A Nucleobase that Releases Reporter Tags upon DNA Oxidation

Journal of the American Chemical Society

Volumn 126, Issue 2, 2004, Pages 416-417

  Okamoto, Akimitsu ^a   Tanaka, Kazuo ^a   Saito, Isao ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

DNA; DOUBLE STRANDED DNA; ETHYLENEDIAMINE; NUCLEIC ACID BASE;

ARTICLE; BIOSENSOR; DEGRADATION; DNA PROBE; DRUG RELEASE; FLUORESCENCE; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; OXIDATION; REPORTER GENE; STOICHIOMETRY; TRANSPORT KINETICS;

BIOSENSING TECHNIQUES; DNA; DNA PROBES; ETHYLENEDIAMINES; FLUORESCENCE; GUANINE; NUCLEOSIDES; OLIGONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION; SPECTROMETRY, FLUORESCENCE;

EID: 0347087291     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038169a     Document Type: Article

References (34)

1. (a) Tyagi, S.; Kramer, F. R. Nat. Biotechnol. 1996, 14, 303-308.
2. (b) Tyagi, S.; Btaru, D. P.; Kramer, F. R. Nat. Biotechnol. 1998, 16, 49-53.
3. (c) Piatek, A. S.; Tyagi, S.; Pol, A. C.; Telenti, A.; Miller, L. P.; Kramer, F. R.; Alland, D. Nat. Biotechnol. 1998, 16, 359-363.
4. (a) Ma, Z.; Taylor, J.-S. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 11159-11163.
5. (b) Ma, Z.; Taylor, J.-S. Bioorg. Med. Chem. 2001, 9, 2501-2510.
6. (c) Okamoto, A.; Tanabe, K.; Inasaki, T.; Saito, I. Angew. Chem., Int. Ed. 2003, 42, 2502-2504.
7. Markiewicz, W. T.; Gröger, G.; Rösch, R.; Zebrowska, A.; Markiewicz, M.; Klotz, M.; Hinz, M.; Godzina, P.; Seliger, H. Nucleic Acids Res. 1997, 25, 3672-3680.
8. For photooxidation of DNA using riboflavin, see: (a) Ito, K.; Inoue, S.; Yamamoto, K.; Kawanishi, S. J. Biol. Chem. 1993, 268, 13221-13227.
9. (b) Kino, K.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 7373-7374.
10. (c) Saito, I.; Nakamura, T.; Nakatani, K.; Yoshioka, Y.; Yamaguchi, K.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 12686-12687.
11. (a) Ikeda, H.; Saito, I. J. Am. Chem. Soc. 1999, 121, 10836-10837.
12. (b) Cadet, J.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Raoul, S.; Ravanat, J.-L. J. Am. Chem. Soc. 1994, 116, 7403-7404.
13. Muller, J. G.; Duarte, V.; Hickerson, R. P.; Burrows, C. J. Nucleic Acids Res. 1998, 26, 2247-2249.
14. 1/2 (0.35 V) was converted to the value versus NHE (0.59 V) by the addition of a constant at 25 °C (0.24 V).
15. Goyal, R. N.; Dryhurst, G. J. Electroanal. Chem. 1982, 135, 75-91.
16. Yanagisawa, H.; Ogawa, Y.; Ueno, M. J. Biol. Chem. 1992, 267, 13320-13326.
17. Hickerson, R. P.; Prat, F.; Mullar, J. G.; Foote, C. S.; Burrows, C. J. J. Am. Chem. Soc. 1999, 121, 9423-9428.
18. For selected examples, see: (a) Hall, D. B.; Holmlin, R. E.; Barton, J. K. Nature 1996, 382, 731-735.
19. (b) Gasper, S. M.; Schuster, G. B. J. Am. Chem. Soc. 1997, 119, 12762-12771.
20. (c) Meggers, E.; Kusch, D.; Spichty, M.; Wille, U.; Giese, B. Angew. Chem., Int. Ed. 1998, 37, 460-462.
21. (d) Núñez, M. E.; Hall, D. B.; Barton, J. K. Chem. Biol. 1999, 6, 85-97.
22. (e) Nakatani, K.; Dohno, C.; Saito, I. J. Am. Chem. Soc. 2000, 122, 5893-5894.
23. (f) Giese, B.; Amaudrut, J.; Köhler, A.-K.; Spormann, M.; Wessely, S. Nature 2001, 412, 318-320.
24. (g) Okamoto, A.; Tanabe, K.; Dohno, C.; Saito, I. Bioorg. Med. Chem. 2002, 10, 713-718.
25. (h) Okamoto, A.; Tanaka, K.; Saito, I. J. Am. Chem. Soc. 2003, 125, 5066-5071.
26. For selected examples, see: (a) Murphy, C. J.; Arkin, M. R.; Jenkins, Y. ; Ghatlia, N. D.; Bossmann, S. H.; Turro, N. J.; Barton, J. K. Science 1993, 262, 1025-1029.
27. (b) Meade, T. J.; Kayyem, J. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 352-354.
28. (c) Lewis, F. D.; Wu, T.; Zhang, Y.; Letsinger, R. L.; Greenfield, S. R. ; Wasielewski, M. R. Science 1997, 277, 673-676.
29. (d) Fukui, K.; Tanaka, K.; Fujitsuka, M.; Watanabe, A.; Ito, O. J. Photochem. Photobiol., B 1999, 50, 18-27.
30. (e) Fiebig, T.; Wan, C.; Kelley, S. O.; Barton, J. K.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1187-1192.
31. (f) Kawai, K.; Takada, T.; Tojo, S.; Ichinose, N.; Majima, T. J. Am. Chem. Soc. 2001, 123, 12688-12689.
32. Nakatani, K.; Dohno, C.; Saito, I. J. Org. Chem. 1999, 64, 6901-6904.
33. The decrease of the fluorescence intensity of TAMRA by photobleaching was less than 5% after 312 nm photoirradiation for 90 min.
34. edaG in intact ODN was also damaged by hot piperidine treatment (90°C, 20 min).