs. Annu. Rev. Biochem. 1989, 58, 351-375.
17. (c) Zwelling, L. A. Topoisomerase II as a Target of Antileukemia Drugs: a Review of Controversial Areas. Hematol. Pathol. 1989, 3, 101-112.
18. (d) Schneider, E.; Hsiang, Y. H.; Liu, L. F. DNA Topoisomerases as Anticancer Drug Targets. Adv. Pharmacol. 1990, 21, 149-183.
19. (e) Bodley, A.; Liu, L. F.; Israel, M.; Seshadri, R.; Silber, R.; Potmesil, M. In DNA Topoisomerases in Cancer; Oxford University Press: New York, 1991; pp 283-298.
20. (f) Capranico, G.; Binaschi, M.; Borgnetto, M. E.; Zunino, F.; Palumbo, M. A Protein-Mediated Mechanism for the DNA Sequence-specific Action of Topoisomerase II Poisons. TiPS 1997, 18, 323-329.
21. (a) Kreuzer, K. N.; Cozzarelli, N. R. Escherichia coli Mutants Thermosensitive for Deoxyribonucleic Acid Gyrase Subunit A: Effects on Deoxyribonucleic Acid Replication, Transcription, and Bacteriophage Growth. J. Bacteriol. 1973, 140, 425-435.
22. (b) Shen, L. S. Molecular Mechanisms of DNA Gyrase Inhibition by Quinolone Antibacterials. Adv. Pharmacol. 1994, 29A, 285-304.
23. (c) Shen, L. L.; Chu, D. T. W. Type II Topoisomerases as Antibacterial Targets. Curr. Pharm. Des. 1996, 2, 195-208.
24. (a) Hussy, P.; Maass, G.; Tümmler, B.; Grosse, F.; Schomburg, U. Effect of 4-Quinolones and Novobiocin on Calf Thymus DNA Polymerase a Primase Complex, Topoisomerase I and II, and Growth of Mammalian Lymphoblasts. Antimicrob. Agents Chemother. 1986, 29, 1073-1078.
25. (b) Oomori, Y.; Yasue, T.; Aoyama, H.; Hirai, K; Suzue, S.; Yokota, T. Effects of Fleroxacin on HeLa Cell Functions and Topoisomerase II. J. Antimicrob. Chemother. 1988, 22 (Suppl. D), 91-97.
26. (c) Hoshino, K.; Sato, K.; Une, T.; Osada, Y. Inhibitory Effects of Quinolones on DNA Gyrase of Escherichia coli and Topoisomerase II of Calf Thymus. Antimicrob. Agents Chemother. 1989, 33, 1818-1818.
27. (d) Barrett, J. F.; Gootz, T. D.; McGuirk, P. R.; Farrel, C. A.; Sokolowski, S. A. Use of in Vitro Topoisomerase II Assay for Studying Quinolone Antibacterial Agents. Antimicrob. Agents Chemother. 1989, 33, 1697-1703.
28. (e) Gootz, T. D.; Osheroff, N. Quinolones and Eukaryotic Topoisomerases. In Quinolone Antimicrobial Agents, 2nd ed.; Hooper, D. C., Wolfson, J. S., Eds.; American Society for Microbiology: Washington, DC, 1993; pp 139-160.
29. (a) Barret, J. F.; Gootz, T. D.; McGuirk, P. R.; Farrel, C. A.; Sokolowski, S. A. Use In Vitro Topoisomerase II Assay for Studying Quinolone Antibacterial Agents. Antimicrob. Agents Chemother. 1989, 33, 1697-1703.
30. (b) Wentland, M. P.; Lesher, G. Y.; Reuman, M.; Pilling, G. M.; Saindane, M. T.; Perni, R. B.; Eisseinstat, M. A.; Weaver, J. D., III; Sing, B.; Rake, J. B.; Coughlin, S. A. Relationship of Structure of Bridged (2,6-Dimethyl-4-pyridinyl)quinolones to Mammalian Topoisomerase II Inhibition. Bioorg. Med. Chem. Lett. 1993, 3, 1711-1716.
31. (c) Wentland, M. P.; Lesher, G. Y.; Reuman, M.; Gruett, M. D.; Sing, B.; Aldous, S. C.; Dorff, P. H.; Rake, J. B.; Coughlin, S. A. Mammalian Topoisomerase II Inhibitory Activity of 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3- quinolinecarboxylic Acid and Related Derivatives. J. Med. Chem. 1993, 36, 2801-2809.
