Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates

European Journal of Medicinal Chemistry

Volumn 67, Issue , 2013, Pages 142-151

  Blau, Lorena ^a   Menegon, Renato Farina ^b   Trossini, Gustavo H G ^c   Molino, João Vitor Dutra ^c   Vital, Drielli Gomes ^c   Cicarelli, Regina Maria Barretto ^a   Passerini, Gabriela Duó ^a   Bosquesi, Priscila Longhin ^a   Chin, Chung Man ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b INSTITUTO DE PESQUISA E DESENVOLVIMENTO   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Chagas disease; Cruzain; Docking; Mutagenicity; Oxidative stress; Thiosemicarbazone

Indexed keywords

2 AMINO 1 (3 NITROPHENYL)ETHAN 1 ONE THIOSEMICARBAZONE; 2 AMINO 1 (4 NITRO) ACETOPHENONE THIOSEMICARBAZONE HEMISUCCINATE AMIDE; 2 AMINO 1 (4 NITRO)ACETOPHENONE THIOSEMICARBAZONE; 2 AMINO 1 PHENYLETHAN 1 ONE THIOSEMICARBAZONE; 2 HIDROXY 1 (4 NITRO) ACETOPHENONE THIOSEMICARBAZONE HEMISUCCINATE ESTER; 2 HYDROXY 1 (4 NITRO)ACETOPHENONE THIOSEMICARBAZONE; 3 AMINO 4 NITROACETOPHENONE THIOSEMICARBAZONE; 3 NITRO 4 AMINOACETOPHENONE THIOSEMICARBAZONE; 4 AMINOACETOPHENONE THIOSEMICARBAZONE; ACETOPHENONE THIOSEMICARBAZONE; AMINOACETOPHENONE THIOSEMICARBAZONE; ANTIPROTOZOAL AGENT; CRUZIPAIN; THIOSEMICARBAZONE DERIVATIVE; TRYPANOTHIONE REDUCTASE; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; BROMINATION; CHAGAS DISEASE; CONCENTRATION RESPONSE; DRUG DESIGN; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MELTING POINT; MOLECULAR DOCKING; MUTAGENIC ACTIVITY; MUTAGENICITY; NONHUMAN; TRYPANOCIDAL ACTIVITY; TRYPANOSOMA CRUZI;

CHAGAS DISEASE; CRUZAIN; DOCKING; FJCDJOPKILSQQC-WUXMJOGZSA-N; IKXKPKRBUBTOBD-WUXMJOGZSA-N; JMULZUQMMLAALR-YRNVUSSQSA-N; JXVGNNBDZQLCNB-MXZHIVQLSA-N; MOLCDPMVIXILLZ-MXZHIVQLSA-N; MUTAGENICITY; NFJPLHYZNDOBTD-IZZDOVSWSA-N; OIHUOBSUZMQSOX-LFYBBSHMSA-N; OXIDATIVE STRESS; QFZNMVFZOBJIQX-MHWRWJLKSA-N; ROSQBCLWTZWMGU-DHZHZOJOSA-N; THIOSEMICARBAZONE; ULDWASCYNZEGGY-MXZHIVQLSA-N; VAOJXJAGBHUCPY-LFYBBSHMSA-N; VNXBTMDXSKKCLJ-XNTDXEJSSA-N;

CHAGAS DISEASE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIOSEMICARBAZONES; TRYPANOSOMA CRUZI;

EID: 84882528324     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.04.022     Document Type: Article

References (43)

