Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 20, 2009, Pages 7131-7137

  Sperry, Jonathan ^a   Lorenzo Castrillejo, Isabel ^b   Brimble, Margaret A ^a   Machín, Felix ^b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b HOSPITAL UNIVERSITARIO NUESTRA SEÑORA DE CANDELARIA   (Spain)

Author keywords

Pyranonaphthoquinone topoisomerase II

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ELEUTHERIN; GYRASE INHIBITOR; NANAOMYCIN A; THYSANONE; UNCLASSIFIED DRUG; VENTILOQUINONE L;

ARTICLE; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG STRUCTURE; ENZYME INHIBITION; NONHUMAN;

ANTINEOPLASTIC AGENTS; DNA TOPOISOMERASES, TYPE II; ENZYME INHIBITORS; NAPHTHOQUINONES; SACCHAROMYCES CEREVISIAE;

EID: 71749103686     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.08.064     Document Type: Article

References (56)

1. McClendon A.K., and Osheroff N. Mutat. Res. 623 (2007) 83
2. Wang J.C. Nat. Rev. Mol. Cell Biol. 3 (2002) 430
3. Champoux J.J. Annu. Rev. Biochem. 70 (2001) 369
4. Holm C., Goto T., Wang J.C., and Botstein D. Cell 41 (1985) 553
5. Heck M.M.S., and Earnshaw W.C. J. Cell Biol. 103 (1986) 2569
6. Heck M.M.S., Hittelman W.N., and Earnshaw W.C. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 1086
7. Osheroff N., Corbett A.H., and Robinson M.J. Adv. Pharmacol. 29B (1994) 105
8. Corbett A.H., and Osheroff N. Chem. Res. Toxicol. 6 (1993) 585
9. Capranico G., and Zunino F. Eur. J. Cancer. 28A (1992) 2055
10. Osheroff N. Biochemistry 28 (1989) 6157
11. Bjornsti M.A., Benedetti P., Viglianti G.A., and Wang J.C. Cancer Res. 49 (1989) 6318
12. Zunino F., and Capranico G. Anticancer Drug Des. 5 (1990) 307
13. Jannatipour M., Liu Y.X., and Nitiss J.L. J. Biol. Chem. 268 (1993) 18586
14. Tanabe K., Ikegami Y., Ishida R., and Andoh T. Cancer Res. 51 (1991) 4903
15. Fortune J.M., and Osheroff N. J. Biol. Chem. 273 (1998) 17643
16. Mao Y., Yu C., Hsieh T.S., Nitiss J.L., Liu A.A., Wang H.M., and Liu L.F. Biochemistry 38 (1999) 10793
17. Sperry J., Bachu P., and Brimble M.A. Nat. Prod. Rep. 25 (2008) 376
18. Lindsey R.H., Bender R.P., and Osheroff N. Chem. Res. Toxicol. 18 (2005) 761
19. Lindsey R.H., Bromberg K.D., Felix C.A., and Osheroff N. Biochemistry 43 (2004) 7563
20. Neder K., Marton L.J., Liu L.F., and Frydman B. Cell Mol. Biol. 44 (1998) 465
21. Krishnan P., and Bastow K.F. Biochem. Pharmacol. 60 (2000) 1367
22. Bender R.P., Ham A.J.L., and Osheroff N. Biochemistry 46 (2007) 2856
23. Jiminéz-Alonso S., Orellana H.C., Estévez-Braun A., Ravelo A.G., Pérez-Sacau E., and Machín F. J. Med. Chem. 51 (2008) 6761
24. Frydman B., Marton L.J., Sun J.S., Neder K., Nitiak D.T., Liu A.A., Wang H.M., and Mao Y. Cancer Res. 57 (1997) 1402
25. Gibson J.S., Andrey O., and Brimble M.A. Synthesis (2007) 2611
