Guanine specific DNA cleavage by photoirradiation of dibenzoyldiazomethane - Oligonucleotide conjugates

Journal of the American Chemical Society

Volumn 119, Issue 33, 1997, Pages 7626-7635

  Nakatani, Kazuhiko ^a   Shirai, Junya ^a   Sando, Shinsuke ^a   Saito, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIBENZOYLMETHANE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; CHEMICAL MODIFICATION; CONJUGATE; DNA CLEAVAGE; DNA SEQUENCE; IRRADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOREACTIVITY;

EID: 0030884569     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970598j     Document Type: Article

References (61)

1. For recent reviews on photoinduced DNA cleavage, see: (a) Saito, I.; Nakatani, K. Bull. Chem. Soc. Jpn. 1996, 69, 3007-3019. (b) Bioorganic Photochemistry, Photochemistry and the Nucleic Acids; Morrison, H., Ed.; John Wiley and Sons: New York, 1990; Vol. 1.
2. For recent reviews on photoinduced DNA cleavage, see: (a) Saito, I.; Nakatani, K. Bull. Chem. Soc. Jpn. 1996, 69, 3007-3019. (b) Bioorganic Photochemistry, Photochemistry and the Nucleic Acids; Morrison, H., Ed.; John Wiley and Sons: New York, 1990; Vol. 1.
3. (a) Kawanishi, S.; Inoue, S.; Sano, S.; Aiba, H. J. Biol. Chem. 1986, 261, 6090-6095.
4. (b) Blazek, E. R.; Peak, J. G.; Peak, M. J. Photochem. Photobiol. 1989, 49, 607-613.
5. (c) Schneider, J. E.; Price, S. Maidlt, L.; Gutteridge, J. M. C.; Floyd, R. A. Nucleic Acids Res. 1990, 18, 631-635.
6. (d) Buchko, G. W.; Cadet, J.; Berger, M.; Ravanat, J.-L. Nucleic Acids Res. 1990, 18, 4847-4851.
7. (e) Devasagayam, T. P. A.; Steenken, S.; Obendorf, M. S. W.; Schulz, W. A.; Sies, H. Biochemistry 1991, 30, 6283-6289.
8. (f) Sies, H.; Menck, C. F. M. Mutat. Res. 1992, 275, 367-375.
9. (g) Ravanat, J.-L.; Cadet, J. Chem. Res. Toxicol. 1995, 8, 379-388.
10. (a) Saito, I.; Takayama, M.; Matsuura, T.; Matsugo, S.; Kawanishi, S. J. Am. Chem. Soc. 1990, 112, 883-884.
11. (b) Matsugo, S.; Kawanishi, S.; Yamamoto, K.; Sugiyama, H.; Matsuura, T.; Saito, I. Angew. Chem., Int. Ed. Engl. 1991, 30, 1351-1353.
12. (c) Saito, I. Pure Appl. Chem. 1992, 64, 1305-1310.
13. For reactions of oxygen radicals with DNA, see a review: Breen, A. P.; Murphy, J. A. Free Radical Biol. Med. 1995, 18, 1033-1077.
14. (a) Barton, J. K. Science 1986, 233, 727-734.
15. (b) Lee, I.; Barton J. K.; Biochemistry, 1993, 32, 6121-6127.
16. (c) Sitlani, A; Long, E. C.; Pyle, A. M.; Barton, J. K. J. Am. Chem. Soc. 1992, 114, 2303-2312.
17. (a) Steenken, S. Chem. Rev. 1989, 89, 503-520.
18. (b) Candeias, L. P.; Steenken, S, J. Am. Chem. Soc. 1993, 115, 2437-2440.
19. Dunn, D. A.; Lin, V. H.; Kochevar, I. E. Biochemistry 1992, 31, 11620-11625.
20. (a) Sugiyama, H.; Tsutsumi, K.; Fujimoto, K.; Saito, I. J. Am. Chem. Soc. 1993, 115, 4443-4448.
21. (b) Saito, I.; Takayama, M.; S. Kawanishi, J. Am. Chem. Soc. 1995, 117, 5590-5591.
22. (c) Saito, I.; Takayama, M.; Sugiyama, H.; Nakatani, K.; Tsuchida, A.; Yamamoto, M. J. Am. Chem. Soc. 1995, 117, 6406-6407.
23. (d) 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.
24. (e) Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063-7068.
25. Ito, K.; Inoue, S.; Yamamoto, K.; Kawanishi, S. J. Biol. Chem. 1993, 268, 13221-13227.
26. Cadet, J.; Berger, M.; Bunchko, G. W.; Joshi, R. C.; Raoul, S.; Ravanet, J.-L. J. Am. Chem. Soc. 1994, 116, 7403-7404.
27. (a) Armitage, B.; Changjun, Y.; Devadoss, C.; Schuster, G. B. J. Am. Chem. Soc. 1994, 116, 9847-9859.
28. (b) Breslia, D.; Schuster, G. B. J. Am. Chem. Soc. 1996, 118, 2313-2319.
29. (c) Ly, D.; Kan, Y.; Armitage, B.; Schuster, G. B. 1996, 118, 8747-8748.
30. Hall, D. B.; Holmlin, R. E.; Barton, J. K. Nature 1996, 382, 731-735.
31. Perrouault, L.; Asseline, U.; Rivallet, C.; Thuong, N. T.; Bisagni, E.; Giovannangeli, C.; Le Doan, T.; Hélène, C. Nature 1990, 344, 358-360.
32. Nielsen, P. E.; Hirort, C.; Sonnichsen, S. H.; Buchardt, O.; Dahl, O.; Norden, B. J. Am. Chem. Soc. 1992, 114, 4967-4975.
