Novel olivacine and ellipticine derivatives: S-16020-2 and related compounds as potential antitumor agents

Drugs of the Future

Volumn 22, Issue 1, 1997, Pages 53-59

  Pierré, Alain ^a   Atassi, Ghanem ^a   Devissaguet, Michele ^b   Bisagni, Emile ^c  

^a INSTITUT DE RECHERCHES SERVIER   (France)

^b INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DOXORUBICIN; ELLIPTICINE; ELLIPTICINE DERIVATIVE; N (2 DIMETHYLAMINOETHYL) 9 HYDROXY 5,6 DIMETHYL 6H PYRIDO[4,3 B]CARBAZOLE 1 CARBOXAMIDE; OLIVACINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; DNA BINDING; DOG; DRUG DESIGN; DRUG SYNTHESIS; IN VITRO STUDY; INTRAVENOUS DRUG ADMINISTRATION; MONKEY; MOUSE; NONHUMAN; RAT; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 0030889790     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.1997.022.01.396562     Document Type: Review

References (50)

1. Goodwin, S., Smith, A.F., Horning, E.G. Alkaloids of Ochrosia elliptica Labill. J Am Chem Soc 1959, 81: 1903.
2. Dalton, L.K., Demerac, S., Elmes, B.C., Loder, J.W., Swan, J.M., Teitei, T. Synthesis of the tumour-inhibitory alkaloids, ellipticine, 9-methoxyellipticine and related pyrido [4,3-b]carbazoles. Aust J Chem 1967, 20: 2715-27.
3. Gribble, G.W. Synthesis and antitumour activity of ellipticine alkaloids and related compounds. In: The alkaloids. A. Brossi (Ed.). Academic Press: London 1990, 39: 239-352.
4. Mathe, G., Hayat, M., De Vassal, F. et al. Methoxy-9-ellipticine lactate, clinical screening: Its action in acute myeloblastic leukemia. Rev Eur Etud Clin Biol 1970, 15: 541.
5. Paoletti, C., Le Pecq, J-B., Dat-Xuong, N. et al. Antitumour activity, pharmacology and toxicity of ellipticine, ellipticinium and 9-hydroxy derivatives: Preliminary clinical trials of 2-methyl-9-hydroxyellipticinium (NSC 264137). Recent Res Cancer Res 1980, 74: 107-23.
6. Le Pecq, J.B., Gosse, C., Dat-Xuong, N., Paoletti, C. Deux nouveaux dérivés antitumoraux: l'hydroxy-9-méthyl-2-ellipticinium acétate et l'hydroxy-9 diméthylellipticinum chlorure: Action sur la leucémie L1210 de souris. CR Acad Sci 1975, 281: 1365-7.
7. Paoletti, C., Cros, S., Dat-Xuong, N., Lecointe, P., Moisand, A. Comparative cytotoxic and antitumoural effects of ellipticine derivatives on mouse L1210 leukemia. Chem Biol Interact 1979, 25: 45-58.
8. Juret, P., Heron, J.F., Couette, J.E., Delozier, T., Le Talaer, Y. Hydroxy-9-methyl-2-ellipticinium for osseous metastases from breast cancer: A 5-year experience. Cancer Treat Rep 1982, 66: 1909-16.
9. Buzdar, A.U., Hortobagyi, G.N., Esparza, L.T. et al. Elliptinium acetate in metastatic breast cancer - A phase 2 study. Oncology 1990, 47: 101-4.
10. Rouessé, J., Spielman, M., Turpin, F., Le Chevalier, T., Azab, M., Mondésir, J.M. Phase 2 study of elliptinium acetate salvage treatment of advanced breast cancer. Eur J Cancer 1993, 29A: 856-9.
11. Marty, M., Jasmin, C., Pouillart, P., Gisselbrecht, C., Gouveia, G., Magdalainat, H. Phase I studies with diethyl N-aminopropyl dipirydoindole (BD40M). Proc Am Soc Clin Oncol 1981, 22: 360.
12. Khayat, D., Borel, C., Azab, M. et al. Phase I study of datelliptium chloride, hydrochloride given by 24-h continuous intravenous infusion. Cancer Chemother Pharmacol 1992, 30: 226-8.
13. Majima, H., Niitani, H., Taguchi, T., Furue, H. Phase I clinical and pharmacokinetic study of SUN4599. Proc Am Soc Clin Oncol 1991, 10: Abst 289.
14. Cappelaere, P., Demaille, M.C., Azab, M., Degardin, M. Phase I study of retelliptine dihydrochloride using daily i.v. infusion for 3 days. Proc Am Soc Clin Oncol 1993, 12: Abst 314.
