Efficient DNA interstrand cross-link formation from a nucleotide radical

Journal of the American Chemical Society

Volumn 127, Issue 11, 2005, Pages 3692-3693

  Hong, In Seok ^a   Greenberg, Marc M ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOUBLE STRANDED DNA; NUCLEOTIDE; PHENYL GROUP; PHENYL SELENIDE; RADICAL; SELENIUM DERIVATIVE; THYMIDINE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ARTICLE; CROSS LINKING; DECOMPOSITION; DNA STRAND; GAMMA RADIATION; MOLECULAR WEIGHT; OXIDATIVE STRESS; STRUCTURE ANALYSIS; THERMODYNAMICS;

DNA; HYDROGEN; MODELS, MOLECULAR; THYMINE;

EID: 15744405105     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042434q     Document Type: Article

References (21)

1. Tomasz, M.; Palom, Y. Pharmacol. Ther. 1997, 76, 73-87.
2. Gates, K. S. In Comprehensive Natural Products Chemistry, DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Elsevier: Amsterdam, 1999.
3. Richter, S. N.; Maggi, S.; Mels, S. C.; Palumbo, M.; Freccero, M. J. Am. Chem. Soc. 2004, 126, 13973-13979.
4. Xu, Y.-j.; Xi, Z.; Zhen, Y.; Goldberg, I. H. Biochemistry 1997, 36, 14975-14984.
5. von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor & Francis: London, 1987.
6. Wagner, J. R.; van Lier, J. E.; Johnston, L. J. Photochem. Photobiol. 1990, 52, 333-343.
7. Romieu, A.; Bellon, S.; Gasparutto, D.; Cadet, J. Org. Lett. 2000, 2, 1085-1088.
8. Anderson, A. S.; Hwang, J. T.; Greenberg, M. M. J. Org. Chem. 2000, 65, 4648-4654.
9. Zhang, Q.; Wang, Y. J. Am. Chem. Soc. 2003, 125, 12795-12802.
10. Hong, I. S.; Greenberg, M. M. Org. Lett. 2004, 6, 5011-5013.
11. See Supporting Information.
12. Paz, M. M.; Hopkins, P. B. J. Am. Chem. Soc. 1997, 119, 5999-6005.
13. Tallman, K. A.; Pratt, D. A.; Porter, N. A. J. Am. Chem. Soc. 2001, 123, 11827-11828.
14. Dussy, A.; Meggers, E.; Giese, B. J. Am. Chem. Soc. 1998, 120, 7399-7403.
15. Nangia, P. S.; Benson, S. W. Int. J. Chem. Kinet. 1980, 12, 29-42.
16. Singer, B.; Sun, L.; Fraenkel-Conrat, H. Biochemistry 1974, 13, 1913-1920.
17. Selzer, R. R.; Elfarra, A. A. Chem. Res. Toxicol. 1996, 9, 875-881.
18. Fujii, T.; Itaya, T. Heterocycles 1998, 48, 359-390.
19. Modeling was carried out using Spartan '02.
20. Cross-link formation can also be explained via formation of the carbocation derived from 1.
21. Friestad, G. Tetrahedron 2001, 57, 5461-5496.