Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group

Journal of Medicinal Chemistry

Volumn 40, Issue 21, 1997, Pages 3456-3465

  Anizon, Fabrice ^a   Belin, Laure ^a   Moreau, Pascale ^a   Sancelme, Martine ^a   Voldoire, Aline ^a   Prudhomme, Michelle ^a   Ollier, Monique ^b   Sevère, Danièle ^c   Riou, Jean François ^c   Bailly, Christian ^d   Fabbro, Doriano ^e   Meyer, Thomas ^e  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b INSERM   (France)

^c SANOFI   (France)

^d CENTRE OSCAR LAMBRET   (France)

^e NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; CHLORINE; DNA; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE INHIBITOR; DRUG ANALOG; METHYL GROUP; NITROGEN; PROTEIN KINASE C; REBECCAMYCIN; SUGAR;

ANIMAL CELL; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; DNA STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMINOGLYCOSIDES; ANIMALS; ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; CARBAZOLES; CELL DIVISION; DNA; DNA FOOTPRINTING; DNA LIGASES; DNA TOPOISOMERASES, TYPE I; DNA TOPOISOMERASES, TYPE II; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; INDOLES; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MONOSACCHARIDES; PROTEIN KINASE C; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 9844260513     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9702084     Document Type: Article

References (38)

