Navegar

Colección

Datos Estadísticas

Artículo

Chao, M.N.; Matiuzzi, C.E.; Storey, M.; Li, C.; Szajnman, S.H.; Docampo, R.; Moreno, S.N.J.; Rodriguez, J.B. "Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii" (2015) ChemMedChem. 10(6):1094-1108
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Abstract As a part of our project aimed at searching for new safe chemotherapeutic agents against parasitic diseases, several compounds structurally related to the antiparasitic agent WC-9 (4-phenoxyphenoxyethyl thiocyanate), which were modified at the terminal phenyl ring, were designed, synthesized, and evaluated as growth inhibitors against Trypanosoma cruzi, the etiological agent of Chagas disease, and Toxoplasma gondii, the parasite responsible of toxoplasmosis. Most of the synthetic analogues exhibited similar antiparasitic activity and were slightly more potent than our lead WC-9. For example, two trifluoromethylated derivatives exhibited ED50 values of 10.0 and 9.2 μM against intracellular T. cruzi, whereas they showed potent action against tachyzoites of T. gondii (ED50 values of 1.6 and 1.9 μM against T. gondii). In addition, analogues of WC-9 in which the terminal aryl group is in the meta position with respect to the alkyl chain bearing the thiocyanate group showed potent inhibitory action against both T. cruzi and T. gondii at the very low micromolar range, which suggests that a para-phenyl substitution pattern is not necessary for biological activity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Registro:

Documento: Artículo
Título:Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii
Autor:Chao, M.N.; Matiuzzi, C.E.; Storey, M.; Li, C.; Szajnman, S.H.; Docampo, R.; Moreno, S.N.J.; Rodriguez, J.B.
Filiación:Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires, C1428EHA, Argentina
Center for Tropical and Emerging Global Diseases, Department of Cellular Biology, University of Georgia, Athens, GA 30602, United States
Palabras clave:antiparasitic agents; biological activity; chemotherapeutic agents; inhibitors; structure-activity relationships; 3 (2 chlorophenoxy)phenoxyethanol; 3 (2 chlorophenoxy)phenoxyethyl 4 toluenesulfonate; 3 (2 chlorophenoxy)phenoxyethyl tetrahydro 2h pyran 2 yl ether; 3 (2 chlorophenoxy)phenoxyethyl thiocyanate; 3 (3 chlorophenoxy)phenoxyethyl tetrahydro 2h pyran 2 yl ether; 4 (pyridin 2 yloxy)phenoxyethanol; 4 (pyridin 2 yloxy)phenoxyethyl 4 toluenesulfonate; 4 (pyridin 2 yloxy)phenoxyethyl tetrahydro 2h pyran 2 yl ether; 4 (pyridin 2 yloxy)phenoxyethyl thiocyanate; 4 benzyloxyphenoxyethyl tetrahydro 2h pyran 2 yl ether; 4 hydroxyphenoxyethyl tetrahydro 2h pyran 2 yl ether; 4 [(3 trifluoro)phenoxy]phenoxyethanol; 4 [(3 trifluoro)phenoxy]phenoxyethyl 4 toluenesulfonate; 4 [(3 trifluoro)phenoxy]phenoxyethyl tetrahydro 2h pyran 2 yl ether; 4 [(3 trifluoro)phenoxy]phenoxyethyl thiocyanate; 4 [(4 trifluoro)phenoxy]phenoxyethanol; 4 [(4 trifluoro)phenoxy]phenoxyethyl 4 toluenesulfonate; 4 [(4 trifluoro)phenoxy]phenoxyethyl tetrahydro 2h pyran 2 yl ether; 4 [(4 trifluoro)phenoxy]phenoxyethyl thiocyanate; alpha naphthyloxyphenylethanol; alpha naphthyloxyphenylethyl 4 toluenesulfonate; alpha naphthyloxyphenylethyl tetrahydro 2h pyran 2 yl ether; alpha naphthyloxyphenylethyl thiocyanate; antiparasitic agent; aryloxyethyl thiocyanate derivative; beta naphthyloxyphenoxyethanol; beta naphthyloxyphenoxyethyl 4 toluenesulfonate; beta naphthyloxyphenoxyethyl tetrahydro 2h pyran 2 yl ether; thiocyanic acid derivative; unclassified drug; unindexed drug; antiprotozoal agent; thiocyanate; thiocyanic acid derivative; antiparasitic activity; antiprotozoal activity; Article; Chagas disease; crystal structure; cytotoxicity; drug screening; drug structure; drug synthesis; in vitro study; microbial growth; nuclear magnetic resonance; priority journal; tachyzoite; Toxoplasma gondii; toxoplasmosis; Trypanosoma cruzi; Vero cell line; animal; Chlorocebus aethiops; drug effects; growth, development and aging; Toxoplasma; Trypanosoma cruzi; Animals; Antiprotozoal Agents; Cercopithecus aethiops; Thiocyanates; Toxoplasma; Trypanosoma cruzi; Vero Cells
Año:2015
Volumen:10
Número:6
Página de inicio:1094
Página de fin:1108
DOI: http://dx.doi.org/10.1002/cmdc.201500100
Título revista:ChemMedChem
Título revista abreviado:ChemMedChem
ISSN:18607179
CODEN:CHEMG
CAS:thiocyanate, 302-04-5; Antiprotozoal Agents; thiocyanate; Thiocyanates
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18607179_v10_n6_p1094_Chao

