Interplay of hydrogen abstraction and radical repair in the generation of single- and double-strand dna damage, by the esperamicins

Journal of the American Chemical Society

Volumn 119, Issue 29, 1997, Pages 6731-6738

  Epstein, Jessica L ^a,b,e   Zhang, Xiaodong ^a,f   Doss, George A ^b   Liesch, Jerrold M ^b   Krishnan, Bala ^c   Stubbe, Joanne ^d   Kozarich, John W ^a,b  

^a Bldg 142   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c BRISTOL MYERS SQUIBB   (United States)

^d MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^e HARVARD UNIVERSITY   (United States)

^f ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOUBLE STRANDED DNA; ESPERAMICIN A1; ESPERAMICIN C; ESPERAMICIN DERIVATIVE; HYDROGEN; RADICAL;

ARTICLE; CYCLIZATION; DNA CLEAVAGE; DNA DAMAGE; DNA REPAIR; PROTON TRANSPORT;

EID: 0030800205     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964355n     Document Type: Article

References (40)

1. Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
2. Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769.
3. Schurig, J. E.; Rose, W. C.; Kamei, H.; Nishiyama, Y.; Bradner, W. T.; Stringfellow, D. A. Invest. New Drugs 1990, 8, 7-15.
4. Long, B. H.; Golik, J.; Forenza, S.; Ward, B.; Rehfuss, R.; Dabrowiak, J. C.; Catino, J. J.; Musial, S. T.; Brookshire, K. W.; Doyle, T. W. Proc. Natl. Acad. Sci. 1989, 86, 2-6.
5. Golik, J.; Clardy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3461-3462.
6. Kiyoto, S.; Nishikawa, M.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H.; Kawai, Y.; Uchida, I.; Hashimoto, M. J. Antibiot. 1985, 38, 840-848.
7. Konishi, M.; Ohkuma, H.; Saitoh, K.; Kawaguchi, H.; Golik, J.; Dubay, G.; Groenewold, G.; Krishnan, B.; Doyle, T. W. J. Antibiot. 1985, 38, 1605-1609.
8. Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235-243.
9. Kishikawa, H.; Jiang, Y.-P.; Goodisman, J.; Dabrowiak, J. C. J. Am. Chem. Soc. 1991, 113, 5434-5440.
10. De Voss, J. J.; Townsend, C. A.; Ding, W. D.; Morton, G. O.; Ellestad, G. A.; Zein, N.; Tabor, A. B.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 9669-9670; Hangeland, J. J.; DeVoss, J. J.; Heath, J. A.; Townsend, C. A.; Ding, W. D.; Ashcroft, J. S.; Ellestad, G. A. J. Am. Chem. Soc. 1992, 114, 9200-9202.
11. De Voss, J. J.; Townsend, C. A.; Ding, W. D.; Morton, G. O.; Ellestad, G. A.; Zein, N.; Tabor, A. B.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 9669-9670; Hangeland, J. J.; DeVoss, J. J.; Heath, J. A.; Townsend, C. A.; Ding, W. D.; Ashcroft, J. S.; Ellestad, G. A. J. Am. Chem. Soc. 1992, 114, 9200-9202.
12. Meschwitz, S. M.; Goldberg, I. H. Proc. Natl. Acad. Sci. 1991, 88, 3047-3051.
13. Meschwitz, S. M.; Schultz, R. G.; Ashley, G. W.; Goldberg, I. H. Biochemistry 1992, 31, 9117-9121.
14. Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe, J. Biochemistry 1991, 30, 2034-2042.
15. Sugiura Y.; Uesawa, Y.; Takahashi, Y.; Kuwahara, J.; Golik, J.; Doyle, T. W. Proc. Natl Acad. Sci. 1989, 86, 7672-7676.
16. Hawley, R. C.; Kiessling, L. L.; Schreiber, S. L. Proc. Natl. Acad. Sci. 1989, 86, 1105-1109.
17. Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnan, B. J. Am. Chem. Soc. 1992, 114, 8763-8767.
18. Yu, L.; Golik, J.; Harrison, R.; Dedon, P. J. Am. Chem. Soc. 1994, 116, 9733-9738.
19. Ikemoto, N.; Kumar, A.; Dedon, P. C.; Danishefsky, S. J.; Patel, D. J. J. Am. Chem. Soc. 1994, 116, 9387-9388.
20. Ajmera, S.; Massof, S.; Kozarich, J. W. J. Labelled Compd. Radiopharm. 1986, 23, 963-968.
21. Zhang, D. X. Ph.D. Thesis Thesis, University of Maryland, 1996.
22. Alam, S. L.; Satterlee, J. D. J. Am. Chem. Soc. 1995, 117, 49-53.
23. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning: a laboratory manual; 2nd ed.; Cold Spring Harbor Laboratory Press: New York, 1989; Vol. 3, p A.1.
24. Wuthrich, K. NMR of Proteins and Nucleic Acids; John Wiley and Sons: New York, 1986.
25. Golik, J.; Dubay, G.; Groenwold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462-3464.
26. Bauer, W.; Vinograd, J. J. Mol. Biol. 1968, 33, 141-171.
27. De Voss, J. J.; Hangeland, J. J.; Townsend, C. A. J. Am. Chem. Soc. 1990, 112, 4554-4556.
28. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146-1147.
29. Harpp, D. N.; Smith, R. A. J. Am. Chem. Soc. 1982, 104, 6045-6053.
30. Langley, D. R.; Golik, J.; Krishnan, B.; Doyle, T. W.; Beveridge, D. L. J. Am. Chem. Soc. 1994, 116, 15-29.
31. Zein, N.; McGahren, W. J.; Morton, G. O.; Ashroft, J.; Ellestad, G. A. J. Am. Chem. Soc. 1989, 111, 6888-6890.
32. Lu, M.; Guo, Q.; Krishnan, B.; Golik, J.; Rosenberg, I. E.; Doyle, T. W.; Kallenback, N. R. J. Biomol. Struct. Dyn. 1991, 9, 285-298.
33. Zheng, S.; Newton, G. L.; Ward, J. F.; Fahey, R. C. Radiat. Res. 1992, 130, 183-193.
34. Sugiyama, H.; Tsutsumi, Y.; Saito, I. J. Am. Chem. Soc. 1990, 112, 6720-6721.
35. Sugiyama, H.; Tsutsumi, Y.; Fujimoto, K.; Saito, I. J. Am. Chem. Soc. 1993, 115, 4443-4448.
36. Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136.
37. von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987, pp 353-374.
38. Prise, K. M.; Gillies, N. E.; Whelan, A.; Newton, G. L.; Fahey, R. C.; Michael, B. D. Int. J. Radiat. Biol. 1995, 67, 393-401.
39. Fahey, R. C.; Vojnovic, B.; Michael, B. D. Int. J. Radiat. Biol. 1991, 59, 885-899.
40. Dedon, P.; Goldberg, I. H. Biochemistry 1992, 31, 1909-1917.