Antitumor agents: Development of highly potent glycosidic duocarmycin analogues for selective cancer therapy

Angewandte Chemie - International Edition

Volumn 45, Issue 39, 2006, Pages 6574-6577

  Tietze, Lutz F ^a   Major, Felix ^a   Schuberth, Ingrid ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Antitumor agents; Cytostatic agents; Duocarmycin; Glycosides; Prodrugs

Indexed keywords

ANTITUMOR AGENTS; CYTOSTATIC AGENTS; DUOCARMYCIN; GLYCOSIDES; PRODRUGS;

ANTIBODIES; DRUG THERAPY; ENZYMES; ONCOLOGY; SYNTHESIS (CHEMICAL); TOXICITY; TUMORS;

DRUG PRODUCTS;

ALKYLATING AGENT; ANTIBODY; DUOCARMYCIN SA; INDOLE DERIVATIVE; PRODRUG; PYRROLE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG SCREENING; HUMAN; NEOPLASM; STREPTOMYCES; SYNTHESIS; TUMOR CELL LINE;

ALKYLATING AGENTS; ANTIBODIES; CELL LINE, TUMOR; DRUG DELIVERY SYSTEMS; HUMANS; INDOLES; NEOPLASMS; PRODRUGS; PYRROLES; STREPTOMYCES; TUMOR STEM CELL ASSAY;

EID: 33749843662     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600936     Document Type: Article

References (55)

