Designing novel antitrypanosomal agents from a mixed graph-theoretical substructural approach

Journal of Computational Chemistry

Volumn 31, Issue 4, 2010, Pages 882-894

  Planche, Alejandro Speck ^a,b   Scotti, Marcus Tulius ^b,c   De Emerenciano, Vicente Paulo ^b   López, América García ^a   Pérez, Enrique Molina ^d,e   Uriarte, Eugenio ^e  

^a UNIVERSIDAD DE ORIENTE   (Cuba)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

^d UNIVERSIDAD DE CAMAGÜEY   (Cuba)

^e UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Antitrypanosomal; Discriminant analysis; Fragment contributions; Graph theoretical descriptors; Massive screening

Indexed keywords

CHAGAS DISEASE; DATA SETS; DESCRIPTORS; FRAGMENT CONTRIBUTIONS; IN-SILICO; MIXED APPROACH; MIXED GRAPH; PARASITE-; RATIONAL DESIGN; SCIENTIFIC COMMUNITY; TOPOLOGICAL SUB-STRUCTURAL MOLECULAR DESIGNS; TRYPANOSOMA CRUZI;

DISCRIMINANT ANALYSIS;

ANTITRYPANOSOMAL AGENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; DISCRIMINANT ANALYSIS; DRUG DESIGN; DRUG EFFECT; DRUG SENSITIVITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RECEIVER OPERATING CHARACTERISTIC; STEREOISOMERISM; SYNTHESIS; TRYPANOSOMA CRUZI;

COMPUTER SIMULATION; DISCRIMINANT ANALYSIS; DRUG DESIGN; MOLECULAR STRUCTURE; PARASITIC SENSITIVITY TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; ROC CURVE; STEREOISOMERISM; TRYPANOCIDAL AGENTS; TRYPANOSOMA CRUZI;

EID: 76249132000     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21374     Document Type: Article

References (80)

