Indoloquinolizidine derivatives as novel and potent apoptosis inducers and cell-cycle blockers

ChemBioChem

Volumn 9, Issue 3, 2008, Pages 401-405

  Wehner, Frank ^a   Nören Müller, Andrea ^a   Müller, Oliver ^a   Reis Corrêa Jr , Ivan ^a   Giannis, Athanassios ^b   Waldmann, Herbert ^a  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Antitumor agents; Apoptosis; Cell cycle; Indoioquinolizidine derivatives; Natural products

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ADENOSINE TRIPHOSPHATE; ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 7; INDOQUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG; INDOLE DERIVATIVE; QUINOLIZIDINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL DEATH; CELL PROLIFERATION; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; ENZYME ASSAY; FLUORESCENCE ACTIVATED CELL SORTING; HELA CELL; HUMAN; HUMAN CELL; IC 50; LUMINESCENCE; PRIORITY JOURNAL; STRUCTURE ANALYSIS; CELL CYCLE; CELL LINE; CHEMISTRY; DRUG EFFECT; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY;

APOPTOSIS; CELL CYCLE; CELL LINE; CELL PROLIFERATION; FLOW CYTOMETRY; HUMANS; INDOLES; MICROSCOPY, FLUORESCENCE; QUINOLIZIDINES;

EID: 48849117900     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200700558     Document Type: Article

References (41)

