Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 3, 2007, Pages 1229-1236

  Filho, Roberto Parise ^a   de Souza Menezes, Carla Maria ^a   Pinto, Pedro Luiz Silva ^b   Paula, Gilberto Alvarenga ^a   Brandt, Carlos Alberto ^c   da Silveira, Maria Amélia Barata ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b INSTITUTO ADOLFO LUTZ   (Brazil)

^c INSTITUTO BUTANTAN   (Brazil)

Author keywords

Molecular modeling; Oxamniquine; Polymeric prodrug; Schistosomicide

Indexed keywords

ANTISCHISTOSOMAL AGENT; OXAMNIQUINE; OXAMNIQUINE ACRYLAMIDE; OXAMNIQUINE METHACRYLATE; OXAMNIQUINE METHACRYLATE COPOLYMER; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG RELEASE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VIVO STUDY; MALE; MOLECULAR MODEL; MOUSE; NONHUMAN; POLYMERIZATION; SCHISTOSOMIASIS; SINGLE DRUG DOSE; THERAPY EFFECT; TREATMENT OUTCOME; TREATMENT RESPONSE;

ACRYLAMIDE; ANIMALS; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; MALE; MESENTERIC VEINS; METHACRYLATES; MICE; MODELS, MOLECULAR; OXAMNIQUINE; PRODRUGS; SCHISTOSOMA MANSONI; SCHISTOSOMIASIS MANSONI; SCHISTOSOMICIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

SCHISTOSOMA MANSONI;

EID: 33845956330     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.11.027     Document Type: Article

References (41)

1. World Web site http://www.who.int/ctd/schistourlhttp://www.who.int/ctd/schisto.
2. Schistosomiasis. Bull. World Health Organ. 1988, 76, 150.
3. Sparg S.G., Van-Staden J., and Jager A.K. J. Ethnopharmacol. 73 (2000) 209
4. Ferreira H.S., and Coutinho E.M. Ann. Trop. Med. Parasitol. 93 (1999) 437
5. Cioli D. Parasitol. Today 14 (1998) 418
6. Coura J.R. Mem. Inst. Oswaldo Cruz 90 (1995) 257
7. Cioli D., Pica-Mattoccia L., and Archer S. Pharmacol. Ther. 68 (1995) 35
8. Shekar K.C. Drugs 42 (1991) 379
9. Parise-Filho R., and Silveira M.A.B. Rev. Bras. Cienc. Farm. 37 (2001) 123
10. Ouchi T., and Ohya Y. Prog. Polym. Sci. 20 (1995) 211
11. Patel H., Raval D.A., and Madanwar D. Angew. Makromol. Chem. 245 (1997) 1
12. Ringsdorf H. J. Polym. Sci. 51 (1975) 135
13. Bundgaard, H., Ed.; Design of Prodrugs; 1985, Elsevier Science: Amsterdam, p 360.
14. Chung M.C., and Ferreira E.I. Quím. Nova 22 (1999) 75
15. Friis, G. J.; Bundgaard, H. Design and Application of Prodrugs. Krogsgaard-Larsen, P., Liljefors, T., Madsen, T., Eds; In A Textbook of Drug Design and Development, 2nd ed.; 1996, Hardwood Academic: Amsterdam, pp 351- 385.
16. Kalcic' I., Zorc B., and Butula I. Int. J. Pharm. 136 (1996) 31
17. Erdmann L., and Uhrich K.E. Biomaterials 21 (2000) 1941
18. Etrych T., Jelínková M., Ríhová B., and Ulbrich K. J. Control. Release 73 (2001) 89
19. Gallardo A., Fernández F., Cifuentes A., Díez-Masa J.C., Bermejo P., Rebuelta M., López-Bravo A., and San Román J. J. Control. Release 72 (2001) 1
20. Jiang H.L., and Zhu K.J. Biomaterials 22 (2001) 211
21. Davaran S., and Entezami A.A. J. Control. Release 47 (1997) 41
22. Wermuth, C. G., Ed.; In The Practice of Medicinal Chemistry; 1996, Academic: London, pp 697-716.
23. Yura H., Yoshmura N., and Hamashima T. Transplant Proc. 30 (1998) 3598
24. Soyez H., Schacht E., and Vanderkerden S. Adv. Drug Delivery Rev. 21 (1996) 81
25. Parise-Filho R., Araújo A.A.S., Santos-Filho M., Matos J.R., and Silveira M.A.B. J. Therm. Anal. Cal. 75 (2004) 487
26. Sheehan J.C., and Hess G.P. J. Am. Chem. Soc. 77 (1955) 1067
27. Mank R., Kala H., and Strube M. Pharmazie 43 (1988) 692
28. San Román J., and Madruga E.L. Polymer 30 (1989) 949
29. Sandler S.R., and Karo W. Polymer Synthesis. In: Wasserman H.H. (Ed). Organic Chemistry. 2nd ed. Vol. 29-I (1992), Academic, San Diego 559-560
30. Erickson J.A., and McLoughlin J.I. J. Org. Chem. 60 (1995) 1626
31. Pellegrino J., and Faria J. Am. J. Trop. Med. Hyg. 14 (1965) 363
32. Pellegrino J., and Siqueira A.F. Rev. Bras. Malariol. Doenças Trop. 8 (1956) 589
33. Drobník J., Kopecek J., Labsky J., Rejmanová P., Exner J., Saudek V., and Kálal J. Makromol. Chem. 177 (1976) 2833
34. Halgren T.A. J. Comput. Chem. 17 (1996) 490
35. Dewar M.J.S., Zoebisch E.G., Heally E.F., and Stweart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902
36. Debnath A.K., Lopez de Compadre R.L., Debnath G., Shusterman A.J., and Hansch C. J. Med. Chem. 34 (1991) 786
37. Lehmann M.W., Singh P., and Evans D.H. J. Electroanal. Chem. 549 (2003) 137
38. Chen C., and Wu J.C. Comput. Chem. 25 (2001) 117
39. Chen P.C., Wu J.C., and Chen S.C. Comput. Chem. 25 (2001) 439
40. Breslow, N. E.; Day, N. E. International Agency for Cancer Research, IARC Scientific Publications: Lyon, n. 82, 1987.
41. Leemis L.M., and Trivedi K.S. Am. Statist. 50 (1996) 63