32. (a) Robinson, M. J.; Martin, B. A.; Gootz, T. D.; McGuirk, P. R.; Maynhian, M.; Sutcliffe, J. A.; Osheroff, M. Effects of Quinolone Derivatives on Eukaryotic Topoisomerase II, a Novel Mechanism for Enhancement of Enzyme Mediated DNA Cleavage. J. Biol. Chem. 1991, 266, 14585-14592.
33. (b) Robinson, M. J.; Martin, B. A.; Gootz, T. D.; Mcguirk, P. R.; Osheroff, N. Effect of Novel Fluoroquinolones on the Catalytic Activities of Eukaryotic Topoisomerase II: Influence of the C-8 Fluorine Group. Antimicrob. Agents Chemother. 1992, 36, 751-756.
34. (c) Elsea, S. H.; Osheroff, N.; Nitiss, J. L. Cytotoxicity of Quinolones toward Eukaryotic Cells. J. Biol. Chem. 1992, 267, 13150-13153.
35. (a) Chu, D. T. W.; Fernandes, P. B.; Claiborne, A. K.; Shen, L. L.; Pernet, A. G. Structure-activity Relationship in Quinolone Antibacterials: Design, Synthesis and Biological Activities of Novel Isothiazoloquinolone. Drugs Exp. Clin. Res. 1988, 14, 379-383.
36. (b) Kohlbrenner, W. E.; Wideburg, N.; Weigl, D.; Saldivar, A.; Chu, D. T. W. Introduction of Calf-thymus Topoisomerase II-mediated Breakage by the Antibacterial Isothiazoloquinolones A-65281 and A-65282. Antimicrob. Agents Chemother. 1992, 36, 81-86.
37. (c) Chu, D. T. W. Isothiazoloquinolones: Antibacterial and Antineoplastic Agents. Drugs Future 1992, 17, 1101-1109.
38. (a) Chu, D. T. W.; Hallas, R.; Clement, J. J.; Alder, J.; McDonald, E.; Plattner, J. J. Synthesis and Antitumor Activities of Quinolone Antineoplastic Agents. Drugs Exptl. Clin. Res. 1992, XVIII, 275-282.
39. (b) Clement, J. J.; Burres, N.; Jarvis, K.; Chu, D. T. W.; Swinirski, J.; Alder, J. Biological Characterization of a Novel Antitumor Quinolone. Cancer Res. 1995, 55, 830-835.
40. (a) Cecchetti, V.; Fravolini, A.; Schiaffella, F.; Tabarrini, O.; Zhou, W.; Pagella, P. G. 1,4-Benzothiazine-2-carboxylic Acid 1-Oxides as Analogues of Antibacterial Quinolones [1]. J. Heterocycl. Chem. 1992, 29, 375-382.
41. (b) Cecchetti, V.; Fravolini, A.; Fringuelli, R.; Schiaffella, F.; Lorenzini, M. C.; Tabarrini, O. 4H-1-Benzothiopyran-4-one-3-carboxylic Acids and 3,4-Dihydro-2H-isothiazolo[5,4-b][1]benzothiopyran-3,4-diones as Quinolone Antibacterial Analogues. J. Heterocycl. Chem. 1993, 30, 1143-1148.
42. (a) Cecchetti, V.; Clementi, S.; Cruciani, G.; Fravolini, A.; Pagella, P. G.; Savino, A.; Tabarrini, O. 6-Aminoquinolones: A New Class of Quinolone Antibacterials? J. Med. Chem. 1995, 38, 973-982.
43. (b) Cecchetti, V.; Fravolini, A.; Lorenzini, M. C.; Tabarrini, O.; Terni, P.; Xin, T. Studies on 6-Aminoquinolones: Synthesis and Antibacterial Evaluation of 6-Amino-8-methyl-quinolones. J. Med. Chem. 1996, 39, 436-445.
44. (a) Huges, G. K.; Lahey, F. N.; Price, J. R.; Webb, L. J. Alkaloids of the Australian Rutaceae. Nature 1948, 162, 223-224.
45. (b) Svoboda, G. H.; Poore, G. A.; Simpson, P. J.; Bodor, G. B. Alkaloids of Acronychia bauen. I. Isolation of the Alkaloids and a Study of the Antitumor and Other Biological Properties of Acronycine. J. Pharm. Sci. 1966, 55, 758-768.