15. Mosher, C.W., Crews, O.P., Acton, E.M., Goodman L. Preparation and antitumour activity of olivacine and some new analogs. J Med Chem 1966, 9: 237-41.
16. Schmutz, J., Hunzicker, F. Die Alkaloide von Aspidosperma Olivaceum M. Arg. Aspidosperma Alkaloid 3. Mitteilung. Pharm Acta Helv 1958, 33: 341-7.
17. Kohn, K.W., Waring, M.J., Glaubiger, D., Friedman, C. Intercalative binding of ellipticine to DNA. Cancer Res 1975, 35: 71-6.
18. Le Pecq, J.B., Dat-Xuong, N., Gosse, C., Paoletti, C. A new antitumoural agent: 9-Hydroxyellipticine. Possibility of a rational design of anticancerous drugs in the series of DNA intercalating drugs. Proc Natl Acad Sci USA 1974, 71: 5078-82.
19. Paoletti, C., Lesca, C., Cros, S., Malvy, C., Auclair, C. Ellipticine and derivatives induce breakage of L1210 cells DNA in vitro. Biochem Pharmacol 1979, 28: 345-50.
20. Zwelling, L.A., Michaels, S., Kerrigan, D., Pommier, Y., Kohn, K.W. Protein-associated deoxyribonucleic acid strand breaks produced in mouse leukemia L1210 cells by ellipticine and 2-methyl-9-hydroxyellipticinium. Biochem Pharmacol 1982, 20: 3261-7.
21. Tewey, K.M., Chen, G.L., Nelson, E.M., Liu, L.F. Intercalative antitumour drugs interfere with the breakage-reunion reaction of mammalian DNA topoisomerase 2. J Biol Chem 1984, 259: 9182-7.
22. Fossé, P., René, B., Charra, M., Paoletti, C., Saucier, J.M. Stimulation of topoisomerase 2-mediated DNA cleavage by ellipticine derivatives: Structure-activity relationship. Mol Pharmacol 1992, 42: 590-5.
23. Auclair, C., Paoletti, C. Bioactivation of the antitumour drugs 9-hydroxyellipticine and derivatives by a peroxidase-hydrogen peroxide system. J Med Chem 1981, 24: 289-95.
24. Dugué, B., Auclair, C., Meunier, B. Covalent binding of elliptinium acetate (NSC264137) to nucleic acids of L1210 cells in culture. Cancer Res 1986, 46; 3828-33.
25. 2-methyl 9-hydroxyolivacinium acetate in the rat: Preliminary identification of biliary 9-(O)-glucuronide and 10-(S)-glutathione conjugates. Xenobiotica 1983, 13: 303-10.
26. Meunier, G., De Montauzon, D., Bernadou, J. et al. The biooxidation ofc ytotoxic ellipticine derivatives: A key to structure-activity relationship studies? Mol Pharmacol 1988, 33: 93-102.
27. Honda, T., Kato, M., Inoue, M. et al. Synthesis and antitumour activity of quaternary ellipticine glycosides, a series of novel and highly active antitumour agents. J Med Chem 1988, 31: 1295-305.
28. Ducrocq, C., Wendling, F., Tourbez-Perrin, M. et al. Structure-activity relationships in a series of newly synthesised 1-amino-substituted ellipticine derivatives. J Med Chem 1980, 23: 1212-6.
29. Roy, M., Monsarrat, B., Cros, S., Lecointe, P., Rivalle, C., Bisagni, E. Cytochrome P-450-mediated O-demethylation of two ellipticine derivatives. Differential effect of the murine Ah locus phenotype. Drug Metab Dispos 1985, 13: 497-502.
30. Cano, J.P., Fabre, G., Bourne, M. et al. In vitro hepatic metabolism of ellipticine derivatives: Application to datelliptium (SR95156B) and retelliptine (SR95325B). Proc Am Assoc Cancer Res 1991, 32: Abst 2062.
31. Atwell, G., Rewcastle, G.W., Baguley, B.C., Denny, W.A. Potential antitumour agents. In vivo solid-tumour activity of derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide. J Med Chem 1987, 30: 664-9.
