Design, synthesis and in vitro cytotoxic studies of novel bis-pyrrolo[2,1][1,4] benzodiazepine-pyrrole and imidazole polyamide conjugates

European Journal of Medicinal Chemistry

Volumn 40, Issue 7, 2005, Pages 641-654

  Kumar, Rohtash ^a   Lown, J William ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Cytotoxicity; DNA minor groove binders; PBD polyamide conjugates; Polyamide; Pyrrolo 2,1 c 1,4 benzodiazepines

Indexed keywords

BENZODIAZEPINE DERIVATIVE; CARBENE; IMIDAZOLE DERIVATIVE; MERCURIC CHLORIDE; POLYAMIDE; PYRROLE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLIZATION; CYTOTOXICITY; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IN VITRO STUDY; MALE;

ANTINEOPLASTIC AGENTS; BENZODIAZEPINES; CELL LINE, TUMOR; CELL SURVIVAL; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; IMIDAZOLES; NYLONS; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 20444402278     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejmech.2005.02.005     Document Type: Article

References (43)

1. D. Henderson, and L.H. Hurley Nat. Med. 6 1995 525
2. L.H. Hurley J. Med. Chem. 32 1989 2027
3. B. Pullman, J. Jortner, Molecular Basis of Specificity in Nucleic Acid-Drug Interactions, 1990;
4. S. Neidle, M. Waring, Molecular Aspects of Anticancer Drug-DNA Interactions, vol. 1, 1993;
5. S. Neidle, M. Waring, Molecular Aspects of Anticancer Drug-DNA Interactions, vol. 2, 1994.
6. M.A. Warpehoski, and L.H. Hurley Chem. Res. Toxicol. 1 1988 315
7. L.H. Hurley, and F.L. Boyd Annu. Rep. Med. Chem. 22 1987 259
8. V.L. Reynolds, L.J. Molineux, D. Kaplan, D.H. Swenson, and L.H. Hurley Biochemistry 24 1985 6628
9. K.E. Rao, and J.W. Lown Chem. Res. Toxicol. 3 1990 262
10. F.E. Hahn Antibiotics III J.W. Corcoran F.E. Hahn Mechanism of Action of Antimicrobial and Antitumor Agents 1975 Springer-Verlag New York pp. 79
11. C. Zimmer, G. Luck, G. Burckhardt, K. Krowicki, and J.W. Lown Molecular Mechanism of Carcinogenic and Antitumor Activity C. Chagas B. Pullman 1986 Adenine Press New York 339 363 pp.
12. C. Zimmer, and U. Wahnert Prog. Biophys. Mol. Biol. 47 1986 31
13. L.H. Hurley, T. Reck, D.E. Thurston, D.R. Langley, K.G. Holden, and R.P. Hertzberg Chem. Res. Toxicol. 1 1988 258
14. S.M. Hecht Bleomycin, Chemical, Biochemical and Biological Aspects 1979 Springer-Valerag New York Ed
15. J. Stubbe, and J.W. Kozarich Chem. Rev. 87 1987 1007
16. D.E. Thurston Molecular Aspects of Anticancer Drug-DNA Interactions 1993 The Macmillan Press Ltd London, UK pp. 54-88
17. R.L. Petrusek, E.L. Uhlenhopp, N. Duteau, and L.H. Hurley J. Biol. Chem. 257 1982 6207
18. D.E. Thurston, and D.S. Bose Chem. Rev. 94 1994 433
19. M.L. Kopka, D.S. Goodsell, I. Baikalov, K. Grzeskowaik, D. Cascio, and R.E. Dickerson Biochemistry 33 1994 13593
20. A. Kamal, Y. Damayanthi, B.S.N. Reddy, B. Lakminarayana, and B.S.P. Reddy Chem. Commun. 1997 1015
21. A. Kamal, B.S.N. Reddy, and B.S.P. Reddy Biorg, Med. Chem. Lett. 7 1997 1825
22. (a) J.W. Lown, Synthesis of sequence-specific agents: lexitropsins, in: S. Neidle, M. Waring (Eds.), Molecular Aspects of Anticancer Drug-DNA Interactions, vol. 1, CRC Press, Boca Raton, 1993, pp. 322.
23. (b) P.B. Dervan, Science 232 (1986) 464;
24. (C) J.W. Trauger, E.E. Baird, P.B. Dervan, Angew. Chem. Int. Ed. Eng. 37 (1998) 1421;
25. (d) M. Mrksich, M.E. Parks, P.B. Dervan, J. Am. Chem. Soc. 116 (1994) 7983.
26. Y. Damayanthi, B.S.P. Reddy, and J.W. Lown J. Org. Chem. 64 1999 290
27. B.S.P. Reddy, Y. Damayanthi, B.S.N. Reddy, and J.W. Lown Anticancer Drug Des. 15 2000 225
28. R. Kumar, and J.W. Lown Oncol. Res. 13 4 2002 221
29. R. Kumar, B.S.N. Reddy, and J.W. Lown Heterocyclic Commun. 8 2002 19
30. R. Kumar, and J.W. Lown Org. Biomol. Chem. 1 19 2003 3327
31. S.J. Gregson, P.W. Howard, T.C. Jenkins, L.R. Kelland, and D.E. Thurston Chem. Commun. 1999 797
32. S.J. Gregson, P.W. Howard, J.A. Hartley, N.A. Brooks, L.J. Adams, and T.C. Jenkins J. Med. Chem. 44 2001 737
33. S.J. Gregson, P.W. Howard, K.E. Corcoran, T.C. Jenkins, L.R. Kelland, and D.E. Thurston Bioorg. Med. Chem. Lett. 11 2001 2859
34. N. Langlois, A.R. Rousseau, C. Gaspard, G.H. Werner, F. Darro, and R. Kiss J. Med. Chem. 44 2001 3754
35. J.D. Farmer, S.M. Rudnicki, and J.W. Suggs Tetrahedron Lett. 29 1988 5105
36. J.D. Farmer, G.R. Gustafson, A. Conti, M.B. Zimmt, and J.W. Suggs Nucleic Acids Res. 19 1991 899
37. D.S. Bose, A.S. Thompson, J.S. Ching, J.A. Hartley, M.D. Berardini, and T.C. Jenkins J. Am. Chem. Soc. 114 1992 4939
38. D.S. Bose, A.S. Thompson, M. Smellie, M.D. Berardini, J.A. Hartley, and T.C. Jenkins Chem. Commun. 1992 1518
39. D.E. Thurston, D.S. Bose, A.S. Thompson, P.W. Howard, A. Leoni, S.J. Croker, T.C. Jenkins, S. Neidle, J.A. Hartley, and L.H. Hurley J. Org. Chem. 61 1996 8141
40. T.C. Jenkins, L.H. Hurley, S. Neidle, and D.E. Thurston J. Med. Chem. 37 1994 4529
41. B.S.P. Reddy, Y. Damayanthi, and J.W. Lown Synlett 14 1999 1112
42. R. Kumar, and J.W. Lown Org. Biomol. Chem. 1 2003 2630
43. R. Kumar, D. Rai, and J.W. Lown Oncol. Res. 14 4-5 2003 247