1. Reviews: a) W. A. Denny, Cancer Invest. 2004, 22, 604-619;
2. b) L. F. Tietze, T. Feuerstein, Curr. Pharm. Des. 2003, 9, 2155-2175;
3. c) L. F. Tietze, T. Feuerstein, Aust. J. Chem. 2003, 56, 841-854;
4. d) W. A. Denny, Eur. J. Med. Chem. 2001, 36, 577-595;
5. e) M. Jung, Mini-Rev. Med. Chem. 2001, 1, 399-407;
6. f) G. Xu, H. L. McLeod, Clin. Cancer Res. 2001, 7, 3314-3324;
7. g) K. N. Syrigos, A. A. Epenetos, Anticancer Res. 1999, 19, 605-614;
8. h) G. M. Dubowchik, M. A. Walker, Pharmacol. Ther. 1999, 83, 67-123;
9. i) C. J. Springer, I. Niculescu-Duvaz, Adv. Drug Delivery Rev. 1997, 26, 151-172;
10. j) L. N. Jungheim, T. A. Shepherd, Chem. Rev. 1994, 94, 1553-1566.
11. K. D. Bagshawe, Br. J. Cancer 1987, 56, 531-532.
12. A. M. Wu, P. D. Senter, Nat. Biotechnol. 2005, 23, 1137-1146.
13. a) T. Arndt, U. Arndt, U Reuning, H. Kessler in Cancer Therapy: Molecular Targets in Tumor-Host Interactions (Ed.: G. F. Weber), Horizon Bioscience, Norfolk, 2005, 93-141;
14. b) D. Ribatti, A. Vacca, F. Merchionne, M. Presta, Mini-Rev. Med. Chem. 2005, 5, 313-317;
15. c) K. A. El Sayed, Mini-Rev. Med. Chem. 2005, 5, 971-993.
16. a) S. Dziadek, D. Kowalczyk, H. Kunz, Angew. Chem. 2005, 117, 7798-7803;
17. Angew. Chem. Int. Ed. 2005, 44, 7624-7630;
18. b) S. Dziadek, A. Hobel, E. Schmitt, H. Kunz, Angew. Chem. 2005, 117, 7803-7808;
19. Angew. Chem. Int. Ed. 2005, 44, 7630-7635.
20. a) M. E. M. Noble, J. A. Endicott, L. N. Johnson, Science 2004, 303, 1800-1805;
21. b) C. Garcia-Echeverria, D. Fabbro, Mini-Rev. Med. Chem. 2004, 4, 273-283.
22. a) M. Langer, F. Kratz, B. Rothen-Rutishauser, H. Wunderli-Allenspach, A. G. Beck-Sickinger, J. Med. Chem. 2001, 44, 1341-1348;
23. b)M. Langer, A. G. Beck-Sickinger, Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 71-93.
24. L. F. Tietze, T. Herzig, T. Feuerstein, I. Schuberth, Eur. J. Org. Chem. 2002, 1634-1645.
25. a) L. F. Tietze, T. Feuerstein, A. Fecher, F. Haunert, O. Panknin, U. Borchers, I. Schuberth, F. Alves, Angew. Chem. 2002, 114, 785-787;
26. Angew. Chem. Int. Ed. 2002, 41, 759-761;
27. b) L. F. Tietze, M. Lieb, T. Herzig, F. Haunert, I. Schuberth, Bioorg. Med. Chem. 2001, 9, 1929-1939;
28. c) L. F. Tietze, T. Herzig, A. Fecher, F. Haunert, I. Schuberth, ChemBioChem 2001, 2, 758-765;
29. d) L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schuberth, Angew. Chem. 1996, 108, 2840-2842;
30. Angew. Chem. Int. Ed. Engl. 1996, 35, 2674-2677.
31. a) G. Wei, N. A. Loktionova, A. E. Pegg, R. C. Moschel, J. Med. Chem. 2005, 48, 256-261;
32. b) H. Cheng, X. Cao, M. Xian, L. Fang, T. B. Cai, J. J. Ji, J. B. Tunac, D. Sun, P. G. Wang, J. Med. Chem. 2005, 48, 645-652;
33. c) M. Y. Torgov, S. C. Alley, C. G. Cerveny, D. Farquhar, P. D. Senter, Bioconjugate Chem. 2005, 16, 717-721;
34. d) E. Bouvier, S. Thirot, F. Schmidt, C. Monneret, Bioorg. Med. Chem. 2004, 12, 969-977;
35. e) T. Kline, M. Y. Torgov, B. A. Mendelsohn, C. G. Cerveny, P. D. Senter, Mol. Pharm. 2004, 1, 9-22;
36. f) E. Bouvier, S. Thirot, F. Schmidt, C. Monneret, Org. Biomol. Chem. 2003, 1, 3343-3352;
37. g) H. Townes, K. Summerville, B. Purnell, M. Hooker, E. Madsen, S. Hudson, M. Lee, Med. Chem. Res. 2002, 12, 248-253;
38. h) N. Amishiro, S. Nagamura, C. Murakata, A. Okamoto, E. Kobayashi, M. Asada, K. Gomi, T. Tamaoki, M. Okabe, N. Yamaguchi, K. Yamaguchi, H. Saito, Bioorg. Med. Chem. 2000, 8, 381-391.
39. a) M. Ichimura, T. Ogawa, K. Takahashi, E. Kobayashi, I. Kawamoto, T. Yasuzawa, I. Takahashi, H. Nakano, J. Antibiot. 1990, 43, 1037-1038;
40. b) M. Ichimura, T. Ogawa, S. Katsumata, K. Takahashi, I. Takahashi, H. Nakano, J. Antibiot. 1991, 44, 1045-1053;
41. c) D. L. Boger, D. S. Johnson, Angew. Chem. 1996, 108, 1542-1580;
42. Angew. Chem. Int. Ed. Engl. 1996, 35, 1438-1474.
43. a) L. F. Tietze, F. Haunert, T. Feuerstein, T. Herzig, Eur. J. Org. Chem. 2003, 562-566;
44. b) R. Baird, S. Winstein, J. Am. Chem. Soc. 1963, 85, 567-578.
45. J. B. J. Milbank, M. Tercel, G. J. Atwell, W. R. Wilson, A. Hogg, W. A. Denny, J. Med. Chem. 1999, 42, 649-658.
46. 3SnH, which was formerly used, was replaced by tris(trimethylsilyl)silane.
47. -1, a = 2.05, (+)-5: 99.9% ee, (-)-5:99.9% ee.
48. L. F. Tietze, F. Major, J. Magull, unpublished results.
49. a) S. Ram, L. D. Spicer, Tetrahedron Lett. 1987, 28, 515-516;
50. b) T. Bieg, W. Szeja, Synthesis 1985, 76-77.
51. a) R. R. Schmidt, Angew. Chem. 1986, 98, 213-236;
52. Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235;
53. b) W. Dullenkopf, J. C. Castro-Palomino, L. Manzoni, R. R. Schmidt, Carbohydr. Res. 1996, 296, 135-147.
54. L. F. Tietze, B. Krewer, H. Frauendorf, F. Major, I. Schuberth, Angew. Chem. 2006, 118, 6720-6724;
55. Angew. Chem. Int. Ed. 2006, 45, 6570-6574.