Experimental and theoretical studies on the selectivity of GGG triplets toward one-electron oxidation in B-form DNA

Journal of the American Chemical Society

Volumn 121, Issue 38, 1999, Pages 8712-8719

  Yoshioka, Yasunori ^a   Kitagawa, Yasutaka ^a   Takano, Yu ^a   Yamaguchi, Kizashi ^a   Nakamura, Takashi ^b   Saito, Isao ^b,c  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOSINE; DNA; GUANINE;

ARTICLE; CALCULATION; ELECTRON; OXIDATION;

EID: 0033615295     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991032t     Document Type: Article

References (57)

1. (a) Saito, I.; Takayama, M.; Sugiyama, H.; Nakamura, T. In DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases; Meunier, B., Ed.; NATO ASI Series; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1996; pp 163-176.
2. (b) Hall, D. B.; Holmin, R. E.; Barton, J. K. Nature 1996, 382, 731.
3. (c) Arkin, M. R.; Stemp, E. D. E.; Pulver, S. C.; Barton, J. K. Chem. Biol. 1997, 4, 389.
4. (d) Holmin, R. E. Dandliker, P. J.; Barton, J. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2714.
5. (e) Hall, D. B.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 5045.
6. (f) Gasper, S, M.; Schuster, G. B. J. Am. Chem. Soc. 1997, 119, 12762.
7. (g) Hall, D. B.; Kelley, S. O.; Barton, J. K. Biochemistry 1998, 37, 15933.
8. (h) Kelley, S. O.; Barton, J. K. Science 1999, 283, 375.
9. (a) Meggers, E.; Michel-Beyerle, M. E.; Giese, B. J. Am. Chem. Soc. 1998, 120, 12950.
10. (b) Ratner, M. Nature 1998, 397, 480.
11. Saito, I.; Nakamura, T.; Nakatani, K.; Yoshioka, Y.; Yamaguchi, K.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 12686.
12. Oxidation potentials of nucleobases, see, for example: (a) Seidel, C. A. M.; Shulz, A.; Sauer, H. M. J. Phys. Chem. 1996, 100, 5541 and references therein. (b) Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617.
13. Oxidation potentials of nucleobases, see, for example: (a) Seidel, C. A. M.; Shulz, A.; Sauer, H. M. J. Phys. Chem. 1996, 100, 5541 and references therein. (b) Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617.
14. For a review, see Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109.
15. (a) Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 699.
16. (b) Sevilla, M. D.; D'Arcy, J. B.; Morehouse, K. M.; Engelhardt, M. L. Photochem. Photobiol. 1979, 29, 37.
17. (c) Graslund, A.; Ehrenberg, A.; Rupprecht, A.; Storm, G. Photochem. Photobiol. 1979, 29, 245.
18. (d) Meggers, E.; Kusch, D.; Spichty, M.; Wille, U. P.; Giese, B. Angew. Chem., Int. Ed. Engl. 1998, 37, 460.
19. Melvin, T.; Botchway, S.; Parker, A. W.; O'Neill, P. J. Chem. Soc., Chem. Commun. 1995, 653.
20. (a) Cullis, P. M.; McClymoun, J. D.; Symons, M. C. R. J. Chem. Soc., Faraday Trans. 1990, 86, 591.
21. (b) Breen, A. P.; Murphy, J. A. Free Radical Biol. Med. 1995, 18, 1033.
22. (c) O'Neill, P.; Fielden, E. M.; Adv. Radiat. Biol 1993, 17, 53.
23. (a) Saito, I.; Takayama, M.; Sugiyama, H.; Nakatani, K.; Tsuchida, A.; Yamamoto, M. J. Am. Chem. Soc. 1995, 117, 6406.
24. (b) Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063.
