Activity of indenoisoquinolines against African trypanosomes

Antimicrobial Agents and Chemotherapy

Volumn 53, Issue 1, 2009, Pages 123-128

  Bakshi, Rahul P ^a   Sang, Dongpei ^a   Morrell, Andrew ^b   Cushman, Mark ^b   Shapiro, Theresa A ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA TOPOISOMERASE; INDENOISOQUINOLINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AFRICAN TRYPANOSOMIASIS; AMINO TERMINAL SEQUENCE; ANIMAL CELL; ANTIPROTOZOAL ACTIVITY; ARTICLE; CARBOXY TERMINAL SEQUENCE; COMPLEX FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA SYNTHESIS; IN VIVO STUDY; MOUSE; NONHUMAN; PARASITEMIA; PRIORITY JOURNAL; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; TRYPANOSOMA BRUCEI;

ANIMALS; DNA, PROTOZOAN; ISOQUINOLINES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI;

EID: 59749093161     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00650-07     Document Type: Article

References (41)

1. Antony, S., K. K. Agama, Z. H. Miao, K. Takagi, M. H. Wright, A. I. Robles, L. Varticovski, M. Nagarajan, A. Morrell, M. Cushman, and Y. Pommier. 2007. Novel indenoisoquinolines NSC 725776 and NSC 724998 produce persistent topoisomerase I cleavage complexes and overcome multidrug resistance. Cancer Res. 67:10397-10405.
2. Bacchi, C. J., M. Vargas, D. Rattendi, B. Goldberg, and W. Zhou. 1998. Antitrypanosomal activity of a new triazine derivative, SIPI 1029, in vitro and in model infections. Antimicrob. Agents Chemother. 42:2718-2721.
3. Bacchi, C. J., and N. Yarlett. 2002. Polyamine metabolism as chemotherapeutic target in protozoan parasites. Mini Rev. Med. Chem. 2:553-563.
4. Bakshi, R. P., and T. A. Shapiro. 2003. DNA topoisomerases as targets for antiprotozoal therapy. Mini Rev. Med. Chem. 3:597-608.
5. Bakshi, R. P., and T. A. Shapiro. 2004. RNA interference of Trypanosoma brucei topoisomerase IB: both subunits are essential. Mol. Biochem. Parasitol. 136:249-255.
6. Berriman, M., E. Ghedin, C. Hertz-Fowler, G. Blandin, H. Renauld, D. C. Bartholomeu, N. J. Lennard, E. Caler, N. E. Hamlin, B. Haas, U. Bohme, L. Hannick, M. A. Aslett, J. Shallom, L. Marcello, L. Hou, B. Wickstead, U. C. Alsmark, C. Arrowsmith, R. J. Atkin, A. J. Barron, F. Bringaud, K. Brooks, M. Carrington, I. Cherevach, T. J. Chillingworth, C. Churcher, L. N. Clark, C. H. Corton, A. Cronin, R. M. Davies, J. Doggett, A. Djikeng, T. Feldblyum, M. C. Field, A. Fraser, I. Goodhead, Z. Hance, D. Harper, B. R. Harris, H. Hauser, J. Hostetler, A. Ivens, K. Jagels, D. Johnson, J. Johnson, K. Jones, A. X. Kerhornou, H. Koo, N. Larke, S. Landfear, C. Larkin, V. Leech, A. Line, A. Lord, A. Macleod, P. J. Mooney, S. Moule, D. M. Martin, G. W. Morgan, K. Mungall, H. Norbertczak, D. Ormond, G. Pai, C. S. Peacock, J. Peterson, M. A. Quail, E. Rabbinowitsch, M. A. Rajandream, C. Reitter, S. L. Salzberg, M. Sanders, S. Schobel, S. Sharp, M. Simmonds, A. J. Simpson, L. Tallon, C. M. Turner, A. Tait, A. R. Tivey, S. Van Aken, D. Walker, D. Wanless, S. Wang, B. White, O. White, S. Whitehead, J. Woodward, J. Wortman, M. D. Adams, T. M. Embley, K. Gull, E. Ullu, J. D. Barry, A. H. Fairlamb, F. Opperdoes, B. G. Barrell, J. E. Donelson, N. Hall, C. M. Fraser, et al. 2005. The genome of the African trypanosome Trypanosoma brucei. Science 309:416-422.
