Anti-tumoral activity of imidazoquines, a new class of antimalarials derived from primaquine

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 24, 2009, Pages 6914-6917

  Fernandes, Iva ^a   Vale, Nuno ^a   de Freitas, Victor ^a   Moreira, Rui ^b   Mateus, Nuno ^a   Gomes, Paula ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

Anti tumoral; Breast cancer; Imidazolidin 4 ones; Malaria; Primaquine; Quinolines

Indexed keywords

ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; IMIDAZOLINE 4 ONE; PRIMAQUINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CELL STRAIN CACO 2; CELL STRAIN MCF 7; CONTROLLED STUDY; HUMAN; HUMAN CELL; IC 50; SOLUBILITY;

ANTIMALARIALS; ANTINEOPLASTIC AGENTS; CACO-2 CELLS; HT29 CELLS; HUMANS; IMIDAZOLIDINES; PRIMAQUINE;

EID: 71849088617     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.10.081     Document Type: Article

References (45)

1. Rosenthal P.J. Antimalarial Chemotherapy: Mechanisms of Action, Resistance and New Directions in Drug Discovery (2001), Humana Press, Totowa, NJ
2. Vale N., Moreira R., and Gomes P. Eur. J. Med. Chem. 44 (2009) 937
3. Suryanaryana V., Meenakshi J., Kirandeep K., Premanand P., Sanjay R.P., and Rahul J. Med. Res. Rev. 27 (2007) 65
4. Hoglund I.P., Silver S., Engstrom M.T., Salo H., Tauber A., Kyyronen H.K., Saarenketo P., Hoffren A.M., Kokko K., Pohjanoksa K., Sallinen J., Savola J.M., Wurster S., and Kallatsa O.A. J. Med. Chem. 49 (2006) 6351
5. Zhou Q., Melkoumian Z.K., Lucktong A., Moniwa M., Davie J.R., and Strobl J.S. J. Biol. Chem. 275 (2000) 35256
6. Martirosyan A.R., Rahim-Bata R., Freeman A.B., Clarke C.D., Howard R.L., and Strobl J.S. Biochem. Pharmacol. 68 (2004) 1729
7. Mahajan A., Yeh S., Nell M., van Rensburg C.E.J., and Chibale K. Bioorg. Med. Chem. Lett. 17 (2007) 5683
8. Shi A., Nguyen T.A., Battina S.K., Rana S., Takemoto D.J., Chiang P.K., and Hua D.H. Bioorg. Med. Chem. Lett. 18 (2008) 3364
9. Gunjan G., Takahiro O., Aibin S., Duy H.H., and Thu Annelise N. Drug Dev. Res. 69 (2008) 526
10. Jones M., Mercer A.E., Stocks P.A., La Pensée L.J.I., Cosstick R., Park B.K., Kennedy M.E., Piantanida I., Ward S.A., Davies J., Bray P.G., Rawe S.L., Baird J., Charidza T., Janneh O., and O'Neill P.M. Bioorg. Med. Chem. Lett. 19 (2009) 2033
11. Rosenthal A.S., Chen X., Liu J.O., West D.C., Hergenrother P.J., Shapiro T.A., and Posner G.H. J. Med. Chem. 52 (2009) 1198
12. Araújo M.J., Bom J., Capela R., Casimiro C., Chambel P., Gomes P., Iley J., Lopes F., Morais J., Moreira R., de Oliveira E., do Rosario V., and Vale N. J. Med. Chem. 48 (2005) 888
13. Chambel P., Capela R., Lopes F., Iley J., Morais J., Gouveia L., Gomes J.R.B., Gomes P., and Moreira R. Tetrahedron 62 (2006) 9883
14. Ferraz R., Gomes J.R.B., de Oliveira E., Moreira R., and Gomes P. J. Org. Chem. 72 (2007) 4189
15. Gomes P., Araújo M.J., Rodrigues M., Vale N., Azevedo Z., Iley J., Chambel P., Morais J., and Moreira R. Tetrahedron 60 (2004) 5551
