DNA interstrand cross-link formation by the 1,4-dioxobutane abasic lesion

Journal of the American Chemical Society

Volumn 131, Issue 42, 2009, Pages 15225-15231

  Guan, Lirui ^a   Greenberg, Marc M ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA DAMAGING AGENTS; DOUBLE-STRAND BREAKS; ELECTROPHILES; HYDROGEN ATOMS; INTERSTRAND CROSS-LINKS; MECHANISTIC STUDIES; MOLECULAR MODELS; NUCLEOTIDE EXCISION REPAIR; PRODUCT STUDIES; SINGLE-STRAND BREAKS;

ALDEHYDES; AMINES; GENES; HYDROGEN; NUCLEIC ACIDS; NUCLEOTIDES;

DNA;

ALDEHYDE; ALKANE DERIVATIVE; AMINE; DNA; ELECTROPHILE; EXOCYCLIC DOUBLE BOND; HYDROGEN; NUCLEOTIDE;

ARTICLE; DNA CROSS LINKING; DNA DAMAGE; EXCISION REPAIR; MOLECULAR MODEL; SINGLE STRANDED DNA BREAK;

BUTANONES; CROSS-LINKING REAGENTS; DNA; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEOTIDES;

EID: 70350329260     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9061695     Document Type: Article

References (49)

