Effect of guanine stacking on the oxidation of 8-oxoguanine in B-DNA

Journal of the American Chemical Society

Volumn 120, Issue 4, 1998, Pages 845-846

  Prat, Ferran ^a   Houk, K N ^a   Foote, Christopher S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYGUANINE; DNA; DNA B; GUANINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DNA DETERMINATION; DNA STRUCTURE; ELECTRON TRANSPORT; ENERGY; NONHUMAN; OXIDATION;

EID: 0032481373     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972331q     Document Type: Article

References (32)

1. Kasai, H.; Yamaizumi, Z.; Berger, M.; Cadet, J. J. Am. Chem. Soc. 1992, 114, 9692-9694.
2. Saito, I.; Takayama, M.; Sugiyama, H.; Nakatani, K.; Tsuchida, A.; Yamamoto, M. J. Am. Chem. Soc. 1995, 117, 6406-6407.
3. Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063-7068.
4. It is still uncertain whether DNA is a true conductor. For a very interesting review about this controversy, see: Taubes, G. Science 1997, 275, 1420-1421.
5. Joenje, H.; Lafleur, M. V. M.; Retel, J. In Biological consequences of oxidative DNA damage; Vigo-Pelfrey, C., Ed.; CRC Press: Boca Raton, FL, 1991; pp 97-113.
6. Shibutani, S.; Takeshita, M.; Grollman, A. P. Nature 1991, 349, 431-434.
7. Friedberg, E. C.; Walker, G. C.; Siede, W. DNA Repair and Mutagenesis; ASM Press: Washington, DC. 1995.
8. Kochevar, I. E.; Dunn, D. A. In Bioorganic Photochemistry; Morrison, H., Ed.; John Wiley & Sons, Inc.; New York, 1990; pp 273-315.
9. Oxidation of 8G generates a complex mixture of products (depending on reaction conditions) which has not been yet fully characterized.
10. Adam, W.; Saha-Moeller, C. R.; Schoenberger, A. J. Am. Chem. Soc. 1997, 119, 719-723.
11. Sheu, C.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 474-477.
12. Sheu, C.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 6439-6442.
13. Schneider, J. E.; Price, S.; L., M.; Gutteridge, J. M. C.; Floyd, R. A. Nucleic Acids Res. 1990, 18, 631-635.
14. Devasagayam, T. P. A.; Steenken, S.; Obendork, M. S. W.; Schulz, W. A.; Sies, H. Biochemistry 1991, 30, 6283-6289.
15. Cullis, P. M.; Malone, M. E.; Merson-Davies, L. A. J. Am. Chem. Soc. 1996, 118, 2775-2781.
16. Cadet, J.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Raoul, S.; Ravanat, J.-L. J. Am. Chem. Soc. 1994, 116, 7403-7404.
17. Sponer, J.; Leszczynski, J.; Hobza, P. J. Phys. Chem. 1996, 100, 5590-5596 and references therein.
18. Vertical IP refers to the most intense transition in ionization experiments and is assumed to involve no change in geometry.
19. Colson, A.-O.; Besler, B.; Close, D. M.; Sevilla, M. D. J. Phys. Chem. 1992, 96, 661-668.
20. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
21. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz Jr., K. M.; M., F. D.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179-5197.
22. A 12° propeller twist for B-form DNA was introduced as a constraint in the calculations.
23. The resulting structures were compared to three different double strands (118d, 119d, and 126d) containing GG sequences, in the Brookhaven Protein Data Bank.
24. Frisch, M. J.; et al. Gaussian 94 (Revision C.2); Gaussian, Inc.: Pittsburgh, PA, 1995.
25. SPARTAN v4.0, Wavefunction, Inc., 18401 Von Karman Ave., #370, Irvine, CA 92715.
26. Hutter, M.; Clark, T. J. Am. Chem. Soc. 1996, 118, 7574-7577.
27. Alhambra, C.; Luque, F. J.; Gago, F.; Orozco, M. J. Phys. Chem. 1997, 101, 3846-3853.
28. Koizume, S.; Inoue, H.; Kamiya, H.; Ohtsuka, E. J. Chem. Soc. Chem. Commun. 1996, 265-266.
29. Gasper, S. M.; Schuster, G. B. J. Am. Chem. Soc. 1997, 119, in press.
30. Bugg, C. E.; Thorns, J. M.; Sundaralingham, M.; Rao, S. T. Biopolymers 1971, 10, 175-219.
31. Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054.
32. Aida, M. J. Theor. Biol. 1988, 130, 327-335 and references therein.