Induction of oxidative stress in Trypanosoma brucei by the antitrypanosomal dihydroquinoline OSU-40

Antimicrobial Agents and Chemotherapy

Volumn 56, Issue 5, 2012, Pages 2428-2434

  He, Shanshan ^a   Dayton, Alex ^b   Kuppusamy, Periannan ^b   Werbovetz, Karl A ^a   Drew, Mark E ^a,c  

^a OHIO STATE UNIVERSITY   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c THE OHIO STATE UNIVERSITY COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYL 1,2 DIHYDRO 2,2,4 TRIMETHYLQUINOLIN 6 YL ACETATE; ANTITRYPANOSOMAL AGENT; DIHYDROQUINOLINE DERIVATIVE; OSU 40; SUPEROXIDE DISMUTASE; SYNTHETASE; TRYPANOTHIONE SYNTHETASE; UNCLASSIFIED DRUG;

ANTIBIOTIC SENSITIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; CELL DENSITY; CELL GROWTH; CONTROLLED STUDY; DOWN REGULATION; DRUG MECHANISM; ELECTRON SPIN RESONANCE; IN VITRO STUDY; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN EXPRESSION; RNA INTERFERENCE; TRYPANOSOMA BRUCEI;

ACETATES; AMIDE SYNTHASES; CELLS, CULTURED; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; INHIBITORY CONCENTRATION 50; OXIDATIVE STRESS; PROTOZOAN PROTEINS; QUINOLINIUM COMPOUNDS; REACTIVE OXYGEN SPECIES; RNA INTERFERENCE; SUPEROXIDE DISMUTASE; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI RHODESIENSE; TRYPANOSOMIASIS, AFRICAN;

EID: 84860153566     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.06386-11     Document Type: Article

References (42)