1. von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor & Francis: London, 1987.
2. Noll, D. M.; Mason, T. M.; Miller, P. S. Chem. Rev. 2006, 106, 277-301.
3. Schärer, O. D. ChemBioChem 2005, 6, 27-32.
4. Cadet, J.; Douki, T.; Gasparutto, D.; Ravanat, J. L. Mutat. Res. 2003, 531, 5-23.
5. Dizdaroglu, M.; Jaruga, P.; Birincioglu, M.; Rodriguez, H. Free Radical Biol. Med. 2002, 32, 1102-1115.
6. Kroeger, K. M.; Hashimoto, M.; Kow, Y. W.; Greenberg, M. M. Biochemistry 2003, 42, 2449-2455.
7. Hashimoto, M.; Greenberg, M. M.; Kow, Y. W.; Hwang, J.-T.; Cunningham, R. P. J. Am. Chem. Soc. 2001, 123, 3161-3162.
8. Makino, K.; Ide, H. J. Biol. Chem. 2003, 278, 25264-25272.
9. Dutta, S.; Chowdhury, G.; Gates, K. S. J. Am. Chem. Soc. 2007, 129, 1852-1853.
10. Regulus, P.; Duroux, B.; Bayle, P.-A.; Favier, A.; Cadet, J.; Ravanat, J.-L. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 14032-14037.
11. Sczepanski, J. T.; Jacobs, A. C.; Greenberg, M. M. J. Am. Chem. Soc. 2008, 130, 9646-9647.
12. Sczepanski, J. T.; Jacobs, A. C.; Majumdar, A.; Greenberg, M. M. J. Am. Chem. Soc. 2009, 131, 11132-11139.
13. Xi, Z.; Goldberg, I. H. In Comprehensive Natural Products Chemistry; Kool, E. T., Ed.; Elsevier: Amsterdam, 1999; Vol.7, pp 553-592.
14. Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191-198.
15. Chen, B.; Bohnert, T.; Zhou, X.; Dedon, P. C. Chem. Res. Toxicol. 2004, 17, 1406-1413.
16. Chin, D. H.; Kappen, L. S.; Goldberg, I. H. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 7070-7074.
17. Georgakilas, A. Mol. BioSyst. 2008, 4, 30-35.
18. Kozmin, S. G.; Sedletska, Y.; Reynaud-Angelin, A.; Gasparutto, D.; Sage, E. Nucleic Acids Res. 2009, 37, 1767-1777.
19. Paap, B.; Wilson, I., D. M.; Sutherland, B. M. Nucleic Acids Res. 2008, 36, 2717-2727.
20. Lomax, M. E.; Gulston, M. K.; O'Neill, P. Radiat. Prot. Dosim. 2002, 99, 63-68.
21. Blaisdell, J. O.; Wallace, S. S. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7426-7430.
22. Gulston, M.; de Lara, C.; Jenner, T.; Davis, E.; O'Neill, P. Nucleic Acids Res. 2004, 32, 1602-1609.
23. Sczepanski, J.; Jacobs, A. C.; Van Houten, B.; Greenberg, M. M. Biochemistry 2009, 7565-7567.
24. Chen, B.; Vu, C. C.; Byrns, M. C.; Dedon, P. C.; Peterson, L. A. Chem. Res. Toxicol. 2006, 19, 982-985.
25. Gingipalli, L.; Dedon, P. C. J. Am. Chem. Soc. 2001, 123, 2664-2665.
26. Byrns, M. C.; Vu, C. C.; Neidigh, J. W.; Abad, J.-L.; Jones, R. A.; Peterson, L. A. Chem. Res. Toxicol. 2006, 19, 414-420.
27. Byrns, M. C.; Predecki, D. P.; Peterson, L. A. Chem. Res. Toxicol. 2002, 15, 373-379.
28. Kodama, T.; Greenberg, M. M. J. Org. Chem. 2005, 70, 9916-9924.
29. Dhar, S.; Kodama, T.; Greenberg, M. M. J. Am. Chem. Soc. 2007, 129, 8702-8703.
30. Aso, M.; Usui, K.; Fukuda, M.; Kakihara, Y.; Goromaru, T.; Suemune, H. Org. Lett. 2006, 15, 3183-3186.
31. Usiv, K.; Aso, M.; Fukuda, M.; Suemune, H. J. Org. Chem. 2008, 73, 241-248.
32. See the Supporting Information.
33. Millard, J. T.; Weidner, M. F.; Kirchner, J. J.; Ribeiro, S.; Hopkins, P. B. Nucleic Acids Res. 1991, 19, 1885-1892.
34. Mueller, R.; et al. J. Med. Chem. 2004, 47, 5183-5197.
35. Bae, S.; Lakshman, M. K. J. Org. Chem. 2008, 73, 3707-3713.
36. Shishkina, I. G.; Johnson, F. Chem. Res. Toxicol. 2000, 13, 907-912.
37. Huang, H.; Greenberg, M. M. J. Org. Chem. 2008, 73, 2695-2703.
38. Mulzer, J.; Angermann, A.; Münch, W. Liebigs Ann. Chem. 1986, 825-838.
39. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C. J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602.
40. Yadav, J. S.; Nirranjan Kumar, N.; Sridhar Reddy, M.; Prasad, A. R. Tetrahedron 2007, 63, 2689-2694.
41. Byrns, M. C.; Vu, C. C.; Peterson, L. A. Chem. Res. Toxicol. 2004, 17, 1607-1613.
42. Bamford, C. H.; Tipper, C. F. H. The Theory of Kinetics; Elsevier: Amsterdam, 1969; Vol.2.
43. Stone, M. P.; Cho, Y.-J.; Huang, H.; Kim, H.-Y.; Kozekov, I. D.; Kozekova, A.; Wang, H.; Minko, I. G.; Lloyd, R. S.; Harris, T. M.; Rizzo, C. J. Acc. Chem. Res. 2008, 41, 793-804.
44. Cho, Y. J.; Wang, H.; Kozekov, I. D.; Kozekova, A.; Kurtz, A. J.; Jacob, J.; Voehler, M.; Smith, J.; Harris, T. M.; Rizzo, C. J.; Lloyd, R. S.; Stone, M. P. Chem. Res. Toxicol. 2006, 19, 1019-1029.
45. Wang, H.; Kozekov, I. D.; Kozekova, A.; Tamura, P. J.; Marnett, L. J.; Harris, T. M.; Rizzo, C. J. Chem. Res. Toxicol. 2006, 19, 1467-1474.
46. Sodum, R. S.; Shapiro, R. Bioorg. Chem. 1988, 16, 272-282
47. Chen, H.-J. C.; Chung, F.-L. Chem. Res. Toxicol. 1994, 7, 857-860
48. Weinert, E. E.; Frankenfield, K. N.; Rokita, S. E. Chem. Res. Toxicol. 2005, 18, 1364-1370.
49. Veldhuyzen, W. F.; Shallop, A. J.; Jones, R. A.; Rokita, S. E. J. Am. Chem. Soc. 2001, 123, 11126-11132.