In vitro activity of N-benzenesulfonylbenzotriazole on Trypanosoma cruzi epimastigote and trypomastigote forms

Experimental Parasitology

Volumn 131, Issue 1, 2012, Pages 57-62

  Becerra, M C ^a   Guinazu N ^a,b   Hergert, L Y ^a,c   Pellegrini, A ^a   Mazzieri, M R ^a   Gea, S ^a   Albesa, I ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

^b UNIVERSIDAD NACIONAL DEL COMAHUE   (Argentina)

^c Universidad Nacional de Villa Maria   (Argentina)

Author keywords

Benzenesulfonylbenzotriazole; Benzotriazole; Prototype; Trypanocidal activity

Indexed keywords

BENZNIDAZOLE; BENZOTRIAZOLE DERIVATIVE; CHLOROQUINE; N BENZENESULFONYLBENZOTRIAZOLE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; EPIMASTIGOTE; FLOW CYTOMETRY; GROWTH INHIBITION; HEMOLYSIS; IC 50; IN VITRO STUDY; INCUBATION TIME; LC 50; MOUSE; NONHUMAN; PRIORITY JOURNAL; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE;

ANIMALS; CELL LINE; CELL SURVIVAL; CHAGAS DISEASE; ERYTHROCYTES; HUMANS; INHIBITORY CONCENTRATION 50; MACROPHAGES; MICE; MICE, INBRED BALB C; NITROIMIDAZOLES; SULFONAMIDES; TRIAZOLES; TRYPANOCIDAL AGENTS; TRYPANOSOMA CRUZI;

PROTOZOA; TRYPANOSOMA CRUZI;

EID: 84860269771     PISSN: 00144894     EISSN: 10902449     Source Type: Journal    
DOI: 10.1016/j.exppara.2012.02.028     Document Type: Article

References (33)

