Abstract:
Glutathionylspermidine synthase (GSS) is a crucial enzyme in the trypanothione biosynthetic pathway and is also an interesting molecular target for drug design. We synthesized a series of amides of a glutathione analogue (L-γ-Glu-L-Leu-Gly-NHR) where R are linear alkyl groups. All of these drugs exhibited marginal biological activity against the responsible agent of Chagas' disease, the protozoan Trypanosoma cruzi.
Registro:
Documento: |
Artículo
|
Título: | Synthesis and biological evaluation of glutathione-like tripeptidesagainstTrypanosoma cruzi |
Autor: | Ravaschino, E.L.; Docampo, R.; Rodriguez, J.B. |
Filiación: | Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EHA, Buenos Aires, Argentina Department of Pathobiology, College of Veterinary Medicine, University of Illinois, 2001 South Lincoln Avenue, Urbana, IL 61802, United States
|
Palabras clave: | American trypanosomiasis; Glutathionylspermidine synthase; Trypanosoma cruzi; Trypanothione; gamma glutamyl alpha benzyl ester leucylgylcyl n 1 butylamide; gamma glutamyl alpha benzyl ester leucylgylcyl n 1 heptylamide; gamma glutamyl alpha benzyl ester leucylgylcyl n 1 hexylamide; gamma glutamyl alpha benzyl ester leucylgylcyl n 1 octylamide; gamma glutamyl alpha benzyl ester leucylgylcyl n 1 pentylamide; gamma glutamyl alpha benzyl ester leucylgylcyl n 1 propylamide; gamma glutamyl alpha benzyl ester leucylgylcyl n ethylamide; gamma glutamyl alpha benzyl ester leucylgylcyl n methylamide; glutathione derivative; glutathionylspermidine synthase; n benzyloxycarbonyl gamma glutamyl alpha benzyl ester leucylgylcyl n 1 butylamide; n benzyloxycarbonyl gamma glutamyl alpha benzyl ester leucylgylcyl n 1 heptylamide; n benzyloxycarbonyl gamma glutamyl alpha benzyl ester leucylgylcyl n 1 hexylamide; n benzyloxycarbonyl gamma glutamyl alpha benzyl ester leucylgylcyl n 1 octylamide; n benzyloxycarbonyl gamma glutamyl alpha benzyl ester leucylgylcyl n 1 pentylamide; n benzyloxycarbonyl gamma glutamyl alpha benzyl ester leucylgylcyl n 1 propylamide; n benzyloxycarbonyl gamma glutamyl alpha benzyl ester leucylgylcyl n ethylamide; n benzyloxycarbonyl gamma glutamyl alpha benzyl ester leucylgylcyl n methylamide; spermidine synthase; tripeptide derivative; unclassified drug; article; Chagas disease; drug screening; drug structure; nonhuman; peptide synthesis; Trypanosoma cruzi |
Año: | 2003
|
Volumen: | 2003
|
Número: | 10
|
Página de inicio: | 298
|
Página de fin: | 313
|
Título revista: | Arkivoc
|
Título revista abreviado: | Arkivoc
|
ISSN: | 14246376
|
CAS: | spermidine synthase, 37277-82-0, 67016-02-8
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p298_Ravaschino |
Referencias:
- Rodriguez, J.B., (2001) Curr. Pharm. Des., 7, pp. 1105-1116
- Urbina, J.A., (2002) Curr. Pharm. Des., 8, pp. 287-295
- Cazzulo, J.J., Stoka, V., Turk, V., (2001) Curr. Pharm. Des., 7, pp. 1143-1156
- Docampo, R., (2001) Curr. Pharm. Des., 7, pp. 1157-1164
- De Lederkremer, R.M., Bertello, L.E., (2001) Curr. Pharm. Des., 7, pp. 1165-1179
- Docampo, R., Moreno, S.N.J., (2001) Curr. Drug Targets Infect. Disord., 1, pp. 51-61
- Augustyns, K., Amssoms, K., Yamani, A., Rajan, P.K., Haemers, A., (2001) Curr. Pharm. Des., 7, pp. 1117-1141
- De Castro, S.L., (1993) Acta Tropica, 53, pp. 83-98
- Docampo, R., Moreno, S.N.J., (1985) Rev. Biochem. Toxicol., 7, pp. 159-204
- Schmidt, A., Krauth-Siegel, R.L., (2002) Curr. Top. Med. Chem., 2, pp. 1239-1259
- D'Silva, C., Daunes, S., (2002) Expert Opin. Investig. Drugs, 11, pp. 217-231
- Muller, S., Liebau, E., Walter, R.D., Krauth-Siegel, R.L., (2003) Trends Parasitol., 19, pp. 320-328
- Krauth-Siegel, R.L., Inhoff, O., (2003) Parasitol. Res., 90, pp. S77-S85
