Photoactivatable prodrugs of highly potent duocarmycin analogues for a selective cancer therapy

Chemistry - A European Journal

Volumn 19, Issue 5, 2013, Pages 1726-1731

  Tietze, Lutz F ^a   Müller, Michael ^a   Duefert, Svenia C ^a   Schmuck, Kianga ^a   Schuberth, Ingrid ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

cancer therapy; cytotoxicity; duocarmycin; photochemistry; prodrugs

Indexed keywords

BIOLOGICAL EVALUATION; CANCER CHEMOTHERAPY; CANCER THERAPY; CYTOTOXIC; DUOCARMYCIN; IN-VITRO; MONO-THERAPY; PHOTOACTIVATABLE; PRODRUGS; PROTECTING GROUP; SIDE EFFECT; UV-A LIGHT;

CHEMOTHERAPY; CYTOTOXICITY; DRUG INTERACTIONS; PHOTOCHEMICAL REACTIONS;

ONCOLOGY;

2 PYRROLIDONE DERIVATIVE; ANTIBODY; ANTINEOPLASTIC AGENT; ANTINEOPLASTIC ANTIBIOTIC; DUOCARMYCIN A; INDOLE DERIVATIVE; PRODRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; NEOPLASM; PHOTOCHEMISTRY; SYNTHESIS; TUMOR CELL LINE;

ANTIBIOTICS, ANTINEOPLASTIC; ANTIBODIES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; HUMANS; INDOLES; MOLECULAR STRUCTURE; NEOPLASMS; PHOTOCHEMISTRY; PRODRUGS; PYRROLIDINONES;

EID: 84872695220     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202773     Document Type: Article

References (49)

