Selective inactivation of triosephosphate isomerase from Trypanosoma cruzi by brevifolin carboxylate derivatives isolated from Geranium bellum Rose

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 20, 2009, Pages 5936-5939

  Gayosso De Lucio, Juan ^a   Torres Valencia, Martin ^a   Rojo Domínguez, Arturo ^b   Nájera Peña, Hugo ^b   Aguirre López, Beatriz ^c   Salas Pacheco, José ^d   Avitia Domínguez, Claudia ^d   Téllez Valencia, Alfredo ^d  

^a UNIVERSIDAD AUTÓNOMA DEL ESTADO DE HIDALGO   (Mexico)

^b DEPARTAMENTO DE PROCESOS Y TECNOLOGÍA   (Mexico)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^d UNIVERSIDAD JUÁREZ DEL ESTADO DE DURANGO   (Mexico)

Author keywords

Brevifolin carboxylate; Molecular docking; Triosephosphate isomerase; Trypanosoma cruzi

Indexed keywords

BUTYLBREVIFOLIN CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; ETHYLBREVIFOLIN CARBOXYLIC ACID; METHYL TRI O METHYLBREVIFOLIN CARBOXYLIC ACID; METHYLBREVIFOLIN CARBOXYLIC ACID; TRIOSEPHOSPHATE ISOMERASE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; DRUG ACTIVATION; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INACTIVATION; GERANIUM; GERANIUM BELLUM; METHYLATION; SIMULATION; SPECTROSCOPY; STRUCTURE ANALYSIS; TRYPANOSOMA CRUZI;

ANIMALS; ANTIPROTOZOAL AGENTS; BINDING SITES; CHAGAS DISEASE; COMPUTER SIMULATION; DRUG DESIGN; ENZYME INHIBITORS; GERANIUM; HUMANS; TAXOIDS; TRIOSE-PHOSPHATE ISOMERASE; TRYPANOSOMA CRUZI;

TRYPANOSOMA CRUZI;

EID: 70349237870     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.08.055     Document Type: Article

References (29)

1. Moncayo A.C., and Ortiz Yanine M.I. Ann. Trop. Med. Parasitol. 100 (2006) 663
2. Schofield C.J., Jannin J., and Salvatella R. Trends Parasitol. 22 (2006) 583
3. Urbina J.A., and Docampo R. Trends Parasitol. 19 (2003) 495
4. Croft S.L. Parasitology 114 (1997) S3
5. Gomez-Puyou A., Saavedra-Lira E., Becker I., Zubillaga R.A., Rojo-Dominguez A., and Perez-Montfort R. Chem. Biol. 2 (1995) 847
6. Velanker S.S., Ray S.S., Gokhale R.S., Balaram H., Balaram P., and Murthy M.R.N. Structure 5 (1997) 751
7. Cortés-Figueroa A.A., Pérez-Torres A., Salaiza N., Cabrera N., Escalona-Montaño A., Rondán A., Aguirre-García M., Gómez-Puyou A., Pérez-Montfort R., and Becker I. Parasitol Res. 102 (2008) 635
8. Maldonado E., Soriano-García M., Moreno A., Cabrera N., Garza-Ramos G., de Gómez-Puyou M., Gómez-Puyou A., and Perez-Montfort R. J. Mol Biol. 283 (1998) 193
9. Waley S.G. J. Biochem. 135 (1973) 165
10. Zabori S., Rudolph R., and Jaenicke R. Z. Naturforsch. 35C (1980) 999
11. Newman D.J., Cragg G.M., and Snader K.M. J. Nat. Prod. 70 (2007) 461
12. Ercil D., Kaloga M., Radtke O., Sakar M., Kiderlen A., and Kolodziej H. Turk. J. Chem. 29 (2005) 437
13. Salem M., and Karl A.W. Curr. Med. Chem. 13 (2006) 2571
14. -1, respectively.
15. 29
16. Tellez-Valencia A., Avila-Rios S., Perez-Montfort R., Rodriguez-Romero A., Tuena de Gomez-Puyou M., Lopez-Calahorra F., and Gomez-Puyou A. Biochem. Biophys. Res. Commun. 295 (2002) 958
17. Pettigrew D.W. Biochemistry 25 (1986) 4711
18. 8 The region on the interface of TcTIM suitable for docking assays was determined using the alfa-sites tool in the same MOE package. Assignation of partial charges and optimal geometry of compound 1 were carried out with the MMFF94 forcefield. For molecular docking of compound 1 in the interface of TcTIM, 5000 random orientations with variations in position and molecular rotation were assessed, and the score for each one of them were calculated by MOE considering spatial compatibility to the binding site, internal energy of the ligand and protein-ligand interactions.
19. Zhong Y., Zuo C., Li F., Ding X., Yao Q., Wu K., Zhang Q., Wang Z., Zhou L.W., Lan J., and Wang X. Zhongguo Zhong Yao Za Zhi. 23 (1998) 363
20. Iizuka T., Moriyama H., and Nagai M. Biol. Pharm. Bull. 29 (2006) 177
21. Iizuka T., Nagai M., Taniguchi A., Moriyama H., and Hoshi K. Biol. Pharm. Bull. 30 (2007) 382
22. Tomczyk M., Drozdowska D., Bielawska A., Bielawski K., and Gudej J. Pharmazie 63 (2008) 389
23. Camacho-Luis A., Gayosso-De-Lucio J.A., Torres-Valencia M.T., Muñoz-Sánchez J.L., Alarcón-Hernández E., López R., and Barrón B.L. J. Mex. Chem. Soc. 52 (2008) 103
24. Fang S.H., Rao Y.K., and Tzeng Y.M. J. Ethnopharmacol. 116 (2008) 333
25. Ostoa-Saloma P., Garza-Ramos G., Ramirez J., Becker I., Berzunza M., Landa A., Gomez-Puyou A., de Gomez-Puyou M., and Perez-Montfort R. Eur. J. Biochem. 244 (1997) 700
26. Mande S.C., Mainfroid V., Kalk K.H., Goraj K., Martial J.A., and Hol W.G. Protein Sci. 3 (1994) 810
27. Pace C.N., Vajdos F., Fee L., Grimsley G., and Gray T. Protein Sci. 4 (1995) 2411
28. Jia-Sheng G., Su-Xian W., Xian L., and Ting-Ru Z. Acta Pharm. Sinca 22 (1987) 28
29. Yoshida T., Itoh H., Matsunaga S., Tanaka R., and Okuda T. Chem. Pharm. Bull. 40 (1992) 53