The effect of a bromide leaving group on the properties of nitro analogs of the duocarmycins as hypoxia-activated prodrugs and phosphate pre-prodrugs for antitumor therapy

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 20, 2011, Pages 5989-5998

  Stevenson, Ralph J ^a   Denny, William A ^a   Ashoorzadeh, Amir ^a   Pruijn, Frederik B ^a   Van Leeuwen, Wouter F ^a   Tercel, Moana ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Antitumor; Basic side chain; Bromide leaving group; DNA minor groove alkylating agent; Duocarmycins; Hypoxic selectivity; Phosphate pre prodrug; Prodrug

Indexed keywords

1 (BROMOMETHYL) 3 (2,2,2 TRIFLUOROACETYL) 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONYL CHLORIDE; 1 (BROMOMETHYL) 5 NITRO 3 (2,2,2 TRIFLUOROACETYL) 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONYL CHLORIDE; 1 (BROMOMETHYL) 9 NITRO 3 (2,2,2 TRIFLUOROACETYL) 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONYL CHLORIDE; 1 (BROMOMETHYL) N (2 HYDROXYETHYL) 3 [3 (4 METHOXYPHENYL)ACRYLOYL] 5 NITRO 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMINDE; 1 (BROMOMETHYL) N (2 HYDROXYETHYL) 3 [3 [4 (2 MORPHOLINOETHOXY)PHENYL]ACRYLOYL] 5 NITRO 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMINDE; 1 (BROMOMETHYL) N (2 HYDROXYETHYL) 3 [5 (2 MORPHOLINOETHOXY) 1H INDOLE 2 CARBONYL] 5 NITRO 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMINDE; 1 (BROMOMETHYL) N (2 HYDROXYETHYL) 5 NITRO 2 3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMIDE; 1 (BROMOMETHYL) N (2 HYDROXYETHYL) 5 NITRO 3 (5,6,7 TRIMETHOXY 1H INDOLE 2 CARBONYL) 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMIDE; 1 [1 (BROMOMETHYL) 1H BENZO[E]INDOL 3(2H) YL] 2,2,2 TRIFLUOROETHANONE; 2 [1 (BROMOMETHYL) 3 [3 (4 METHOXYPHENYL)ACRYLOYL] 5 NITRO 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMIDO]ETHYL DIHYDROGEN PHOSPHATE; 2 [1 (BROMOMETHYL) 3 [3 [4 (2 MORPHOLINOETHOXY)PHENYL]ACRYLOYL] 5 NITRO 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMIDO]ETHYL DIHYDROGEN PHOSPHATE TRIFLUOROACETATE; 2 [1 (BROMOMETHYL) 3 [5 (2 MORPHOLINOETHOXY) 1H INDOLE 2 CARBONYL] 5 NITRO 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMIDO]ETHYL DIHYDROGEN PHOSPHATE TRIFLUOROACETATE; 2 [1 (BROMOMETHYL) 5 NITRO 3 (5,6,7 TRIMETHOXY 1H INDOLE 2 CARBONYL) 2,3 DIHYDRO 1H BENZO[E]INDOLE 7 SULFONAMIDO]ETHYL DIHYDROGEN PHOSPHATE; 7 SULFONAMIDE; BROMIDE; DUOCARMYCIN DERIVATIVE; DUOCARMYCIN SA; NITRO DERIVATIVE; NITRO SECO 1,2,9,9A TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL 4 ONE; PHOSPHATE; PRODRUG; UNCLASSIFIED DRUG;

ACUTE TOXICITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER THERAPY; CELL KILLING; CELL STRAIN HT29; CONTROLLED STUDY; DNA BINDING; DRUG CYTOTOXICITY; DRUG MEGADOSE; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYPOXIA; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; TUMOR XENOGRAFT;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; ANTINEOPLASTIC AGENTS, ALKYLATING; BROMIDES; CELL HYPOXIA; FEMALE; HUMANS; INDOLES; MALE; MICE; MICE, NUDE; PHOSPHATES; PRODRUGS; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP; UTERINE CERVICAL NEOPLASMS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 80053288064     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.08.045     Document Type: Article

References (38)

