Inhibition of tubulin polymerization by 5,6-dihydroindolo[2,1- a]isoquinoline derivatives

Journal of Medicinal Chemistry

Volumn 40, Issue 22, 1997, Pages 3524-3533

  Goldbrunner, Michael ^a   Loidl, Günther ^a   Polossek, Thomas ^a   Mannschreck, Albrecht ^a   Von Angerer, Erwin ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

12 FORMYL 5,6 DIHYDRO 3,9 DIHYDROXY 6 PROPYLINDOLO[2,1 A]ISOQUINOLINE; 2 METHOXYESTRADIOL; 5,6 DIHYDROINDOLO[2,1 A]ISOQUINOLINE DERIVATIVE; 6 BUTYL 12 FORMYL 5,6 DIHYDRO 3,9 DIHYDROXYINDOLO[2,1 A]ISOQUINOLINE; 6 METHOXY 2 PHENYL 4 QUINOLONE; COLCHICINE; COMBRETASTATIN A4; ISOQUINOLINE DERIVATIVE; PODOPHYLLOTOXIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CONTROLLED STUDY; CYTOSTASIS; DRUG ACTIVITY; DRUG BINDING SITE; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY;

ANIMALS; ANTINEOPLASTIC AGENTS; CATTLE; COLCHICINE; HUMANS; INDOLES; ISOQUINOLINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; POLYMERS; PROTEIN BINDING; SPECTROPHOTOMETRY, INFRARED; TUBULIN; TUBULIN MODULATORS; TUMOR CELLS, CULTURED;

EID: 0030668053     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970177c     Document Type: Article

References (30)

