Synthesis and topoisomerase I inhibitory properties of luotonin A analogues

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 23, 2004, Pages 6287-6299

  Cagir, Ali ^a   Eisenhauer, Brian M ^a   Gao, Rong ^a   Thomas, Shannon J ^a   Hecht, Sidney M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Camptothecin; Luotonin A; Structure activity relationships; Topoisomerase I DNA inhibition

Indexed keywords

1,2 DIHYDROPYRROLO[3,4 B]QUINOLIN 3 ONE; 16 HYDROXYLUOTONIN A; 16 METHOXYLUOTONIN A; 16,17,18,19 TETRAHYDROLUOTONIN A; 17 CHLOROISOLUOTONIN A; 17 CHLOROLUOTONIN A; 17 CYANOISOLUOTONIN A; 17 CYANOLUOTONIN A; 17 FLUOROISOLUOTONIN A; 17 FLUOROLUOTONIN A; 17,18 DIFLUOROLUOTONIN A; 17,18 DIMETHOXYLUOTONIN A; 17,18,19 TRIMETHOXYLUOTONIN A; 18 METHYLLUOTONIN A; ANTHRANILIC ACID DERIVATIVE; CAMPTOTHECIN; DICHLOROMETHANE; DNA; DNA TOPOISOMERASE; DNA TOPOISOMERASE INHIBITOR; ISOLUOTONIN A; LUOTONIN A; LUOTONIN A DERIVATIVE; PHOSPHORUS DERIVATIVE; PHOSPHORUS OXYCHLORIDE; QUINOLINE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; COVALENT BOND; CYTOTOXICITY TEST; DRUG ACTIVITY; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; ISOMER; PROTEIN EXPRESSION; PROTEIN STABILITY; REACTION ANALYSIS; YEAST;

DNA; DNA TOPOISOMERASES, TYPE I; HUMANS; ORGANISMS, GENETICALLY MODIFIED; PYRROLES; QUINONES; SACCHAROMYCES CEREVISIAE; SOLVENTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 7444265432     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.08.052     Document Type: Article

References (58)

