Intramolecular photoinduced electron transfer to anthraquinones linked to duplex DNA: The effect of gaps and traps on long-range radical cation migration

Journal of the American Chemical Society

Volumn 119, Issue 52, 1997, Pages 12762-12771

  Gasper, Susan M ^a   Schuster, Gary B ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE DERIVATIVE; CATION; DOUBLE STRANDED DNA; OLIGONUCLEOTIDE;

ARTICLE; DNA DAMAGE; DNA DRUG COMPLEX; DNA STRUCTURE; ELECTRON TRANSPORT; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET RADIATION;

EID: 0031593021     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972496z     Document Type: Article

References (53)

1. Frenkel, K. Pharmacol. Ther. 1992, 53.
2. Breen, A. P.; Murphy, J. A. Free Radical Biol. Med. 1995, 18, 1033-1077.
3. Cheng, K. C.; Cahill, D. S.; Kasai, H.; Nishimura, S.; Loeb, L. A. J. Biol. Chem. 1992, 267.
4. Boon, P. J.; Cullis, P. M.; Symons, M. C. R.; Wren, B. W. J. Chem. Soc., Perkin Trans. 2 1984, 1393-1399.
5. Wolf, P. G.; Jones, D. D.; Candeias, L. P.; O'Neill, P. Int. J. Radiat. Biol. 1993, 64, 7-18.
6. Melvin, T.; Plumb, M. A.; Botchway, S. W.; O'Neill, P.; Parker, A. W. Photochem. Photobiol. 1995, 61, 584-591.
7. Steenken, S. Chem. Rev. 1989, 89, 503.
8. Cadet, J.; Vigny, P. Bioorganic Photochemistry: Photochemistry and the Nucleic Acids; John Wiley and Sons: New York, 1990; Vol. 1.
9. Johnston, D. H.; Glasgow, K. C.; Thorp, H. H. J. Am. Chem. Soc. 1995, 117, 8993.
10. O'Neill, P.; Fielden, E. M. Adv. Radiat. Biol. 1993, 17, 53-120.
11. Armitage, B. A.; Yu, C.; Devadoss, C.; Schuster, G. B. J. Am. Chem. Soc. 1994, 116, 9847-9859.
12. Ly, D.; Kan, Y.; Armitage, B.; Schuster, G. B. J. Am. Chem. Soc. 1996, 118, 8747-8748.
13. Breslin, D. T.; Schuster, G. B. J. Am. Chem. Soc. 1996, 118, 2311-2319.
14. Saito, I.; Takayama, M.; Sugiyama, H.; Nakatani, K.; Tsuchida, A.; Yamamoto, M. J. Am. Chem. Soc. 1995, 117, 6406-6407.
15. Lincoln, P.; Tuite, E.; Norden, B. J. Am. Chem. Soc. 1997, 119, 1454-1455.
16. Olson, E. J. C.; Hu, D.; Herman, A.; Barbara, P. F. J. Phys. Chem. B 1997, 101, 299-303.
17. Orson, F. M.; Kinsey, B. M.; McShan, W. M. Nucleic Acids Res. 1994, 22, 479-484.
18. Boutonne, A. S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Helene, C. Angew. Chem., Im. Ed. Engl. 1994, 33, 2462-2465.
19. Schubert, F.; Knaf, A.; Moller, U.; Chec, D. Nucleosides Nucleotides 1995, 14, 1437-1443.
20. Meade, T. J.; Kayyem, J. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 352-354.
21. Hall, D. B.; Holmlin, R. E.; Barton, J. K. Nature 1996, 382, 731-735.
22. Dandliker, P. J.; Holmlin, R. E.; Barton, J. K. Science 1997, 275, 1465-1468.
23. Mestre, B.; Jakobs, A.; Pratviel, G.; Meunier, B. Biochemistry 1996, 35, 9140-9149.
24. Boutorine, A. S.; Brault, D.; Takasugi, M.; Delgado, O.; Helene, C. J. Am. Chem. Soc. 1996, 118, 9469-9476.
25. Fukui, K.; Morimoto, M.; Segawa, H.; Tanaka, K.; Shimidzu, T. Bioconjugate Chem. 1996, 7, 349-355.