1. M. Goldbaum, M.L. Barreto, Commentary: the contribution and example of Carlos Chagas, Int. J. Epidemiol. 37 (2008) 697-698.
2. J.R. Coura, L.C. Dias, Epidemiology, control and surveillance of Chagas disease: 100 years after its discovery, Mem. Inst. Oswaldo Cruz 104 (S1) (2009) 31-40.
3. WHO - Word Health Organization, Chagas Disease: Special Programme for Research and Training in Tropical Disease, TDR, 2008.
4. DNDi - Drugs for Neglected Disease Initiative, 2008.
5. G.A. Schmunis, Epidemiology of Chagas disease in non-endemic countries: the role of international migration, Mem. Inst. Oswaldo Cruz 102 (2007) 75-85. (Pubitemid 350146006)
6. J.A. Urbina, Specific chemotherapy of Chagas disease: relevance, current limitations and new approaches, Acta Trop. 115 (2010) 55-68.
7. V.G. Duschak, A.S. Couto, An insight on targets and patented drugs for chemotherapy of Chagas Disease, Recent Patents Anti-Infect. Drug Discov. 2 (2007) 19-51.
8. J.H. Mckerrow, P.J. Rosenthal, R. Swenerton, P. Doyle, Development of protease inhibitors for protozoan infections, Curr. Opin. Infect. Dis. 21 (2008) 668-672.
9. J.A. Urbina, Chemotherapy of Chagas disease, Curr. Pharm. Des. 8 (2002) 287-295. (Pubitemid 34449884)
10. J.A. Urbina, R. DoCampo, Specific chemotherapy of Chagas disease: controversis and advances, Trends Pasitol. 19 (2003) 495-501. (Pubitemid 37329658)
11. G. Le Loup, G. Pialoux, F.X. Lescure, Update in treatment of Chagas disease, Curr. Opin. Infect. Dis. 24 (2011) 428-434.
12. P. Veiga-Santos, E.S. Barrias, J.F. Santos, T.L. De Barros Moreira, T.M. De Carvalho, J.A. Urbina, W. De Souza, Effects of amiodarone and posaconazole on the growth and ultrastructure of Trypanosoma cruzi, Int. J. Antimicrob. Agent 40 (2012) 61-71.
13. N. Chamond, N. Coatnoan, P. Minoprio, Immunotherapy of Trypanosoma cruzi infections, Curr. Drug Targets Immune Endocr. Metabol. Disord. 2 (2002) 247-254.
14. H. Tokiwa, Y. Ohnishi, Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment, CRC Crit. Rev. Toxicol. 17 (1986) 23-60.
15. H.S. Rosenkranz, R.O. Mermelstein, All nitro-containing chemicals were not created equal, Mutat. Res. 114 (1983) 217-267.
16. P.L. Olive, Correlation between metabolic reduction rates and electron affinity of nitroheterocycles, Cancer Res. 39 (1979) 4512-4515. (Pubitemid 10197614)
17. S.N. Moreno, R.P. Mason, R.P.A. Muniz, F.S. Cruz, R. Docampo, Generation of free radicals from metronidazole and other nitroimidazoles by Trichomonas foetus, J. Biol. Chem. 158 (1983) 4051-4054. (Pubitemid 13080621)
18. M.A. La-Scalea, G.H.G. Trossini, C.M.S. Menezes, M.C. Chung, E.I. Ferreira, Electrochemical reduction using glassy carbon electrode in aqueous medium of a potential anti-Chagas drug: NFOH, J. Eletrochem. Soc. 157 (2009) F93-F97.
19. B. Bonnet, D. Soullez, S. Girault, L. Maes, E. Davioud-Charvet, Trypanothione reductase inhibition/trypanomicidal activity relationships in a 1,4-bis(3-aminopropyl)piperazine series, Bioorg. Med. Chem. 8 (2000) 95-103. (Pubitemid 30125658)
20. R.L. Lopez De Compadre, A.K. Debnath, A.J. Shusterman, C. Hansch, LUMO energies and hydrophobicity as determinants of mutagenicity by nitroaromatic compounds in Salmonella typhimurium, Environ. Mol. Mutagen. 15 (1990) 44-55. (Pubitemid 20071321)
21. R.L. Lopez De Compadre, A.J. Shusterman, C. Hansch, The role of hydrophobicity in the Ames test. The correlation of the mutagenicity of nitropolycyclic hydrocarbons with partition coefficients and molecular orbital indices, Int. J. Quantum Chem. 34 (1988) 91-101.
22. J.J. Cazzulo, M.C.I. Cazzulo Franke, J. Martinez, B.M. Franke De Cazzulo, Some kinetic properties of a cysteine proteinase (cruzipain) from Trypanosoma cruzi, Biochim. Biophys. Acta 1037 (1990) 186-191. (Pubitemid 20043410)
23. J.J. Cazzulo, V. Hellman, R. Couso, A.J. Parodi, Amino acid and carbohydrate composition of a lysosomal cysteine proteinase from Trypanossoma cruzi. Absence of phosphorylated mannose residues, Mol. Biochem. Parasitol. 38 (1990) 41-48. (Pubitemid 20008183)
24. L.C. Alves, R.L. Melo, M.H.S. Cezari, S.J. Sanderson, J.C. Mottram, G.H. Coombs, L. Juliano, M.A. Juliano, Analysis of the S-2 subsite specificities of the recombinant cysteine proteinases CPB of Leishmaniamexicana; and cruzain of Trypanosoma cruzi using fluorescent substrates containing non-natural basic amino acids, Mol. Biochem. Parasitol. 117 (2001) 137-143. (Pubitemid 32972274)
25. M.E. Mcgrath, A.E. Eakin, J.C. Engel, J.H. Mckerrow, C.S. Craik, R.J. Fletterick, The crystal struture of cruzain: a therapeutic target for Chagas disease, J. Mol. Biol. 247 (1995) 251-259.