Referencias:

  • Urbina, J.A., (1997) Parasitology, 114, pp. S91-S99
  • Urbina, J.A., (2002) Curr. Pharm. Des., 8, pp. 287-295
  • Buckner, F.S., Urbina, J.A., (2012) Int. J. Parasitol. Drugs Drug Resist., 2, pp. 236-242
  • Lepesheva, G.I., Villalta, F., Waterman, M.R., (2011) Adv. Parasitol., 75, pp. 65-87
  • Docampo, R., Schmuñis, G., (1997) Parasitol. Today, 13, pp. 129-130
  • Urbina, J.A., Concepciõn, J.L., Rancel, S., Bisbal, G., Lira, R., (2002) Mol. Biochem. Parasitol., 125, pp. 35-45
  • Urbina, J.A., Payares, G., Molina, J., Sanoja, C., Liendo, A., Lazardi, K., Piras, M.M., Ryley, J.F., (1996) Science, 273, pp. 969-971
  • Cinque, G.M., Szajnman, S.H., Zhong, L., Docampo, R., Schvartzapel, A.J., Rodriguez, J.B., Gros, E.G., (1998) J. Med. Chem., 41, pp. 1540-1554
  • Szajnman, S.H., Yan, W., Bailey, B.N., Docampo, R., Elhalem, E., Rodriguez, J.B., (2000) J. Med. Chem., 43, pp. 1826-1840
  • Elhalem, E., Bailey, B.N., Docampo, R., Ujváry, I., Szajnman, S.H., Rodriguez, J.B., (2002) J. Med. Chem., 45, pp. 3984-3999
  • Urbina, J.A., Concepcion, J.L., Montalvetti, A., Rodriguez, J.B., Docampo, R., (2003) Antimicrob. Agents Chemother., 47, pp. 2047-2050
  • Concepcion, J.L., Gonzalez-Pacanowska, D., Urbina, J.A., (1998) Arch. Biochem. Biophys., 352, pp. 114-120
  • Nair, S.C., Brooks, C.F., Goodman, C.D., Sturm, A., McFadden, G.I., Sundriyal, S., Anglin, J.L., Striepen, B., (2011) J. Exp. Med., 208, pp. 1547-1559
  • Coppens, I., Sinai, A.P., Joiner, K.A., (2000) J. Cell Biol., 149, pp. 167-180
  • Grellier, P., Valentin, A., Millerioux, V., Schrevel, J., Rigomier, D., (1994) Antimicrob. Agents Chemother., 38, pp. 1144-1148
  • Pradines, B., Torrentino-Madamet, M., Fontaine, A., Henry, M., Baret, E., Mosnier, J., Briolant, S., Rogier, C., (2007) Antimicrob. Agents Chemother., 51, pp. 2654-2655
  • Bessoff, K., Sateriale, A., Lee, K.K., Huston, C.D., (2013) Antimicrob. Agents Chemother., 57, pp. 1804-1814
  • Cortez, E., Stumbo, A.C., Olieveira, M., Barbosa, H.S., Carvalho, L., (2009) Int. J. Antimcrob. Agents, 33, pp. 185-186
  • Li, Z.H., Ramakrishnan, S., Striepen, B., Moreno, S.N., (2013) PLoS Pathog., 9
  • Lin, F.Y., Liu, Y.L., Li, K., Cao, R., Zhu, W., Axelson, J., Pang, R., Oldfield, E., (2012) J. Med. Chem., 55, pp. 4367-4372
  • Shang, N., Li, Q., Ko, T.P., Chan, H.C., Li, J., Zheng, Y., Huang, C.H., Guo, R.T., (2014) PLoS Pathog., 10
  • Schvartzapel, A.J., Zhong, L., Docampo, R., Rodriguez, J.B., Gros, E.G., (1997) J. Med. Chem., 40, pp. 2314-2322
  • García Liñares, G., Gismondi, S., Osa Codesido, N., Moreno, S.N.J., Docampo, R., Rodriguez, J.B., (2007) Bioorg. Med. Chem. Lett., 17, pp. 5068-5071
  • Elicio, P.D., Chao, M.N., Galizzi, M., Li, C., Szajnman, S.H., Docampo, R., Moreno, S.N.J., Rodriguez, J.B., (2013) Eur. J. Med. Chem., 69, pp. 480-489
  • Linares, G.E.G., Ravaschino, E.L., Rodriguez, J.B., (2006) Curr. Med. Chem., 13, pp. 335-360
  • Maiti, D., Buchwald, S.L., (2009) J. Am. Chem. Soc., 131, pp. 17423-17429
  • Bhayana, B., Fors, B.P., Buchwald, S.L., (2009) Org. Lett., 11, pp. 3954-3957
  • Fors, B.P., Watson, D.A., Biscoe, M.R., Buchwald, S.L., (2008) J. Am. Chem. Soc., 130, pp. 13552-13554
  • Evans, D.A., Katz, J.L., West, T.R., (1998) Tetrahedron Lett., 39, pp. 2937-2940
  • Chan, D.M.T., Monaco, K.L., Wang, R.-P., Winters, M.P., (1998) Tetrahedron Lett., 39, pp. 2933-2936
  • Schvartzapel, A.J., Fichera, L., Esteva, M., Rodriguez, J.B., Gros, E.G., (1995) Helv. Chim. Acta, 78, pp. 1207-1214
  • Inkster, J.A.H., Liu, K., Ait-Mohand, S., Schaffer, P., Guérin, B., Ruth, T.J., Storr, T., (2012) Chem. Eur. J., 18, pp. 11079-11087
  • Imperiali, B., Roy, R.S., (1995) J. Org. Chem., 60, pp. 1891-1894
  • Canavaci, A.M., Bustamante, J.M., Padilla, A.M., Pereza Brandan, C.M., Simpson, L.J., Xu, D., Boehlke, C.L., Tarleton, R.L., (2010) PLoS Neglected Trop. Dis., 4, p. e740
  • Recher, M., Barboza, A.P., Li, Z.-H., Galizzi, M., Ferrer-Casal, M., Szajnman, S.H., Docampo, R., Rodriguez, J.B., (2013) Eur. J. Med. Chem., 60, pp. 431-440
  • Gubbels, M.J., Li, C., Striepen, B., (2003) Antimicrob. Agents Chemother., 47, pp. 309-316
  • Agrawal, S., Van Dooren, G.G., Beatty, W.L., Striepen, B., (2009) J. Biol. Chem., 284, pp. 33683-33691