- Moncayo, A., (1995) Eleventh Programme Report of the UNDP/World Bank/WHO Special Program for Research and Training in Tropical Diseases (TDR), pp. 67-75. , World Health Organization: Geneva
- De Souza, W., (1984) Int. Rev. Cytol., 86, pp. 197-283
- Docampo, R., Schmuñis, G.A., (1997) Parasitol. Today, 13, pp. 129-130
- Urbina, J.A., (1999) J. Mol. Med., 77, pp. 332-338
- Brener, Z., (1979) Pharmacol. Ther., 7, pp. 71-90
- Rodriguez, J.B., Gros, E.G., (1995) Curr. Med. Chem., 2, pp. 723-742
- Shames, S., Fairlamb, A.H., Cerami, A., Walsh, C.T., (1986) Biochemistry, 25, pp. 3519-3526
- Fairlamb, A.H., Blackburn, P., Ultrich, P., Chait, B.T., Cerami, A., (1985) Science, 227, pp. 1485-1487
- Smith, K., Nadeau, K., Walsh, C.T., Fairlamb, A.H., (1992) Protein Sci., 1, pp. 874-883
- Jacoby, E.M., Schlichting, I., Lantwin, C.B., Kabsch, W., Krauth-Siegel, R.L., (1996) Proteins, 24, pp. 73-80
- Zhang, Y., Bond, C.S., Bailey, S., Cunningham, M.L., Fairlamb, A.H., Hunter, W.N., (1996) Protein Sci., 5, pp. 52-61
- Bailey, S., Smith, K., Fairlamb, A.H., Hunter, W.N., (1993) Eur. J. Biochem., 213, pp. 67-75
- De Craecker, S., Verbruggen, C., Rajan, P.K., Smith, K., Haemers, A., Fairlamb, A.H., (1997) Mol. Biochem. Parasitol., 84, pp. 25-32
- Fan, C., Moews, P.C., Walsh, C.T., Knox, J.R., (1994) Science, 266, pp. 439-443
- Hiratake, J., Kato, H., Oda, J., (1994) J. Am. Chem. Soc., 116, pp. 12059-12060
- Verbruggen, C., De Craecker, S., Rajan, P.K., Jiago, X.-Y., Borloo, M., Smith, K., Fairlamb, A.H., Haemers, A., (1996) Bioorg. Med. Chem. Lett., 6, pp. 253-258
- Chen, S., Coward, J.K., (1998) J. Org. Chem., 63, pp. 502-509
- Chen, S., Lin, C.-H., Walsh, C.T., Coward, J.K., (1997) Bioorg. Med. Chem. Lett., 7, pp. 505-510
- Amssoms, K., Oza, S.L., Ravaschino, E., Yamani, A., Lambeir, A., Rajan, P., Bal, G., Haemers, A., (2002) Bioorg. Med. Chem. Lett., 12, pp. 2553-2556
- Amssoms, K., Oza, S.L., Augustyns, K., Yamani, A., Lambeir, A.M., Bal, G., Van Der Veken, P., Haemers, A., (2002) Bioorg. Med. Chem. Lett., 12, pp. 2703-2705
- D'Silva, C., Daunes, S., Rock, P., Yardley, V., Croft, S.L., (2000) J. Med. Chem., 43, pp. 2072-2078
- Daunes, S., D'Silva, C., Kendrick, H., Yardley, V., Croft, S.L., (2001) J. Med. Chem., 44, pp. 2976-2983
- Chen, S., Lin, C.-H., Kwon, D.S., Walsh, C.T., Coward, J.K., (1997) J. Med. Chem., 40, pp. 3842-3850
- Kwon, D.S., Lin, C.-H., Chen, S., Coward, J.K., Walsh, C.T., Bollinger Jr., J.M., (1997) J. Biol. Chem., 272, pp. 2429-2436
- Schvartzapel, A.J., Zhong, L., Docampo, R., Rodriguez, J.B., Gros, E.G., (1997) J. Med. Chem., 40, pp. 2314-2322
Citas:
---------- APA ----------
Ravaschino, E.L., Docampo, R. & Rodriguez, J.B.
(2003)
. Synthesis and biological evaluation of glutathione-like tripeptidesagainstTrypanosoma cruzi. Arkivoc, 2003(10), 298-313.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p298_Ravaschino [ ]
---------- CHICAGO ----------
Ravaschino, E.L., Docampo, R., Rodriguez, J.B.
"Synthesis and biological evaluation of glutathione-like tripeptidesagainstTrypanosoma cruzi"
. Arkivoc 2003, no. 10
(2003) : 298-313.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p298_Ravaschino [ ]
---------- MLA ----------
Ravaschino, E.L., Docampo, R., Rodriguez, J.B.
"Synthesis and biological evaluation of glutathione-like tripeptidesagainstTrypanosoma cruzi"
. Arkivoc, vol. 2003, no. 10, 2003, pp. 298-313.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p298_Ravaschino [ ]
---------- VANCOUVER ----------
Ravaschino, E.L., Docampo, R., Rodriguez, J.B. Synthesis and biological evaluation of glutathione-like tripeptidesagainstTrypanosoma cruzi. Arkivoc. 2003;2003(10):298-313.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2003_n10_p298_Ravaschino [ ]