7. Bodley, A. L., A. K. Chakraborty, S. Xie, C. Burri, and T. A. Shapiro. 2003. An unusual type IB topoisomerase from African trypanosomes. Proc. Natl. Acad. Sci. USA 100:7539-7544.
8. Bodley, A. L., M. W. McGarry, and T. A. Shapiro. 1995. Drug cytotoxicity assay for African trypanosomes and Leishmania species. J. Infect. Dis. 172:1157-1159.
9. Bodley, A. L., and T. A. Shapiro. 1995. Molecular and cytotoxic effects of camptothecin, a topoisomerase I inhibitor, on trypanosomes and Leishmania. Proc. Natl. Acad. Sci. USA 92:3726-3730.
10. Bodley, A. L., M. C. Wani, M. E. Wall, and T. A. Shapiro. 1995. Antitrypanosomal activity of camptothecin analogs. Structure-activity correlations. Biochem. Pharmacol. 50:937-942.
11. Burri, C., A. L. Bodley, and T. A. Shapiro. 1996. Topoisomerases in kinetoplastids. Parasitol. Today 12:226-231.
12. Cook, J. A., and J. B. Mitchell. 1989. Viability measurements in mammalian cell systems. Anal. Biochem. 179:1-7.
13. Das, A., A. Dasgupta, T. Sengupta, and H. K. Majumder. 2004. Topoisomerases of kinetoplastid parasites as potential chemotherapeutic targets. Trends Parasitol. 20:381-387.
14. Docampo, R., and S. N. Moreno. 2003. Current chemotherapy of human African trypanosomiasis. Parasitol. Res. 90(Supp. 1):S10-S13.
15. Ersfeld, K., S. E. Melville, and K. Gull. 1999. Nuclear and genome organization of Trypanosoma brucei. Parasitol. Today 15:58-63.
16. Fortune, J. M., and N. Osheroff. 2000. Topoisomerase II as a target for anticancer drugs: when enzymes stop being nice. Prog. Nucleic Acid Res. Mol. Biol. 64:221-253.
17. Holford, N. H., and L. B. Sheiner. 1981. Understanding the dose-effect relationship: clinical application of pharmacokinetic- pharmacodynamic models. Clin. Pharmacokinet. 6:429-453.
18. Hsiang, Y. H., R. Hertzberg, S. Hecht, and L. F. Liu. 1985. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J. Biol. Chem. 260:14873-14878.
19. Ioanoviciu, A., S. Antony, Y. Pommier, B. L. Staker, L. Stewart, and M. Cushman. 2005. Synthesis and mechanism of action studies of a series of norindenoisoquinoline topoisomerase I poisons reveal an inhibitor with a flipped orientation in the ternary DNA-enzyme-inhibitor complex as determined by X-ray crystallographic analysis. J. Med. Chem. 48:4803-4814.
20. Kohlhagen, G., K. D. Paull, M. Cushman, P. Nagafuji, and Y. Pommier. 1998. Protein-linked DNA strand breaks induced by NSC 314622, a novel noncamptothecin topoisomerase I poison. Mol. Pharmacol. 54:50-58.
21. Leppard, J. B., and J. J. Champoux. 2005. Human DNA topoisomerase I: relaxation, roles, and damage control. Chromosoma 114:75-85.
22. Liu, L. F., S. D. Desai, T. K. Li, Y. Mao, M. Sun, and S. P. Sim. 2000. Mechanism of action of camptothecin. Ann. N. Y. Acad. Sci. 922:1-10.
23. Mattern, M. R., S. M. Mong, H. F. Bartus, C. K. Mirabelli, S. T. Crooke, and R. K. Johnson. 1987. Relationship between the intracellular effects of camptothecin and the inhibition of DNA topoisomerase I in cultured L1210 cells. Cancer Res. 47:1793-1798.
24. Maxwell, A. 1999. DNA gyrase as a drug target. Biochem. Soc. Trans. 27:48-53.
25. McHugh, M. M., R. D. Sigmund, and T. A. Beerman. 1990. Effects of minor groove binding drugs on camptothecin-induced DNA lesions in L1210 nuclei. Biochem. Pharmacol. 39:707-714.
26. Morrell, A., S. Antony, G. Kohlhagen, Y. Pommier, and M. Cushman. 2004. Synthesis of nitrated indenoisoquinolines as topoisomerase I inhibitors. Bioorg. Med. Chem. Lett. 14:3659-3663.
