Comparative analysis of DNA alkylation by conjugates between pyrrole-imidazole hairpin polyamides and chlorambucil or seco-CBI

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 3, 2010, Pages 1236-1243

  Minoshima, Masafumi ^a   Bando, Toshikazu ^a   Shinohara, Ken ichi ^a   Kashiwazaki, Gengo ^a   Nishijima, Shigeki ^a   Sugiyama, Hiroshi ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Alkylating agent; Antitumor agent; DNA alkylation; Minor groove binder; Pyrrole imidazole polyamide

Indexed keywords

1 METHYLIMIDAZOLE; 1 METHYLPYRROLE; CHLORAMBUCIL; IMIDAZOLE; INDOLE DERIVATIVE; POLYAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; CYTOTOXICITY; DNA ALKYLATION; DNA SEQUENCE; DRUG STRUCTURE; GEOMETRY; HUMAN; HUMAN CELL; POLYACRYLAMIDE GEL ELECTROPHORESIS;

ANTINEOPLASTIC AGENTS, ALKYLATING; CELL LINE, TUMOR; CELL SURVIVAL; CHLORAMBUCIL; DNA; HUMANS; IMIDAZOLES; LYMPHOCYTES; MOLECULAR STRUCTURE; NEOPLASMS; NYLONS; PYRROLES;

EID: 75149139919     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.12.033     Document Type: Article

References (45)

