Luotonin A. A Naturally Occurring Human DNA Topoisomerase I Poison

Journal of the American Chemical Society

Volumn 125, Issue 45, 2003, Pages 13628-13629

  Cagir, Ali ^a   Jones, Shannon H ^a   Gao, Rong ^a   Eisenhauer, Brian M ^a   Hecht, Sidney M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; CYTOTOXIC AGENT; DNA; DNA TOPOISOMERASE; FUNCTIONAL GROUP; LUOTONIN A; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CYTOTOXICITY; DNA TOPOISOMERASE DNA BINARY COMPLEX; DRUG DESIGN; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; IC 50; MOLECULAR INTERACTION; MOLECULAR STABILITY; NONHUMAN; SACCHAROMYCES CEREVISIAE;

ALKALOIDS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; DNA; DNA TOPOISOMERASES, TYPE I; ENZYME INHIBITORS; HUMANS; PYRROLES; QUINONES;

EID: 0242407122     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0368857     Document Type: Article

References (46)

1. (a) Takimoto, C. H.; Wright, J.; Arbuck, S. G. Biochim. Biophys. Acta 1998, 1400, 107.
2. (b) O'Leary, J.; Muggia, F. M. Eur. J. Cancer 1998, 34, 1500.
3. (c) Saltz, L. B.; Cox, J. V.; Blanke, C.; Rosen, L. S.; Fehrenbacher, L. ; Moore, M. J.; Maroun, J. A.; Ackland, S. P.; Locker, P. K.; Pirotta, N.; Elfring, G. L.; Miller, L. L. N. Engl. J. Med. 2000, 343, 905.
4. (d) Ozols, R. F. Int. J. Gynecol. Cancer 2000, 10, 33.
5. (e) Vanhoefer, U.; Harstrick, A.; Achterrath, W.; Cao, S.; Seeber, S.; Rustum, Y. M. J. Clin. Oncol. 2001, 19, 1501.
6. (f) Ulukan, H.; Swaan, P. W. Drugs 2002, 62, 2039.
7. (g) Garcia-Carbonero, R.; Supko, J. G. Clin. Cancer Res. 2002, 8, 641.
8. (a) Wall, M. E.; Wani, M. C.; Nicholas, A. W.; Manikumar, G.; Tele, C.; Moore, L.; Truesdale, A.; Leitner, P.; Besterman, J. M. J. Med. Chem. 1993, 36, 2689.
9. (b) Yaegashi, T.; Sawada, S.; Nagata, H.; Furuta, T.; Yokokura, T.; Miyasaka, T. Chem. Pharm. Bull. 1994, 42, 2518.
10. (c) Lackey, K.; Besterman, J. M.; Fletcher, W.; Leitner, P.; Morton, B.; Sternbach, D. D. J. Med. Chem. 1995, 38, 906.
11. (d) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; McIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uchling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395.
12. (e) Lackey, K.; Sternbach, D. D.; Croom, D. K.; Emerson, D. L.; Evans, M. G.; Leitner, P. L.; Luzzio, M. J.; McIntyre, G.; Vuong, A.; Yates, J.; Besterman, J. M. J. Med. Chem. 1996, 39, 713.
13. (f) Lavergne, O.; Lesueur-Ginot, L.; Pla Rodas, F.; Bigg, D. C. H. Bioorg. Med. Chem. Lett. 1997, 7, 2235.
14. (g) Lavergne, O.; Lesueur-Ginot, L.; Pla Rodas, F.; Kasprzyk, P. G.; Pommier, J.; Demarquay, D.; Prévost, G.; Ulibarri, G.; Rolland, A.; Schiano-Liberatore, A.-M.; Harnett, J.; Pons, D.; Camara, J. Bigg, D. C. H. J. Med. Chem. 1998, 41, 5410.
15. (h) Garbarda, A. E.; Du, W.; Isarno, T.; Tangirala, R. S.; Curran, D. P. Tetrahedron 2002, 58, 6329.
16. (a) Hsiang, Y.-H.; Hertzberg, R.; Hecht, S. M.; Liu, L. F. J. Biol. Chem. 1985, 260, 14873.
