905
Views
22
CrossRef citations to date
0
Altmetric
Research Article

Cruzain inhibition by hydroxymethylnitrofurazone and nitrofurazone: investigation of a new target in Trypanosoma cruzi

, , , , , , , , & show all
Pages 62-67 | Received 09 Dec 2008, Accepted 26 Mar 2009, Published online: 23 Dec 2009

References

  • World Health Organization. Geneva: WHO, 2002. http://www.who.int/topics/chagas_disease/en/.
  • Coura JR, de Castro SL. A critical review on Chagas’ disease chemotherapy. Mem Inst Oswaldo Cruz 2002;97:3–24.
  • Moncayo A. Chagas’ disease: current epidemiological trends after the interruption of vectorial and transfusional transmission in the Southern Cone countries. Mem Inst Oswaldo Cruz 2003;98:577–91.
  • Moncayo A, Ortiz Yanine MI. An update on Chagas’ disease (human American trypanosomiasis). Ann Trop Med Parasitol 2006;100:663–77.
  • de Andrade ALSS, Zicker F, de Oliveira RM, Silva SAE, Luquetti A, Travassos LR, et al. Randomised trial of efficacy of benznidazole in treatment of early Trypanosoma cruzi infection. Lancet 1996;348:1407–13.
  • Dodd MC, Stillman WB. The in vitro bacteriostatic action of some simple furan derivatives. J Pharmacol ExpTher 1944;82:11–18.
  • Andrade ZA, Brenner Z. Ação da nitrofurazona (5-nitro-2-furaldeído-semicarbazona) sobre as formas intracelulares do Trypanosoma cruzi na doença de Chagas experimental. Rev Inst Med Trop S Paulo 1969;11:222–8.
  • Henderson GB, Ulrich P, Fairlamb AH, Rosenberg I, Pereira M, Sela M, et al. Engineering the substrate specificity of glutathione reductase toward that of trypanothione reduction. Proc Natl Acad Sci USA 1988;88:8769–73.
  • La-Scalea MA, Chung MC, Cruz ML, Serrano SHP, Ferreira EI. Dissociation and electrooxidation of primaquine diphosphate as an approach to the study of anti-chagas prodrugs mechanism of action. Bioeletrochemistry 2001;53:55–9.
  • Chung MC, Guido RVC, Martinelli TF, Goncalves MF, Polli MC, Botelho KCA, et al. Synthesis and in vitro evaluation of potential antichagasic hydroxymethylnitrofurazone (NFOH-121): a new nitrofurazone prodrug. Bioorg Med Chem 2003;11:4779–83.
  • Sajid M, McKerrow JH. Cysteine proteases of parasitic organisms. Mol Biochem Parasitol 2002;120:1–21.
  • Cazzulo JJ, Stoka V, Turk V. Cruzipain, the major cysteine proteinase from the protozoan parasite Trypanosoma cruzi. Biol Chem 1997;378:1–10.
  • McGrath ME. The lysosomal cysteine proteases. Annu Rev Biophys Biomol Struct 1999;28:181.
  • Melo RL, Pozzo RCB, Alves LC, Perissutti E, Caliendo G, Santagada V, et al. Synthesis and hydrolysis by cathepsin B of fluorogenic substrates with the general structure benzolyl-X-ARG-MCA containing non-natural basic amino acids at position X. Biochim Biophys Acta 2001;1547:82–94.
  • Alves LC, Melo RL, Cezari MHS, Sanderson SJ, Mottram JC, Coombs GH, et al. Analysis of the S-2 subsite specificities of the recombinant cysteine proteinases CPB of Leishmania mexicana, and cruzain of Trypanosoma cruzi, using fluorescent substrates containing non-natural basic amino acids. Mol Biochem Parasitol 2001;117:137–43.
  • Brak K, Doyle PS, MacKerrow JH, Ellman JA. Identification of a new class of nonpeptidic inhibitors of cruzain. J Am Chem Soc 2008;130:6404–10.
  • Du XH, Guo C, Hansell E, Doyle PS, Caffrey CR, Holler TP, et al. Synthesis and structure-activity relationship study of potent trypanocidal thiosemicarbazone inhibitors of the trypanosomal cysteine protease cruzain. J Med Chem 2002;45:2695–707.
  • Aguirre G, Boiani L, Cerecetto H, Fernandez M, Gonzalez M, Denicola A, et al. In vitro activity and mechanism of action against the protozoan parasite Trypanosoma cruzi of 5-nitrofuryl containing thiosemicarbazones. Bioorg Med Chem 2004;12:4885–93.
  • Gasteiger J. The central role of chemoinformatics. Chemometr Intell Lab Syst 2006;82:200–9.
  • Stahl M, Guba W, Kansy M. Integrating molecular design resources within modern drug discovery research: the Roche experience. Drug Discov Today 2006;11:326–33.
  • Parise R, Menezes CMS, Pinto PLS, Paula GA, Brandt CA, da Silveira MAB. Design, synthesis and in vivo evaluation of oxaminiquine methacrylate and acrylamide prodrugs. Bioorg Med Chem 2007;15:1229–36.
  • Rosselli FP, Albuquerque CN, Da Silva ABF. A chemometric study of megazol derivatives with activity against Trypanosoma equiperdum. SAR QSAR Environ Res 2006;17:533–47.
  • Doriguetto AC, Silva CHTD, Ellena J, Trossini GHG, Chin CM, Ferreira EI. 5-Nitro-2-furaldehyde N-(hydroxymethyl)semicarbazone. Acta Crystallogr 2005;E-61:2099–101.
  • Eakin AE, Mills AA, Harth G, McKerrow JH, Craik CS. The sequence, organization, and expression of the major cysteine protease (cruzain) from Trypanosoma cruzi. J Biol Chem 1992;267:7411–20.
  • Leatherbarrow RJ. GraFit Version 5. Horley, UK: Erithacus Software Ltd., 2001.
  • Halgren TA. Merck molecular force field. I. Basis, form, scope, parametrization, and performance of MMFF94. J Comp Chem 1996;17:490–519.
  • Debnath AK, Decompadre RLL, Debnath G, Shusterman AJ, Hansch C. Structure activity relationship of mutagenic aromatic and heteroaromatic nitro-compounds – correlation with molecular-orbital energies and hydrophobicity. J Med Chem 1991;34:786–97.
  • Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP. The development and use of quantum-mechanical molecular-models .76. AM1 – a new general-purpose quantum-mechanical molecular-model. J Am Chem Soc 1985;107:3902–9.
  • Lehmann MW, Singh P, Evans DH. Potential inversion in the reduction of trans-2,3-dinitro-2-butene. J Electroanal Chem 2003;549:137–43.
  • Chen C, Wu JC. Correlations between theorical and experiemtnal determination of heat of formation of cartain aromatic nitro compounds. Comp Chem 2001;25:117–24.
  • Chen PC, Wu JC, Chen SC. Correlations between theoretical and experimental determination of heat of formation of certain aliphatic nitro compounds. Comp Chem 2001;25:439–45.
  • La Scalea MA, Menezes CMS, Juliao MSD, Chung MC, Serrano SHP, Ferreira EI. Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity. J Braz Chem Soc 2005;16:774–82.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.