1. Polossek, T.; Ambros, R.; von Angerer, S.; Brandl, G.; Mannschreck, A.; von Angerer, E. 6-Alkyl-12-formylindolo[2,1-α]isoquinolines. Syntheses, estrogen receptor binding affinities, and stereospecific cytostatic activity. J. Med. Chem. 1992, 35, 3537-3547.
2. Cushman, M.; Nagarathnam, D.; Gopal, D.; He, H. M.; Lin, C. M.; Hamel, E. Synthesis and evaluation of analogues of (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents. J. Med. Chem. 1992, 35, 2293-2306.
3. Lin, C. M.; Singh, S. B.; Chu, P. S.; Dempcy, R. O.; Schmidt, J. M.; Pettit, G. R.; Hamel, E. Interactions of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: a structure-activity study. Mol. Pharmacol. 1988, 34, 200-208.
4. Cushman, M.; He, H.-M.; Lin, C. M.; Hamel, E. Synthesis and evaluation of a series of benzylaniline hydrochlorides as potential cytotoxic and antimitotic agents acting by inhibition of tubulin polymerization. J. Med. Chem. 1993, 36, 2817-2821.
5. Edwards, M. L.; Stemerick, D. M.; Sunkara, P. S. Chalcones: a new class of antimitotic agents. J. Med. Chem. 1990, 33, 1948-1954.
6. Getahun, Z.; Jurd, L.; Chu, P. S.; Lin, C. M.; Hamel, E. Synthesis of alkoxy-substituted diaryl compounds and correlation of ring separation with inhibition of tubulin polymerization: differential enhancement of inhibitory effects under suboptimal polymerization reaction conditions. J. Med. Chem. 1992, 35, 1058-1067.
7. Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A. K.; Lin, C. M.; Hamel, E. Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization. J. Med. Chem. 1991, 34, 2579-2588.
8. Shi, Q.; Chen, K.; Li, L.; Chang, J. J.; Autry, C.; Kozuka, M.; Konoshima, T.; Estes, J. R.; Lin, C. M.; Hamel, E.; et al. Antitumor agents, 154. Cytotoxic and antimitotic flavonols from Polanisia dodecandra. J. Nat. Prod. 1995, 58, 475-482.
9. Lichius, J. J.; Thoison, O.; Montagnac, A.; Pais, M.; Gueritte Voegelein, F.; Sevenet, T.; Cosson, J. P.; Hadi, A. H. Antimitotic and cytotoxic flavonols from Zieridium pseudobtusifolium and Acronychia porteri. J. Nat. Prod. 1994, 57, 1012-1016.
10. Hastie, S. B. Interactions of colchicine with tubulin. Pharmacol. Ther. 1991, 51, 377-401.
11. Cortese, F.; Bhattacharyya, B.; Wolff, J. Podophyllotoxin as a probe for the colchicine binding site of tubulin. J. Biol. Chem. 1977, 252, 1134-1140.
12. Tomioka, K.; Ishiguro, T.; Mizuguchi, H.; Komeshima, N.; Koga, K.; Taukagoshi, S.; Tauruo, T.; Tashiro, T.; Tamida, S.; Kishi, T. Absolute structure-activity relationships of steganacin congeners and analogues. J. Med. Chem. 1991, 34, 54-57.
13. Lin, C. M.; Ho, H. H.; Pettit, G. R.; Hamel, E. Antimitotic natural products combrestatin A-4 and combrestatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry 1989, 28, 6984-6991.
14. Kuo, S. C.; Lee, H. Z.; Juang, J. P.; Lin, Y. T.; Wu, T. S.; Chang, J. J.; Lednicer, D.; Paull, K. D.; Lin, C. M.; Hamel, E.; et al. Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4′-substituted phenyl)-4-quinolones and related compounds: identification as antimitotic agents interacting with tubulin. J. Med. Chem. 1993, 36, 1146-1156.
15. Li, L.; Wang, H.-K.; Kuo, S.-C.; Wu, T.-S.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K.-H. Antitumor agents 155. Synthesis and biological evaluation of 3′,6,7-substituted 2-phenyl-4-quinolones as antimicrotubule agents. J. Med. Chem. 1994, 37, 3400-3407.
16. Lin, C. M.; Kang, G. J.; Roach, M. C.; Jiang, J. B.; Hesson, D. P.; Luduena, R.F.; Hamel, E. Investigation of the mechanism of the interaction of tubulin with derivatives of 2-styrylquinazolin-4(3H)-one. Mol. Pharmacol. 1991, 40, 827-832.
17. Jiang, J. B.; Hesson, D. P.; Dusak, B. A.; Dexter, D. L.; Kang, G. J.; Hamel, E. Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization. J. Med. Chem. 1990, 33, 1721-1728.
18. De Ines, C.; Leynadier, D.; Barasoain, I.; Peyrot, V.; Garcia, P.; Briand, C.; Rener, G. A.; Temple, C., Jr. Inhibition of microtubules and cell cycle arrest by a new 1-deaza-7,8-dihydropteridine antitumor drug, CI 980, and by its chiral isomer, NSC 613863. Cancer Res. 1994, 54, 75-84.
19. D'Amato, R. J.; Lin, C. M.; Flynn, E.; Folkman, J.; Hamel, E. 2-Methoxyestradiol, an endogenous mammalian metabolite, inhibits tubulin polymerization by interacting at the colchicine site. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3964-3968.
20. Hamel, E.; Lin, C. M.; Flynn, E.; D'Amato, R. J. Interactions of 2-methoxyestradiol, an endogenous mammalian metabolite, with unpolymerized tubulin and with tubulin polymers. Biochemistry 1996, 35, 1304-1310.
21. Lobert, S.; Vulevic, B.; Correia, J. J. Interaction of vinca alkaloids with tubulin: a comparison of vinblastine, vincristine, and vinorelbine. Biochemistry 1996, 35, 6806-6814.
22. Hamel, E. Natural products which interact with tubulin in the vinca domain: maytansine, rhizoxin, phomopsin A, dolastatins 10 and 15 and halichondrin B. Pharmacol. Ther. 1992, 55, 31-51.
23. Aizu-Yokota, E.; Ichinoseki, K.; Sato, Y. Microtubule disruption induced by estradiol in estrogen receptor-positive and -negative human breast cancer cell lines. Carcinogenesis 1994, 15, 1875-1880.
24. Blokhin, A. V.; Yoo, H. D.; Geralds, R. S.; Nagle, D. G.; Gerwick, W. H.; Hamel, E. Characterization of the interaction of the marine cyanobacterial natural product curacin A with the colchicine site of tubulin and initial structure-activity studies with analogues. Mol. Pharmacol. 1995, 48, 523-531.
25. Biberger, C. 2-Phenylindole mit schwefelhaltigen Seitenketten. Synthese und biologische Charakterisierung neuer Estrogenan-tagonisten. Ph.D. Thesis, Universität Regensburg, 1996.
26. Hodgson, S.T. Discovery of 1069C-A novel synthetic antitumour agent with low cross-resitance potential. In Medicinal Chemistry. Principles and Practice; King, F. D., Ed.; Royal Society of Chemistry: Cambridge, 1994; pp 241-254.
27. Cushman, M.; He, H. M.; Katzenellenbogen, J. A.; Lin, C. M.; Hamel, E. Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site. J. Med. Chem. 1995, 38, 2041-2049.
28. Li, L.; Wang, H.-K.; Kuo, S.-C.; Wu, T.-S.; Lednicer, D.; Lin, C. M.; Hamel, E.; Lee, K.-H. Antitumor agents. 150. 2′,3′,4′,5′,5,6,7-substituted 2-phenyl-4-quinolones and related compounds: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization. J. Med. Chem. 1994, 37, 1126-1135.
29. Hamel, E.; Blokhin, A. V.; Nagle, D. G.; Yoo, H.-D.; Gerwick, W. H. Limitations in the use of tubulin polymerization assays as a screen for the identification of new antimitotic agent; the potent marine natural product curacin A as an example. Drug Dev. Res. 1995, 34, 110-120.
30. Koller, H.; Rimböck, K. H.; Mannschreck, A. High-pressure liquid chromatography on triacetylcellulose. Characterization of a sorbent for separation of enantiomers. J. Chromatogr. 1983, 282, 89-94.