17. (b) Kohn, K. W.; Pommier, Y. Ann. N.Y. Acad. Sci. 2000, 922, 11.
18. (a) Xiao, X.-H.; Qou, G.-L.; Wang, H.-L.; Lui, L.-S.; Zheng, Y.-L.; Jia, Z.-J.; Deng, Z.-B. Chin J. Pharmacol. Toxicol. 1988, 232.
19. (b) Ma, Z. Z.; Hano, Y.; Nomura, T.; Chen, Y.-J. Heterocycles 1997, 46, 541.
20. Yadav, J. S.; Reddy, B. V. S. Tetrahedron Lett. 2002, 43, 1905.
21. (a) Hutchinson, C. R. Tetrahedron 1981, 37, 1047.
22. (b) Hertzberg, R. P.; Caranfa, M. J.; Holden, K. G.; Jakas, D. R.; Gallagher, G.; Mattern, M. R.; Mong, S.-M.; Bartus, J. O.; Johnson, R. K.; Kingsbury, W. D. J. Med. Chem. 1989, 32, 715.
23. Lesueur-Ginot, L.; Demarquay, D.; Kiss, R.; Kasprzyk, P. G.; Dassonneville, L.; Bailly, C.; Camara, J.; Lavergne, O.; Bigg, D. C. Cancer Res. 1999, 59, 2939.
24. Wall, M. E.; Wani, M. C. Annu. Rev. Pharmacol. Toxicol. 1977, 17, 117.
25. Pommier, Y.; Tanizawa, A.; Kohn, K. W. Adv. Pharmacol. 1994, 29B, 73.
26. Prepared by modification of: (a) Wang, H.; Ganesan, A. Tetrahedron Lett. 1998, 39, 9097.
27. (b) Dallavalle, S.; Merlini, L. Tetrahedron Lett. 2002, 43, 1835.
28. Bjornsti, M. A.; Benedetti, P.; Viglianti, G. A.; Wang, J. C. Cancer Res. 1989, 49, 6318.
29. Treatment of the same yeast strain lacking the plasmid with 1 μM 1 or 2 produced no cytotoxicity. Note: cytotoxic agents such as 1 and 2 should be handled with caution.
30. (a) Redinbo, M. R.; Stewart, L.; Kuhn, P.; Champoux, J. J.; Hol. W. G. Science 1998, 279, 1504.
31. (b) Stewart, L.; Redinbo, M. R.; Qui, X.; Hol, W. G.; Champoux, J. J. Science 1998, 279, 1534.
32. (c) Staker, B. L.; Hjerrild, K.; Feese, M. D., Behnke, C. A.; Burgin, A. B.; Stewart, L. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 15387.
33. (a) Fan, Y.; Weinstein, J. N.: Kohn, K. W.; Shi, L. M.; Pommier, Y. J. Med. Chem. 1988, 31, 2216.
34. (b) Kerrigan, J. E.; Pilch, D. S. Biochemistry 2001, 40, 9792.
35. (c) Laco, G. S.; Collins, J. R.; Luke, B. T.; Kroth, H.; Sayer, J. M.; Jerina, D. M.; Pommier, Y. Biochemistry 2002, 41, 1428.
36. Jaxel, C.; Kohn, K. W.; Wani, M. C.; Wall, M. E.; Pommier, Y. Cancer Res. 1989, 49, 1465.
37. Wang, X.; Zhou, X.; Hecht, S. M. Biochemistry 1999, 38, 4374.
38. Hertzberg, R. P.; Caranfa, M. J.; Hecht, S. M. Biochemistry 1989, 28, 4629.
39. 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.
40. (a) Ma, Z.-Z.; Hano, Y.; Nomura, T.; Chen, Y.-J. Heterocycles 1999, 51, 1593.
41. (b) Kelly, T. R.; Chamberland, S.; Silva, R. A. Tetrahedron Lett. 1999, 40, 2723.
42. (c) Molina, P.; Terraga, A.; Gonzalez-Tejero, A. Synthesis-Stuttgart 2000, 11, 1523.
43. (d) Toyota, M.; Komori, C.; Ihara, M. Heterocycles 2002, 56, 101.
44. (e) Osborne, D.; Stevenson, P. J. Tetrahedron Lett. 2002, 43, 5469.
45. (f) Lee, E. S.; Park, J.-G.; Jahng, Y. Tetrahedron Lett. 2003, 44, 1883.
46. (g) Harayama, T.; Morikami, Y.; Shigeta, Y.; Abe, H.; Takeuchi, Y. Synlett 2003, 6, 847.