Dual molecules as new antimalarials

Combinatorial Chemistry and High Throughput Screening

Volumn 8, Issue 1, 2005, Pages 49-62

  Salom Roig, Xavier J ^a   Hamzé, Abdallah ^a   Calas, Michèle ^a   Vial, Henri J ^b  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b CNRS   (France)

Author keywords

Antimalarials; Bis amidines; Bis thiazolium salts; Bisquaternary ammonium salts; Choline analogues; Hemozoin; Malarial pigment; Phosphatidylcholine; Phospholipid; Plasmodium falciparum; Prodrug

Indexed keywords

AMMONIUM DERIVATIVE; ANTIMALARIAL AGENT;

CRYSTAL STRUCTURE; CYTOTOXICITY; DOSE RESPONSE; DRUG ABSORPTION; DRUG EFFECT; DRUG EFFICACY; DRUG POTENCY; DRUG SPECIFICITY; DRUG STRUCTURE; ENZYME REGULATION; IC 50; IN VIVO STUDY; INTRACELLULAR TRANSPORT; MALARIA; MULTIDRUG RESISTANCE; NONHUMAN; PHOSPHOLIPID METABOLISM; PLASMODIUM; PLASMODIUM FALCIPARUM; PLASMODIUM VINCKEI; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIMALARIALS; CHOLINE; PENTAMIDINE; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

PLASMODIUM CYNOMOLGI; PLASMODIUM FALCIPARUM; PLASMODIUM VINCKEI; PRIMATES;

EID: 12844284664     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/1386207053328219     Document Type: Review

References (56)