1. Barrett D., Tanaka A., Harada K., Ohki H., Watabe E., Maki K., Ikeda F. Synthesis and biological activity of novel macrocyclic antifungals: acylated conjugates of the ornithine moiety of the lipopeptidolactone FR901469. Bioorganic and Medicinal Chemistry Letters 2001, 11:479-482.
2. Cardoso J., Soares M.J., Menna-Barreto R.F., Le Bloas R., Sotomaior V., Goldenberg S., Krieger M.A. Inhibition of proteasome activity blocks Trypanosoma cruzi growth and metacyclogenesis. Parasitology Research 2008, 103:941-951.
3. Carrera-Silva E.A., Guiñazu N., Pellegrini A., Cano R.C., Arocena A., Aoki M.P., Gea S. Importance of TLR2 on hepatic immune and non-immune cells to attenuate the strong inflammatory liver response during Trypanosoma cruzi acute infection. PLoS Neglected Tropical Diseases 2010, 4(11):e863.
4. Carta A., Loriga M., Piras S., Paglietti G., Ferrone M., Fermeglia M., Pricl S., La Colla P., Collu G., Sanna T., Loddo R. Synthesis and anti-picornaviridae in vitro activity of a new class of helicase inhibitors the N,N'-bis[4-(1H(2H)-benzotriazol-1(2)-yl)phenyl] alkyldicarboxamides. Medicinal Chemistry 2007, 3:520-532.
5. Castro J.A., Diaz de Toranzo E.G. Toxic effects of nifurtimox and benznidazole, two drugs used against American trypanosomiasis (Chagas' disease). Biomedical and Environmental Sciences 1988, 1:19-33.
6. De Souza E.M., da Silva P.B., Nefertiti A.S., Ismail M.A., Arafa R.K., Tao B., Nixon-Smith C.K., Boykin D.W., Soeiro M.N. Trypanocidal activity and selectivity in vitro of aromatic amidine compounds upon bloodstream and intracellular forms of Trypanosoma cruzi. Experimental Parasitology 2011, 127:429-435.
7. DECOS, Dutch Expert Committee on Occupational Standards, 2000. 1,2,3-Benzotriazole, The Hague, Health Council of the Netherlands.
8. Deolindo P., Teixeira-Ferreira A.S., Melo E.J., Arnholdt A.C., Souza W., Alves E.W., DaMatta R.A. Programmed cell death in Trypanosoma cruzi induced by Bothrops jararaca venom. Memórias do Instituto Oswaldo Cruz 2005, 100:33-38.
9. Dixit P.P., Patil V.J., Nair P.S., Jain S., Sinha N., Arora S.K. Synthesis of 1-[3-(4-benzotriazol-1/2-yl-3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-3-substituted-thiourea derivatives as antituberculosis agents. European Journal of Medicinal Chemistry 2006, 41:423-428.
10. Erlanson D.A. Fragment-based lead discovery: a chemical update. Current Opinion in Biotechnology 2006, 17:643-652.
11. Finney D.J. Probit Analysis 1971, Cambridge University Press, London, 333-343. third ed.
12. Guiñazú N., Pellegrini A., Carrera-Silva E.A., Aoki M.P., Cabanillas A.M., Gironés N., Fresno M., Cano R., Gea S. Immunisation with a major Trypanosoma cruzi antigen promotes pro-inflammatory cytokines, nitric oxide production and increases TLR2 expression. International Journal for Parasitology 2007, 37:1243-1254.
13. Hergert L., Nieto M.J., Becerra M.C., Albesa I., Mazzieri M.R. Synthesis of N-benzenesulfonylbenzotriazole derivatives and evaluation of their antimicrobial activity. Letters in Drug Design and Discovery 2008, 5:313-318.
14. Hotez P.J., Molyneux D.H., Fenwick A., Kumaresan J., Sachs S.E., Sachs J.D., Savioli L. Control of neglected tropical diseases. The New England Journal of Medicine 2007, 357:1018-1027.
15. Jannin J., Villa L. An overview of Chagas disease treatment. Memórias Instituto Oswaldo Cruz 2007, 102:95-97.
16. Jorqueira A., Gouvêa R.M., Ferreira V.F., da Silva M.N., de Souza M.C., Zuma A.A., Cavalcanti D.F., Araújo H.P., Santos D.O., Bourguignon S.C. Oxyrane derivative of alpha-lapachone is potent growth inhibitor of Trypanosoma cruzi epimastigote forms. Parasitology Research 2006, 99:429-433.
17. Katritzky A.R., Shobana N., Pernak J., Afridi A.S., Wei-qiang F. Sulfonyl derivatives of benzotriazole: part 1. A novel approach to the activation of carboxylic acids. Tetrahedron 1992, 48:7817-7822.
18. Lamas M.C., Villaggi L., Nocito I., Bassani G., Leonardi D., Pascutti F., Serra E., Salomón C.J. Development of parenteral formulations and evaluation of the biological activity of the trypanocide drug benznidazole. International Journal of Pharmaceutics 2006, 307:239-243.
19. Li P., Zhao L. Developing early formulations: practice and perspective. International Journal of Pharmaceutics 2007, 341:1-19.
20. Luize P.S., Ueda-Nakamura T., Dias Filho B.P., Cortez D.A., Nakamura C.V. Activity of neolignans isolated from Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi. Biological and Pharmaceutical Bulletin 2006, 29:2126-2130.
21. Moncayo A., Silveira A.C. Current epidemiological trends for Chagas disease in Latin America and future challenges in epidemiology, surveillance and health policy. Memórias Instituto Oswaldo Cruz 2009, 104:17-30.
22. Nanjunda Swamy S., Basappa A., Sarala G., Priya B.S., Gaonkar S.L., Shashidhara Prasad J., Rangappa K.S. Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: antimicrobial studies. Bioorganic and Medicinal Chemistry Letters 2006, 16:999-1004.
23. Pagliero R.J., Lusvarghi S., Pierini A.B., Brun R., Mazzieri M.R. Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4 tetrahydroquinolines. Bioorganic and Medicinal Chemistry 2010, 18:142-150.
24. Pagliero R., Pierini A., Brun R., Mazzieri M.R. Design, synthesis and 3D characterization of 1-benzenesulfonyl-1,2,3,4-tetrahydroquinolines as lead scaffold for antiparasitic drug. Letters in Drug Design and Discovery 2010, 7:461-470.
25. Ramana M.M.V., Kudav N.A. O-Hydroxybenzoyl ureas in the synthesis of 1-hydroxyxanthones. Chemistry and Industry (London) 1985, 31-32.
26. Sibley D. Invasion and intracellular survival by protozoan parasites. Immunological Reviews 2011, 240:72-91.
27. Sülsen V., Güida C., Coussio J., Paveto C., Muschietti L., Martino V. In vitro evaluation of trypanocidal activity in plants used in Argentine traditional medicine. Parasitology Research 2006, 98:370-374.
28. Urbina, J.A., Lira, R., Visbal, G., Bartrolí, J., 2000. In vitro antiproliferative effects and mechanism of action of the new triazole derivative UR-9825 against the protozoan parasite Trypanosoma (Schizotrypanum)cruz. Antimicrobial Agents and Chemotherapy 44 (Erratum in: Antimicrobial Agents and Chemotherapy 2000; 44, 2924).
29. Urbina J.A., Docampo R. Specific chemotherapy of Chagas disease: controversies and advances. Trends in Parasitology 2003, 19:495-501.
30. Urbina J.A., Payares G., Sanoja C., Molina J., Lira R., Brener Z., Romanha A.J. Parasitological cure of acute and chronic experimental Chagas disease using the long-acting experimental triazole TAK-187. Activity against drug-resistant Trypanosoma cruzi strains. International Journal of Antimicrobial Agents 2003, 21:39-48.
31. Valdez R.H., Tonin L.T., Ueda-Nakamura T., Dias Filho B.P., Morgado-Diaz J.A., Sarragiotto M.H., Nakamura C.V. Biological activity of 1,2,3,4-tetrahydro-beta-carboline-3-carboxamides against Trypanosoma cruzi. Acta Tropica 2009, 110:7-14.
32. Villarreal D., Barnabé C., Sereno D., Tibayrenc M. Lack of correlation between in vitro susceptibility to benznidazole and phylogenetic diversity of Trypanosoma cruzi, the agent of Chagas disease. Experimental Parasitology 2004, 108:24-31.
33. Yong V., Schmitz V., Vannier-Santos M.A., de Lima A.P., Lalmanach G., Juliano L., Gauthier F., Scharfstein J. Altered expression of cruzipain and a cathepsin B-like target in a Trypanosoma cruzi cell line displaying resistance to synthetic inhibitors of cysteine-proteinases. Molecular Biochemistry and Parasitology 2000, 109:47-59.