Citas:

---------- APA ----------
Chao, M.N., Matiuzzi, C.E., Storey, M., Li, C., Szajnman, S.H., Docampo, R., Moreno, S.N.J.,..., Rodriguez, J.B. (2015) . Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii. ChemMedChem, 10(6), 1094-1108.
http://dx.doi.org/10.1002/cmdc.201500100
---------- CHICAGO ----------
Chao, M.N., Matiuzzi, C.E., Storey, M., Li, C., Szajnman, S.H., Docampo, R., et al. "Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii" . ChemMedChem 10, no. 6 (2015) : 1094-1108.
http://dx.doi.org/10.1002/cmdc.201500100
---------- MLA ----------
Chao, M.N., Matiuzzi, C.E., Storey, M., Li, C., Szajnman, S.H., Docampo, R., et al. "Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii" . ChemMedChem, vol. 10, no. 6, 2015, pp. 1094-1108.
http://dx.doi.org/10.1002/cmdc.201500100
---------- VANCOUVER ----------
Chao, M.N., Matiuzzi, C.E., Storey, M., Li, C., Szajnman, S.H., Docampo, R., et al. Aryloxyethyl thiocyanates are potent growth inhibitors of Trypanosoma cruzi and Toxoplasma gondii. ChemMedChem. 2015;10(6):1094-1108.
http://dx.doi.org/10.1002/cmdc.201500100