Sequence-specific modification of guanosine in DNA by a C60-linked deoxyoligonucleotide: Evidence for a non-singlet oxygen mechanism

Tetrahedron

Volumn 52, Issue 14, 1996, Pages 5179-5189

  An, Yi Zhong ^a   Chen, Chi Hong B ^a   Anderson, Jamey L ^a   Sigman, David S ^a   Foote, Christopher S ^a   Rubin, Yves ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYRIBONUCLEOTIDE; FULLERENE DERIVATIVE;

ARTICLE; DNA DAMAGE; DNA STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; HYBRIDIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0029961154     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00123-8     Document Type: Article

References (23)

1. (a) Arbogast, J. W.; Darmanyan, A. O.; Foote, C. S.; Rubin, Y.; Diederich, F. N.; Alvarez, M. M.; Anz, S. J.; Whetten, R. L. J. Phys. Chem. 1991, 95, 11-12.
2. (b) Arbogast, J. W.; Foote, C. S.; Kao, M. J. Am. Chem. Soc. 1992, 114, 2277-2279.
3. (c) Foote, C. S. in Topics in Current Chemistry, Electron Transfer I; Vol 169; Matthay, J., Ed.; Springer-Verlag, New York, 1994, pp 347-363.
4. (a) Tokuyama, H.; Yamago, S.; Nakamura, E.; Shiraki, T.; Sugiura, Y. J. Am. Chem. Soc. 1993, 115, 7918-7919.
5. (b) Boutorine, A. S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Hélène, C. Angew. Chem. Int. Ed. Engl. 1994, 33, 2462-2465.
6. (a) Friedman, S. H.; Decamp, D. L.; Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6506-6509.
7. (b) Shinazi, R. F.; Sijbesma, R. P.; Srdanov, G.; Hill, C. L.; Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707-1710.
8. (c) Toniolo, C.; Bianco, A.; Maggini, M.; Scorrano, G.; Prato, M.; Marastoni, M.; Tomatis, R.; Spisani, S.; Palú, G.; Balir, E. D. J. Med. Chem. 1994, 37, 4558-4562.
9. (a) An, Y. Z.; Anderson, J. L.; Rubin, Y. J. Org. Chem. 1993, 58, 4799-4801.
10. (b) Ganapathi, P. S.; Friedman, S. H.; Kenyon, G. L.; Rubin, Y. J. Org. Chem. 1995, 60, 2954-2955.
11. Anderson, J. L.; An, Y. Z.; Rubin, Y.; Foote, C. S. J. Am. Chem. Soc. 1994, 116, 9763-9764.
12. (a) Sheu, C.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 10446-10447.
13. (b) Sheu, C. M.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 474-477.
14. Durland, R. H.; Kessler, D. J.; Gunnell, S.; Duvie, M.; Pettitt, B. M.; Hogan, M. E. Biochemistry 1991, 30, 9246-9255.
15. Chen, C. H. B.; Mazumder, A.; Constant, J. F.; Sigman, D. S. Bioconjugate Chemistry 1993, 4, 69-77.
16. Foote, C. S. in Singlet Oxygen; Wasserman, H. H.; Murray, R. W., Eds.; Academic Press: New York, 1979; pp 139-171.
17. Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1989, 111, 1094-1099.
18. Kanner, R. C.; Foote, C. S. J. Am. Chem. Soc. 1992, 114, 682-688.
19. Zhang, X. J.; Romero, A.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 11024-11025.
20. (a) Tokuyama, H.; Isobe, H.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2753-2754.
21. (b) Mikami, K.; Matsumoto, S. Synlett 1995, 229-230.
22. Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Millar, J. R. A.; Parkinson, J. A.; Sadler, I. H.; Taylor, A. T. J. Chem. Soc., Chem. Commun. 1995, 1171-1172.
23. Chu, B. C. F.; Wahl, G. M.; Orgel, L. E. Nucleic Acids Res. 1983, 11, 6513-6529.