Synthesis and in vitro evaluation of potential antichagasic dipeptide prodrugs of primaquine

Journal of Pharmaceutical Sciences

Volumn 86, Issue 10, 1997, Pages 1127-1131

  Chung, M C ^a   Goncalves M F ^b   Colli, W ^b   Ferreira, E I ^b   Miranda, M T M ^b  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CRUZIPAIN; LYSYLARGININE PRIMAQUINE; PHENYLALANINE PRIMAQUINE; PHENYLARGININE PRIMAQUINE; PRIMAQUINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIPROTOZOAL ACTIVITY; ARTICLE; CHAGAS DISEASE; DRUG CONFORMATION; DRUG EFFICACY; DRUG SYNTHESIS; ENDEMIC DISEASE; NONHUMAN; SOUTH AND CENTRAL AMERICA; TRYPANOSOMA CRUZI;

EID: 0030885357     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js970006v     Document Type: Article

References (40)

1. Brener, Z.; Cançado, J. R. In Trypanosoma cruzi e Doença de Chagas. Brener, Z.; Andrade, Z. A., Eds.; Guanabara Koogan: Rio de Janeiro, 1979; pp 362-424.
2. Dias, J. C. P. Arq. Bras. Cardiol. 1994, 63, 451-455.
3. Korolkovas, A. Essentials of Medicinal Chemistry, 2nd ed.; Wiley-Interscience: New York, 1988, p 1204.
4. Moncayo, A. Wld. Hlth Statist. Quart. 1992, 45, 276-279.
5. Who Technical Report Series- Control of Chagas' Disease, Geneva, 1991.
6. Kirchhoff, L. V. Rev. Soc. Bras. Med. Trop. 1993, 26, 21-22.
7. Dias, J. C. P. Doença de Chagas- Clínica e Terapêutica. Sucam-Superintendência de Campanhas de Saúde Pública, Ministério da Saúde, Brasília, DF, 1990.
8. Howard, J. E.; Rios, C.; Ebensperger, I.; Olivos, P. Bol. Chil. Parasitol. 1967, 12, 42-45.
9. Pizzi, T. Proc. Soc. Exp. Biol. Med. 1951, 78, 643-644.
10. Augusto, O.; Alves, M. J.; Colli, W.; Filardi, L. S.; Brener, Z. Biochem. Biophys. Res. Commun. 1986, 135, 1029-1034.
11. Bundgaard, H. Drugs Fut. 1991, 16, 443-458.
12. Bundgaard, H., Ed.; Prodrug Design; Elsevier: Amsterdam, 1985.
13. Singh, G.; Sharma, P. D. Indian J. Pharm. Sci. 1994, 56, 69-79.
14. Laakso, T.; Stjarnkvist, P.; Sjoholm, I. J. Pharm Sci. 1987, 76, 134-140.
15. Trouet, A.; Masquelier, M.; Baurain, R.; Deprez-de-Campeneere, D. Proc. Natl Acad. Sci. USA 1982, 79, 626-629.
16. Borissova, R.; Lammek, B.; Stjarnkvist, D.; Sjoholm, I. J. Pharm. Sci. 1995, 84, 249-255.
17. Carl, P. L.; Chakravarty, P. K.; Katzenellenbogen, J. A.; Weber, M. J. Proc. Natl. Acad. Sci. USA 1980, 77, 2224-2228.
18. Tubaro, E.; Raffaldoni, E. Boll. Chim. Farm. 1960, 100, 9-22.
19. Kawamura, M.; Fujisawa, S. Yakugaku Zasshi 1971, 91, 885-889.
20. Nuldeman, A.; McCaully, R. J.; Bell, S. C. J. Pharm. Sci. 1974, 63, 1880-1885.
21. Bundgaard, H.; Larsen, C.; Thorbek, P. Int. J. Pharm. 1984, 18, 67-77.
22. Yamaoka, Y.; Roberts, R. D.; Stella, V. J. J. Pharm. Sci. 1983, 72, 400-405.
23. Clerici, C.; Gentili, G.; Poschetti, E.; Santucci, C.; Aburbeh, A. G.; Natalini, B.; Pellicciari, R.; Morelli, A. Dig. Dis. Sci. 1994, 39, 2601-2606.
24. Deleted in proof.
25. Trouet, A.; Baurain, R.; Deprez-de-Campeneere, D., Masquelier, M.; Pirson, P. In Targeting of Drugs; Gregoriadis, G.; Senior, J.; Trouet, A., Eds.; Plenum: New York, 1982; pp 19-30.
26. Chakravarty, P. K.; Carl, P. L.; Weber, M. J.; Katzenellenbogen, J. A. J. Med. Chem. 1983, 26, 633-638.
27. Duncan, R.; Kopeckova-Rejmanova, P; Strohalm, J.; Hume, C.; Cable, H. C.; Pohl, J.; Lloyd, J. B.; Kopecek, J. Br. J. Cancer 1987, 55, 165-174.
28. Selective Toxicity; Albert, A., Ed.; Wiley: New York, 1981.
29. McGrath, M. E.; Eakin, A. E.; Engel, J. C.; McKerrow, J. H.; Craik, C. S.; Fletterick, R. J. J. Mol. Biol. 1995, 247, 251-259.
30. (a) McKerrow, J. H.; McGrath, M. E.; Engel, J. C. Parasitol. Today 1995, 11, 279-282.
31. (b) McKerrow, J. H.; Sun, E.; Rosenthal, P. J.; Bouvier, J. Ann. Rev. Microbiol. 1993, 47, 821-853.
32. Cazzulo, J. J.; Cazzullo Franke, M. C. I.; Martinez, J.; Franke de Cazzullo, B.M. Biochim. Biophys. Acta 1990, 1037, 186-191.
33. Scharfstein, J.; Schechter, M.; Senna, M.; Peralta, J. M.; Mendonça-Previato, L.; Milles, M. A. J. Immunol. 1986, 137, 1336-1341.
34. Harth, G.; Andrews, N.; Mills, A. A.; Engel, J. C.; Smith, R.; McKerrow, J. H. Mol. Biochem. Parasitol. 1993, 58, 17-24.
35. Bodanszky, M. Peptide Chemistry - A Practical Textbook, 2nd ed.; Springer-Verlag: Berlin, 1993.
36. Bodansky, M. Principles of Peptide Synthesis; Springer-Verlag: Berlin, 1984.
37. Dulbecco, R.; Freeman, G. Virology 1959, 8, 396-397.
38. Kristensen, S.; Grislingaas, A. L.; Greenhill, J. V.; Skjetne, T.; Karlsen, J.; Tonnesen, H. H. Int. J. Pharm. 1993, 100, 15-23.
39. Falmagne, J. B. Biochem. Pharmacol. 1988, 37, 2683-2690.
40. Philip, A.; Kepler, J. A.; Jonhson, B. H.; Carroll, F. I. J. Med. Chem. 1988, 31, 870-874.