27. Morrell, A., M. Jayaraman, M. Nagarajan, B. M. Fox, M. R. Meckley, A. Ioanoviciu, Y. Pommier, S. Antony, M. Hollingshead, and M. Cushman. 2006. Evaluation of indenoisoquinoline topoisomerase I inhibitors using a hollow fiber assay. Bioorg. Med. Chem. Lett. 16:4395-4399.
28. Nagarajan, M., A. Morrell, B. C. Fort, M. R. Meckley, S. Antony, G. Kohlhagen, Y. Pommier, and M. Cushman. 2004. Synthesis and anticancer activity of simplified indenoisoquinoline topoisomerase I inhibitors lacking substituents on the aromatic rings. J. Med. Chem. 47:5651-5661.
29. Nagarajan, M., A. Morrell, A. Ioanoviciu, S. Antony, G. Kohlhagen, K. Agama, M. Hollingshead, Y. Pommier, and M. Cushman. 2006. Synthesis and evaluation of indenoisoquinoline topoisomerase I inhibitors substituted with nitrogen heterocycles. J. Med. Chem. 49:6283-6289.
30. Nagarajan, M., X. Xiao, S. Antony, G. Kohlhagen, Y. Pommier, and M. Cushman. 2003. Design, synthesis, and biological evaluation of indenoisoquinoline topoisomerase I inhibitors featuring polyamine side chains on the lactam nitrogen. J. Med. Chem. 46:5712-5724.
31. O'Sullivan, M. C., Q. Zhou, Z. Li, T. B. Durham, D. Rattendi, S. Lane, and C. J. Bacchi. 1997. Polyamine derivatives as inhibitors of trypanothione reductase and assessment of their trypanocidal activities. Bioorg. Med. Chem. 5:2145-2155.
32. Pantazis, P., J. A. Early, A. J. Kozielski, J. T. Mendoza, H. R. Hinz, and B. C. Giovanella. 1993. Regression of human breast carcinoma tumors in immunodeficient mice treated with 9-nitrocamptothecin: differential response of nontumorigenic and tumorigenic human breast cells in vitro. Cancer Res. 53:1577-1582.
33. Pantazis, P., H. R. Hinz, J. T. Mendoza, A. J. Kozielski, L. J. Williams, Jr., J. S. Stehlin, Jr., and B. C. Giovanella. 1992. Complete inhibition of growth followed by death of human malignant melanoma cells in vitro and regression of human melanoma xenografts in immunodeficient mice induced by camptothecins. Cancer Res. 52:3980-3987.
34. Pommier, Y., P. Pourquier, Y. Fan, and D. Strumberg. 1998. Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme. Biochim. Biophys. Acta 1400:83-105.
35. Staker, B. L., M. D. Feese, M. Cushman, Y. Pommier, D. Zembower, L. Stewart, and A. B. Burgin. 2005. Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex. J. Med. Chem. 48:2336-2345.
36. Strumberg, D., Y. Pommier, K. Paull, M. Jayaraman, P. Nagafuji, and M. Cushman. 1999. Synthesis of cytotoxic indenoisoquinoline topoisomerase I poisons. J. Med. Chem. 42:446-457.
37. Trask, D. K., J. A. DiDonato, and M. T. Muller. 1984. Rapid detection and isolation of covalent DNA/protein complexes: application to topoisomerase I and II. EMBO J. 3:671-676.
38. Wang, J. C. 2002. Cellular roles of DNA topoisomerases: a molecular perspective. Nat. Rev. Mol. Cell Biol. 3:430-440.
39. Wani, M. C., A. W. Nicholas, G. Manikumar, and M. E. Wall. 1987. Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations. J. Med. Chem. 30:1774-1779.
40. Welburn, S. C., and M. Odiit. 2002. Recent developments in human African trypanosomiasis. Curr. Opin. Infect. Dis. 15:477-484.
41. Witola, W. H., N. Inoue, K. Ohashi, and M. Onuma. 2004. RNA-interference silencing of the adenosine transporter-1 gene in Trypanosoma evansi confers resistance to diminazene aceturate. Exp. Parasitol. 107:47-57.