1. World Health Organization Report, TDR (2005), Progress 2003-2004, 17th program Report, Available at http://www.who.int/tdr/publicatios/publicatios/pdf/ pr17/chagas.pdf.
2. Urbina, J. A, Curr Pharm Des 2002, 8, 287.
3. Urbina, J. A.; Docampo, R. Trends Parasitol 2003, 19, 495.
4. Docampo, R.; Moreno, S. N. J. In. Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1984; pp. 243-288.
5. Muelas, S.; Suárez, M.; Pérez, R.; Rodríguez, H.; Ochoa, C.; Escario, J. A.; Gómez-Barrio, A. Mem Inst Oswaldo Cruz 2002, 97, 269.
6. Muelas-Serrano, S.; Le-Senne, A.; Fenádez-Portillo, C.; Nogal, J. J.; Ochoa, C.; Gómez-Barrio, A. Mem Inst Oswaldo Cruz 2002, 97, 553.
7. Hansch, C.; Leo, A. QSAR: Fundamentals and Applications in Chemistry and Biology; American Chemical Society: Washington, DC, 1995.
8. Kubinyi, H. In Methods and Principles in Medicinal Chemistry; Manhnhold, R.; Krogsgaard-Larsen, P.; Timmerman, H., Eds.; VCH: New York, 1993.
9. Kier, L. B.; Hall, L. H. Molecular Connectivity in. Chemistry and Drug Research; Academic Press: New York, 1976.
10. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Activity Analysis; Research Studies Press: Letchworth, Herts, 1986.
11. Ivanciuc, O. In Handbook of Chemoinformatics; Gasteiger, J., Ed.; Wiley-VCH.: 2003; pp. 103-138.
12. Ivanciuc, O. In Handbook of Chemoinformatics; Gasteiger, J., Ed.; Wiley-VCH: 2003; pp. 981-1003.
13. Garcia-Domenech, R.; Garcia, F. J.; Soler, R. M.; Gálvez, J.; AntonFos, G. M.; De Julián-Ortiz, J. V. Quant Struc-Act Rel 1.996, 15, 1.
14. Julián-Ortiz, J. V.; Gálvez, J.; Muñoz-Collado, C; Garcia-Domenech, R.; Gimeno-Cardona, C. J Med Chem 1999, 42, 3308.
15. De Gregorio Alapont, C.; Garcia-Domenech, R.; Gálvez, J.; Ros, M. J.; Wolski, S.; García, M. D. Bioorg Med Chem Lett 2000, 10, 2033.
16. Gozalbes, R.; Brun-Pascaud, M.; Gálvez, J.; Garcia-Domenech, R.; Girard, P. M.; Doucet, J. P.; Derouin, F. Antimicrob Agents Chemother 2000, 44, 2764.
17. Kubinyi, H.; Kehrhahn, O. H. J Med Chem 1976, 19, 578.
18. Kubinyi, H. J Med Chem 1.976, 19, 587.
19. Bonse, S.; Santelli-Rouvier, C.; Barbe, J.; Krauth-Siegel, R. L. J Med Chem 1999, 42, 5448.
20. De Koning, H. P. Int J Parasitol 2001, 31,511.
21. Elhalem, E.; Bailey, B. N.; Docampo, R.; Ujváry, I.; Szajnman, S. H.; Rodríguez, L. B. J Med Chem. 2002, 45, 3984.
22. Avila, J. L.; Rojas, T.; Avila, A.; Polegre, M. A.; Robins, R. K. Antimicrob Agents Chemother 1987, 31, 447.
23. Oliveira, R. B.; Passos, A. P. F.; Alves, R. O.; Romanha, A. J.; Prado, M. A. F.; Dias De Sousa Filho, J.; Alves, R. J. Mem Inst Oswaldo Cruz 2003, 98, 141.
24. Carvalho, S. A.; Da Silva, E. F.; Santa-Rita, R. M.; De Castro, S. L.; Fraga, C. A. M. Bioorg Med Chem Lett 2004, 14, 5967.
25. Cerecetto, H.; Di. Maio, R.; Gonzalez, M.; Risso, M.; Sagrara, G.; Seoane, G.; Denicola, A.; Peluffo, G.; Quijano, C.; Stoppani, A. O.; Paulino, M.; Olea-Azar, C.; Basombrio, M. A. Eur J Med Chem 2000, 35, 343.
26. Gilbert, I. H. Biochim. Biophys Acta 2002, 1587, 249.
27. Du, X.; Guo, Ch; Hansell, E.; Doyle, P. S.; Caffrey, C. R.; Holler, T. P.; Mckerrow, J. H.; Cohen, F. E. J Med Chem 2002, 45, 2695.