26. Arkin, M. R.; Stemp, E. D.; Pulver, S. C.; Barton, J. K. Chem. Biol. 1997, 4, 389-400.
27. Mon, K.; Subasinghe, C.; Cohen, J. S. FEBS Lett. 1989 249, 213-218.
28. Kalnik, M. W.; Chang, C. N.; Grollman, A. P.; Patel, D. J. Biochemistry 1988, 27, 924-931.
29. Loeb, L. A.; Preston, B. D. Annu. Rev. Genet. 1986, 20, 201-230.
30. Breslin, D. T.; Coury, J. E.; Anderson, J. R.; McFail-Isom, L.; Kan, Y.; Williams, L. D.; Bottomley, L. A.; Schuster, G. B. J. Am. Chem. Soc. 1997, 119, 5043-5044.
31. Hertzberg, R. P.; Dervan, P. B. J. Am. Chem. Soc. 1982, 102, 313-315.
32. The inclusion of catalase, with or without SOD, causes an increase in the observed piperidine-dependent cleavage quantum efficiency without any change in the cleavage pattern.
33. Floyd, R. A.; West, M. S.; Eneff, K. L.; Schneider, J. E. Arch. Biochem. Biophys. 1989, 273, 106-111.
34. Schneider, J. E.; Price, S.; Maidt, L.; Gutteridge, J. M. C.; Floyd, R. A. Nucleic Acids Res. 1990, 18, 631-635.
35. Devasagayam, T. P. A.; Steenken, S.; Obendort, M. S. W.; Schulz, W. A.; Sies, H. Biochemistry 1991, 30, 6283-6289.
36. Rogers, M. A. J.; Snowden, P. T. J. Am. Chem. Soc. 1982, 104, 5541-5543.
37. Showen, K. B., Showen, R. L. Solvent Isotope Effects on Enzyme Systems; Academic Press: New York, 1982; Vol. 87.
38. Boutorine, A. S.; Brault, D.; Takasugi, M.; Delgado, O.; Helene, C. J. Am. Chem. Soc. 1996, 118, 9469-9476.
39. Veal, J. M.; Wilson, W. D. J. Biomol. Struct. Dyn. 1991, 8, 1119-1145.
40. Private communication with Professor Wilson of Georgia State University.
41. Pratt, F.; Hou, C.-C.; Foote, C. S. J. Am. Chem. Soc. 1997, 119, 5051-5052.
42. Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617-618.
43. Beratan, D. N.; Priyadarshy, S.; Risser, S. M. Chem. Biol. 1997, 4, 3-8.
44. Lipscomb, L. A.; Peek, M. E.; Morningstar, M. L.; Verghis, S. M.; Miller, E. M.; Rich, A.; Essigmann, J. M.; Williams, L. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 719-723.
45. Oda, Y.; Uesugi, S.; Ikehara, M.; Nishimura, S.; Kawase, Y.; Ishikawa, H.; Inoue, H.; Ohtsuka, E. Nucleic Acids Res. 1991, 19, 1407-1412.
46. Sheu, C.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 6439-6442.
47. Cullis, P. M.; Malone, M. E.; Merson-Davies, L. A. J. Am. Chem. Soc. 1996, 118, 2775-2781.
48. Lerman, L. S. Proc. Natl. Acad. Sci. U.S.A. 1963, 49, 94.
49. Guckian, K. M.; Schweitzer, B. A.; Ren, R., X-F.; Sheils, L. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182-8183.
50. Hall, D. B.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 5045-5046.
51. Cuniasse, P.; Fazakerley, G. V.; Guschlbauer, W.; Kaplan, B. E.; Sowers, L. C. J. Mol. Biol. 1990, 213, 303-314.
52. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning. A Laboratory Manual, 2nd ed.; Cold Spring Harbor Press: Cold Spring Harbor, NY, 1989.
53. Brown, T.; Hunter, W. N.; Kneale, G.; Kennard, O. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 2402.