26. E. Del Nery, M.A. Juliano, A.P. Lima, J. Scharfstein, L. Juliano, Kininogenase activity by the major cysteinyl proteinase (cruzipain) from Trypanosoma cruzi, J. Biol. Chem. 272 (1997) 25713-25718. (Pubitemid 27438889)
27. A. Bocedi, L. Gradoni, E. Menegatti, P. Ascenzi, Kinetics of parasite cysteine proteinase inactivation by NO-donors, Biochem. Biophys. Res. Commun. 315 (2004) 710-718. (Pubitemid 38229401)
28. X. Du, C. Guo, E. Hansell, P.S. Doyle, C.R. Caffrey, T.P. Holler, J.H. Mckerrow, F.E. Cohen, Synthesis and structure-activity relationship study of potent trypanocidal thiosemicarbazone inhibitors of the trypanosomal cysteine protease cruzain, J. Med. Chem. 45 (2002) 2695-2707. (Pubitemid 34627642)
29. D.C. Greenbaum, Z. Mackey, E. Hansell, P. Doyle, J. Gut, C.R. Caffrey, J. Lehrman, P.J. Rosenthal, J.H. Mckerrow, K. Chibale, Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi, J. Med. Chem. 47 (2004) 3212-3219. (Pubitemid 38702713)
30. N. Fujii, J.P. Mallari, E.J. Hansell, Z. Mackey, P. Doyle, Y.M. Zhou, P.J. Rosenthal, J.H. Mckerrow, R.K. Guy, Discovery of potent thiosemicarbazone inhibitors of rhodesain and cruzain, Bioorg. Med. Chem. Lett. 15 (2005) 121.
31. R. Siles, S.-E. Chen, M. Zhou, K.G. Pinney, M.L. Trawick, Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas disease, Bioorg. Med. Chem. Lett. 16 (2006) 4405-4409. (Pubitemid 44018080)
32. G.H.G. Trossini, A. Malvezzi, A.T. Do Amaral, C.O. Rangel-Yagui, M.A. Izidoro, M.H. Cezari, L. Juliano, M.C. Chung, C.M.S. Menezes, E.I. Ferreira, Cruzain inhibition by hydroxymethylnitrofurazone and nitrofurazone: investigation of a new target in Trypanosoma cruzi, J. Enzym. Inhib. Med. Chem. 25 (2010) 62-67.
33. M.E. Caputto, A. Ciccarelli, F. Frank, A.G. Moglioni, G.Y. Moltrasio, D. Vega, E. Lombardo, L.M. Finkielsztein, Synthesis and biological evaluation of some novel 1-indanone thiazolylhydrazone derivatives as anti-Trypanosoma cruzi agents, Eur. J. Med. Chem. 55 (2012) 155-163.
34. P.F. Carneiro, S.B. do Nascimento, A.V. Pinto, M. do C.F.R. Pinto, G.C. Lechuga, D.O. Santos, H.M. dos Santos Júnior, J.A.L.C. Resende, S.C. Bourguignon, V.F. Ferreira, New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms, Bioorg. Med. Chem. 20 (2012) 4995-5000.
35. S.A. Carvalho, L.O. Feitosa, M. Soares, T.E.M.M. Costa, M.G. Henriques, K. Salomão, S.L. de Castro, M. Kaiser, R. Brun, J.M. Wardell, S.M.S.V. Wardell, G.H.G. Trossini, A.D. Andricopulo, E.F. da Silva, C.A.M. Fraga, Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents, Eur. J. Med. Chem. 54 (2012) 512-521.
36. J.D. Maya, S. Bollo, L.J. Nuñez-Vergara, J.A. Squella, Y. Repetto, A. Morello, J. Périé, G. Chauvière, Trypanosoma cruzi: effect and mode of action of nitroimidazole and nitrofuran derivatives, Biochem. Pharmacol. 65 (2003) 999-1006. (Pubitemid 36293683)
37. F. Lecaille, J. Cotton, J.H. Mckerrow, M. Ferrer-Di Martino, E. Boll-Bataille, F. Gauthier, G. Lalmanach, Reversible inhibition of cathepsin L-like proteases by 4-mer pseudopeptides, FEBS Lett. 507 (2001) 362-366. (Pubitemid 33030266)
38. R.N. Prabhu, D. Pandiarajan, R. Ramesh, Ruthenium(II) mediated C-H activation of substituted acetophenone thiosemicarbazones: synthesis, structural characterization, luminescence and electrochemical properties, J. Organomet. Chem. 694 (2009) 4170-4177.
39. S. Witek, J. Bielawski, A. Bielawska, New pesticides and intermediates. Part VII. Some azaalkenyl derivatives of N-phenylurea and N-phenylcarbamic acid, Polish J. Chem. 55 (1981) 2589-2600.
40. H.R. Fatondji, F. Gbaguidi, S. Kpoviessi, J. Bero, V. Hannaert, J. Quetin-Leclercq, J. Poupaert, M. Moudachirou, G.C. Accrombessi, Synthesis, characterization and trypanocidal activity of some aromatic thiosemicarbazones and their 1,3,4-thiadiazolines derivatives, Afr. J. Pure Appl. Chem. 5 (2011) 59-64.
41. A. Dutta, S. Bandyopadhyay, C. Mandal, M. Chatterjee, Development of a modified MTT assay for screening antimonial resistant field isolated of Indian visceral leishmaniosis, Parasitol. Int. 54 (2005) 119-122. (Pubitemid 40615210)
42. S. Muelas-Serrano, J. Nogal-Ruiz, A. Gómez-Barrio, Setting of a colorimetric method to determine de viability of Trypanosoma cruzi epimastigotes, Parasitol. Res. 86 (2000) 999-1002.
43. M. Hayashi, T. Morita, Y. Kodama, T. Sofuni, M. Ishidate Jr., The micronucleus assay with mouse peripheral blood reticulocytes using acridine orange-coated slides, Mutat. Res. 245 (1990) 245-249.