1. W.R. Wilson, S.M. Stribbling, F.B. Pruijn, S.P. Syddall, A.V. Patterson, H.D.S. Liyanage, E. Smith, K.J. Botting, and M. Tercel Mol. Cancer Ther. 8 2009 2903
2. M. Tercel, G.J. Atwell, S. Yang, R.J. Stevenson, K.J. Botting, M. Boyd, E. Smith, R.F. Anderson, W.A. Denny, W.R. Wilson, and F.B. Pruijn J. Med. Chem. 52 2009 7258
3. M. Tercel, S. Yang, G.J. Atwell, E. Smith, Y. Gu, R.F. Anderson, W.A. Denny, W.R. Wilson, and F.B. Pruijn Bioorg. Med. Chem. 18 2010 4997
4. M. Tercel, G.J. Atwell, S. Yang, A. Ashoorzadeh, R.J. Stevenson, K.J. Botting, Y. Gu, S.Y. Mehta, W.A. Denny, W.R. Wilson, and F.B. Pruijn Angew. Chem., Int. Ed. 50 2011 2606
5. A. Ashoorzadeh, G.J. Atwell, F.B. Pruijn, W.R. Wilson, M. Tercel, W.A. Denny, and R.J. Stevenson Bioorg. Med. Chem. 19 2011 4851
6. Tercel, M.; Lee, H. H.; Yang, S.; Liyanage, H. D. S.; Mehta, S. Y.; Boyd, P. D. W.; Jaiswal, J. K.; Tan, K. L.; Pruijn, F. B. Chem. Med. Chem. 2011, in press. 10.2/cmdc.200.
7. J.A. Bertout, S.A. Patel, and M.C. Simon Nat. Rev. Cancer 8 2008 967
8. S.R. McKeown, R.L. Cowen, and K.J. Williams J. Clin. Oncol. 19 2007 427
9. Y. Chen, and L. Hu Med. Res. Rev. 29 2009 29
10. W.R. Wilson, and M.P. Hay Nat. Rev. Cancer 11 2011 393
11. M. Ichimura, T. Ogawa, K. Takahashi, E. Kobayashi, I. Kawamoto, T. Yasuzawa, I. Takahashi, and H. Nakano J. Antibiot. 43 1990 1037
12. D.L. Boger, and D.S. Johnson Angew. Chem., Int. Ed. 35 1996 1438
13. N. Pavlidis, S. Aamdal, A. Awada, H. Calvert, P. Fumoleau, R. Sorio, C. Punt, J. Verwij, A. van Oosterom, R. Morant, J. Wanders, and A.R. Hanauske Cancer Chemother. Pharmacol. 46 2000 167
14. S.N. Markovic, V.J. Suman, A.M. Vukov, T.R. Fitch, D.W. Hillman, A.A. Adjei, S.R. Alberts, J.S. Kaur, T.A. Braich, J.M. Leitch, and E.T. Creagan Am. J. Clin. Oncol. 25 2002 308
15. L.F. Tietze, T. Feuerstein, A. Fecher, F. Haunert, O. Panknin, U. Borchers, I. Schuberth, and F. Alves Angew. Chem., Int. Ed. 41 2002 759
16. L.F. Tietze, F. Major, and I. Schuberth Angew. Chem., Int. Ed. 45 2006 6574
17. D.L. Boger, and R.M. Garbaccio J. Org. Chem. 64 1999 8350
18. H. Townes, K. Summerville, B. Purnell, M. Hooker, E. Madsen, S. Hudson, and M. Lee Med. Chem. Res. 11 2002 248
19. J. Wei, J.D. Trzupek, T.J. Rayl, M.A. Broward, G.A. Vielhauer, S.J. Weir, I. Hwang, and D.L. Boger J. Am. Chem. Soc. 129 2007 15391
20. J.B.J. Milbank, R.J. Stevenson, D.C. Ware, J.Y.C. Chang, M. Tercel, G.-O. Ahn, W.R. Wilson, and W.A. Denny J. Med. Chem. 52 2009 6822
21. G.-L. Lu, R.J. Stevenson, J.Y.C. Chang, P.A. Brothers, D.C. Ware, W.R. Wilson, W.A. Denny, and M. Tercel Bioorg. Med. Chem. 19 2011 4861
22. L. Ducry, and B. Stump Bioconjug. Chem. 21 2010 5
23. G.J. Atwell, M. Tercel, M. Boyd, W.R. Wilson, and W.A. Denny J. Org. Chem. 63 1998 9414
24. M.A. Gieseg, J. Matejovic, and W.A. Denny Anti-Cancer Drug Des. 14 1999 77
25. Q.-T.X. Le, J. Moon, M. Redman, S.K. Williamson, P.N. Lara Jr., Z. Goldberg, L.E. Gaspar, J.J. Crowley, D.F. Moore Jr., and D.R. Gandara J. Clin. Oncol. 27 2009 3014
26. M.B. Jameson, D. Rischin, M. Pegram, J. Gutheil, A.V. Patterson, W.A. Denny, and W.R. Wilson Cancer Chemother. Pharmacol. 65 2010 791
27. T. Ogawa, M. Ichimura, S. Katsumata, M. Morimoto, and K. Takahashi J. Antibiot. 42 1989 1299
28. S. Nagamura, Y. Kanda, E. Kobayashi, K. Gomi, and H. Saito Chem. Pharm. Bull. 43 1995 1530
29. S. Nagamura, E. Kobayashi, K. Gomi, and H. Saito Bioorg. Med. Chem. 4 1996 1379
30. S. Nagamura, A. Asai, Y. Kanda, E. Kobayashi, K. Gomi, and H. Saito Chem. Pharm. Bull. 44 1996 1723
31. S. Nagamura, A. Asai, N. Amishiro, E. Kobayashi, K. Gomi, and H. Saito J. Med. Chem. 40 1997 972
32. N. Amishiro, S. Nagamura, E. Kobayashi, K. Gomi, and H. Saito J. Med. Chem. 42 1999 669
33. N. Amishiro, S. Nagamura, E. Kobayashi, A. Okamoto, K. Gomi, and H. Saito Chem. Pharm. Bull. 47 1999 1393
34. A. Asai, S. Nagamura, E. Kobayashi, K. Gomi, and H. Saito Bioorg. Med. Chem. Lett. 9 1999 2995
35. N. Amishiro, S. Nagamura, E. Kobayashi, A. Okamoto, K. Gomi, M. Okabe, and H. Saito Bioorg. Med. Chem. 8 2000 1637
36. Szekely, Z; McDonnell, M. G. PCT US Appl. 2009, US 20090118349A1.
37. Tercel, M.; Pruijn, F. B.; Stevenson, R. J.; Yang, S.; Lee, H. H.; Youte, J. J. T. PCT Int. Appl. 2010, WO 2010027280A1.
38. L.F. Tietze, and F. Major Eur. J. Org. Chem. 2006 2314