1. M.E. Wall, M.C. Wani, C.E. Cook, K.H. Palmer, A.T. McPhail, and G.A. Sim J. Am. Chem. Soc. 88 1966 3888
2. C.H. Takimoto, J. Wright, and S.G. Arbuck Biochim. Biophys. Acta 1400 1998 107
3. J. O'Leary, and F.M. Muggia Eur. J. Cancer 34 1998 1500
4. L.B. Saltz, J.V. Cox, C. Blanke, L.S. Rosen, L. Fechrenbacher, M.J. Moore, J.A. Maroun, S.P. Ackland, P.K. Locker, N. Pirotta, G.L. Elfring, and L.L. Miller New Engl. J. Med. 343 2000 905
5. R.F. Ozols Int. J. Gynecol. Cancer 10 2000 33
6. U. Vanhoefer, A. Harstrick, W. Achterrath, S. Cao, S. Seeber, and Y.M. Rustum J. Clin. Oncol. 19 2001 1501
7. H. Ulukan, and P.W. Swaan Drugs 62 2002 2039
8. R. Garcia-Carbenero, and J.G. Supko Clin. Cancer Res. 8 2002 641
9. M.E. Wall, M.C. Wani, A.W. Nicholas, G. Manikumar, C. Tele, L. Moore, A. Truesdale, P. Leitner, and J.M. Besterman J. Med. Chem. 36 1993 2689
10. T. Yaegashi, S. Sawada, H. Nagata, T. Furuta, T. Yokokura, and T. Miyasaka Chem. Pharm. Bull. 42 1994 2518
11. K. Lackey, J.M. Besterman, W. Fletcher, P. Leitner, B. Morton, and D.D. Sternbach J. Med. Chem. 38 1995 906
12. M.J. Luzzio, J.M. Besterman, D.L. Emerson, M.G. Evans, K. Lackey, P.L. Leitner, G. McIntyre, B. Morton, P.L. Myers, M. Peel, J.M. Sisco, D.D. Sternbach, W.-Q. Tong, A. Truesdale, D.E. Uehling, A. Vuong, and J. Yates J. Med. Chem. 38 1995 395
13. K. Lackey, D.D. Sternbach, D.K. Croom, D.L. Emerson, M.G. Evans, P.L. Leitner, M.J. Luzzio, G. McIntyre, A. Vuong, J. Yates, and J.M. Besterman J. Med. Chem. 39 1996 713
14. O. Lavergne, L. Lesueur-Ginot, F. PlaRodas, and D.C.H. Bigg Bioorg. Med. Chem. Lett. 7 1997 2235
15. O. Lavergne, L. Lesueur-Ginot, F. PlaRodas, P.G. Kasprzyk, J. Pommier, D. Demarquay, G. Prevost, G. Ulibarri, A. Rolland, A.-M. Schiano-Liberatore, J. Harnett, D. Pons, J. Camara, and D.C.H. Bigg J. Med. Chem. 41 1998 5410
16. A.E. Garbarda, W. Du, T. Isarno, R.S. Tangirala, and D.P. Curran Tetrahedron 58 2002 6329
17. J.C. Wang Annu. Rev. Biochem. 65 1996 635
18. J.C.Q. Wang Rev. Biophys. 31 1998 107
19. Y. Pommier Biochimie 80 1998 255
20. J. Champoux J. Annu. Rev. Biochem. 70 2002 369
21. Y. Pommier, P. Pourquier, Y. Fan, and D. Strumberg Biochim. Biophys. Acta 1400 1998 83
22. M.R. Redinbo, J.J. Champoux, and W.G.J. Hol Biochemistry 39 2000 6832
23. Y.-H. Hsiang, R. Hertzberg, S. Hecht, and L.F. Liu J. Biol. Chem. 260 1985 14873
24. Y.-H. Hsiang, L.F. Liu, M.E. Wall, M.C. Wani, A.W. Nicholas, G. Manikumar, S. Kirschenbaum, R. Silber, and M. Potmesil Cancer Res. 49 1989 4385
25. J.M. Covey, C. Jaxel, K.W. Kohn, and Y. Pommier Cancer Res. 49 1989 5016
26. Y.-H. Hsiang, M.G. Lihou, and L.F. Liu Cancer Res. 49 1989 5077
27. Y. Fan, J.N. Weinstein, K.W. Kohn, L.M. Shi, and Y. Pommmier J. Med. Chem. 41 1998 2216
28. J.E. Kerrigan, and D.S. Pilch Biochemistry 40 2001 9792
29. G.S. Laco, J.R. Collins, B.T. Luke, H. Kroth, J.M. Sayer, D.M. Jerina, and Y. Pommier Biochemistry 41 2002 1428
30. M.R. Redinbo, L. Stewart, P. Kuhn, J.J. Champoux, and W.G.J. Hol Science 279 1998 1504
31. B.L. Staker, K. Hjerrild, M.D. Feese, C.A. Behnke, A.B. Burgin Jr., and L. Stewart Proc. Natl. Acad. Sci. U.S.A. 99 2002 15387
32. L. Stewart, M.R. Redinbo, X. Qui, W.G. Hol, and J.J. Champoux Science 279 1998 1534
33. C. Jaxel, K.W. Kohn, M.C. Wani, M.E. Wall, and Y. Pommier Cancer Res. 49 1989 1465
34. X. Wang, X. Zhou, and S.M. Hecht Biochemistry 38 1999 4374
35. R.P. Hertzberg, M.J. Caranfa, and S.M. Hecht Biochemistry 28 1989 4629
36. A. Cagir, S.H. Jones, R. Gao, B.M. Eisenhauer, and S.M. Hecht J. Am. Chem. Soc. 125 2003 13628
37. X.-H. Xiao, G.-L. Qou, H.-L. Wang, L.-S. Lui, Y.-L. Zheng, Z.-J. Jia, and Z.-B. Deng Chin. J. Pharmacol. Toxicol. 1988 232
38. Z.Z. Ma, Y. Hano, T. Nomura, and Y.J. Chen Heterocycles 46 1997 541
39. M.A. Bjornsti, P. Benedetti, G.A. Viglianti, and J.C. Wang Cancer Res. 49 1989 6318
40. A. Cagir, S.H. Jones, B.M. Eisenhauer, R. Gao, and S.M. Hecht Bioorg. Med. Chem. Lett. 14 2004 2051
41. E.S. Lee, J.-G. Park, and Y. Jahng Tetrahedron Lett. 44 2003 1883
42. D. Osborne, and P.J. Stevenson Tetrahedron Lett. 43 2002 5469
43. S. Dallavalle, and L. Merlini Tetrahedron Lett. 43 2002 1835
44. J.S. Yadav, and B.V.S. Reddy Tetrahedron Lett. 43 2002 1905
45. H. Wang, and A. Ganesan Tetrahedron Lett. 39 1998 9097
46. Z.-Z. Ma, Y. Hano, T. Nomura, and Y.-J. Chen Heterocycles 51 1999 1593
47. T.R. Kelly, S. Chamberland, and R.A. Silva Tetrahedron Lett. 40 1999 2723
48. P. Molina, A. Tarraga, and A. Gonzalez-Tejero Synthesis-Stuttgart 11 2000 1523
49. M. Toyota, C. Komori, and M. Ihara Heterocycles 56 2002 101
50. T. Harayama, Y. Morikami, Y. Shigeta, H. Abe, and Y. Takeuchi Synlett 6 2003 847
51. S.B. Mhaske, and N.P. Argade J. Org. Chem. 69 2004 14563
52. S. Danishefsky, T.A. Bryson, and J. Puthenpurayil J. Org. Chem. 40 1975 796
53. T. Sugasawa, T. Toyota, K. Sasakura, and T. Hidaka Chem. Pharm. Bull. 19 1971 1971
54. T. Tanaka, K. Mashimo, and M. Wagatsuma Tetrahedron Lett. 30 1971 2803
55. Repetition of these experiments at 50 μM concentration indicated surprisingly little difference, presumably reflecting the limited aqueous solubility of the luotonin A analogues
56. M.E. Wall, M.C. Wani, A.W. Nicholas, G. Manikumar, G. Tele, L. Moore, A. Truesdale, P. Leitner, and J.M. Besterman J. Med. Chem. 36 1993 2689
57. W.D. Kingsbury, J.C. Boehm, D.R. Jakas, K.G. Holden, S.M. Hecht, G. Gallagher, M.J. Caranfa, F.L. McCabe, L.F. Faucette, R.K. Johnson, and R.P. Hertzberg J. Med. Chem. 34 1991 98
58. M.L. Quan, W.C. Dominguez, J.V. Duncia, C.A. Kettner, C.D. Ellis, A.Y. Liauw, J.M. Park, J.B. Santella, R.M. Knabb, M.J. Thoolen, P.C. Weber, and R.R. Wexler Bioorg. Med. Chem. Lett. 13 1997 1595