Anti-protozoal activity of diamine derivatives

Biomedicine and Pharmacotherapy

Volumn 65, Issue 1, 2011, Pages 60-62

  Giordani, R B ^a   Araujo D P ^b   Duarte, M ^a   Zuanazzi, J A ^a   Tasca, T ^a   De Almeida, M V ^b  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b FEDERAL UNIVERSITY OF JUIZ DE FORA   (Brazil)

Author keywords

Diamine; Giardia lamblia; Lipophilicity; Trichomonas vaginalis

Indexed keywords

DIAMINE DERIVATIVE; METRONIDAZOLE; N DODECYL 1,4 BUTANEDIAMINE; N HEXADECIL 1,4 BUTANEDIAMINE; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; COMPARATIVE STUDY; GIARDIA LAMBLIA; GROWTH INHIBITION; IN VITRO STUDY; LIPOPHILICITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; TRICHOMONAS VAGINALIS;

ANTIPROTOZOAL AGENTS; DIAMINES; GIARDIA LAMBLIA; STRUCTURE-ACTIVITY RELATIONSHIP; TRICHOMONAS VAGINALIS;

EID: 79951675998     PISSN: 07533322     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biopha.2010.10.006     Document Type: Article

References (26)

1. Savioli L., Smith H., Thompson A. Giardia and cryptosporidium join the neglected diseases initiative. Trends Parasitol 2006, 22:203-208.
2. World Health Organization Global prevalence and incidence of selected curable sexually transmitted infections 2001, WHO, Geneva, p. 1-120.
3. Laga M., Manoka A., Kivuvu M., Malele B., Tulza M., et al. Nonulcerative sexually transmitted diseases as risk factors for HIV-1 transmission in women: results from a cohort study. AIDS 1993, 7:95-102.
4. Sorvillo F., Smith L., Kerndt P., Ash L. Trichomonas vaginalis, HIV, and Africans. Emerg Infect Dis 2001, 7:927-932.
5. Sadjjadi S.M., Alborzi A.W., Mostovfi H. Comparative clinical trial of mebendazole and metronidazole in giardiasis of children. J Trop Pediatr 2001, 47:176-178.
6. Upcroft P., Upcroft J.A. Drug targets and mechanisms of resistance in the anaerobic protozoa. Clin Microbiol Rev 2001, 14:150-164.
7. Reis I.A., Martinez M.P., Yarlett N., Johnson P.J., Silva-Filho F.C., Vannier-Santos M.A. Inhibition of polyamine synthesis arrests trichomonad growth and induces destruction of hydrogenosomes. Antimicrob Agents Chemother 1999, 43:1919-1923.
8. Casero R.A., Wobster P.M. Terminally alkylated polyamine analogues as chemotherapeutic agents. J Med Chem 2001, 44:1-26.
9. Bacchi C.J., Yarlett N. Polyamine metabolism as chemotherapeutic target in protozoan parasites. Mini Rev Med Chem 2002, 2:553-563.
10. Reguera R.M., Tekwani B.L., Balaña-Fouce R. Polyamine transport in parasites: a potential target for new antiparasitic drug development. Comp Biochem Physiol 2005, 140:151-164.
11. Muller IB, Das Gupta R, Luersen K, Wrenger C, Walter RD. Assessing the polyamine metabolism of Plasmodium falciparum as chemotherapeutic target. Mol Biochem Parasitol 2008;160:1-7.
12. Muller S., Coombs G.H., Walker R.D. Targeting polyamines of parasitic protozoa in chemotherapy. Trends Parasitol 2001, 17:242-249.
13. Sánchez-Sancho F., Campillo N.E., Páez J.A. Chagas disease: progress and new perspectives. Amino Acids 2010, 38:645-651.
14. Algranati I.D. Polyamine metabolism in Trypanosoma cruzi: studies on the expression and regulation of heterologous genes involved in polyamine biosynthesis. Curr Med Chem 2010, 17:423-452.
15. Vannier-Santos M.A., Menezes D., Oliveira M.F., de Mello F.G. The putrescine analogue 1,4-diamino-2-butanone affects polyamine synthesis, transport, ultrastructure and intracellular survival in Leishmania amazonensis. Microbiol 2008, 154:3104-3111.
16. General procedure for the preparation of N-substituted diamine dihydrochloride salts 1-10. To a solution of 1,4-butanediamine or 1,6-hexanediamine (20mmol) in 25mL of ethanol at reflux was slowly added the alkyl mesylate (20mmol). The reaction mixture was maintained under reflux during 20h. The solvent was evaporated under reduced pressure and the residue was extracted with water/dichlorometane (3×). The organic phase was evaporated under reduced pressure and the residue purified by recrystalization from hexane. After that, these compounds were redissolved in methanol and concentrated HCl was added until pH ∼2. The corresponding dihydrochloride salts were purified by simple recrystallization furnishing compounds 1-10 in 45-73% yield.
17. Giordani R.B., de Almeida M.V., Fernandes E., Da Costa C.F., De Carli J.A., Tasca T., et al. procedure for the preparation of N-su anti-Trichomonas vaginalis activity of synthetic lipophilic diamine and amino alcohol derivatives. Biomed Pharmacother 2009, 63:613-617.
18. De Almeida M.V., Saraiva M.F., Souza M.V.N., Da Costa C.F., Vicente F.R.S., Lourenço M.C.S. Synthesis and antitubercular activity of lipophilic moxifloxacin and gatifloxacin derivatives. Bioorg Med Chem Lett 2007, 17:5661-5664.
19. Da Costa C.F., Coimbra E.S., Braga F.G., dos Reis R.C.N., da Silva A.D., de Almeida M.V. Preparation and antileishmanial activity of lipophilic N-alkyl diamines. Biomed Pharmacother 2009, 63:40-42.
20. Junior C.O.R., Le Hyaric M., Da Costa C.F., Correa T.A., Taveira A.F., Araujo D.P., et al. Preparation and antitubercular activity of lipophilic diamines and amino alcohols. Mem Inst Oswaldo Cruz 2009, 104:703-705.
21. Taveira A.F., Le Hyaric M., Dos Reis E.F.C., Araújo D.P., Ferreira A.P., Souza M.A., et al. Preparation and antitubercular activities of alkylated amino alcohols and their glycosylated derivatives. Bioorg Med Chem 2007, 15:7789-7794.
22. Dos Reis E.F.C., Junior C.O.R., Alves L.L., Ferreira A.P., De Almeida M.V. Synthesis and immunosuppressive activity of lipophilic amino alcohols and diamines. Chem Biol Drug Des 2008, 72:596-598.
23. De Almeida M.V., Le Hyaric M., Amarante G.W., Lourenço M.C.S., Lima Brandão M.L. Synthesis of amphiphilic galactopyranosyl diamines and amino alcohols as antitubercular agents. Eur J Med Chem 2007, 42:1076-1083.
24. Junior COR, Alves RO, Rezende CAM, Da Costa CF, Silva H, Le Hyaric M, et al. Trypanocidal activity of lipophilic diamines and amino alcohols. Biomed Pharmacother 2010;64:624-6.
25. Bénéré E., da Luz R.A., Vermeersch M., Cos P., Maes L. A new quantitative in vitro microculture method for Giardia duodenalis trophozoites. J Microbiol Methods 2007, 71:101-106.
26. Duarte M., Giordani R.B., De Carli G.A., Zuanazzi J.A.S., Macedo A.J., Tasca T. A quantitative resazurin-assay to determinate the viability of Trichomonas vaginalis and the cytotoxicity of organic solvents and surfactant agents. Exp Parasitol 2009, 123:195-198.