46. (c) Gout, P. W.; Dunn, B. P.; Beer, C. T. Effect of Acronycine on Nucleic Acid Synthesis and Population Growth in Mammalian Tumor Cell Cultures. J. Cell. Physiol. 1971, 78, 127-138.
47. (d) Schneider, J.; Evans, E. L.; Grunberg, E.; Fryer, R. I. Synthesis and Biological Activity of Acronycine Analogues. J. Med. Chem. 1972, 15, 266-270.
48. (a) Wu, T.-S.; Furukawa, H. Structure of Four New Acridone Alkaloids from Glycosmis citrifolia (Willd.) Lindl. Heterocycles 1982, 19, 1047-1051.
49. (b) Su, T. L.; Köhler, B.; Chou, T.-C.; Chun, M. W.; Watanable, K. A. Synthesis of the Acridone Alkaloids Glyfoline and Congeners. Structure-Activity Relationship Studies of Cytotoxic Acridones. J. Med. Chem. 1992, 35, 2703-2710.
50. (a) Yamashita, Y.; Kawada, S.; Nakano, H. Biochem. Pharmacol. 1990, 39, 737-744.
51. (b) Barnes, S.; Peterson, G. T. Biochemical Targets of the Isoflavone Genistein in Tumor Cell Lines. Proc. Soc. Exp. Biol. Med. 1995, 208, 103-108.
52. (c) Markovits, J.; Linassier, C.; Fosse, P.; Couprie, J.; Pierre, J.; Jaquemin-Sablon, A.; Saucier, J. M.; Le Pecq, J. B.; Larsen, A. K. Inhibitory Effects of the Tyrosine Kinase Inhibitor Genistein on Mammalia DNA Topoisomerase II. Cancer Res. 1989, 49, 5111-5117.
53. (d) Constantinou, A.; Kiguchi, K.; Huberman, E. Induction Differentiation and DNA Strand Breakage in Human HL-60 and K-562 Leukemia Cells by Genistein. Cancer Res. 1990, 50, 2618-2624.
54. (e) McCabe, M. J., Jr.; Orrenius, S. Genistein Induces Apoptosis in Immature Human Thymocytes by Inhibiting Topoisomerase-II. Biochem. Biophys. Res. Commun. 1993, 194, 944-950.
55. (f) Capranico, G.; Palumbo, M.; Tinelli, S.; Mabilia, M.; Pozzan, A.; Zunino, F. Conformational Drug Determinants of the Sequence Specifity of Drug-Stimulated Topoisomerase II DNA Cleavage. J. Mol. Biol. 1994, 235, 1218-1230.
56. Radl, S.; Kovàrovà, L. Preparation of Some Substituted 9,10-Dihydro-1-hydroxy-9-Oxoacridine Derivatives. Collect. Czech. Chem. Commun. 1992, 57, 212-215.
57. Nocentini, G.; Barzi, A. A Predictive Screening Model for in Vitro Selection of Agents with Potential Antitumor Activity. Arzneim.-Forsch. / Drug Res. 1995, 45 (II), 1306-1311.
58. Goldstein, H.; Schaaf, E. 5-Nitro- and 3-Nitro-2,4-dichlorobenzoic Acids. Helv. Chim. Acta 1957, 40, 1187-1188.
59. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria Grown Aerobically; Approved Standard M7-A3; National Committee for Clinical Laboratory Standards (NC-CCLS): Villanova, PA, 1993.
60. (a) Scudiero, D. A.; Shoemaker, R. H.; Paull, K. D.; Monks, A.; Tierney, S.; Nofriger, T. H.; Cunens, M. J.; Seniff, D.; Boyd, M. R. Evaluation of a Soluble Tetrazolium/formazan Assay for Cell Growth and Drug Sensitivity in Culture Using Human and other Tumor Cell Lines. Cancer Res. 1988, 48, 4827-4833.
61. (b) Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytoxicity Assay. J. Immunol. Methods 1983, 65, 55-63.
62. TopoGEN Technical Bulletin. A Decatenation-Supercoiling Assay Using Kinetoplast DNA Suitable for Prokaryotic and Eukaryotic Type II Topoisomerases. TopoNOTES 1993, 1 (1).
63. Tewey, K. M.; Rowe, T. C.; Yang, L.; Halligan, B. D.; Liu, L. F. Adriamycin-Induced DNA Damage Mediated by Mammalian DNA Topoisomerase II. Science 1984, 226, 466-468.