1. Sachs, J.; Malaney, P. Nature 2002, 415, 680-685.
2. Hay, S. I.; Guerra, C. A.; Tatem, A. J.; Noor, A. M.; Snow, R. W. Lancet Infect Dis. 2004, 4, 327-336.
3. Carter, R.; Mendis, K. N. Clin. Microbiol. Rev. 2002, 15, 564-594.
4. Breman, J. G.; Egan, A.; Keusch, G. T. Am. J. Trop. Med. Hyg. 2001, 64, iv-vii.
5. White, N. J. J. Clin. Invest. 2004, 113, 1084-1092.
6. Olliaro, P. Pharmacol. Ther. 2001, 89, 207-219.
7. Biagini, G. A.; O'Neill, P. M.; Nzila, A.; Ward, S. A.; Bray, P. G. Trends in Parasitology 2003, 19, 479-487.
8. Schmid, G.; Hotheinz, W. J. Am. Chem. Soc. 1983, 105, 624-625.
9. Avery, M. A.; Jennings-White, C.; Chong, W. K. M. Tetrahedron Lett. 1987, 28, 4629-4632.
10. Liu, H.; Yeh, W. L.; Chew, S. W. Tetrahedron Lett. 1993, 35, 4435-4438.
11. Yadav, J. S.; Satheesh Babu, R.; Sabitha, G. Tetrahedron Lett. 2002, 44, 387-389.
12. Haynes, R. K. Curr. Opin. Infect. Dis. 2001, 14, 719-726.
13. Borstnik, K.; Paik, I. H.; Posner, G. H. Mini-Rev. Med. Chem. 2002, 2, 573-583.
14. Ridley, R. G. Nature 2002, 415, 686-693.
15. Fidock, D. A.; Rosenthal, P. J.; Croft, S. L.; Brun, R.; Nwaka, S. Nat Rev Drug Discov. 2004, 3, 509-520.
16. Vial, H. J.; Thuet, M. J.; Ancelin, M. L.; Philippot, J. R.; Chavis, C. Biochem. Pharmacol. 1984, 33, 2761-2770.
17. Ancelin, M. L.; Vial, H. J.; Philippot, J. R. Biochem. Pharmacol. 1985, 34, 4068-4071.
18. Sherman, I. Malaria, Parasite Biology, pathogenesis and Protection; ASM Press: Washington DC, 1998; 573.
19. Gardner, M. J.; Shallom, S. J.; Carlton, J. M.; Salzberg, S. L.; Nene, V.; Shoaibi, A.; Ciecko, A.; Lynn, J.; Rizzo, M.; Weaver, B.; Jarrahi, B.; Brenner, M.; Parvizi, B.; Tallon, L.; Moazzez, A.; Granger, D.; Fujii, C.; Hansen, C.; Pederson, J.; Feldblyum, T.; Peterson, J.; Suh, B.; Angiuoli, S.; Pertea, M.; Allen, J.; Selengut, J.; White, O.; Cummings, L. M.; Smith, H. O.; Adams, M. D.; Venter, J. C.; Carucci, D. J.; Hoffman, S. L.; Fraser, C. M. Nature 2002, 419, 531-534.
20. Holz, G. G. Bull. Wld. Hlth. Organiz (WHO) 1977, 55, 237-248.
21. Vial, H. J.; Ancelin, M. L. Subcell. Biochem. 1992, 18, 259-306.
22. Vial, H.; Ancelin, M. Malarial Lipids. Malaria: Parasite Biology, Biogenesis, Protection; ASM Press: Washington DC, 1998; pp. 159-175.
23. Vial, H. J.; Calas, M. Inhibitors of Phospholipid Metabolism. Antimalarial Chemotherapy, mechanisms of action, modes of resistance, and new directions in drug development; Humana Press: Totowa, NJ, 2001; pp. 347-365.
24. Calas, M.; Cordina, G.; Bompart, J.; Ben Bari, M.; Jei, T.; Ancelin, M. L.; Vial, H. J. Med. Chem. 1997, 40, 3557-3566.
25. Ancelin, M. L.; Calas, M.; Bompart, J.; Cordina, G.; Martin, D.; Ben Bari, M.; Jei, T.; Druilhe, P.; Vial, H. J. Blood 1998, 91, 1426-1437.
26. Calas, M.; Ancelin, M. L.; Cordina, G.; Portefaix, P.; Piquet, G.; Vidal-Sailhan, V.; Vial, H. J. Med. Chem. 2000, 43, 505-516.
27. Ancelin, M. L.; Calas, M.; Vidal Sailhan, V.; Herbute, S.; Ringwald, P.; Vial, H. J. Antimicrob. Agents Chemother. 2003, 47, 2590-2597.
28. Ancelin, M. L.; Calas, M.; Bonhoure, A.; Herbute, S.; Vial, H. J. Antimicrob. Agents Chemother. 2003, 47, 2598-2605.
29. Wengelnik, K.; Vidal, V.; Ancelin, M. L.; Cathiard, A. M.; Morgat, J. L.; Kocken, C. H.; Calas, M.; Herrera, S.; Thomas, A. W.; Vial, H. J. Science 2002, 295, 1311-1314.