32. Jasztold-Howorko, R., Landras, C., Pierré, A. et al. Synthesis and evaluation of 9-hydroxy-5-methyl-(and 5,6-dimethyl)-6H-pyrido[4,3-b]carbazole-1-N-[(dialkylamino)alkyl]carboxamides, a new promising series of antitumour olivacine derivatives. J Med Chem 1994, 37: 2445-52.
33. Suffness, M., Cordell, G. Antitumour alkaloids. In: The Alkaloids. A. Brossi (Ed.). Academic Press: London 1985, 89-142.
34. 6-dimethyl-9-hydroxyellipticinium acetate. Evidence for the formation of an electrophilic quinone-iminium derivative. Biochem Pharmacol 1987, 36: 2599-604.
35. 6-methylated derivative of elliptinium acetate, an antitumour agent. Drug Metab Dispos 1988, 16: 316-21.
36. Maftouh, M., Besselievre, R., Monsarrat, B. et al. Synthesis and cytotoxic activity of hydroxylated derivatives of olivacine in relation with their biotransformation. J Med Chem 1985, 28: 708-14.
37. Ruckdeschel, J.C., Modi, S.P., El-Hamouly, W., Portuese, E., Archer, S. N-Methylcarbamate derivatives of ellipticine and olivacine with cytotoxic activity against four human lung cancer cell lines. J Med Chem 1992, 35: 4854-7.
38. Chevalier-Multon, M.C., Jacquemin-Sablon, A., Besselievre, R., Husson, H.P., LePecq, J.B. Comparative cytotoxicities of a series of ellipticine and olivacine derivatives on multidrug resistant cells of human and marine origins. Anti-Cancer Drug Des 1990, 5: 319-55.
39. 2-methyl-9-hydroxyellipticinium acetate. Comparative disposition of this drug with its olivacinium isomer in rat bile. Drug Metab Dispos 1984, 12: 111-9.
40. Le Mee, S., Markovits, J., Pierre, A. et al. In vitro studies of S16020-2, a new antitumour pyridocarbazole derivative. 5th Conf DNA Topoisomerases Ther (Oct 3-6, New York) 1994, 36.
41. Léonce, S., Pérez, V., Casabianca-Pignede, M.R. et al. In vitro cytotoxicity of S16020-2, a new olivacine derivative. Invest New Drugs 1996, 14: 169-80.
42. Léonce, S., Anstett, M., Pérez, V., Pierré, A., Atassi, G. Cell cycle effect and cytotoxicity of S16020-2-2, a new olivacine derivative. Anal Cell Pathol 1994, 6: 270.
43. Le Mee, S., Markovits, J., Pierre, A. et al. Selection and characterization of a Chinese hamster cell line resistant to S16020-2 (NSC-659687), a new antitumour DNA topoisomerase 2 inhibitor, pyridocarbazole derivative. 6th Conf DNA Topoisomerases Ther (Sept 6-8, Amsterdam) 1995, 36.
44. Guilbaud, N., Kraus-Berthier, L., Saint-Dizier, D. et al. In vivo antitumour activity of S16020-2, a new olivacine derivative. Cancer Chemother Pharmacol 1996, 38: 513-21.
45. Pierre, A., Guilbaud, N., Kraus-Berthier, L. et al. In vitro and in vivo antitumour activity of S16020-2 (NSC D-659687), a new olivacine derivative. Proc Am Assoc Cancer Res 1994, 35: Abst 2371.
46. Guilbaud, N., Kraus-Berthier, L., Saint-Dizier, D. et al. Antitumour activity of S16020-2 in two orthotopic models of lung cancer. Anticancer Drugs, submitted.
47. Besselievre, R., Husson, H.P. Une synthèse efficace de la (±) guatambuine et de l'olivacine. a) Tetrahedron Lett 1976, 22: 1873-6. b) Tetrahedron 1981, (Suppl. 1): 241-6.
48. Besselievre, R., Husson, H.P. Une synthèse efficace de la (±) guatambuine et de l'olivacine. a) Tetrahedron Lett 1976, 22: 1873-6. b) Tetrahedron 1981, (Suppl. 1): 241-6.
49. Donato, M.T., Goethals, F., Gómez-Lechon, M.J. et al. Toxicicity of the antitumoral drug datelliptium in hepatic cells: Use of models in vitro for the prediction of toxicity in vivo. Toxicol In Vitro 1992, 6 (4): 295-302.
50. 2-methyl-9-hydroxyellipticinium acetate in rat: A defect of urinary concentrating ability. Ren Fail 1991, 13 (4): 243-51.