The topopyrones poison human DNA topoisomerases I and II

Journal of the American Chemical Society

Volumn 130, Issue 39, 2008, Pages 12888-12889

  Khan, Qasim A ^a   Elban, Mark A ^b   Hecht, Sidney M ^a,b  

^a ARIZONA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMICAL CHARACTERIZATION; CHEMICAL EQUATIONS; DNA TOPOISOMERASE; NATURAL PRODUCTS; NATURALLY OCCURRING; TOPOISOMERASE I; TOPOISOMERASES; TOTAL SYNTHESIS;

ANTIBODIES; CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; DNA; GENES;

NUCLEIC ACIDS;

ANTHRAQUINONE DERIVATIVE; DNA; DNA BINDING PROTEIN; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE II ALPHA; ENZYME INHIBITOR; PYRONE DERIVATIVE; TUMOR ANTIGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; METABOLISM; NUCLEOTIDE SEQUENCE;

ANTHRAQUINONES; ANTIGENS, NEOPLASM; BASE SEQUENCE; DNA; DNA TOPOISOMERASES, TYPE I; DNA TOPOISOMERASES, TYPE II, EUKARYOTIC; DNA-BINDING PROTEINS; ENZYME INHIBITORS; HUMANS; PYRONES;

EID: 58149159944     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805421b     Document Type: Article

References (30)

1. (a) Wang, J. C. Nat. Rev. Mol. Cell Biol. 2002, 3, 430-440.
2. (b) Pommier, Y. Nat. Rev.Cancer 2006, 6, 789-802.
3. (a) Nelson, E. M.; Tewey, K. M.; Liu, L. F. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 1361-1365.
4. (b) Hsiang, Y. H.; Hertzberg, R.; Hecht, S.; Liu, L. F. J. Biol. Chem. 1985, 260, 14873-14878.
5. (a) Wang, J. C. Annu. Rev. Biochem. 1996, 65, 635-692.
6. (b) Champoux, J. J. Annu. Rev. Biochem. 2001, 70, 369-413.
7. Liu, L. F.; Liu, C. C.; Alberts, B. M. Cell 1980, 19, 697-707.
8. (a) Chen, A. Y.; Liu, L. F. Annu. Rev. Pharmacol. Toxicol. 1994, 34, 191-218.
9. (b) Wilstermann, A. M.; Osheroff, N. Curr. Top. Med. Chem. 2003, 3, 321-338.
10. Potmesil, M. Cancer Res. 1994, 54, 1431-1439.
11. Bailly, C.; Riou, J. F.; Colson, P.; Houssier, C.; Rodrigues-Pereira, E.; Prudhomme, M. Biochemistry 1997, 36, 3917-3929.
12. Marchand, C.; Antony, S.; Kohn, K. W.; Cushman, M.; Ioanoviciu, A.; Staker, B. L.; Burgin, A. B.; Stewart, L.; Pommier, Y. Mol. Cancer Ther. 2006, 5, 287-295.
13. Khan, Q. A.; Pilch, D. S. J. Mol. Biol. 2007, 365, 561-569.
14. Zhou, B.-N.; Johnson, R. K.; Mattern, M. R.; Wang, X.; Hecht, S. M.; Beck, H. T.; Ortiz, A.; Kingston, D. G. I. J. Nat. Prod. 2000, 63, 217-221.
15. (a) Kanai, Y.; Ishiyama, D.; Senda, H.; Iwatani, W.; Takahashi, H.; Konno, H.; Tokumasu, S.; Kanazawa, S. J. Antibiot. (Tokyo) 2000, 53, 863-872.
16. (b) Ishiyama, D.; Kanai, Y.; Senda, H.; Iwatani, W.; Takahashi, H.; Konno, H.; Kanazawa, S. J. Antibiot. (Tokyo) 2000, 53, 873-878.
17. Sun, D.; Hansen, M.; Clement, J. J.; Hurley, L. H. Biochemistry 1993, 32, 8068-8074.
18. (a) Tan, J. S.; Ciufolini, M. A. Org. Lett. 2006, 8, 4771-4774.
19. (b) Gattinoni, S.; Merlini, L.; Dallavelle, S. Tetrahedron Lett. 2007, 48, 1049-1051.
20. (c) Elban, M. A.; Hecht, S. M. J. Org. Chem. 2008, 73, 785-793.
21. Bonven, B. J.; Gocke, E.; Westergaard, O. Cell 1985, 41, 541-551.
22. (a) Pommier, Y.; Kohlhagen, G.; Kohn, K. W.; Leteurtre, F.; Wani, M. C.; Wall, M. E. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8861-8865.
23. (b) Tanizawa, A.; Kohn, K. W.; Kohlhagen, G.; Leteurtre, F.; Pommier, Y. Biochemistry 1995, 34, 7200-7206.
24. Interestingly, the concentration dependence of binary complex stabilization by some of the topopyrones was not concentration dependent, perhaps reflecting direct DNA binding at higher concentrations.
25. Topoisomerase IIR is associated with mitototic chromosomes and is preferentially expressed in proliferating cells: Heck, M. M.; Hittleman, W. N.; Earnshaw, W. C. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 1086-1090.
26. Whereas topoisomerase II levels do not change significantly during the cell cycle: Capranico, G.; Tinelli, S.; Austin, C. A.; Fisher, M. L.; Zunino, F. Biochim. Biophys. Acta 1992, 1132, 43-48.
27. Pommier, Y.; Capranico, G.; Orr, A.; Kohn, K. W. J. Mol. Biol. 1991, 222, 909-924.
28. The incubations for the experiments in Figures 2-4 were carried out in 10 mM Tris-HCl, pH 7.5, for 30 min (see Supporting Information).
29. Examples of other reported dual topoisomerase poisons include: (a) Leteurtre, F.; Fujimori, A.; Tanizawa, A.; Chhabra, A.; Mazumder, A.; Kohlhagen, G.; Nakano, H.; Pommier, Y. J. Biol. Chem. 1994, 269, 28702-28707.
30. (b) Rao, V. A.; Agama, K.; Holbeck, S.; Pommier, Y. Cancer Res. 2007, 67, 9971-9979.