28. Jonckers, T. H. M.; Van Miert, S.; Cimanga, K.; Baillo, C.h; Colson, P.; De Pauw-Gillet, M. C.; Van Den Heuvel, H.; Claeys, M.; Lemière, F.; Esmans, E. L.; Rozenski, J.; Quirijnen, L.; Maes, L.; Dommisse, R.; Lemière, G. L.; Vlietinck, A.; Pieters, L. J Med Chem 2002, 45, 3497.
29. Prieto, J. J.; Talevi, A.; Bruno-Blanch, L. E. Mol Divers 2006, 10, 361.
30. Mcgrath, M. E.; Eakin, A. E.; Engel, J. C.; Mckerrow, J. H.; Craik, C. S.; Fletterick, R. J. J Mol Biol 1995, 247, 251.
31. Eakin, A. E.; Guerra, A.; Focia, P. J.; Torres-Martinez, J.; Craig, S. P., III, Antimicrob Agents Chemother 1997, 41, 1686.
32. Chowdhury, S. F.; Bernier Villamor, V. B.; Guerrero, R. H.; Leal, I.; Bran, R.; Croft, S. L.; Goodman, J. M.; Maes, L.; Ruiz-Perez, L. M.; Gonzalez-Pacanowska, D.; Gilbert, I. H. J Med Chem 1999, 42, 4300.
33. Blankenfeldt, W.; Nowicki, C.; Montemartini-Kalisz, M.; Kalisz, H. M.; Hecht, H. J. Protein Sci 1999, 8, 2406.
34. Zuccotto, F.; Zvelebil, M.; Brun, R.; Chowdhury, S. F.; Di Lucrezia, R.; Leal, I.; Maes, L.; Ruiz-Perez, L. M.; Gonzalez-Pacanowska, D.; Gilbert, I. H. Eur J Med Chem 2001, 36, 395.
35. Buckner, F.; Yokoyama, K.; Lockman, J.; Aikenhead, K.; Ohkanda, J.; Sadilek, M.; Sebti, S.; Van Voorhis, W.; Hamilton, A.; Gelb, M. H. PNAS 2003, 100, 15149.
36. Montero-Torres, A.; Vega, M. C.; Marrero-Ponce, Y.; Rolon, M.; Gómez-Barrio, A.; Escario, J. A.; Aran, V. J.; Martínez- Fernández, A. R.; Meneses-Marcel, A. Bioorg Med Chem 2005, 13, 6264.
37. Prado-Prado, F. J.; González-Díaz, H.; Martinez De La Vega, O.; Ubeira, F. M.; Chou, K. Ch Bioorg Med Chem 2008, 16, 5871.
38. Viswanadhan, V. N.; Chose, A. K.; Revankar, G. R.; Robins, R. K. J Chem Inf Comput Sci 1989, 29, 163.
39. Viswanadhan, V. N.; Reddy, M. R.; Bacquet, R. J.; Erion, M. D. J Comput Chem 1993, 14, 1019.
40. Estrada, E.; Molina, E. J Mol Graph Model 2001, 20, 54.
41. Estrada, E. J Chem Inf Comput Sci 1996, 36, 844.
42. Estrada, E. J Chem. Inf Comput Sci 1997, 37, 320.
43. Estrada, E. J Chem Inf Comput Sci 1998, 38, 23.
44. Estrada, E. J Chem Soc Faraday Trans 1998, 94, 1407.
45. Estrada, E. J Chem Inf Comput Sci 1999, 39, 90.
46. Estrada, E.; Peña, A.; Garcia-Domenech R. J Comput-Aided Mol Des 1998, 12, 583.
47. Estrada, E.; Gutiérrez, Y. J Chromatogr A. 1999, 858, 187.
48. Estrada, E.; Gutiérrez, Y.; González, H. J Chem Inf Comput Sci 2000, 40, 1386.
49. Estrada, E.; Peña, A. Bioorg Med Chem 2000, 8, 2755.
50. Estrada, E.; Uriarte, E.; Montero, A.; Tejeira, M.; Santana, L.; De Clercq, E. J Med Chem 2000, 43, 1975.
51. Pérez-Gonález, M.; González-Díaz, H.; Molina-Ruiz, R.; Cabrera, M. A.; Ramos De Armas, R. J Chem Inf Comput Sci 2003, 43, 1192.
52. Pérez-Gonález, M.; Morales Helguera, A.; Morales Rodríguez, Y. Electron J Mol Des 2004, 3, 750.
53. Estrada, E. J Chem Inf Comput Sci 1995, 35, 31.
54. Estrada, E.; Uriarte, E. SAR QSAR Environ Res 2001, 12, 309.
55. Estrada, E.; Molina, E.; Uriarte, E. SAR QSAR Environ Res 2001, 12, 445.
56. Estrada, E.; Uriarte, E. Curr Med Chem 2001, 8, 1573.