16. Vale N., Collins M.S., Gut J., Ferraz R., Rosenthal P.J., Cushion M.T., Moreira R., and Gomes P. Bioorg. Med. Chem. Lett. 18 (2008) 485
17. Vale N., Matos J., Gut J., Nogueira F., do Rosario V., Rosenthal P.J., Moreira R., and Gomes P. Bioorg. Med. Chem. Lett. 18 (2008) 4150
18. Vale N., Nogueira F., do Rosário V.E., Gomes P., and Moreira R. Eur. J. Med. Chem. 44 (2009) 2506
19. Vale, N.; Prudêncio, M.; Marques, C. A.; Collins, M. S.; Gut, J.; Nogueira, F.; Matos, J.; Rosenthal, P. J.; Cushion, M. T.; do Rosário, V. E.; Mota, M. M.; Moreira, R.; Gomes, P. J. Med. Chem. ahead-of-print (doi:10.1021/jm900738c).
20. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107
21. Monks A., Scudiero D., Skehan P., Shoemaker R., Paul K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A., et al. J. Natl. Cancer Inst. 83 (1991) 757
22. http://www.vcclab.org/lab/alogps.
23. http://www.organic-chemistry.org/prog/peo.
24. Hall H.K. J. Am. Chem. Soc. 79 (2002) 5441
25. Dawson R.M.C., Elliott D.C., Elliott W.H., and Jones K.M. Data for Biochemical Research (1959), Oxford University Press
26. Elliott J.J., and Mason S.F. J. Chem. Soc. (Resumed) (1959) 2352
27. Santos C., Morais J., Gouveia L., De Clercq E., Pannecouque C., Nielsen C.U., Steffansen B., Moreira R., and Gomes P. ChemMedChem 3 (2008) 970
28. Santos C.R., Capela R., Pereira C.S.G.P., Valente E., Gouveia L., Pannecouque C., De Clercq E., Moreira R., and Gomes P. Eur. J. Med. Chem. 44 (2009) 2339
29. Portela M.J., Moreira R., Valente E., Constantino L., Iley J., Pinto J., Rosa R., Cravo P., and do Rosario V.E. Pharm. Res. 16 (1999) 949
30. In: Niazi S.K. (Ed). Handbook of Preformulation: Chemical, Biological, and Botanical Drugs (2006), CRC Press
31. Parkin D.M. Lancet Oncol. 2 (2001) 533
32. Yip A.Y., and Chow L.W. Breast Cancer 13 (2006) 192
33. Parkin D.M., and Leticia M.G.F. Breast J. 12 (2006) S70
34. Foley M., and Tilley L. Pharmacol. Ther. 79 (1998) 55
35. Zhou Q., McCracken M.A., and Strobl J.S. Breast Cancer 75 (2002) 107
36. Savarino A., Lucia M.B., Giordano F., and Cauda R. Lancet Oncol. 7 (2006) 792
37. Vazquez-Vivar J., and Augusto O. Free Radical Res. 7 (1990) 383
38. Šimunović M., Perković I., Zorc B., Ester K., Kralj M., Hadjipavlou-Litina D., and Pontiki E. Bioorg. Med. Chem. 17 (2009) 5605
39. Pugh C.W., Gleadle J.I., and Maxwell P.H. Breast Cancer Res. 3 (2001) 313
40. Knowles H.J., and Harris A.L. Breast Cancer Res. 3 (2001) 318
41. Williams K.J., Cowen R.L., and Stratford I.J. Breast Cancer Res. 3 (2001) 328
42. Van den. Eynden G.G., Van der Auwera I., Van Laere S.J., Colpaert C.G., Turley H., Harris A.L., Van Dam P., Dirix L.Y., Vermeulen P.B., and Van Marck E.A. Br. J. Cancer 93 (2005) 1128
43. Kim J.-W., Gao P., and Dang C.V. Cancer Metast. Rev. 26 (2007) 291
44. Milani M., and Harris A.L. Eur. J. Cancer 44 (2008) 2766
45. Gago-Domíngeuz M., Jiang X., and Castelao J.E. Breast Cancer J. 9 (2007) 201