Evaluation of novel epothilone analogues by means of a common pharmacophore and a QSAR pseudoreceptor model for taxanes and epothilones

ChemMedChem

Volumn 5, Issue 1, 2010, Pages 35-40

  Forli, Stefano ^a,c   Manetti, Fabrizio ^a   Altmann, Karl Heinz ^b   Botta, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b ETH ZURICH   (Switzerland)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Antitumor agents; Epothilones; Molecular modeling; Pharmacophores; Taxanes

Indexed keywords

EPOTHILONE DERIVATIVE; PACLITAXEL; TAXANE DERIVATIVE;

ARTICLE; BINDING SITE; CANCER CELL; CRYSTALLOGRAPHY; DRUG BINDING; HUMAN; HUMAN CELL; IC 50; MUTAGENESIS; NUCLEAR MAGNETIC RESONANCE; PHARMACOPHORE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; UTERINE CERVIX CARCINOMA;

ANTINEOPLASTIC AGENTS; EPOTHILONES; PACLITAXEL; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS; TUBULIN;

EID: 74849137129     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200900303     Document Type: Article

References (34)

1. J. Winkler, P. H. Axelson, Bioorg. Med. Chem. Lett. 1996, 6, 2963-2966.
2. a) H. L. Lowe, K. H. Downing, E. Nogales, J. Mol. Biol. 2001, 313, 1045-1057;
3. b) J. P. Snyder, J. H. Nettles, B. Cornett, K. H. Downing, E. Nogales, Proc. Natl. Acad. Sci. USA 2001, 98, 5312-5316.
4. a) M. Wang, X. Xia, Y. Kim, D. Hwang, J. M. Jansen, M. Botta, D. C. Liotta, J. P. Snyder, Org. Lett. 1999, 1, 43-46;
5. b) P. Giannakakou, R. Gussio, E. Nogales, K. H. Downing, D. Zaharevitz, B. Bollbuck, G. Poy, D. Sachett, K. C. Nicolaou, T. Fojo, Proc. Natl. Acad. Sci. USA 2000, 97, 2904-2909;
6. I. Ojima, S. Chakravarty, T. Inoue, S. Lin, L. He, S. B. Horwitz, S. D. Kuduk, S. J. Danishefsky, Proc. Natl. Acad. Sci. USA 1999, 96, 4256-4261.
7. a) F. Manetti, S. Forli, L. Maccari, F. Corelli, M. Botta, Farmaco 2003, 58, 357-661;
8. b) F. Manetti, L. Maccari, F. Corelli, M. Botta, Curr. Top. Med. Chem. 2004, 4, 203-217.
9. J. H. Nettles, H. Li, B. Cornett, J. M. Krahn, J. P. Snyder, K. H. Downing, Science 2004, 305, 866-869.
10. W. Zhan, Y. Jiang, P. J. Brodie, D. G. Kingston, D. C. Liotta, J. P. Snyder, Org. Lett. 2008, 10, 1565-1568.
11. M. Reese, V. M. Sànchez-Pedregal, K. Kibicek, J. Meiler, M. J. J. Blommers, C. Griesinger, T. Carlomagno, Angew. Chem. 2007, 119, 1896-1900;
12. Angew. Chem. Int. Ed. 2007, 46, 1864-1868.
13. K.-H. Altmann, B. Pfeiffer, S. Arseniyadis, B. A. Pratt, K. C. Nicolaou, ChemMedChem 2007, 2, 396-423.
14. R. M. Buey, J. F. Díaz, J. M. Andreu, A. O'Brate, P. Giannakakou, K. C. Nicolaou, P. K. Sasmal, A. Ritzén, K. Namoto, Chem. Biol. 2004, 11, 225-236.
15. a) F. Cachoux, T. Isarno, M. Wartmann, K.-H. Altmann, ChemBioChem 2006, 7, 54-57;
16. b) G. Bold, S. Wojeik, G. Caravatti, R. Lindauer, C. Stierlin, J. Gertsch, M. Wartmann, K.-H. Altmann, ChemMedChem 2006, 1, 37-40.
17. a) M. Wartmann, K.-H. Altmann, Curr. Appl. Phys. Curr. Rev. Med. Chem. Anticancer Agents 2002, 2, 123-148;
18. b) K.-H. Altmann, G. Bold, G. Caravatti, N. End, A. Flörsheimer, V. Guagnano, T. O'Reilly, M. Wartmann, Chimia 2000, 54, 612-621;
19. K.-H. Altmann, A. Flörsheimer, G. Bold, G. Caravatti, M. Wartmann, Chimia 2004, 58, 686-690;
20. F. Feyen, J. Gertsch, M. Wartmann, K.-H. Altmann, Chimia 2007, 61, 143-146.
21. a) F. Feyen, J. Gertsch, M. Wartmann, K.-H. Altmann, Angew. Chem. 2006, 118, 6013-6017;
22. Angew. Chem. Int. Ed. 2006, 45, 5880-5885.
23. K. C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, T. Je, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, P. N. King, M. R. V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. 1997, 109, 2181-2187;
24. Angew. Chem. Int. Ed. Engl. 1997, 36, 2097-2103.
25. K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120-2153;
26. Angew. Chem. Int. Ed. 1998, 37, 2014-2045.
27. F. Cachoux, T. Isarno, M. Wartmann, K.-H. Altmann, Angew. Chem. 2005, 117, 7636-7640;
28. Angew. Chem. Int. Ed. 2005, 44, 7469-7473.
29. M. Sefkow, M. Kiffe, D. Schummer, G. Höfle, Bioorg. Med. Chem. Lett. 1998, 8, 3025-3030.
30. M. Erdélyi, B. Pfeiffer, K. Hauenstein, J. Fohrer, K.-H. Altmann, T. Carlomagno, J. Med. Chem. 2008, 51, 1469-1473.
31. a) A. Rivkin, F. Yoshimura, G. Fumihiko, A. E. Gabarda, Y. S. Cho, T.-C. Chou, H. Dong, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 10913-10922;
32. b) T.-C. Chou, H. Dong, X. Zhang, W. P. Tong, S. J. Danishefsky, Cancer Res. 2005, 65, 9445-9454.
33. M. Gurrath, G. Müller, H. D. Höltje, Perspect. Drug Discovery Des. 1998, 12-14, 135-157.
34. K. C. Nicolaou, R. Scarpelli, B. Bollbuck, B. Werschkun, M. M. A. Pereira, M. Wartmann, K.-H. Altmann, D. Zaharevitz, R. Gussio, P. Giannakakou, Chem. Biol. 2000, 7, 593-599.