1. Chen, A. Y.; Liu, L. F. DNA topoisomerases: essential enzymes and lethal targets. Annu. Rev. Pharmacol. Toxicol. 1994, 34, 191-218.
2. Pommier, Y.; Tanizawa, A. Mammalian DNA topoisomerase I and its inhibitors. In Cancer Chemotherapy, Hickman, J. A., Tritton, T. R., Eds.; Blackwell Scientific Publication: Oxford, U.K., 1993.
3. Gupta, M.; Fujimori, A.; Pommier, Y. Eukaryotic DNA topoisomerase I. Biochim. Biophys. Acta 1995, 1262, 1-14.
4. Tanizawa, A.; Kohn, K. W.; Kollhagen, G.; Leteurtre, F.; Pommier, Y. Differential stabilization of eukaryotic DNA topoisomerase I cleavable complexes by camptothecin derivatives. Biochemistry 1995, 34, 7200-7206.
5. Sawada, S.; Yokokura, T.; Miyasaka, T. Synthesis and antitumor activity of A-ring or E-lactone modified water-soluble prodrugs of 20(S)-camptothecin, including development of irinotecan hydrochloride trihydrate (CPT-11). Curr. Pharm. Des. 1995, 1, 113-132.
6. Fujii, N.; Yamashita, Y.; Saitoh, Y.; Nakano, H. Induction of mammalian topoisomerase I-mediated DNA cleavage and DNA unwinding by bulgarein. J. Biol. Chem. 1993, 268, 13160-13165.
7. Makhey, D.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. Protoberberine alkaloids and related compounds as dual inhibitors of mammalian topoisomerases I and II. Med. Chem. Res. 1994, 5, 1-12.
8. Gatto, B.; Sanders, M. M.; Yu, C.; Wu, H.-Y.; Makhey, D.; LaVoie, E. J.; Liu, L. F. Identification of topoisomerase I as the cytotoxic target of the protoberberine alkaloid coralyne. Cancer Res. 1996, 56, 2795-2800.
9. Yamashita, Y.; Fujii, N.; Murakata, C.; Ashizawa, T.; Okabe, M.; Nakano, H. Induction of mammalian DNA topoisomerase I mediated DNA cleavage by antitumor indolocarbazole derivatives. Biochemistry 1992, 31, 12069-12075.
10. Yoshinari, T.; Yamada, A.; Uemura, D.; Nomura, K.; Arakawa, H.; Kojiri, K.; Yoshida, E.; Suda, H.; Okura, A. Induction of topoisomerase I-mediated DNA cleavage by a new indolocarbazole, ED-110. Cancer Res. 1993, 53, 490-494.
11. Yoshinari, T.; Matsumoto, M.; Arakawa, H.; Okada, H.; Noguchi, K.; Suda, H.; Okura, A.; Nishimura, S. Novel antitumor indolocarbazole compound 6-N-formylamino-12,13-dihydro-1,11-dihydroxy-13-(β-D-glucopyranosyl)-5H- indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione (NB-506): induction of topoisomerase I-mediated DNA cleavage and mechanisms of cell line-selective cytotoxicity. Cancer Res. 1995, 55, 1310-1315.
12. Arakawa, H.; Iguchi, T.; Morita, M.; Yoshinari, T.; Kojiri, K.; Suda, H.; Okura, A.; Nishimura, S. Novel indolocarbazole compound 6-N-formylamino-12,13-dihydro-1,11-dihydroxy-13-(β-D-glucopyranosyl)-5H- indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione (NB-506): its potent antitumor activities in mice Cancer Res. 1995, 55, 1316-1320.
13. Nettleton, D. E.; Doyle, T. W.; Krishnan, B.; Matsumoto, G. K.; Clardy, J. Isolation and structure of rebeccamycin - a new antitumor antibiotic from Nocardia aerocolonigenes. Tetrahedron Lett. 1985, 26, 4011-4014.
14. Bush, J. A.; Long, B. H.; Catino, J. J.; Bradner, W. T.; Tomita, K. Production and biological activity of rebeccamycin, a novel antitumor agent. J. Antibiot. 1987, 40, 668-678.
15. Rodrigues-Pereira, E.; Belin, L.; Sancelme, M.; Prudhomme, M.; Ollier, M.; Rapp, M.; Servère, D.; Riou, J. F.; Fabbro, D. Structure-activity relationships in a series of substituted indolocarbazoles: topoisomerase I and protein kinase C inhibition and antitumoral and antimicrobial properties. J. Med. Chem. 1996, 39, 4471-4477.
16. Bailly, C.; Riou, J. F.; Colson, P.; Houssier, C.; Rodrigues-Pereira, E.; Prudhomme, M. Sequence-selective DNA cleavage by mammalian topoisomerase I induced by DNA-intercalating indolocarbazole analogues of rebeccamycin. Biochemistry 1997, 36, 3917-3929.
17. Nishizuka, Y. The molecular heterogeneity of protein kinase C and its implications for cellular regulation. Nature 1988, 334, 661-665.
18. Qatsha, K. A.; Rudolph, C.; Marmé, D.; Schächtele, C.; May, W. S. Gö 6976, a selective inhibitor of protein kinase C, is a potent antagonist of human immunodeficiency virus 1 induction from latent/low level-producing reservoir cells in vitro. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 4674-4678.
19. Matson, J. A.; Claridge, C.; Bush, J. A.; Titus, J.; Bradner, W. T.; Doyle, T. W.; Koran, A. C.; Patel, M. AT2433-A1, AT2433-A2, AT2433-B1 and AT2433-B2 novel antitumor antibiotic compounds produced by Actinomadura melliaura. J. Antibiot. 1989, 42, 1547-1555.
20. Toullec, D.; Pianetti, P.; Coste, H.; Bellevergue, P.; Grand-Perret, T.; Ajakane, M.; Baudet, V.; Boissin, P.; Boursier, E.; Loriolle, F.; Duhamel, L.; Charon, D.; Kirilovsky, J. The bisindolylmaleimide GF 109203X is a potent and selective inhibitor of protein kinase C. J. Biol. Chem. 1991, 266, 15771-15781.
21. Brenner, M.; Rexhausen, H.; Steffan, B.; Steiglich, W. Synthesis of arcyriarubin B and related bisindolylmaleimides. Tetrahedron 1988, 44, 2887-2892.
22. Tanaka, S.; Ohkubo, M.; Kojiri, K.; Suda, H.; Yamada, A.; Uemure, D. A new indolopyrrolocarbazole antitumor substance, ED-110, a derivative of BE-13793C. J. Antibiot. 1992, 45, 1797-1798.
23. Kaneko, T.; Wong, H.; Okamato, K. T.; Clardy, J. Two synthetic approaches to rebeccamycin. Tetrahedron Lett. 1985, 26, 4015-4018.
24. Gallant, M.; Link, J. T.; Danishefsky, S. J. A stereoselective synthesis of indole-β-N-glycosides: An application to the synthesis of rebeccamycin. J. Org. Chem. 1993, 58, 343-349.
25. Flowers, H. M.; Levy, A.; Sharon, N. Synthesis of 2-O-α-L-fucopyranosyl-L-fucopyranose. Carbohydr. Res. 1967, 4, 189-195.
26. Lambert, J. B.; Wharry, S. M. Conformational analysis of 5-thio-D-glucose. J. Org. Chem. 1981, 46, 3193-3196.
27. Fahre, S.; Prudhomme, M.; Sancelme, M.; Rapp, M. Indolocarbazole protein kinase C inhibitors from rebeccamycin. BioMed. Chem. 1994, 2, 73-77.
28. Waring, M. J.; Bailly, C. DNA recognition by intercalators and hybrid molecules. J. Mol. Recognit. 1994, 7, 109-122.
29. Tazi, J. Unpublished results.
30. Drew, H. R.; Travers, A. A. DNA structural variations in the E. coli tyr T promoter. Cell 1984, 37, 491-502.
31. Bailly, C.; Waring, M. J. Comparison of different footprinting methodologies for detecting binding sites for a small ligand on DNA. J. Biomol. Struct. Dyn. 1995, 12, 869-898.
32. Halligan, B. D.; Edwards, K. A.; Liu, L. F. Purification and characterization of a type II DNA topoisomerase from bovine calf thymus. J. Biol. Chem. 1985, 260, 2475-2482.
33. Riou, J. F.; Helissey, P.; Grondard, L.; Giorgi-Renault, S. Inhibition of eukaryotic DNA topoisomerase I and II activities by indoloquinolinedione derivatives. Mol. Pharmacol. 1991, 40, 699-706.
34. Riou, J. F.; Fosse, P.; Nguyen, C. H.; Larsen, A. K.; Bissery, M. C.; Grondard, L.; Saucier, J. M.; Bisagni, E.; Lavelle, F. Intoplicine (RP 60475) and its derivatives, a new class of antitumor agents inhibiting both topoisomerase I and II activities. Cancer Res. 1993, 53, 5987-5993.
35. Riou, J. F.; Naudin, A.; Lavalle, F. Effects of taxotere on murine and human tumor cell lines. Biochem. Biophys. Res. Commun. 1992, 187, 164-170.
36. Marte, B. M.; Meyer, T.; Stabel, S.; Gesche, J. R.; Jaken, S.; Fabbro, D.; Hynes, N. E. Protein kinase C and mammary cell differentiation: involvement of protein kinase C-α in the induction of β-casein expression. Cell Growth Diff. 1994, 5, 239-247.
37. McGlynn, E.; Liebetanz, J.; Reutener, S.; Wood, J.; Lydon, N. B.; Hofstetter, H.; Vanek, M.; Meyer, T.; Fabbro, D. Expression and partial characterization of rat protein kinase C-δ and protein kinase C-ζ in insect cells using recombinant baculovirus. J. Cell. Biochem. 1992, 49, 239-250.
38. Ferrari, S.; Thomas, G. Micro- and macropurification methods for protein kinases. Methods Enzymol 1991, 200, 159-169.