Design, synthesis and antimalarial/anticancer evaluation of spermidine linked artemisinin conjugates designed to exploit polyamine transporters in Plasmodium falciparum and HL-60 cancer cell lines

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 7, 2010, Pages 2586-2597

  Chadwick, James ^a   Jones, Michael ^a   Mercer, Amy E ^a   Stocks, Paul A ^b   Ward, Stephen A ^b   Park, B Kevin ^a   O'Neill, Paul M ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b LIVERPOOL SCHOOL OF TROPICAL MEDICINE   (United Kingdom)

Author keywords

Artemisinin; Cancer; Malaria; Polyamine

Indexed keywords

ARTEMISININ DERIVATIVE; SPERMIDINE DERIVATIVE;

ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN HL 60; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; ARTEMISININS; BIOGENIC POLYAMINES; CARRIER PROTEINS; COLORING AGENTS; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HL-60 CELLS; HUMANS; PLASMODIUM FALCIPARUM; SPERMIDINE; TETRAZOLIUM SALTS; THIAZOLES;

PLASMODIUM FALCIPARUM;

EID: 77950030227     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.02.035     Document Type: Article

References (50)

1. Liu J.-M., Ni M.-Y., Fan J.-F., Tu Y.-Y., Wu Z.-H., Wu Y.-L., and Chou W.-S. Acta Chim. Sinica 37 (1979) 129
2. Woerdenbag H.J., Moskal T.A., Pras N., Malingre T.M., El Feraly F.S., Kampinga H.H., and Konings A.W.T. J. Nat. Prod. 56 (1993) 849
3. Beekman A.C., Woerdenbag H.J., Kampinga H.H., and Konings A.W.T. Phytother. Res. 10 (1996) 140
4. Beekman A.C., Barentsen A.R.W., Woerdenbag H.J., VanUden W., Pras N., Konings A.W.T., ElFeraly F.S., Galal A.M., and Wikstrom H.V. J. Nat. Prod. 60 (1997) 325
5. Beekman A.C., Wierenga P.K., Woerdenbag H.J., Van Uden W., Pras N., Konings A.W.T., El-Feraly F.S., Galal A.M., and Wikstrom H.V. Planta Med. 64 (1998) 615
6. Jeyadevan J.P., Bray P.G., Chadwick J., Mercer A.E., Byrne A., Ward S.A., Park B.K., Williams D.P., Cosstick R., Davies J., Higson A.P., Irving E., Posner G.H., and O'Neill P.M. J. Med. Chem. 47 (2004) 1290
7. Posner G.H., Ploypradith P., Hapangama W., Wang D.S., Cumming J.N., Dolan P., Kensler T.W., Klinedinst D., Shapiro T.A., Zheng Q.Y., Murray C.K., Pilkington L.G., Jayasinghe L.R., Bray J.F., and Daughenbaugh R. Bioorg. Med. Chem. 5 (1997) 1257
8. Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.H., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S.J., and Shapiro T.A. J. Med. Chem. 42 (1999) 4275
9. Jung M., Lee S., Ham J., Lee K., Kim H., and Kim S.K. J. Med. Chem. 46 (2003) 987
10. Posner G.H., D'Angelo J., O'Neill P.M., and Mercer A. Expert Opin. Ther. Patents 16 (2006) 1665
11. Jaracz S., Chen J., Kuznetsova L.V., and Ojima L. Bioorg. Med. Chem. 13 (2005) 5043
12. Nakase I., Gallis B., Takatani-Nakase T., Oh S., Lacoste E., Singh N.P., Goodlett D.R., Tanaka S., Futaki S., Lai H., and Sasaki T. Cancer Lett. 274 (2009) 290
13. Cohen G.M., Cullis P.M., Hartley J.A., Mather A., Symons M.C.R., and Wheelhouse R.T. J. Chem. Soc., Chem. Commun. (1992) 298
14. Holley J.L., Mather A., Wheelhouse R.T., Cullis P.M., Hartley J.A., Bingham J.P., and Cohen G.M. Cancer Res. 52 (1992) 4190
15. Li Y.L., Eiseman J.L., Sentz D.L., Rogers F.A., Pan S.S., Hu L.T., Egorin M.J., and Callery P.S. J. Med. Chem. 39 (1996) 339