57. Estrada, E.; Molina, E.; Perdomo-Lopez, I. J Chem Inf Comput Sci 2001, 41, 1015.
58. Lima Leite, A. C.; Souza De Lima, R.; Moreira, D. R.; Cardoso, M. V.; Gouveia De Brito, A. C.; Farias Dos Santos, L. M. Bioorg Med Chem 2006, 14, 3749.
59. Rolón, M.; Seco, E. M.; Vega, C.; Nogal, J. J.; Escario, J. A.; Gómez-Barrio, A.; Malpartida, F. Int J Antimicrob Agents 2006, 28, 104.
60. Gonzalez, J. L.; Stephens, C. E.; Wenzler, T.; Brun, R.; Tanious, F. A.; Wilson, W. D.; Barszcz, T.; Werbovets, K. A.; Boykin, D. W. Eur J Med Chem 2007, 42, 552.
61. Gerpe, A.; Odreman-Nuñez, I.; Draper, P.; Boiani, L.; Urbina, J. A.; Gonzalez, M.; Cerecetto, H. Bioorg Med Chem 2008, 16, 569.
62. Caterina, M. C.; Perillo, I. A.; Boiani, L.; Pezaroglo, H.; Cerecetto, H.; González, M.; Salerno, A. Bioorg Med Chem 2008, 16, 2226.
63. Porcal, W.; Hernández, P.; Boiani, L.; Boiani, M.; Ferreira, A.; Chidichimo, A.; Cazzulo, J. J.; Olea-Azar, C.; González, M.; Cerecetto, H. Bioorg Med Chem 2008, 16, 6995.
64. O'neil, M. J.; Heckelman, P. E.; Koch, C. B.; Roman, K. J.; Kenny, C. M.; D'arecca, M. R. THE MERCK INDEX: An Encyclopedia of Chemical, Drugs and Biologicals, MERCK & Co., Inc: Whitehouse Station, NJ, USA, 2006.
65. PubChem Database, Available at: http://pubchem.ncbi.nlm.nih.gov/.
66. 66. Hyperchem™ Release 7.01 for Windows (Molecular Modeling System). © 2002, Hypercube, Inc.
67. Talete srl, DRAGON for Windows (Software for Molecular Descriptor Calculations). Version 5.4, 2006, Available at: http://www.tal.ete. mi.it/dragon.htm.
68. Platts, J. A.; Butina, D.; Abraham, M. H.; Hersey, A. J Chem Inf Comput Sci 1999, 39, 835.
69. Estrada, E.; Gutiérrez, Y. MODESLAB 1.5. © 2002-2004. Available at: www.modeslab.com.
70. Kowalski, R. B.; Wold, S. Handbook of Statistic; Krishnaiah, P. R.; Kanal, L. N., Eds.; North Holland Publishing Company: Amsterdam, 1982; pp. 673-697.
71. Johnson, R. A.; Wiehern, D. W. Applied Multivariate Statistical Analysis, Prentice-Hall: NJ, 1998.
72. StatSoft, Inc. 2001TATISTICA (data analysis software system), version 6. Available at: www.statsoft.com.
73. Buryak, A.; Severin, K. J Comb Chem 2006, 8, 540.
74. Estrada, E. Topological Indices and Related Descriptors in QSAR and QSPR; Dellivers, J.; Balaban, A. T., Eds.; Gordon, and Breach: Amsterdam, 1999; pp. 403-453.
75. Fawcett, T. ROC Graphs: Notes and Practical Considerations for Researchers. Tech. Rep. HPL. 2003-4, Palo Alto, 2004.
76. Hanley, J. A.; Mcneil, B. J. Radiology 1982, 143, 29.
77. MATLAB Version 6.5. © 1984-2002. The MathWorks, Inc. Available at: http://www.mathworks.com.
78. Van Waterbeemd, H. Methods and Principles in Medicinal Chemistry; Van Waterbeemd, H.; Manhnhold, R.; Krogsgaard-Larsen, P.; Timmerman, H., Eds.; VCH: Weinhiem, 1.995; pp. 283-293.
79. Da Silva Ferreira, W.; Freire-De-Lima, L.; Barbosa Saraiva, V.; Alisson-Silva, F.; Mendoça-Previato, L.; Previato, J. O.; Echevarria, A.; Freire De Lima, M. E. Bioorg Med Chem 2008, 16, 2984.
80. Brain-Isasi, S.; Quezada, C.; Pessoa, H.; Morello, A.; Kogan, M. J.; Álvarez-Lueje, A. Bioorg Med Chem 2008, 7622.