ESR, electrochemical, molecular modeling and biological evaluation of 4-substituted and 1,4-disubstituted 7-nitroquinoxalin-2-ones as potential anti-Trypanosoma cruzi agents

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 78, Issue 3, 2011, Pages 1004-1012

  Aguilera Venegas, Benjamín ^a   Olea Azar, Claudio ^a   Norambuena, Ester ^b   Arán, Vicente J ^c   Mendizábal, Fernando ^a   Lapier, Michel ^a   Maya, Juan Diego ^d   Kemmerling, Ulrike ^d   López Muñoz, Rodrigo ^d  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSIDAD METROPOLITANA DE CIENCIAS DE LA EDUCACIÓN   (Chile)

^c INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^d UNIVERSITY OF CHILE   (Chile)

Author keywords

Chagas' disease; Epimastigote; ESR; Molecular Modeling; Nitroquinoxaline; Trypomastigote

Indexed keywords

CHAGAS' DISEASE; EPIMASTIGOTE; ESR; NITROQUINOXALINE; TRYPOMASTIGOTE;

DERIVATIVES; ELECTROCHEMISTRY; ELECTROLYTIC REDUCTION; ENZYME ACTIVITY; FREE RADICAL REACTIONS; HYDROGEN; MOLECULAR MODELING;

CYCLIC VOLTAMMETRY;

ANTITRYPANOSOMAL AGENT; NITROGEN DERIVATIVE; OXIDOREDUCTASE; QUINOXALINE DERIVATIVE; TRYPANOTHIONE REDUCTASE;

ANIMAL; ARTICLE; CELL LINE; CHAGAS DISEASE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; ENZYMOLOGY; HUMAN; METHODOLOGY; OXIDATION REDUCTION REACTION; TRYPANOSOMA CRUZI;

ANIMALS; CELL LINE; CHAGAS DISEASE; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NADH, NADPH OXIDOREDUCTASES; NITROGEN COMPOUNDS; OXIDATION-REDUCTION; QUINOXALINES; TRYPANOCIDAL AGENTS; TRYPANOSOMA CRUZI;

EID: 79951517485     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2010.12.017     Document Type: Article

References (45)