33. Quadda, J. C.; Levy, M. J., Jr.; Hecht, S. M. J. Am. Chem. Soc. 1993, 115, 12171-12172.
34. (a) Nakatani, K.; Isoe, S.; Maekawa, S.; Saito, I. Tetrahedron Lett. 1994, 35, 605-608.
35. (b) Saito, I.; Sakurai, T.; Kurimoto, T.; Takayama, M. Tetrahedron Lett. 1994, 35, 4797-4800.
36. (c) Nakatani, K.; Maekawa, S.; Tanabe, K.; Saito, I. J. Am. Chem. Soc. 1995, 117, 10635-10644.
37. Condorelli, G.; Costanzo, L. L.; De Guidi, G.; Giuffrida, S.; Sortino, S. Photochem. Photobiol. 1995, 62, 155-161.
38. Matsugo, S.; Nakano, S.; Adachi, K.; Konishi, T. J. Chem. Soc., Chem. Commun. 1995, 311-312.
39. Wender, P. A.; Touami, S. M.; Alayrac, C.; Philipp. U. C. J. Am. Chem. Soc. 1996, 118, 6522-6533.
40. (a) Nielsen, P. E.; Jeepsen, C.; Egholm, M.; Buchardt, O. Nucleic Acids Res. 1988, 16, 3877-3888.
41. (b) Henriksen, U.; Larsen, C.; Karup, G., Jeepsen, C.; Nielsen, P. E.; Buchardt, O. Photochem. Photobiol. 1991, 53, 299-305.
42. (a) Chatterjee, M.; Rokita, S. E. J. Am. Chem. Soc. 1990, 112, 6397-6397.
43. (b) Chatterjee, M.; Rokita, S. E. J. Am. Chem. Soc. 1994, 116, 1690-1697.
44. Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc. 1994, 116, 2653-2654.
45. Nakatani, K.; Shirai, J.; Tamaki, R.; Saito, I. Tetrahedron Lett. 1995, 36, 5363-5366.
46. (a) Baumann, N. Helv. Chim. Acta 1972, 55, 2716-2723.
47. (b) Tomioka, H.; Hayashi, N.; Asano, T.; Izawa, Y. Bull. Chem. Soc. Jpn. 1983, 56, 758-761.
48. For reviews on chemical nucleases, see: (a) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666-690 (b) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98-104.
49. For reviews on chemical nucleases, see: (a) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666-690 (b) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98-104.
50. For recent examples of photoactivatable oligonucleotide conjugates, see: (a) Boutorine, A. S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 2462-2465. (b) Magda, D.; Wright, M.; Miller, R. A.; Sessler, J. L.; Sansom, P. I. J. Am. Chem. Soc. 1995, 117, 3629-3630. (c) Sessler, J. L., Sansom, P. I.; Král, V.; O'Connor, D.; Iverson, B. J. Am. Chem. Soc. 1996, 118, 12322-12330, and references cited therein. See also ref 21b.
51. For recent examples of photoactivatable oligonucleotide conjugates, see: (a) Boutorine, A. S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 2462-2465. (b) Magda, D.; Wright, M.; Miller, R. A.; Sessler, J. L.; Sansom, P. I. J. Am. Chem. Soc. 1995, 117, 3629-3630. (c) Sessler, J. L., Sansom, P. I.; Král, V.; O'Connor, D.; Iverson, B. J. Am. Chem. Soc. 1996, 118, 12322-12330, and references cited therein. See also ref 21b.
52. For recent examples of photoactivatable oligonucleotide conjugates, see: (a) Boutorine, A. S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 2462-2465. (b) Magda, D.; Wright, M.; Miller, R. A.; Sessler, J. L.; Sansom, P. I. J. Am. Chem. Soc. 1995, 117, 3629-3630. (c) Sessler, J. L., Sansom, P. I.; Král, V.; O'Connor, D.; Iverson, B. J. Am. Chem. Soc. 1996, 118, 12322-12330, and references cited therein. See also ref 21b.
53. Maxam, A. M.; Gilbert, W. Methods Enzymol. 1980, 65, 499-560.
54. Baker, B. F.; Dervan P. B. J. Am. Chem. Soc. 1989, 111, 2700-2712.
55. (a) Maxam, A. M.; Gilbert, W. Proc. Natl. Acad Sci. U.S.A. 1977, 74, 560-564.
56. (b) Nishikawa K.; Adams, B. L.; Hecht, S. M. J. Am. Chem. Soc. 1982, 104, 326-328 and references cited therein.
57. Raoul, S.; Cadet, J. J. Am. Chem. Soc. 1996, 118, 1892-1898.
58. (a) Sheu, C.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 474-477.
59. (b) Sheu, C.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 6439-6442.
60. Nagai, K.; Hecht, S. M. J. Biol. Chem. 1991, 266, 23994-24002.
61. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning. A Laboratory Mannual, 2nd ed.; Cold Spring Harbor Laboratories Press: Cold Spring Harbor, NY, 1989.