Interstrand cross-links generated by abasic sites in duplex DNA

Journal of the American Chemical Society

Volumn 129, Issue 7, 2007, Pages 1852-1853

  Dutta, Sanjay ^a   Chowdhury, Goutam ^a   Gates, Kent S ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DOUBLE STRANDED DNA; GUANINE; HETEROCYCLIC COMPOUND; IMINE; METHOXYAMINE; OXIME; URACIL;

ARTICLE; CROSS LINKING; DNA DAMAGE; DNA HELIX; DNA MODIFICATION; DNA SEQUENCE; HYDROLYSIS; MASS SPECTROMETRY; QUANTUM YIELD; REDUCTION;

ALDEHYDES; BASE SEQUENCE; BINDING SITES; CROSS-LINKING REAGENTS; DNA; DNA DAMAGE; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION;

EID: 33847323023     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067294u     Document Type: Article

References (31)

1. Evans, A. R.; Limp-Foster, M.; Kelley, M. R. Mutat. Res. 2000, 461, 83-108.
2. Lhomme, J.; Constant, J.-F.; Demeunynck, M. Biopolymers 2000, 52, 65-83.
3. Loeb, L. A.; Preston, B. D. Ann. Rev. Genet. 1986, 20, 201-230.
4. Boiteux, S.; Guillet, M. DNA Repair 2004, 3, 1-12.
5. For examples of abasic sites stemming from DNA alkylation, see: Gates, K. S.; Nooner, T.; Dutta, S. Chem. Res. Toxicol. 2004, 17, 839-856.
6. Nooner, T.; Dutta, S.; Gates, K. S. Chem. Res. Toxicol. 2004, 17, 942-949.
7. Freese, E.; Cashel, M. Biochim. Biophys. Acta 1964, 91, 67-77.
8. Burnotte, J.; Verly, W. G. Biochim. Biophys. Acta 1972, 262, 449-452.
9. Goffin, C.; Verly, W. G. FEBS Lett. 1983, 161, 140-144.
10. Goffin, C.; Verly, W. G. Biochim. Biophys. Acta 1984, 783, 1-5.
11. Mittal, A.; Musarrat, J. Med. Sci. Res. 1990, 18, 633-635.
12. Prakash, A. S.; Gibson, N. W. Carcinogenesis 1992, 13, 425-431.
13. Noll, D. M.; Mason, T. M.; Miller, P. S. Chem. Rev. 2006, 106, 277-301.
14. Schärer, O. D. ChemBioChem 2005, 6, 27-32.
15. Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723-2795.
16. Grossman, K. F.; Ward, A. M.; Matkovic, M. E.; Folias, A. E.; Moses, R. E. Mutat. Res. 2001, 487, 73-83.
17. Reddy, M.; Vasquez, K. M. Radiat. Res. 2005, 164, 345-356.
18. Wilde, J. A.; Bolton, P. H.; Mazumdar, A.; Manoharan, M.; Gerlt, J. A. J. Am. Chem. Soc. 1989, 111, 1894-1896.
19. (a) Riggins, J. N.; Daniels, J. S.; Rouzer, C. A.; Marnett, L. J. J. Am. Chem. Soc. 2004, 126, 8237-8243.
20. (b) Wang, M.; McIntee, E. J.; Cheng, G.; Shi, Y.; Villalta, P. W.; Hecht, S. S. Chem. Res. Toxicol. 2000, 13, 1149-1157.
21. (c) Chaw, Y. F. M.; Crane, L. E.; Lange, P.; Shapiro, R. Biochemistry 1980, 19, 5525-5531. In early work, Verly and coworkers (ref 4) proposed that abasic-site-derived cross-link formation might involve a Schiff base linkage.
22. Kozekov, I. D.; Nechev, L. V.; Moseley, M. S.; Harris, C. M. Rizzo, C. J.; Stone, M. P.; Harris, T. M. J. Am. Chem. Soc. 2003, 125, 50-61.
23. For examples involving interstrand cross-linking of non-natural DNA via reductive amination, see: Manoharan, M.; Andrade, L. K.; Cook, P. D. Org. Lett. 1999, 1, 311-314.
24. Dohno, C.; Okamoto, A.; Saito, I. J. Am. Chem. Soc. 2005, 127, 16681-16684.
25. Duplexes with an adenine residue opposing the abasic site retain a right-handed, B-helical structure in solution (see: Withka, J. M.; Wilde, J. A.; Bolton, P. H.; Mazumder, A.; Gerlt, J. A. Biochemistry 1991, 30, 9931-9940
26. and Cuniasse, P.; Fazakerley, G. V.; Guschbauer, W.; Kaplan, B. E.; Sowers, L. C. J. Mol. Biol. 1990, 213, 303-314).
27. In general, however, abasic-site-containing duplexes have the potential to display considerable structural diversity (see: ref 1, Hoehn, S. T.; Turner, C. J.; Stubbe, J. Nucleic Acids Res. 2001, 29, 3413-3423,
28. and Berger, R. D.; Bolton, P. H. J. Biol. Chem. 1998, 273, 155565-15573).
29. Lindahl, T. Ljunquist, S.; Siegert, W.; Nyberg, B.; Sperens, B. J. Biol. Chem. 1977, 252, 3286-3294. Treatment with UDG cleanly generates AP sites (>99% yield) in all of the duplex substrates used here (see Supporting Information).
30. Talpaert-Borle, M.; Liuzzi, M. Biochim. Biophys. Acta 1983, 740, 410-16.
31. Rosa, S.; Fortini, P.; Karran, P.; Bignami, M.; Dogliotti, E. Nucleic Acids Res. 1991, 19, 5569-5574.