1. C.J. Schofield, J. Jannin, and R. Salvatella Trends in Parasitology 22 2006 583 588
2. J.A. Urbina, and R. Docampo Trends in Parasitology 19 2003 495 501
3. R. Docampo Chemico-Biological Interactions 73 1990 1 27
4. R. Docampo, and A.O.M. Stoppani Archives of Biochemistry and Biophysics 197 1979 317 321
5. J.D. Maya, Y. Repetto, M. AgosIn, J.M. Ojeda, R. Tellez, C. Gaule, and A. Morello Molecular and Biochemical Parasitology 86 1997 101 106
6. C.M. Sreider, L. Grinblat, and A.O.M. Stoppani Biochemical Pharmacology 40 1990 1849 1857
7. M.M. de Mecca, S.L. Fanelli, L.C. Bartel, C.R. de Castro, E.G. Díaz, and J.A. Castro Life Sciences 81 2007 144 152
8. J.A. Castro, M.M. deMecca, and L.C. Bartel Human and Experimental Toxicology 25 2006 471 479
9. W.H. Koppenol Free Radical Biology and Medicine 15 1993 645 651
10. S. Cuzzocrea, D.P. Riley, A.P. Caputi, and D. Salvemini Pharmacological Reviews 53 2001 135 159
11. J.R. Coura, and S.L.d. Castro Memórias do Instituto Oswaldo Cruz 97 2002 3 24
12. C. Jullian, J. Morales-Montecinos, G. Zapata-Torres, B. Aguilera, J. Rodriguez, V. Arán, and C. Olea-Azar Bioorganic & Medicinal Chemistry 16 2008 5078 5084
13. J. Rodríguez, A. Gerpe, G. Aguirre, U. Kemmerling, O.E. Piro, V.J. Arán, J.D. Maya, C. Olea-Azar, M. González, and H. Cerecetto European Journal of Medicinal Chemistry 44 2009 1545 1553
14. J. Rodríguez, C. Olea-Azar, G. Barriga, C. Folch, A. Gerpe, H. Cerecetto, and M. González Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 70 2008 557 563
15. V.J. Arán, C. Ochoa, L. Boiani, P. Buccino, H. Cerecetto, A. Gerpe, M. González, D. Montero, J.J. Nogal, A. Gómez-Barrio, A. Azqueta, A. López de Ceráin, O.E. Piro, and E.E. Castellano Bioorganic & Medicinal Chemistry 13 2005 3197 3207
16. L. Boiani, A. Gerpe, V.J. Arán, S. Torres de Ortiz, E. Serna, N. Vera de Bilbao, L. Sanabria, G. Yaluff, H. Nakayama, A. Rojas de Arias, J.D. Maya, J.A. Morello, H. Cerecetto, and M. González European Journal of Medicinal Chemistry 44 2009 1034 1040
17. L. Otero, G. Aguirre, L. Boiani, A. Denicola, C. Rigol, C. Olea-Azar, J.D. Maya, A. Morello, M. González, D. Gambino, and H. Cerecetto European Journal of Medicinal Chemistry 41 2006 1231 1239
18. M. Vieites, L. Otero, D. Santos, C. Olea-Azar, E. Norambuena, G. Aguirre, H. Cerecetto, M. González, U. Kemmerling, A. Morello, J. Diego Maya, and D. Gambino Journal of Inorganic Biochemistry 103 2009 411 418
19. M. Vieites, L. Otero, D. Santos, J. Toloza, R. Figueroa, E. Norambuena, C. Olea-Azar, G. Aguirre, H. Cerecetto, M. González, A. Morello, J.D. Maya, B. Garat, and D. Gambino Journal of Inorganic Biochemistry 102 2008 1033 1043
20. Y. Marrero-Ponce, O. Rivera-Borroto, A. Meneses-Marcel, J. Escario, A. Gómez Barrio, V. Arán, M. Martins Alho, D. Montero Pereira, J. Nogal, F. Torrens, F. Ibarra-Velarde, Y. Vera Montenegro, A. Huesca-Guillén, N. Rivera, and C. Vogel QSAR & Combinatorial Science 28 2009 9 26
21. A. Meneses-Marcel, Y. Marrero-Ponce, Y. Machado-Tugores, A. Montero-Torres, D.M. Pereira, J.A. Escario, J.J. Nogal-Ruiz, C. Ochoa, V.J. Arán, A.R. Martínez-Fernández, and R.N. García Sánchez Bioorganic & Medicinal Chemistry Letters 15 2005 3838 3843
22. M.A.M. Alho, Y. Marrero-Ponce, A. Meneses-Marcel, Y.M. Tugores, A. Montero-Torres, F. Pérez-Giménez, A. Gómez-Barrio, J.J. Nogal, R.N. García-Sánchez, M.C. Vega, M. Rolón, A.R. Martínez-Fernández, J.A. Escario, N. Rivera, F. Ibarra-Velarde, M. Mondragón, R. Mondragón, R. Chicharro, and V.J. Arán Antiprotozoan lead discovery by aligning dry and wet screening: prediction, synthesis, and biological assay of novel quinoxalinones Proceedings of the 12th International Electronic Conference on Synthetic Organic Chemistry 2008
23. F. Irigoín, L. Cibils, M.A. Comini, S.R. Wilkinson, L. Flohé, and R. Radi Free Radical Biology and Medicine 45 2008 733 742
24. M. Faundez, L. Pino, P. Letelier, C. Ortiz, R. Lopez, C. Seguel, J. Ferreira, M. Pavani, A. Morello, and J.D. Maya Antimicrob. Agents Chemother. 49 2005 126 130
25. S. Muelas-Serrano, J.J. Nogal-Ruiz, and A. Gómez-Barrio Parasitology Research 86 2000 999 1002
26. M.L. Cunningham, M.J.J.M. Zvelebil, and A.H. Fairlamb European Journal of Biochemistry 221 1994 285 295
27. S. Baillet, E. Buisine, D. Horvath, L. Maes, B. Bonnet, and C. Sergheraert Bioorganic & Medicinal Chemistry 4 1996 891 899
28. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart Journal of the American Chemical Society 107 1985 3902 3909
29. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople GAUSSIAN' 98. Revision A.11.2 ed. 2001 Gaussian Inc. Pittsburgh, PA
30. M. D'Amore, R. Improta, and V. Barone Journal of Physical Chemistry A 107 2003 6264 6269
31. A.D. Becke Physical Reviews A 38 1988 3098 3100
32. C.T. Lee, W.T. Yang, and R.G. Parr Physical Reviews B 37 1988 785 789
33. V. Barone, and M. Cossi Journal of Physical Chemistry A 102 1998 1995 2001
34. M. Cossi, V. Barone, R. Cammi, and J. Tomasi Chemical Physical Letters 255 1996 327 335
35. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson Journal of Computational Chemistry 19 1998 1639 1662
36. J.A. Bautista-Martínez, I. González, and M. Aguilar-Martínez Electrochimica Acta 49 2004 3403 3411
37. S. Bollo, L.J. Núñez-Vergara, M. Bontá, G. Chauviere, J. Périé, and J.A. Squella Journal of Electroanalytical Chemistry 511 2001 46 54
38. J. Carbajo, S. Bollo, L.J. Núñez-Vergara, A. Campero, and J.A. Squella Journal of Electroanalytical Chemistry 531 2002 187 194
39. A.H. Fairlamb, and A. Cerami Annual Review of Microbiology 46 1992 695 729
40. Y. Zhang, C.S. Bond, S. Bailey, M.L. Cunningham, A.H. Fairlamb, and W.N. Hunter Protein Science 5 1996 52 61
41. G. Aguirre, E. Cabrera, H. Cerecetto, R. Di Maio, M. González, G. Seoane, A. Duffaut, A. Denicola, M.J. Gil, and V. Martínez-Merino European Journal of Medicinal Chemistry 39 2004 421 431
42. C.S. Bond, Y. Zhang, M. Berriman, M.L. Cunningham, A.H. Fairlamb, and W.N. Hunter Structure 7 1999 81 89
43. C.H. Faerman, S.N. Savvides, C. Strickland, M.A. Breidenbach, J.A. Ponasik, B. Ganem, D. Ripoll, R. Luise Krauth-Siegel, and P. Andrew Karplus Bioorganic & Medicinal Chemistry 4 1996 1247 1253
44. B. Bonnet, D. Soullez, E. Davioud-Charvet, V. Landry, D. Horvath, and C. Sergheraert Bioorganic & Medicinal Chemistry 5 1997 1249 1256
45. M.O.F. Khan, S.E. Austin, C. Chan, H. Yin, D. Marks, S.N. Vaghjiani, H. Kendrick, V. Yardley, S.L. Croft, and K.T. Douglas J. Med. Chem. 43 2000 3148 3156