Water-soluble 2-amino-1,8-naphthyridine as a novel DNA binding photosensitizer for one-electron oxidation of DNA

Tetrahedron Letters

Volumn 40, Issue 33, 1999, Pages 6029-6032

  Nakatani, Kazuhiko ^a   Sando, Shinsuke ^a   Yoshida, Kohzo ^a   Saito, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; NAPHTHYRIDINE DERIVATIVE; PHOTOSENSITIZING AGENT;

ARTICLE; DNA BINDING; DNA CLEAVAGE; DRUG STRUCTURE; OXIDATION; POLYACRYLAMIDE GEL ELECTROPHORESIS;

EID: 0033551754     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01189-2     Document Type: Article

References (22)

1. (a) Gottesfeld, J. M.; Neely, L.; Trauger, J. W.; Baird, E. E.; Dervan, P. B. Nature 1997, 387, 202- 205.
2. (b) Trauger, J. W.; Baird, E. E.; Dervan, P. B. J. Am. Chem. Soc. 1998, 120, 3534-3535.
3. Hurley, L. H.; Draves, P. H. In Molecular Aspects of Anticancer Drug-DNA Interactions: Neidel, S.; Waring, M., Eds.; CRC: Ann Arbor, MI, 1993; Vol. 1, p 89.
4. (a) Nakatani, K.; Okamoto, A.; Saito, I. Angew. Chem. Int. Ed. Engl. 1997, 36, 2794-2797.
5. (b) Nakatani, K.; Okamoto, A.; Matsuno, T.; Saito, I. J. Am. Chem. Soc. 1998, 120, 11219-11225.
6. Nakatani, K.; Shirai, J.; Sando, S.; Saito, I. J. Am. Chem. Soc. 1997, 119, 7626-7635.
7. (a) Nakatani, K.; Dohno, C.; Nakamura, T.; Saito, I. Tetrahedron Lett. 1998, 39, 2779-2782.
8. (b) Nakatani, K.; Fujisawa, K.; Dohno, C.; Nakamura, T.; Saito, I. Tetrahedron Lett. 1998, 39, 5995- 5998.
9. For a recent review on one-electron oxidation, see: Burrows, C. J.; Muller, J. G. Chem. Revs. 1998, 98, 1109-1154.
10. Brown, E. V. J. Org. Chem. 1965, 30, 1607-1610.
11. +] 217.1089, found 217.1087.
12. For recent reports for small molecule-DNA interactions using BIAcore technique, see: (a) Hendrix, M.; Scott Priestley, E.; Joyce, G. F.; Wong, C-H. J. Am. Chem. Soc. 1997, 119, 3641-3648.
13. (b) Alper, P. B.; Hendrix, M.; Sears, P.; Wong, C-H. J. Am. Chem. Soc. 1998, 120, 1965-1978.
14. l-1 where r is the ratio of bound concentration of 1 to the concentration of DNA phosphate; c is the concentration of 1 free in solution; K is the association constant; l is the neighbor exclusion value.
15. McGhee, J. D.; Von Hippel, P. H. J. Mol. Biol. 1974, 86, 469-489.
16. (a) Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1996, 118, 7063-7068.
17. (b) Saito, I.; Nakamura, T.; Nakatani, K.; Yoshioka, Y.; Yamaguchi, K.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 12686- 12687.
18. (a) Cadet, J.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Raoul, S.; Ravanat, J. -L. J. Am. Chem. Soc. 1994, 116, 7403-7404.
19. (b) Raoul, S.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Morin, B.; Weifeid, M.; Cadet, J. J. Chem. Soc. Perkin Trans. 2 1996, 371-381.
20. (c) Cullis, P. M.; Malone, M. E.; Merson-Davia, L. A. J. Am. Chem. Soc. 1996, 118, 2775-2781.
21. 15
22. Kino, K.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 7373-7374.