1. Hurley L.H. Nat. Rev. Cancer 2 (2002) 188
2. Rajski S.R., and Williams R.M. Chem. Rev. 98 (1998) 2723
3. Baker B.F., and Dervan P.B. J. Am. Chem. Soc. 107 (1985) 8266
4. Broggini M., Erba E., Ponti M., Ballinari D., Ceroni C., Spreafico F., and D'Incaici M. Cancer Res. 51 (1991) 199
5. Broggini M., Coley H.M., Mongelli N., Pesenti E., Wyatt M.D., Hartley J.A., and D'Incaici M. Nucleic Acids Res. 23 (1995) 81
6. Hurley L.H., Lee C.-S., McGovren J.P., Warpehoski M.A., Mitchell M.A., Kelly R.C., and Aristoff P.A. Biochemistry 27 (1988) 3886
7. Yasuzawa T., Muroi K., Ichimura M., Takahashi I., Ogawa T., Takahashi K., Sano H., and Saitoh Y. Chem. Pharm. Bull. 43 (1995) 378
8. For recent review, see:. Dervan P.B., Poulin-Kerstien A.T., Fechter E.J., and Edelson B.S. Top. Curr. Chem. 253 (2005) 1
9. Dervan P.B., and Edelson B.S. Curr. Opin. Struct. Biol. 13 (2003) 284
10. Gottesfeld J.M., Neely L., Trauger J.W., Baird E.E., and Dervan P.B. Nature 387 (1997) 202
11. Olenyuk B.Z., Zhang G.-J., Klco J.M., Nickols N.G., Kaelin Jr. W.G., and Dervan P.B. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 16768
12. Nickols N.G., and Dervan P.B. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 10418
13. For recent review, see:. Bando T., and Sugiyama H. Acc. Chem. Res. 39 (2006) 935
14. Boger D.L., and Johnson D.S. Angew. Chem., Int. Ed. 35 (1996) 1438
15. Boger D.L., and Munk S.A. J. Am. Chem. Soc. 114 (1992) 5487
16. Bando T., Iida H., Tao Z.-F., Narita A., Fukuda N., Yamori T., and Sugiyama H. Chem. Biol. 10 (2003) 751
17. Bando T., Sasaki S., Minoshima M., Shinohara K., Dohno C., Narita A., and Sugiyama H. Bioconjugate Chem. 17 (2006) 715
18. Minoshima M., Bando T., Sasaki S., Shinohara K., Shimizu T., Fujimoto J., and Sugiyama H. J. Am. Chem. Soc. 129 (2007) 5384
19. Sasaki S., Bando T., Minoshima M., Shinohara K., and Sugiyama H. Chem. Eur. J. 18 (2008) 864
20. Oyoshi T., Kawakami W., Narita A., Bando T., and Sugiyama H. J. Am. Chem. Soc. 125 (2003) 4752
21. Shinohara K., Narita A., Oyoshi T., Bando T., Teraoka H., and Sugiyama H. J. Am. Chem. Soc. 126 (2004) 5113
22. Shinohara K., Sasaki S., Minoshima M., Bando T., and Sugiyama H. Nucleic Acids Res. 34 (2006) 1189
23. Dickinson L.A., Burnett R., Melander C., Edelson B.S., Arora P.S., Dervan P.B., and Gottesfeld J.M. Chem. Biol. 11 (2004) 1583
24. Alvarez D., Chou C.J., Latella L., Zeitlin S.G., Ku S., Puri P.L., Dervan P.B., and Gottesfeld J.M. Cell Cycle 5 (2006) 1537
25. Chou C.J., Farkas M.E., Tsai S.M., Alvarez D., Dervan P.B., and Gottesfeld J.M. Mol. Cancer Ther. 7 (2008) 769
26. Chou C.J., O'Hare T., Lefebvre S., Alvarez D., Tyner J.W., Eide C.A., Druker B.J., and Gottesfeld J.M. PLoS ONE 3 (2008) e3593
27. Tsai S.M., Farkas M.E., Chou C.J., Gottesfeld J.M., and Dervan P.B. Nucleic Acids Res. 35 (2007) 307
28. Baird E.E., and Dervan P.B. J. Am. Chem. Soc. 118 (1996) 6141
29. Wurtz N.R., Turner J.M., Baird E.E., and Dervan P.B. Org. Lett. 3 (2001) 1201
30. Belitsky J.M., Nguyen D.H., Wurtz N.R., and Dervan P.B. Bioorg. Med. Chem. 10 (2002) 2767
31. Sasaki S., Bando T., Minoshima M., Shimizu T., Shinohara K., Takaoka T., and Sugiyama H. J. Am. Chem. Soc. 128 (2006) 12162
32. Bando T., Narita A., Saito I., and Sugiyama H. Chem. Eur. J. 8 (2002) 4781
33. Bando T., Narita A., Saito I., and Sugiyama H. J. Am. Chem. Soc. 125 (2003) 3471
34. Bando T., Narita A., Asada K., Ayame H., and Sugiyama H. J. Am. Chem. Soc. 126 (2004) 8948
35. Bando T., Narita A., Sasaki S., and Sugiyama H. J. Am. Chem. Soc. 127 (2005) 13890
36. Farkas M.E., Tsai S.M., and Dervan P.B. Bioorg. Med. Chem. 15 (2007) 6927
37. Chang A.Y., and Dervan P.B. J. Am. Chem. Soc. 122 (2000) 4856
38. Wurtz N.R., and Dervan P.B. Chem. Biol. 7 (2000) 153
39. Wang Y.-D., Dziegielewski J., Wurtz N.R., Dziegielewska B., Dervan P.B., and Beerman T.A. Nucleic Acids Res. 31 (2003) 1208
40. Bosanquet A.G. Cancer Chemother. Pharmacol. 14 (1985) 83
41. Giraud I., Rapp M., Maurizis J.-C., and Madelmont J.-C. J. Med. Chem. 45 (2002) 2116
42. Edelson B.S., Best T.P., Olenyuk N.G., Nickols N.G., Doss R.M., Foister S., Heckel A., and Dervan P.B. Nucleic Acids Res. 32 (2004) 2802
43. Brooks N., McHugh P.J., Lee M., and Hartley J.A. Chem. Biol. 7 (2000) 659
44. Bando T., Narita A., Iwai A., Kihara K., and Sugiyama H. J. Am. Chem. Soc. 126 (2004) 3406
45. Shinohara K., Bando T., Sasaki S., Sakakibara Y., Minoshima M., and Sugiyama H. Cancer Sci. 97 (2006) 219