Molecular design of a pyrrole-imidazole hairpin polyamides for effective DNA alkylation

Chemistry - A European Journal

Volumn 8, Issue 20, 2002, Pages 4781-4790

  Bando, Toshikazu ^a   Narita, Akihiko ^a   Saito, Isao ^b   Sugiyama, Hiroshi ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Antitumor agents; DNA cleavage; DNA recognition; Molecular recognition; Nucleic acid

Indexed keywords

ALKYLATION; DNA; ELECTROPHORESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS (CHEMICAL);

MOLECULAR DESIGN; VINYL-LINKER PAIRING;

POLYAMIDES;

ANTINEOPLASTIC AGENT; CYCLOPROPYLPYRROLOINDOLE; CYTOSINE; DNA; DNA FRAGMENT; DUOCARMYCIN A; GUANINE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; NUCLEIC ACID; NUCLEOTIDE; NYLON; OLIGONUCLEOTIDE; POLYAMIDE; PYRROLE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ALKYLATION; ARTICLE; BASE MISPAIRING; BASE PAIRING; CHEMICAL STRUCTURE; CHEMISTRY; CONCENTRATION RESPONSE; CONFORMATION; CONJUGATE; DENATURING GRADIENT GEL ELECTROPHORESIS; DNA ALKYLATION; DNA SEQUENCE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR GENETICS; MOLECULAR RECOGNITION; NUCLEOTIDE SEQUENCE; SYNTHESIS; TEMPERATURE;

ALKYLATION; BASE PAIRING; BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; DRUG DESIGN; IMIDAZOLES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; NYLONS; OLIGONUCLEOTIDES; PYRROLES; TEMPERATURE;

EID: 0037131501     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021018)8:20<4781::AID-CHEM4781>3.0.CO;2-J     Document Type: Article

References (35)

1. a) P. B. Dervan, Bioorg. Med. Chem. 2001, 9, 2215-2235; D. E. Wemmer, P. B. Dervan, Curr. Opin. Struct. Biol. 1997, 7, 355-361;
2. a) P. B. Dervan, Bioorg. Med. Chem. 2001, 9, 2215-2235; D. E. Wemmer, P. B. Dervan, Curr. Opin. Struct. Biol. 1997, 7, 355-361;
3. b) J. W. Trauger, E. E. Baird, P. B. Dervan, Nature 1996, 382, 559-561;
4. c) J. M. Turner. E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1997, 119, 7636-7644:
5. d) S. E. Swalley, E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1997, 119, 6953-6961;
6. e) S. E. Swalley, E. E. Baird, P. B. Dervan, Chem. Eur. J. 1997, 3, 1600-1607;
7. f) J. W. Trauger, E. E. Baird, P. B. Dervan, Angew. Chem. 1998, 110, 1489-1492; Angew. Chem. Int. Ed. 1998, 37, 1421-1423.
8. f) J. W. Trauger, E. E. Baird, P. B. Dervan, Angew. Chem. 1998, 110, 1489-1492; Angew. Chem. Int. Ed. 1998, 37, 1421-1423.
9. a) S. White, E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1997, 119, 8756-8765;
10. b) P. B. Dervan, R. W. Burli, Curr. Opin. Chem. Biol. 1999, 3, 688-693;
11. c) C. L. Kielkopf, E. E. Baird, P. B. Dervan, D. C. Rees, Nat. Struct. Biol. 1998, 5, 104-109.
12. a) C. L. Kielkopf, S. White, J. W. Szewczyk, J. M. Turner, E. E. Baird, P. B. Dervan, D. C. Rees, Science 1998, 282, 111-115;
13. b) S. White, J. W. Szewczyk, J. M. Turner, E. E. Baird, P. B. Dervan, Nature 1998, 391, 468-471.
14. a) J. W. Trauger, E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1998, 120, 3534-3535;
15. b) J. M. Turner, S. E. Swalley, E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1998, 120, 6219-6226;
16. c) R. E. Bremer, E. E. Baird, P. B. Dervan, Chem. Biol. 1998, 5, 119-133.
17. a) J. M. Gottesfeld, L. Neely, J. W. Trauger, E. E. Baird, P. B. Dervan, Nature 1997, 387, 202-205;
18. b) L. A. Dickinson, R. J. Gulizia, J. W. Trauger, E. E. Baird, D. E. Mosier, J. M. Gottesfeld, P. B. Dervan, Proc. Natl. Acad. Sci. USA 1998, 95, 12890-12895.
19. A. Y. Chang, P. B. Dervan, J. Am. Chem. Soc. 2000, 122, 4856-4864.
20. a) P. Wittung-Stafshede, Science 1998, 281, 657-658;
21. b) C. Denison, T. Kodadek, Chem. Biol. 1998, 5, R129-R145.
22. a) D. L. Boger, T. Ishizaki, H. Zarrinmayeh, J. Org. Chem. 1990, 55, 4499-4502;
23. b) D. L. Boger, J. A. McKie, T. Nishi, T. Ogiku, J. Am. Chem. Soc. 1997, 119, 311-325;
24. c) J. R. Schnell, R. R. Ketchem, D. L. Boger, W. J. Chazin, J. Am. Chem. Soc. 1999, 121, 5645-5652.
25. Z.-F. Tao, T. Fujiwara, I. Saito, H. Sugiyama, J. Am. Chem. Soc. 1999, 121, 4961-4967.
26. Z.-F. Tao, I. Saito, H. Sugiyama, J. Am. Chem. Soc. 2000, 122, 1602-1608.
27. T. Bando, H. Iida, I. Saito. H. Sugiyama, J. Am. Chem. Soc. 2001, 123, 5158-5159.
28. S. Nagamura, A. Asai, Y. Kanda, E. Kobayashi, K. Gomi, H. Saito, Chem. Pharm. Bull. 1996, 44, 1723-1730.
29. Z.-F. Tao, T. Fujiwara, I. Saito, H. Sugiyama, Angew. Chem. 1999, 111, 692-695; Angew. Chem. Int. Ed. 1999, 38, 650-652.
30. Z.-F. Tao, T. Fujiwara, I. Saito, H. Sugiyama, Angew. Chem. 1999, 111, 692-695; Angew. Chem. Int. Ed. 1999, 38, 650-652.
31. a) H. Sugiyama, M. Hosoda, I. Saito, A. Asai, H. Saito, Tetrahedron Lett. 1990, 31, 7197-7200;
32. b) H. Sugiyama, K. Ohmori, K. L. Chan, M. Hosoda, A. Asai, H. Saito, I. Saito, Tetrahedron Lett. 1993, 34, 2179-2182;
33. c) H. Sugiyama, T. Fujiwara, A. Ura, T. Tashiro, K. Yamamoto, S. Kawanishi, I. Saito, Chem. Res. Toxicol. 1994, 7, 673-683.
34. R. P. Lamamie de Clairac, B. H. Geierstanger, M. Mrksin, P. B. Dervan, D. E. Wemmer, J. Am. Chem. Soc. 1997, 119, 7909-7916.
35. H. Sugiyama, C. Lian, M. Isomura, I. Saito, A. H.-J. Wang, Proc. Natl. Acad. Sci. USA 1996, 93, 14405-14410.