Synthesis and biological evaluation of epothilone A dimeric compounds

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 21, 2009, Pages 7435-7440

  Passarella, Daniele ^a   Comi, Daniela ^a   Cappelletti, Graziella ^a   Cartelli, Daniele ^a   Gertsch, Juerg ^b   Quesada, Ana R ^c   Borlak, Jürgen ^d   Altmann, Karl Heinz ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b ETH ZURICH   (Switzerland)

^c UNIVERSITY OF MÁLAGA   (Spain)

^d FRAUNHOFER INSTITUTE FOR TOXICOLOGY AND EXPERIMENTAL MEDICINE   (Germany)

Author keywords

Epothilone a; Inhibition of angiogenesis; Tubulin polymerization

Indexed keywords

EPOTHILONE DERIVATIVE; TUBULIN; ANGIOGENESIS INHIBITOR; EPOTHILONE A; TUBULIN MODULATOR;

ANGIOGENESIS; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL CULTURE; CELL DIFFERENTIATION; CELL MIGRATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG SYNTHESIS; ENDOTHELIUM CELL; HUMAN; HUMAN TISSUE; MICROTUBULE ASSEMBLY; CELL MOTION; CHEMISTRY; CYTOLOGY; DIMERIZATION; DRUG SCREENING; METABOLISM; SYNTHESIS; TUMOR CELL LINE;

ANGIOGENESIS INHIBITORS; CELL DIFFERENTIATION; CELL LINE, TUMOR; CELL MOVEMENT; DIMERIZATION; DRUG SCREENING ASSAYS, ANTITUMOR; ENDOTHELIAL CELLS; EPOTHILONES; HUMANS; TUBULIN; TUBULIN MODULATORS;

EID: 73949160187     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.09.032     Document Type: Article

References (24)

1. (a) Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014-2045
2. (b) Attard, G.; Greystoke, A.; Kaye, S.; De Bono, S. Pathologie Biologie 2006, 54, 74-82.
3. (a) Höfle. G.; Bedorf, N.; Gerth, K. and Reichenbach, H.; German Patent Disclosure, DE 4138042, 1993 (Priority Nov. 19, 1991);
4. Chem. Abstr. 1993, 120, 52841.
5. (b) Gerth, K.; Bedorf, N.: Höfle, C.; Irschik. H.; Reichenbach, H. J. Antibiot. 1996, 49, 560-564.
6. (a) Lee, F. Y. F.; Borzilleri, R.; Fairchild, C. R.; Kim, S.-H.; Long, B. H.; ReventosSuarez, C.; Vite, G. D.: Rose, W. C.; Kramer, R. A. Clin. Cancer Res. 2001, 7, 1429-1437
7. (b) Cortes, J.; Baselga, J. Oncologist 2007, 12, 271-280
8. Rivera, E.; Lee, J.; Davies, A. Oncologist 2008, 13, 1207-1223
9. Kaminskas, E.; Jiang, X.; Aziz, R.; Bullock, J.; Kasliwal, R.; Harapanhalli, R.; Pope, S.; Sridhara, R.; Leighton, J.; Booth, B.; Dagher, R.; Justice, R.; Pazdur, R. Clin. Cancer Res. 2008, 14, 4378-4384
10. (e) Hunt, J. T. Mol. Cancer. Ther. 2009, 8, 275-281.
11. Thorpe, P. E.; Chaplin, D. J.; Blakey, D. C. Cancer Res. 2003, 63, 1144-1147.
12. Jain, R. K. Science 2005, 307, 58-62.
13. Gertsch, J.; Meyer, S.; Müller, M.; Altmann, K.-H. ChemBioChem 2009, 10, 166-175.
14. Nicolaou, K. C.; Hepworth, D.; King, N. P.; Finlay, M. R. V.; Scarpelli, R.; Pereira, M. M. A.; Bollbuck, B.; Bogot, A.; Werschkun, B.; Winsigger, N. Chem. Eur. J. 2000, 6, 2783-2800.
15. For other epothilones analogues see: (a) Nicolaou, K. C.; Scarpelli, R.; Bollbuck, B.; Werschkun, B.; Pereira, M. M.; Wartmann, M.; Altmann, K.-. H.; Zaharevitz, D.; Gussio, R.; Giannakakou, P. Chem. Biol. 2000, 7, 593-599
16. (b) Watkins, E. B.; Chittiboyina, A. G.; Jung, J. C.: Avery, M. A. Curr. Pharm. Design 2005, 11, 1615-1653.
17. For other example of selective functionalization of C7-OH see: Sefkoe, M.; Kiffe, M.: Schummer, D.; Höfle, G. Bioorg. Med. Chem. Lett. 1998, 8, 3025-3030.
18. Reamon-Buettner, S. M.; Borlak, J. Cancer Res. 2008, 68, 7587-7596.
19. Folkman, J. Nat. Med. 1995, 1, 27-31.
20. Rodríguez-Nieto, S.; Chavarría, T.; Martínez-Poveda, B.; Sánchez-Jiménez, F.; Quesada, A. R.; Medina, M. A. Biochem. Biophys. Res. Commun 2002, 293, 497-500.
21. Martínez-Poveda, B.; Quesada, A. R.; Medina, M. A. Eur. J. Pharm. 2005, 516, 97-103.
22. Meyer, T.; Regenass, U.; Fabbro, D.; Alteri, E.; Rösel, J.; Müller, M.; Caravatti, G.; Matter, A. Int. J. Cancer 1989, 43, 851-856.
23. Nicolaou, K. C.; Scarpelli, R.; Bollbuck, B.; Werschkun, B.; Pereira, M. M.; Wartmann, M.; Altmann, K.-H.; Zaharevitz, D.; Gussio, R.; Giannakakou, P. Chem. Blol. 2000, 7, 593-599.
24. Rodriguez-Nieto, S.; Medina, M. A: Quesada, A. R. Anticancer Res. 2001, 21, 3457-3460.