16. Phanstiel O., Price H.L., Wang L., Juusola J., Kline M., and Shah S.M. J. Org. Chem. 65 (2000) 5590
17. Porter C.W., Bergeron R.J., and Stolowich N.J. Cancer Res. 42 (1982) 4072
18. Siddiqui A.Q., Merson-Davies L., and Cullis P.M. J. Chem. Soc., Perkin Trans. 1 (1999) 3243
19. Stark P.A., Thrall B.D., Meadows G.G., and Abdelmonem M.M. J. Med. Chem. 35 (1992) 4264
20. Wang Q., Wu L.M., Zhao Y., Zhang X.L., and Wang N.P. Yaoxue Xuebao 37 (2002) 477
21. Cohen S.S.A. A Guide to the Polyamines (1998), Oxford University Press, New York
22. Thomas T., and Thomas T.J. Cell. Mol. Life Sci. 58 (2001) 244
23. Seppanen P., Alhonenhongisto L., and Janne J. Eur. J. Biochem. 110 (1980) 7
24. Seppanen P., Alhonenhongisto L., and Janne J. Biochim. Biophys. Acta 674 (1981) 169
25. McCormack S.A., and Johnson L.R. Am. J. Physiol. 256 (1989) G868
26. Felschow D.M., Mi Z., Stanek J., Frei J., and Porter C.W. Biochem. J. 328 (1997) 889
27. Rinehart C.A., and Chen K.Y. J. Biol. Chem. 259 (1984) 4750
28. Minchin R.F., Martin R.L., and Ilett K.F. Life Sci. 45 (1989) 63
29. Cullis P.M., Green R.E., Merson-Davies L., and Travis N. Chem. Biol. 6 (1999) 717
30. Bergeron R.J., Feng Y., Weimar W.R., McManis J.S., Dimova H., Porter C., Raisler B., and Phanstiel O. J. Med. Chem. 40 (1997) 1475
31. Bergeron R.J., McManis J.S., Weimar W.R., Schreier K.M., Gao F.L., Wu Q.H., Ortizocasio J., Luchetta G.R., Porter C., and Vinson J.R.T. J. Med. Chem. 38 (1995) 2278
32. Seiler N., Delcros J.G., and Moulinoux J.P. Int. J. Biochem. Cell Biol. 28 (1996) 843
33. Feuerstein B.G., Williams L.D., Basu H.S., and Marton L.J. J. Cell. Biochem. 46 (1991) 37
34. Wu W.M., Yao Z.J., Wu Y.L., Kun J.A., Wang Y.F., Chen H.B., Shan F., and Li Y. Chem. Commun. (1996) 2213
35. Wu Y.L., Chen H.B., Jiang K., Li Y., Shan F., Wang D.Y., Wang Y.F., Wu W.M., Wu Y.K., Yao Z.J., Yue Z.Y., and Zhou C.M. Pure Appl. Chem. 71 (1999) 1139
36. O'Neill P.M., Pugh M., Stachulski A.V., Ward S.A., Davies J., and Park B.K. J. Chem. Soc., Perkin Trans. 1 (2001) 2682
37. O'Neill P.M., Searle N.L., Kan K.W., Storr R.C., Maggs J.L., Ward S.A., Raynes K., and Park B.K. J. Med. Chem. 42 (1999) 5487
38. Hindley S., Ward S.A., Storr R.C., Searle N.L., Bray P.G., Park B.K., Davies J., and O'Neill P.M. J. Med. Chem. 45 (2002) 1052
39. Brossi A., Venugopalan B., Gerpe L.D., Yeh H.J.C., Flippenanderson J.L., Buchs P., Luo X.D., Milhous W., and Peters W. J. Med. Chem. 31 (1988) 645
40. Krapcho A.P., and Kuell C.S. Synth. Commun. 20 (1990) 2559
41. Hu W.Q., and Hesse M. Helv. Chim. Acta 79 (1996) 548
42. Ando T., and Yamawaki J. Chem. Lett. (1979) 45
43. Mercer A.E., Maggs J.L., Sun X.M., Cohen G.M., Chadwick J., O'Neill P.M., and Park B.K. J. Biol. Chem. 282 (2007) 9372
44. Zhou H.J., Wang Z., and Li A. Anti-Cancer Drugs 19 (2008) 247
45. Walters J.D., and Wojcik M.S. Leukemia Res. 18 (1994) 703
46. Ramya T.N.C., Surolia N., and Surolia A. Biochem. Biophys. Res. Commun. 348 (2006) 579
47. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923
48. Mosmann T.J. Immunol. Methods 65 (1983) 55
49. Jensen J.B., and Trager W. J. Parasitol. 63 (1977) 883
50. Desjardins R.E.C.J., Haynes D., and Chulay D.J. Antimicrob. Agents Chemother. 16 (1979) 710