1. Ariyanayagam MR, Oza SL, Guther MLS, Fairlamb AH. 2005. Phenotypic analysis of trypanothione synthetase knockdown in the African trypanosome. Biochem. J. 391:425-432. (Pubitemid 41532441)
2. Barrett MP, Boykin DW, Brun R, Tidwell RR. 2007. Human African trypanosomiasis: pharmacological re-engagement with a neglected disease. Br. J. Pharmacol. 152:1155-1171. (Pubitemid 350242432)
3. Burkard G, Fragoso CM, Roditi I. 2007. Highly efficient stable transformation of bloodstream forms of Trypanosoma brucei. Mol. Biochem. Parasitol. 153:220-223. (Pubitemid 46654247)
4. Burri C. 2010. Chemotherapy against human African trypanosomiasis: is there a road to success? Parasitology 137:1987-1994.
5. Cenas N, Arscott D, Williams C, Jr, Blanchard J. 1994. Mechanism of reduction of quinones by Trypanosoma congolense trypanothione reductase. Biochemistry 33:2509-2515. (Pubitemid 24099658)
6. Cerecetto H, et al. 1999. 1,2,5-Oxadiazole N-oxide derivatives and related compounds as potential antitrypanosomal drugs: structure-activity relationships. J. Med. Chem. 42:1941-1950. (Pubitemid 29269627)
7. Comini MA, et al. 2004. Validation of Trypanosoma brucei trypanothione synthetase as drug target. Free Radic. Biol. Med. 36:1289-1302. (Pubitemid 38526323)
8. Docampo R, Moreno SNJ. 1984. Free radical metabolites in the mode of action of chemotherapeutic agents and phagocytic cells on Trypanosoma cruzi. Rev. Infect. Dis. 6:223-238.
9. Docampo R, et al. 1981. Mechanism of nifurtimox toxicity in different forms of Trypanosoma cruzi. Biochem. Pharmacol. 30:1947-1951. (Pubitemid 11071504)
10. Docampo R, Stoppani AOM. 1979. Generation of superoxide anion and hydrogen peroxide induced by nifurtimox in Trypanosoma cruzi. Arch. Biochem. Biophys. 197:317-321. (Pubitemid 10226733)
11. Fotie J, et al. 2010. Antitrypanosomal activity of 1,2-dihydroquinolin-6- ols and their ester derivatives. J. Med. Chem. 53:966-982.
12. Gershkovich P, et al. 2011. Simultaneous determination of a novel antitrypanosomal compound (OSU-36) and its ester derivative (OSU-40) in plasma by HPLC: application to first pharmacokinetic study in rats. J. Pharm. Pharm. Sci. 14:36-45.
13. Henderson G, et al. 1988. "Subversive" substrates for the enzyme trypanothione disulfide reductase: alternative approach to chemotherapy of Chagas disease. Proc. Natl. Acad. Sci. U. S. A. 85:5374-5378.
14. Hirumi H, Hirumi K. 1989. Continuous cultivation of Trypanosoma brucei blood stream forms in a medium containing a low concentration of serum protein without feeder cell layers. J. Parasitol. 75:985-989. (Pubitemid 20099178)
15. Imlay JA. 2003. Pathways of oxidative damage. Annu. Rev. Microbiol. 57:395-418. (Pubitemid 37392949)
16. Jaeger T, Flohe L. 2006. The thiol-based redox networks of pathogens: unexploited targets in the search for new drugs. Biofactors 27:109-120. (Pubitemid 44444593)
17. Krauth-Siegel RL, Comini MA. 2008. Redox control in trypanosomatids, parasitic protozoa with trypanothione-based thiol metabolism. Biochim. Biophys. Acta 1780:1236-1248.
18. Krauth-Siegel RL, Meiering SK, Schmidt H. 2003. The parasite-specific trypanothione metabolism of trypanosoma and leishmania. Biol. Chem. 384:539-549. (Pubitemid 36609170)
19. Kuppusamy P. 2004. EPR spectroscopy in biology and medicine. Antioxid. Redox Signal. 6:583-585. (Pubitemid 38625377)
20. Livak KJ, Schmittgen TD. 2001. Analysis of relative gene expression data using real-time quantitative PCR and the 2(-Delta Delta C(T)) method. Methods 25:402-408. (Pubitemid 34164012)
21. Maya JD, et al. 2007. Mode of action of natural and synthetic drugs against Trypanosoma cruzi and their interaction with the mammalian host. Comp. Biochem. Physiol. A Mol. Integr. Physiol. 146:601-620. (Pubitemid 46341910)
22. Opigo J, Woodrow C. 2009. NECT trial: more than a small victory over sleeping sickness. Lancet 374:7-9.
23. Otero L, et al. 2006. Novel antitrypanosomal agents based on palladium nitrofurylthiosemicarbazone complexes: DNA and redox metabolism as potential therapeutic targets. J. Med. Chem. 49:3322-3331. (Pubitemid 43830530)
24. Patterson S, et al. 2011. Dihydroquinazolines as a novel class of Trypanosoma brucei trypanothione reductase inhibitors: discovery, synthesis, and characterization of their binding mode by protein crystallography. J. Med. Chem. 54:6514-6530.
25. Perez-Pineiro R, et al. 2009. Development of a novel virtual screening cascade protocol to identify potential trypanothione reductase inhibitors. J. Med. Chem. 52:1670-1680.
26. Porcal W, et al. 2008. New trypanocidal hybrid compounds from the association of hydrazone moieties and benzofuroxan heterocycle. Bioorg. Med. Chem. 16:6995-7004.
27. Prathalingham SR, Wilkinson SR, Horn D, Kelly JM. 2007. Deletion of the Trypanosoma brucei superoxide dismutase gene sodb1 increases sensitivity to nifurtimox and benznidazole. Antimicrob. Agents Chemother. 51:755-758. (Pubitemid 46185302)
28. Raj L, et al. 2011. Selective killing of cancer cells by a small molecule targeting the stress response to ROS. Nature 475:231-234.
29. Reid CS, et al. 2011. Synthesis and antitrypanosomal evaluation of derivatives of N-benzyl-1,2-dihydroquinolin-6-ols: effect of core substitutions and salt formation. Bioorg. Med. Chem. 19:513-523.
30. Salmon-Chemin L, et al. 2001. 2-and 3-substituted 1,4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity. J. Med. Chem. 44:548-565. (Pubitemid 32156097)
31. Schmidt A, Krauth-Siegel RL. 2002. Enzymes of the trypanothione metabolism as targets for antitrypanosomal drug development. Curr. Top. Med. Chem. 2:1239-1259.
32. Torrie LS, et al. 2009. Chemical validation of trypanothione synthetase: a potential drug target for human trypanosomiasis. J. Biol. Chem. 284:36137-36145.
33. Trachootham D, Alexandre J, Huang P. 2009. Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? Nat. Rev. Drug Discov. 8:579-591.
34. Turrens JF. 2004. Oxidative stress and antioxidant defenses: a target for the treatment of diseases caused by parasitic protozoa. Mol. Aspects Med. 25:211-220. (Pubitemid 38401943)
35. Verrax J, et al. 2011. Redox-active quinones and ascorbate: an innovative cancer therapy that exploits the vulnerability of cancer cells to oxidative stress. Anticancer Agents Med. Chem. 11:213-221.
36. Villamena FA, Hadad CM, Zweier JL. 2003. Kinetic study and theoretical analysis of hydroxyl radical trapping and spin adduct decay of alkoxycarbonyl and dialkoxyphosphoryl nitrones in aqueous media. J. Phys. Chem. A 107:4407-4414.
37. Villamena FA, Zweier JL. 2004. Detection of reactive oxygen and nitrogen species by EPR spin trapping. Antioxid. Redox Signal. 6:619-629. (Pubitemid 38625382)
38. Wang ZF, Morris JC, Drew ME, Englund PT. 2000. Inhibition of Trypanosoma brucei gene expression by RNA interference using an integratable vector with opposing T7 promoters. J. Biol. Chem. 275:40174-40179. (Pubitemid 32064646)
39. WHO. 23 May 2011, posting date. New cases of African trypanosomiasis continue to drop. World Health Organization, Geneva, Switzerland. http://www.who.int/neglected-diseases/disease-management/HAT-cases-drop/en/ index.html.
40. Wilkinson SR, et al. 2006. Functional characterisation of the iron superoxide dismutase gene repertoire in Trypanosoma brucei. Free Radic. Biol. Med. 40:198-209. (Pubitemid 43069346)
41. Wyllie S, et al. 2009. Dissecting the essentiality of the bifunctional trypanothione synthetase-amidase in Trypanosoma brucei using chemical and genetic methods. Mol. Microbiol. 74:529-540.
42. Yun O, Priotto G, Tong J, Flevaud L, Chappuis F. 2010. NECT is next: implementing the new drug combination therapy for Trypanosoma brucei gambiense sleeping sickness. PLoS Negl. Trop. Dis. 4:e720.