30. Bitsch, R.; Wolf, M.; Möller, J.; Heuzeroth, L.; Gruneklee, D., 1991, 5, 292-296. Ann. Nutr. Metab. 1991, 5, 292-296.
31. Baker, H.; Franck, O. J. Nutr. Sci. Vitaminol 1976, 22 (suppl.), 63-68.
32. Ishikura, T.; Senou, T.; Ishihara, H.; Kato, T.; Ito, T. Intern. J. of Pharm 1995, 116, 5-63.
33. Changeux, J. P.; Galzani, J. L.; Devillers-Thiéry, A.; Bertrand, D. Quart. Rev. Biophys. 1992, 52, 395-432.
34. Christopher, A. Lipinski, F. L., Beryl, W. Dominy, Paul, J. Feeney. Advanced Drug Delivery Reviews 1997, 23, 3-25.
35. Biagini, G. A.; Richier, E.; Bray, P. G.; Calas, M.; Vial, H.; Ward, S. A. Antimicrob. Agents Chemother. 2003, 47, 2584-2589.
36. Roggero, R.; Zufferey, R.; Nastase, M.; Richier, E.; Calas, M.; Vial, H.; Ben Mamoun, C. Antimicrob. Agents Chemother. 2004, In Press.
37. Stead, A. M.; Bray, P. G.; Edwards, I. G.; DeKoning, H. P.; Elford, B. C.; Stocks, P. A.; Ward, S. A. Mol. Pharmacol. 2001, 59, 1298-1306.
38. Biagini, G. A.; Pasini, E.; Hughes, R. H.; De Koning, H. P.; Vial, H.; Ward, S. A.; Bray, P. G. Blood 2004, In Press.
39. Vial, H. J.; Thuet, M. J.; Philippot, J. R. J. Protozool. 1982, 29, 258-263.
40. Francis, S. E.; Sullivan, D. J. Jr.; Goldberg, D. E. Annu. Rev. Microbiol. 1997, 51, 97-123.
41. Fitch, C. D. Life Sci. 2004, 74, 1957-1972.
42. Ancelin, M. L.; Parant, M.; Thuet, M. J.; Philippen, J. R.; Vial, H. J. Biochem. J. 1991, 273 (Pt. 3), 701-709.
43. Vial, H. J.; Eldin, P.; Martin, D.; Gannoun, L.; Calas, M.; Ancelin, M. L. Novariis Found. Symp. 1999, 226, 74-83; discussion 83-78.
44. Ferguson, S. S. G.; Diksic, M.; Collier, B. J. Neurochem. 1991, 57, 915-921.
45. Barrow, R. B.; Ing, H. R. Brit. J. Pharmacol. 1948, 3, 298-304.
46. Roberts, E. Neurochem. Res. 1992, 17, 509-528.
47. Mohamed, A. I.; Brun, R.; Easterbrook, J. D.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. J. Med. Chem. 2003, 46, 4761-4769.
48. Bell, C. A.; Hall, J. E.; Kyle, D. E.; Gorogl, M.; Ohemeng, K. A.; Allen, M. A.; Tidwell, R. R. Antimicrob. Agents Chemother. 1990, 34, 1381-1386.
49. Mayence, A.; Eynde, J. J. V.; Krogstad, F. M.; Donald, J. K.; Cushion, M. T.; Huang, T. L. J. Med. Chem. 2004, 47, 2700-2705.
50. Mayence, A.; Eynde, J. J. V.; Huang, T. L. Bioorganic and Medicinal Chemistry Letters 2004, 14, 1625-1628.
51. Egan, T. J.; Marques, H. M. Coordination Chemistry Reviews 1999, 190-192, 493-517.
52. Kelly, J. X.; Winter, R.; Peyton, D. H.; Hinrichs, D. J.; Riscoe, M. Antimicrobial Agents and Chemotherapy 2002, 144-150.
53. Alzeer, J.; Chollet, J.; Heinze-Krauss, I.; Hubschwerlen, C.; Matile, H.; Ridley, R. G. J. Med. Chem. 2000, 43, 560-568.
54. Ridley, R. G.; Matile, H.; Jaquet, C.; Dorn, A.; Hofheinz, W.; Leupin, W.; Masciadri, R.; Theil, F. P.; Richter, W. F.; Girometta, M. A.; Guenzi, A.; Urwyler, H.; Gocke, E.; Potthast, J. M.; Csato, M.; Thomas, A.; Peters, W. Antimicrob. Agents Chemother. 1997, 41, 677-686.
55. Peters, W.; Li, Z. L.; Robinson, B. L.; Warhurst, D. C. Ann. Trop. Med. Parasitol. 1986, 80, 483-489.
56. O'Neill, P. M.; Miller, A.; Bishop, L. P.; Hindley, S.; Maggs, J. L.; Ward, S. A.; Roberts, S. M.; Scheinmann, F.; Stachulski, A. V.; Posner, G. H.; Park, B. K. J. Med. Chem. 2001, 44, 58-68.