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Original Article

Inhibition of Leishmania infantum trypanothione reductase by diaryl sulfide derivatives

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Pages 304-310 | Received 03 Aug 2016, Accepted 28 Sep 2016, Published online: 18 Jan 2017

References

  • Desjeux P. Leishmaniasis: current situation and new perspectives. Comp Immunol Microbiol Infect Dis 2004;27:305–18.
  • Hotez PJ, Savioli L, Fenwick A. Neglected tropical diseases of the Middle East and North Africa: review of their prevalence, distribution, and opportunities for control. PLoS Neglected Trop Dis [Online] 2012;6:e1475. Available from: http://journals.plos.org/plosntds/article?id=10.1371/journal.pntd.0001475.
  • Colotti G, Baiocco P, Fiorillo A, et al. Structural insights into the enzymes of the trypanothione pathway: targets for antileishmaniasis drugs. Future Med Chem 2013;5:1861–75.
  • Fiorillo A, Colotti G, Boffi A, et al. The crystal structures of the tryparedoxin-tryparedoxin peroxidase couple unveil the structural determinants of Leishmania detoxification pathway. PLoS Negl Trop Dis [Online] 2012;6:e1781. Available from: http://journals.plos.org/plosntds/article?id=10.1371%2Fjournal.pntd.0001781.
  • Dumas C, Ouellette M, Tovar J, et al. Disruption of the trypanothione reductase gene of Leishmania decreases its ability to survive oxidative stress in macrophages. EMBO J 1997;16:2590–8.
  • Baiocco P, Colotti G, Franceschini S, Ilari A. Molecular basis of antimony treatment in leishmaniasis. J Med Chem 2009;52:2603–12.
  • Ilari A, Baiocco P, Messori L, et al. A gold-containing drug against parasitic polyamine metabolism: the X-ray structure of trypanothione reductase from Leishmania infantum in complex with auranofin reveals a dual mechanism of enzyme inhibition. Amino Acids 2012;42:803–11.
  • Baiocco P, Ilari A, Ceci P, et al. Inhibitory effect of silver nanoparticles on trypanothione reductase activity and Leishmania infantum proliferation. ACS Med Chem Lett 2010;2:230–3.
  • Ilari A, Fiorillo A, Baiocco P, et al. Targeting polyamine metabolism for finding new drugs against leishmaniasis: a review. Mini Rev Med Chem 2015;15:243–52.
  • Spinks D, Torrie LS, Thompson S, et al. Design, synthesis and biological evaluation of Trypanosoma brucei trypanothione synthetase inhibitors. ChemMedChem 2012;7:95–106.
  • Spinks D, Shanks EJ, Cleghorn LA, et al. Investigation of trypanothione reductase as a drug target in Trypanosoma brucei. ChemMedChem 2009;4:2060–9.
  • Massa S, Di Santo R, Costi R, et al. Synthesis of novel HEPT analogues with anti-HIV-1 activity. Med Chem Res 1994;4:554–62.
  • Costi R, Di Santo R, Artico M, et al. Structure-activity relationship studies on potential non-nucleoside DABO-like inhibitors of HIV-1 reverse transcriptase. Antivir Chem Chemother 2000;11:117–33.
  • Okauchi T, Kuramoto K, Kitamura M. Facile preparation of aryl sulfides using palladium catalysis under mild conditions. Synlett 2010;2891–4.
  • Sereno D, Lemesre JL. Use of an enzymatic micromethod to quantify amastigote stage of Leishmania amazonensis in vitro. Parasitol Res 1997;83:401–3.
  • Baiocco P, Franceschini S, Ilari A, Colotti G. Trypanothione reductase from Leishmania infantum: cloning, expression, purification, crystallization and preliminary X-ray data analysis. Protein Pept Lett 2009;16:196–200.
  • Mueller U, Darowski N, Fuchs MR, et al. Facilities for macromolecular crystallography at the Helmholtz-Zentrum Berlin. J Synchrotron Radiat 2012;19:442–9.
  • Kabsch W. XDS. Acta Crystallogr D Biol Crystallogr 2010;66:125–32.
  • Vagin AA, Teplyakov A. Molecular replacement with MOLREP. Acta Crystallogr D Biol Crystallogr 2010;66:22–5.
  • Murshudov GN, Vagin AA, Dodson EJ. Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr D Biol Crystallogr 1997;53:240–55.
  • Emsley P, Cowtan K. Coot: model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr 2004;60:2126–32.
  • Stump B, Eberle C, Kaiser M, et al. Diaryl sulfide-based inhibitors of trypanothione reductase: inhibition potency, revised binding mode and antiprotozoal activities. Org Biomol Chem 2008;6:3935–47.
  • Baiocco P, Poce G, Alfonso S, et al. Inhibition of Leishmania infantum Trypanothione Reductase by Azole-Based Compounds: a Comparative Analysis with Its Physiological Substrate by X-ray Crystallography. ChemMedChem 2013;8:1175–83.
  • Krieger S, Schwarz W, Ariyanayagam MR, et al. Trypanosomes lacking trypanothione reductase are avirulent and show increased sensitivity to oxidative stress. Mol. Microbiol 2000;35:542–52.