25. Stemp, E. D. E.; Arkin, M. R.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 2921.
26. Breslin D. T.; Schuster, G. B. J. Am. Chem. Soc. 1996, 118, 2311.
27. (b) Ly, D.; Kan, Y.; Armitage, B.; Schuster, G. B. J. Am. Chem. Soc. 1996, 118, 8747.
28. (c) Armitage B.; Ly, D.; Koch, T.; Frydenlund, H.; Ørum, H.; Batz, H. G.; Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 12320.
29. (a) Ito, K.; Inoue, S.; Yamamoto, K.; Kawanishi, S. J. Biol. Chem. 1993, 268, 13221.
30. (b) Kino, K.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 7373.
31. (a) Nakatani, K.; Dohno, C.; Nakamura, T.; Saito, I. Tetrahedron Lett. 1998, 39, 2779.
32. (b) Nakatani, K.; Fujisawa, K.; Dohno, C.; Nakamura, T.; Saito, I. Tetrahedron Lett. 1998, 39, 5995.
33. Ito, K.; Kawanishi, S. Biochemistry 1997, 36, 1774.
34. Muller, J. G.; Hickerson, R. P.; Perez, R. J.; Burrows, C. J. J. Am. Chem. Soc. 1997, 119, 1501.
35. Shin, H.-C; Tnag, N.; Burrows, C. J.; Rokita, S. E. J. Am. Chem. Soc. 1998, 120, 3284.
36. (a) Melvin, T.; Plumb, M. A.; Botchway, S. W.; O'Neill, P.; Parker, A. W. Photochem. Photobiol. 1995, 61, 584.
37. (b) Spassky, A.; Angelov, D. Biochemistry 1997, 36, 6571.
38. (a) Patterson, S. E.; Coxon, J. M. Strekowski, L. Bioorg. Med. Chem. 1997, 5, 277.
39. (b) Hutter, M.; Clark, T. J. Am. Chem. Soc. 1996, 118, 7574.
40. (c) Colson, A.-O.; Besler, B.; Close, D. M.; Sevilla, M. D. J. Phys. Chem. 1992, 96, 661.
41. (d) Sponer, J.; Leszczynski, J.; Hobza, P. J. Phys. Chem. 1996, 100, 5590.
42. (e) Part, F.; Houk, K. N.; Foote, C. S. J. Am. Chem. Soc. 1998, 120, 845.
43. (a) Maxam, A. M.; Gilbert, W. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 560.
44. (b) Maniatis, T.; Fritsch, E. F.; Sambrook, J. Molecular Cloning; Cold Spring Harbor Laboratory Press: Plainview, NY, 1982.
45. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning: A laboratory Manual, 2nd ed.; Cold Spring Harbor Laboratory Press: Plainview, NY, 1989.
46. Maxam, A. M.; Gilbert, W. In Methods in Enzymology; Grossman, L., Moldave, K., Eds.; Academic Press: New York, 1980; Vol. 65, p 499.
47. (a) Rickwood, D.; Hames, B. D. Gel Electrophoresis of Nucleic Acids: A Practical Approach, 2nd ed.; IRL Press: New York, 1990.
48. (b) Brown, T. A. DNA Sequencing: The Basics: IRL Press: New York, 1994.
49. (a) Arnott, S.; Hukins, D. W. L. Biochem. Biophys. Res. Commun. 1972, 47, 1504.
50. (b) Arnott, S.; Selsing, E. J. Mol. Biol. 1974, 88, 509.
51. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Oritiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
52. Jortner, J.; Bixon, M.; Langenbacher, T.; Michel-Beyerle, M. E. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12759.
53. Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1989, 111, 1094.
54. Hildebrand, K.; Schulte-Frohlinde, D. Free Radical Res. Commun. 1990, 11, 195.
55. (a) Cadet, J.; Berger, M.; Buchko, C. W.; Joshi, P. C.; Raoul, S.; Ravana, J.-L. J. Am. Chem. Soc. 1994, 116, 7403.
56. (b) Viala, C.; Pratviel, G.; Claparols, C.; Meunier, B. J. Am. Chem. Soc. 1998, 120, 11548.
57. Bernstein, R.; Part, F.; Foote, C. S. J. Am. Chem. Soc. 1999, 121, 464.