11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8598-8606

  Feng, Wei ^a   Satyanarayana, Mavurapu ^a   Tsai, Yuan Chin ^b   Liu, Angela A ^b   Liu, Leroy F ^b,c   LaVoie, Edmond J ^a,c  

^a RUTGERS UNIVERSITY   (United States)

^b RUTGERS ROBERT WOOD JOHNSON MEDICAL SCHOOL   (United States)

^c RUTGERS CANCER INSTITUTE OF NEW JERSEY   (United States)

Author keywords

Antitumor agents; Benzo i phenanthridines; Cytotoxicity; Multidrug resistance; Photocyclization; Topoisomerase I

Indexed keywords

2,3 DIMETHOXY 8,9 METHYLENEDIOXYBENZO[I]PHENANTHRIDINE DERIVATIVE; DNA TOPOISOMERASE; PHENANTHRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DNA TOPOISOMERASES, TYPE I; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; LEUKEMIA, LYMPHOID; PHENANTHRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 51449119022     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.018     Document Type: Article

References (35)

1. Champoux J.J. Annu. Rev. Biochem. 70 (2001) 369
2. Wang J.C. Nat. Rev. Mol. Cell Biol. 3 (2002) 430
3. Li T.K., and Liu L.F. Annu. Rev. Pharmacol. Toxicol. 41 (2001) 53
4. Pommier Y. Nat. Rev. Cancer 6 (2006) 789
5. Hsaing Y.H., Hertsberg R., Hecht S., and Liu L.F. J. Biol. Chem. 260 (1985) 14873
6. Burke T.G., and Mi Z. J. Med. Chem. 36 (1993) 2580
7. Burke T.G., and Mi Z. Anal. Biochem. 212 (1993) 285
8. Bom D., Curran D.P., Chavan A.J., Kruszewski S., Zimmer S., Fraley K.A., and Burke T.G. J. Med. Chem. 42 (1999) 3018
9. Chu X., Kato Y., and Sugiyama Y. Cancer Res. 57 (1997) 1934
10. Kawabata S., Oka M., Shiozawa K., Tsukamoto K., Nakatomi K., Soda H., Fududa M., Ikegami Y., Sugahara K., Yamada Y., Kamihira S., Doyle L.A., Ross D.D., and Kohno S. Biochem. Biophys. Res. Commun. 280 (2001) 1216
11. Robey R.W., Medina-Perez W.Y., Nishiyama K., Lahusen T., Miyake K., Litman T., Senderowicz A.M., Ross D.D., and Bates S.E. Clin. Cancer Res. 7 (2001) 145
12. Mattern M.R., Hofmann G.A., Polsky R.M., Funk L.R., McCabe F.L., and Johnson R.K. Oncol. Res. 5 (1993) 467
13. Erlichman C., Boerner S.A., Hallgren C.G., Spieker R., Wang X.-Y., James C.D., Scheffer G.L., Maliepaard M., Ross D.D., Bible K.C., and Kaufmann S.H. Cancer Res. 61 (2001) 739
14. Yang C.-H., Schneider E., Kuo M.-L., Volk E.L., Rocchi E., and Chen T.-C. Biochem. Pharmacol. 60 (2000) 831
15. Ross D.D. Leukemia 14 (2000) 467-473
16. Ruchelman A.L., Singh S.K., Wu X.H., Ray A., Yang J.-M., Li T.-K., Liu A., Liu L.F., and LaVoie E.J. Bioorg. Med. Chem. Lett. 12 (2002) 3333
17. Ruchelman A.L., Singh S.K., Ray A., Wu X., Yang J.-M., Li T.-K., Liu A., Liu L.F., and LaVoie E.J. Bioorg. Med. Chem. 11 (2003) 2061
18. Li T.-K., Houghton P.J., Desai S.D., Daroui P., Liu A.A., Hars E.S., Ruchelman A.L., LaVoie E.J., and Liu L.F. Cancer Res. 63 (2003) 8400
19. Ruchelman A.L., Zhou N., Liu A., Liu L.F., and LaVoie E.J. J. Med. Chem. 48 (2005) 792
20. Ruchelman A.L., Singh S.K., Ray A., Wu X., Yang J.-M., Zhou N., Liu A., Liu L.F., and LaVoie E.J. Bioorg. Med. Chem. 12 (2004) 795
21. Corey E.J., and Fuchs P.L. Tetrahedron Lett. 13 (1972) 3769
22. Sai H., Ogiku T., Nishitani T., Hiramatsu H., Horikawa H., and Iwasaki T. Synthesis (1995) 582
23. Margolis B.J., Long K.A., Laird D.L., Ruble J.C., and Pulley S.R. J. Org. Chem. 72 (2007) 2232
24. Stille J.K. Angew. Chem. Int. Ed. 25 (1986) 508
25. Amin S., Hecht S.S., LaVoie E., and Hoffmann D. J. Med. Chem. 22 (1979) 1336
26. Ruchelman A.L., Zhu S., Zhou N., Liu A., Liu L.F., and LaVoie E.J. Bioorg. Med. Chem. Lett. 15 (2005) 5585
27. Zhu S., Ruchelman A.L., Zhou N., Liu A., Liu L.F., and LaVoie E.J. Bioorg. Med. Chem. 13 (2005) 6782
28. Andoh T., Ishii K., Suzuki Y., Ikegami Y., Kusunoki Y., Takemoto Y., and Okada K. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 5565
29. Woessner R.D., Eng W.K., Hofmann G.A., Rieman D.J., McCabe F.L., Hertzberg R.P., Mattern M.R., Tan K.B., and Johnson R.K. Oncol. Res. 4 (1992) 481
30. Gervasoni Jr. J.E., Fields S.Z., Krishna S., Baker M.A., Rosado M., Thuraisamy K., Hindenburg A.A., and Taub R.N. Cancer Res. 51 (1991) 4955
31. Makhey D., Yu C., Liu A., Liu L.F., and LaVoie E.J. Bioorg. Med. Chem. 8 (2000) 1171
32. Maniatis T., Fritsch E.F., and Sambrook J. Molecular Cloning, a Laboratory Manual (2000), Cold Spring Harbor Laboratory, Cold Spring Harbor, NY pp 149-185
33. Tewey K.M., Rowe T.C., Yang L., Hallogan B.C., and Liu L.F. Science 226 (1984) 466
34. Gatto B., Sanders M.M., Yu C., Wu H.-Y., Makhey D., LaVoie E.J., and Liu L.F. Cancer Res. 56 (1996) 2795
35. Wang H., Mao Y., Chen A., Zhou N., LaVoie E.J., and Liu L.F. Biochemistry 40 (2001) 3316