1. L. F. Tietze, K. Schmuck, Curr. Pharm. Des. 2011, 17, 3527-3547
2. L. F. Tietze, B. Krewer, J. M. von Hof, H. Frauendorf, I. Schuberth, Toxins 2009, 1, 134-150
3. L. F. Tietze, B. Krewer, Anti-Cancer Agents Med. Chem. 2009, 9, 304-325
4. L. F. Tietze, B. Krewer, Chem. Biol. Drug Des. 2009, 74, 205-2011
5. K. D. Bagshawe, Curr. Drug Targets 2009, 10, 152-157
6. F. Kratz, I. A. Müller, C. Ryppa, A. Warnecke, ChemMedChem 2008, 3, 20-53
7. K. D. Bagshawe, Expert Rev. Anticancer Ther. 2006, 6, 1421-1431
8. W. A. Denny, Cancer Invest. 2004, 22, 604-619
9. G. Xu, H. L. McLeod, Clin. Cancer Res. 2001, 7, 3314-3324.
10. L. F. Tietze, J. M. von Hof, M. Müller, B. Krewer, I. Schuberth, Angew. Chem. 2010, 122, 7494-7497
11. Angew. Chem. Int. Ed. 2010, 49, 7336-7339
12. L. F. Tietze, K. Schmuck, H. J. Schuster, M. Müller, I. Schuberth, Chem. Eur. J. 2011, 17, 1922-1929
13. L. F. Tietze, B. Krewer, H. Frauendorf, Eur. J. Mass Spectrom. 2009, 15, 661-672
14. L. F. Tietze, B. Krewer, H. Frauendorf, Anal. Bioanal. Chem. 2009, 395, 437-448
15. F. Alves, C. Dullin, J. Napp, J. Missbach-Guentner, K. Jannasch, J. Mathejczyk, L. A. Pardo, W. Stühmer, L. F. Tietze, Eur. J. Radiol. 2009, 70, 286-293.
16. T. Wirth, K. Schmuck, L. F. Tietze, S. A. Sieber, Angew. Chem. 2012, 124, 2928-2931
17. Angew. Chem. Int. Ed. 2012, 51, 2874-2877.
18. R. J. Stevenson, W. A. Denny, M. Tercel, F. B. Pruijn, A. Ashoorzadeh, J. Med. Chem. 2012, 55, 2780-2802
19. A. L. Wolfe, K. K. Duncan, N. K. Parelkar, S. J. Weir, G. A. Vielhauer, D. L. Boger, J. Med. Chem. 2012, 55, 5878-5886
20. M. Tercel, G. J. Atwell, S. Yang, A. Ashoorzadeh, R. J. Stevenson, K. J. Botting, Y. Gu, S. Mehta, W. A. Denny, W. R. Wilson, F. B. Pruijn, Angew. Chem. 2011, 123, 2654-2657
21. Angew. Chem. Int. Ed. 2011, 50, 2606-2609
22. J. P. Lajiness, W. M. Robertson, I. Dunwiddie, M. A. Broward, G. A. Vielhauer, S. J. Weir, D. L. Boger, J. Med. Chem. 2010, 53, 7731-7738
23. Y. Wang, H. Yuan, S. C. Wright, H. Wang, J. W. Larrick, Bioorg. Med. Chem. 2003, 11, 1569-1575.
24. T. Dougherty, B. W. Henderson, C. J. Gomer, G. Jori, D. Kessel, M. Korbelik, J. Moan, Q. Peng, J. Natl. Cancer Inst. 1998, 90, 889-905
25. K. Plaetzer, B. Krammer, J. Berlanda, F. Berr, T. Kiesslich, Lasers Med. Sci. 2009, 24, 259-268.
26. O. Bourdon, V. Mosqueira, Ph. Legrand, J. Blais, J. Photochem. Photobiol. B: Biol. 2000, 55, 164-171
27. C. J. Gomer, Photochem. Photobiol. 1991, 54, 1093-1107
28. E. Reddi, J. Photochem. Photobiol. B 1997, 37, 189-195
29. L. Morlet, V. Vonarx-Coinsmann, P. Lenz, M.-T. Foultier, L. Xavier de Brito, C. Stewart, T. Patrice, J. Photochem. Photobiol. B: Biol. 1995, 28, 25-32
30. L. Ma, J. Moan, K. Berg, Int. J. Cancer 1994, 57, 883-888.
31. N. J. Farrer, J. A. Woods, L. Salassa, Y. Zhao, K. S. Robinson, G. Clarkson, F. S. Mackay, P. J. Sadler, Angew. Chem. 2010, 122, 9089-9092
32. Angew. Chem. Int. Ed. 2010, 49, 8905-8908
33. R. Reinhard, B. F. Schmidt, J. Org. Chem. 1998, 63, 2434-2441. Further photoactivatable prodrugs
34. Y. Wei, Y. Yan, D. Pei, B. Gong, Bioorg. Med. Chem. Lett. 1998, 8, 2419-2422
35. D. V. Santi, C. J. McHenry, H. Somer, Biochemistry 1974, 13, 471
36. Z. Zhang, H. Hatta, T. Ito, S. Nishimoto, Org. Biomol. Chem. 2005, 3, 592-596
37. W. Lin, D. Peng, B. Wang, L. Long, C. Guo, J. Yuan, Eur. J. Org. Chem. 2008, 793-796
38. C. H. Self, S. Thompson, Nat. Med. 1996, 2, 817-819.
39. B. C. Wilson, Can. J. Gastroenterol. 2002, 393-396
40. M. Seshadri, D. A. Bellnier, L. A. Vaughan, J. A. Spernyak, R. Mazurchuk, T. H. Foster, B. W. Henderson, Clin. Cancer Res. 2008, 14, 2796-2805
41. K. H. Kim, J.-J. Park, Gut and Liver 2010, 4, 39-43.
42. G. Mayer, A. Heckel, Angew. Chem. 2006, 118, 5020-5042
43. Angew. Chem. Int. Ed. 2006, 45, 4900-4921.
44. K. Schaper, M. Etinski, T. Fleig, Photochem. Photobiol. 2009, 85, 1075-1081
45. F. Bley, K. Schaper, H. Görner, Photochem. Photobiol. 2008, 84, 162-171
46. T. Schmierer, F. Bley, K. Schaper, P. Gilch, Photochem. Photobiol. 2010, 86, 1247-1254.
47. J. W. Walker, H. Martin, F. R. Schmitt, R. J. Barsotti, Biochemistry 1993, 32, 1338-1345
48. W. A. Boyle, S. Muralidharan, G. M. Maher, J. M. Nerbonne, J. Photochem. Photobiol. B 1997, 41, 233-244
49. D. Gilbert, K. Funk, B. Dekowski, R. Lechler, S. Keller, F. Möhrlen, S. Frings, V. Hagen, ChemBioChem 2007, 8, 89-97.