The effect of sulfonate leaving groups on the hypoxia-selective toxicity of nitro analogs of the duocarmycins

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 16, 2011, Pages 4851-4860

  Ashoorzadeh, Amir ^a   Atwell, Graham J ^a   Pruijn, Frederik B ^a   Wilson, William R ^a   Tercel, Moana ^a   Denny, William A ^a   Stevenson, Ralph J ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Antitumor; Cyclopropylindoline; DNA minor groove alkylator; Hypoxic selectivity; Neutral side chain; Prodrug; Sulfonate leaving group

Indexed keywords

1[1 (CHLOROMETHYL) 5 NITRO 1H BENZOL[E]INDOL 3(2H) YL] 3 (3 HYDROXY 4 METHOXYPHENYL)PROP 2 EN 1 ONE; [1 (CHLOROMETHYL) 5 AMINO 1H BENZOL[E]INDOL 3(2H) YL][5 (2 HYDROXYETHOXY) 1H INDOL 2 YL]METHANONE; [1 (CHLOROMETHYL) 5 NITRO 1H BENZOL[E]INDOL 3(2H) YL][5 (2 HYDROXYETHOXY) 1H INDOL 2 YL]METHANONE; [3 (5 METHOXY 1H INDOLE 2 CARBONYL) 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL 4 METHYLBENZENESULFONATE; [3 [3 (3 HYDROXY 4 METHOXYPHENYL)ACRYLOYL] 5 NITRO 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL PHENYLMETHANESULFONATE; [3 [5 (2 HYDROXYETHOXY) 1H INDOLE 2 CARBONYL] 5 NITRO 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL 4 METHYLBENZENESULFONATE; [3 [5 (2 HYDROXYETHOXY) 1H INDOLE 2 CARBONYL] 5 NITRO 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL PHENYLMETHANESULFONATE; [3 [5 [2 (DIMETHYLAMINO)ETHOXY] 1H INDOLE 2 CARBONYL] 5 NITRO 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL CYCLOHEXANESULFONATE; [3 [5 [2 (DIMETHYLAMINO)ETHOXY] 1H INDOLE 2 CARBONYL] 5 NITRO 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL PHENYLMETHANESULFONATE; [5 AMINO 3 (5,6,7 TRIMETHOXY 1H INDOLE 2 CARBONYL) 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL CYCLOHEXANESULFONATE; [5 AMINO 3 (5,6,7 TRIMETHOXY 1H INDOLE 2 CARBONYL) 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL PHENYLMETHANESULFONATE; [5 NITRO 3 (5,6,7 TRIMETHOXY 1H INDOLE 2 CARBONYL) 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL 4 METHYLBENZENESULFONATE; [5 NITRO 3 (5,6,7 TRIMETHOXY 1H INDOLE 2 CARBONYL) 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL CYCLOHEXANESULFONATE; [5 NITRO 3 (5,6,7 TRIMETHOXY 1H INDOLE 2 CARBONYL) 2,3 DIHYDRO 1H BENZ[E]INDOL 1 YL]METHYL PHENYLMETHANESULFONATE; ALKYLATING AGENT; ANTINEOPLASTIC AGENT; DUOCARMYCIN SA; NITRO DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL HYPOXIA; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; NONHUMAN; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ACTIVITY RELATION;

ALKANESULFONATES; ANTINEOPLASTIC AGENTS, ALKYLATING; CELL HYPOXIA; DNA; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; INDOLES; NITRO COMPOUNDS; PRODRUGS; PYRROLIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 79961170149     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.073     Document Type: Article

References (24)

1. D.L. Boger, and D.S. Johnson Angew. Chem., Int. Ed. 35 1996 1438
2. T. Yasuzawa, Y. Saitoh, M. Ichimura, I. Takahashi, and H. Sano J. Antibiot. 44 1991 445
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. D.L. Boger, T. Ishizaki, P.A. Kitos, and O. Suntornwat J. Org. Chem. 55 1990 5823
5. 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
6. H. Townes, K. Summerville, B. Purnell, M. Hooker, E. Madsen, S. Hudson, and M. Lee Med. Chem. Res. 11 2002 248
7. 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
8. 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
9. 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
10. G.J. Atwell, M. Tercel, M. Boyd, W.R. Wilson, and W.A. Denny J. Org. Chem. 63 1998 9414
11. M. Tercel, M.A. Gieseg, J.B. Milbank, M. Boyd, J.Y. Fan, L.K. Tan, W.R. Wilson, and W.A. Denny Chem. Res. Toxicol. 12 1999 700
12. G.J. Atwell, W.R. Wilson, and W.A. Denny Bioorg. Med. Chem. Lett. 7 1997 1493
13. W.R. Wilson, and M.P. Hay Nat. Rev. Cancer 11 2011 393
14. Y. Chen, and L. Hu Med. Res. Rev. 29 2009 29
15. G.J. Atwell, J.B.J. Milbank, W.R. Wilson, A. Hogg, and W.A. Denny J. Med. Chem. 42 1999 3400
16. A. Panthananickal, C. Hansch, and A. Leo J. Med. Chem. 21 1978 16
17. P. Jaramillo, L.R. Domingo, and P. Perez Chem. Phys. Lett. 420 2006 95
18. D.Y. Pacheco, N.K. Stratton, and N.W. Gibson Cancer Res. 49 1989 5108
19. L.F. Tietze, and B. Birgit Krewer Anti-Cancer Agents Med. Chem. 9 2009 304
20. Denny, W. A.; Wilson, W. R.; Stevenson, R. J.; Tercel, M.; Atwell, G. J.; Yang, S.; Patterson, A. V.; Pruijn, F. B. PCT Int. Appl. WO 2006043839A1, 2006.
21. J.B.J. Milbank, M. Tercel, G.J. Atwell, W.R. Wilson, A. Hogg, and W.A. Denny J. Med. Chem. 42 1999 649
22. G.-O. Ahn, K.J. Botting, A.V. Patterson, D.C. Ware, M. Tercel, and W.R. Wilson Biochem. Pharmacol. 71 2006 1683
23. Su, J.; Wang, J.; Wilson, W. A. Personal communication.
24. M.P. Hay, S.A. Gamage, M.S. Kovacs, F.B. Pruijn, R.F. Anderson, A.V. Patterson, W.R. Wilson, J.M. Brown, and W.A. Denny J. Med. Chem. 46 2003 169