1. I. Chowdhury, B. Tharakan, G. K. Bhat, Cell. Mol. Biol. Lett. 2006, 11, 506-525.
2. S. Elmore, Toxicol. Pathol. 2007, 35, 495-516.
3. K. Taylor, D. Micha, M. Ranson, C. Dive, Expert. Opin. Investig. Drugs 2006, 15, 669-690.
4. A. Russo, M. Terrasi, V. Agnese, D. Santini, V. Bazan, Ann. Oncol. 2006, 17 Suppl. 7, vii115-vii123.
5. R. Gerl, D. L. Vaux, Carcinogenesis 2005, 26, 263-270.
6. C. Gey, S. Kyrylenko, L. Hennig, L. H. Nguyen, A. Buttner, H. D. Pham, A. Giannis, Angew. Chem. 2007, 119, 5311-5314;
7. C. Gey, S. Kyrylenko, L. Hennig, L. H. Nguyen, A. Buttner, H. D. Pham, A. Giannis, Angew. Chem. Int. Ed. 2007, 46, 5219-5222.
8. N. Sunder-Plassmann, V. Sarli, M. Gartner, M. Utz, J. Seiler, S. Huemmer, T. U. Mayer, T. Surrey, A. Giannis, Bioorg. Med. Chem. 2005, 13, 6094-6111.
9. P. T. Daniel, U. Koert, J. Schuppan, Angew. Chem. 2006, 118, 886-908;
10. P. T. Daniel, U. Koert, J. Schuppan, Angew. Chem. Int. Ed. 2006, 45, 872-893.
11. H. Matsuda, K. Yoshida, K. Miyagawa, Y. Nemoto, Y. Asao, M. Yoshikawa, Bioorg. Med. Chem. Lett. 2006, 16, 1567-1573.
12. H. Okamura, K. Yoshida, H. Morimoto, T. Haneji, J. Cell. Biochem. 2005, 94, 117-125.
13. M. Frederich, M. Bentires-Alj, M. Tits, L. Angenot, R. Greimers, J. Gielen, V. Bours, M. P. Merville, J. Pharmacol. Exp. Ther. 2003, 304, 1103-1110.
14. C. Ito, M. Itoigawa, K. Nakao, T. Murata, M. Tsuboi, N. Kaneda, H. Furukawa, Phytomedicine 2006, 13, 359-365.
15. X. Deng, F. Yin, X. Lu, B. Cai, W. Yin, Toxicol. Sci. 2006, 91, 59-69.
16. X. K. Deng, W. Yin, W. D. Li, F. Z. Yin, X. Y. Lu, X. C. Zhang, Z. C. Hua, B. C. Cai, J. Ethnopharmacol. 2006, 106, 179-186.
17. a) A. Noren-Muller, I. Reis-Corrêa, Jr., H. Prinz, C. Rosenbaum, K. Saxena, H. J. Schwalbe, D. Vestweber, G. Cagna, S. Schunk, O. Schwarz, H. Schiewe, H. Waldmann, Proc. Natl. Acad. Sci. USA 2006, 103, 10606-10611;
18. b) I. R. Corrêa, Jr., A. Noren-Muller, H. Ambrosi, S. Jakupovic, K. Saxena, H. Schwalbe, H. Prinz, M. Kaiser, H. Waldmann, Chem. Asian J. 2007, 2, 1109-1126.
19. a) O. Barun, S. Sommer, H. Waldmann, Angew. Chem. 2004, 116, 3258-3261;
20. O. Barun, S. Sommer, H. Waldmann, Angew. Chem. Int. Ed. 2004, 43, 3195-3199;
21. b) S. Sommer, H. Waldmann, Chem. Commun. 2005, 5684-5686;
22. c) O. Barun, K. Kumar, S. Sommer, A. Langerak, T. U. Mayer, O. Müller, H. Waldmann, Eur. J. Org. Chem. 2005, 4773-4788;
23. d) A. B. Garcia, T. Lessmann, J. Umarye, V. Mamane, S. Sommer, H. Waldmann, Chem. Commun. 2006, 3868-3870;
24. e) J. D. Umarye, T. Lessmann, A. B. Garcia, V. Mamane, S. Sommer, H. Waldmann, Chem. Eur. J. 2007, 13, 3305-3319;
25. f) V. Mamane, A. B. García, J. D. Umarye, T. Lessmann, S. Sommer, H. Waldmann, Tetrahedron 2007, 63, 5754-5767;
26. g) M. A. Sanz, T. Voigt, H. Waldmann, Adv. Synth. Catal. 2006, 348, 1511-1515;
27. h) C. Rosenbaum, P. Baumhof, R. Mazitschek, O. Müller, A. Giannis, H. Waldmann, Angew. Chem. 2004, 116, 226-230;
28. C. Rosenbaum, P. Baumhof, R. Mazitschek, O. Müller, A. Giannis, H. Waldmann, Angew. Chem. Int. Ed. 2004, 43, 224-228;
29. i) C. Rosenbaum, C. Katzka, A. Marzinzik, H. Waldmann, Chem. Commun. 2003, 1822-1823;
30. j) B. Meseguer, D. Alonso-Díaz, N. Griebenow, T. Herget, H. Waldmann, Angew. Chem. 1999, 111, 3083-3087;
31. B. Meseguer, D. Alonso-Díaz, N. Griebenow, T. Herget, H. Waldmann, Angew. Chem. Int. Ed. 1999, 38, 2902-2906;
32. k) B. Meseguer, D. Alonso-Díaz, N. Griebenow, T. Herget, H. Waldmann, Chem. Eur. J. 2000, 6, 3943-3957;
33. l) D. Brohm, S. Metzger, A. Bhargava, O. Müller, F. Lieb, H. Waldmann, Angew. Chem. 2002, 114, 319-323;
34. D. Brohm, S. Metzger, A. Bhargava, O. Müller, F. Lieb, H. Waldmann, Angew. Chem. Int. Ed. 2002, 41, 307-311;
35. m) D. Brohm, N. Philippe, S. Metzger, A. Bhargava, O. Müller, F. Lieb, H. Waldmann, J. Am. Chem. Soc. 2002, 124, 13171-13178;
36. n) P. Stahl, L. Kissau, R. Matzischek, A. Huwe, P. Furet, A. Giannis, H. Waldmann, J. Am. Chem. Soc. 2001, 123, 11586-11593;
37. o) P. Stahl, L. Kissau, R. Matzischek, A. Giannis, H. Waldmann, Angew. Chem. 2002, 114, 1222-1226;
38. P. Stahl, L. Kissau, R. Matzischek, A. Giannis, H. Waldmann, Angew. Chem. Int. Ed. 2002, 41, 1174-1178;
39. p) M. A. Koch, L.-O. Wittenberg, S. Basu, D. A. Jeyaraj, E. Gourzoulidou, K. Reinecke, A. Odermatt, H. Waldmann, Proc. Natl. Acad. Sci. USA 2004, 101, 16721-16726;
40. q) M. A. Koch, A. Schuffenhauer, M. Scheck, M. Casaulta, A. Odermatt, H. Waldmann, Proc. Natl. Acad. Sci. USA 2005, 102, 17272-17277.
41. Natural-product inspired compounds were obtained from Analyticon Discovery GmbH (Potsdam, Germany).