Hypoxic selectivity and solubility - Investigating the properties of A-ring substituted nitro seco-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-ones (nitroCBIs) as hypoxia-activated prodrugs for antitumor therapy

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 14, 2010, Pages 4997-5006

  Tercel, Moana ^a   Yang, Shangjin ^a   Atwell, Graham J ^a   Smith, Eileen ^a   Gu, Yongchuan ^a   Anderson, Robert F ^a,b   Denny, William A ^a   Wilson, William R ^a   Pruijn, Frederik B ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Anticancer agent; DNA alkylating agent; Duocarmycin; Hypoxia; Prodrug

Indexed keywords

1 (CHLOROMETHYL 3 [5 [2 (DIMETHYLAMINO)ETHOXY]INDOL 2 CARBONYL] N [2 (DIMETHYLAMINO)ETHYL] 5 NITRO 1,2 DIHYDRO 3H BENZO[E]INDOLE 7 SULFONAMIDE; ANTINEOPLASTIC AGENT; CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; NITRO DERIVATIVE; NITRO SECO 1,2,9,9A TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL 4 ONE; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CELL HYPOXIA; DRUG BLOOD LEVEL; DRUG CYTOTOXICITY; DRUG METABOLISM; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SOLUBILITY; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; MALE; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; TUMOR CELL;

ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; CELL HYPOXIA; CELL LINE, TUMOR; CELL SURVIVAL; CYCLOPROPANES; DNA; HUMANS; INDOLES; MICE; NEOPLASMS; PRODRUGS; SOLUBILITY;

EID: 77955320882     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.06.001     Document Type: Article

References (18)

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. J.M. Brown, and W.R. Wilson Nat. Rev. Cancer 4 2004 437
3. S.R. McKeown, R.L. Cowen, and K.J. Williams Clin. Oncol. 19 2007 427
4. Y. Chen, and L. Hu Med. Res. Rev. 29 2009 29
5. 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
6. 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
7. J.-X. Duan, H. Jiao, J. Kaizerman, T. Stanton, J.W. Evans, L. Lan, G. Lorente, M. Banica, D. Jung, J. Wang, H. Ma, X. Li, Z. Yang, R.M. Hoffman, W.S. Ammons, C.P. Hart, and M. Matteucci J. Med. Chem. 51 2008 2412
8. M.R. Albertella, P.M. Loadman, P.H. Jones, R.M. Phillips, R. Rampling, N. Burnet, C. Alcock, A. Anthoney, E. Vjaters, C.R. Dunk, P.A. Harris, A. Wong, A.S. Lalani, and C.J. Twelves Clin. Cancer Res. 14 2008 1096
9. G.J. Atwell, M. Tercel, M. Boyd, W.R. Wilson, and W.A. Denny J. Org. Chem. 63 1998 9414
10. M.A. Gieseg, J. Matejovic, and W.A. Denny Anti-Cancer Drug Des. 14 1999 77
11. D.L. Boger, and D.S. Johnson Angew. Chem., Int. Ed. 35 1996 1438
12. M. Searcey Curr. Pharm. Des. 8 2002 1375
13. 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
14. J.J. Talley, S.R. Bertenshaw, D.L. Brown, J.S. Carter, M.J. Graneto, M.S. Kellogg, C.M. Koboldt, J. Yuan, Y.Y. Zhang, and K. Seibert J. Med. Chem. 43 2000 1661
15. R.N.V.S. Mamidi, R. Mullangi, J. Kota, R. Bhamidipati, A.A. Khan, K. Katneni, S. Datla, S.K. Singh, K.Y. Rao, C.S. Rao, N.R. Srinivas, and R. Rajagopalan Biopharm. Drug Dispos. 23 2002 273
16. J.B. Milbank, M. Tercel, G.J. Atwell, W.R. Wilson, A. Hogg, and W.A. Denny J. Med. Chem. 42 1999 649
17. 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
18. M.P. Hay, K.O. Hicks, F.B. Pruijn, K. Pchalek, B.G. Siim, W.R. Wilson, and W.A. Denny J. Med. Chem. 50 2007 6392