26. Schmid H., Meijer T.M., and Ebnöther A. Helv. Chim. Acta 33 (1950) 595
27. Hara H., Maruyama N., Yamashita S., Hayashi Y., Lee K.H., Bastow K.F., Chairul, Marumoto R., and Imakura Y. Chem. Pharm. Bull. 45 (1997) 1714
28. Hauser F.M., and Rhee R.P. J. Org. Chem. 43 (1978) 178
29. Kraus G.A., and Sugimoto H. Tetrahedron Lett. (1978) 2263
30. Rathwell K., and Brimble M.A. Synthesis (2007) 643
31. Mal D., and Pahari P. Chem. Rev. 107 (2007) 1892
32. Brimble M.A., Duncalf L.J., and Nairn M.R. Nat. Prod. Rep. 16 (1999) 267
33. Brimble M.A., Nairn M.R., and Prabaharan H. Tetrahedron 56 (2000) 1937
34. Bachu P., Sperry J., and Brimble M.A. Tetrahedron 64 (2008) 4827
35. Jammula S.R., Pepalla S.B., Telikepalli H., Rao K.V.J., and Thomson R.H. Phytochemistry 30 (1991) 3741
36. Sperry J.S., Sejberg J.J.P., Stiemke F.M., and Brimble M.A. Org. Biomol. Chem. 7 (2009) 2599
37. Sperry J., Ying Yuen T., and Brimble M.A. Synthesis (2009) 2561
38. Singh S.B., Cordingley M.G., Ball R.G., Smith J.L., Dombrowski A.W., and Goetz M.A. Tetrahedron Lett. 32 (1991) 5279
39. Evans G.E., Leeper F.J., Murphy J.A., and Staunton J. J. Chem. Soc., Chem. Commun. (1979) 205
40. Dodd J.H., and Weinreb S.M. Tetrahedron Lett. (1979) 3593
41. Omura S., Tanaka H., Koyama Y., Oiwa R., Katagiri M., Awaya J., Nagai T., and Hata T. J. Antibiot. (Tokyo) 27 (1974) 363
42. Tanaka H., Marumo H., Nagai T., Okada M., Taniguchi K., and Omura S. J. Antibiot. (Tokyo) 28 (1975) 925
43. Nakagawa A., Fukamachi N., Yamaki K., Hayashi M., Ohishi S., Kobayashi B., and Omura S. J. Antibiot. (Tokyo) 40 (1987) 1075
44. Tatsuta K., Akimoto K., Annaka M., Ohno Y., and Kinoshita M. Bull. Chem. Soc. Jpn. 58 (1985) 1699
45. Brimble M.A., Bachu P., and Sperry J. Synthesis (2007) 2887
46. Bachu P., Sperry J., and Brimble M.A. Tetrahedron 64 (2008) 3343
47. Buchanan M.S., Gill M., and Yu J. J. Chem. Soc., Perkin Trans. 1 (1997) 919
48. Buchanan M.S., Gill M., and Yu J. Aust. J. Chem. 50 (1997) 1081
49. Sperry J., Gibson J.S., Sejberg J.J.P., and Brimble M.A. Org. Biomol. Chem. 6 (2008) 4261
50. Spitzner J.R., Chung I.K., and Muller M.T. Nucleic Acids Res. 18 (1990) 1
51. Nitiss J., and Wang J.C. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 7501
52. Perego P., Jimenez G.S., Gatti L., Howell S.B., and Zunino F. Pharmacol. Rev. 52 (2000) 477
53. Bey E.A., Bentle M.S., Reinicke K.E., Dong Y., Yang C.R., Girard L., Minna J.D., Bornmann W.G., Gao J.M., and Boothman D.A. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 11832
54. Pink J.J., Planchon S.M., Tagliarino C., Varnes M.E., Siegel D., and Boothman D.A. J. Biol. Chem. 275 (2000) 5416
55. Meng L.H., and Ding J. Acta Pharm. Sin. 28 (2007) 1460
56. Casey J.T., O'Cleirigh C., Walsh P.K., and O'Shea D.G. J. Microbiol. Methods 58 (2004) 327