Redox-active antiparasitic drugs

Antioxidants and Redox Signaling

Volumn 17, Issue 4, 2012, Pages 555-582

  Pal, Chinmay ^a   Bandyopadhyay, Uday ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; AMODIAQUINE; AMOPYROQUINE; ANTIOXIDANT; ANTIPARASITIC AGENT; CHALCONE DERIVATIVE; CLOTRIMAZOLE; DOXORUBICIN; GLYCOCONJUGATE; HALOFANTRINE; ISOXAZOLE DERIVATIVE; KETOCONAZOLE; MEFLOQUINE; MEPACRINE; MICONAZOLE; MITOMYCIN C; NAPHTHAZARIN; NAPHTHOQUINONE; NITRO DERIVATIVE; PEROXYNITRITE; PLUMBAGIN; PYRONARIDINE; QUINIDINE; QUININE; QUINOL QUINOLINE HYBRID COMPOUND; REACTIVE OXYGEN METABOLITE; TEBUQUINE; TRIFLUPROMAZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; WITHAFERIN A;

AMEBIASIS; ANTIMALARIAL ACTIVITY; DRUG SENSITIVITY; DRUG STRUCTURE; ENTAMOEBA HISTOLYTICA; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME STRUCTURE; HUMAN; LEISHMANIA DONOVANI; LEISHMANIASIS; NONHUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PARASITEMIA; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; PROTEIN TARGETING; REVIEW; SCHISTOSOMA MANSONI; TRICHOMONAS VAGINALIS; TRICHOMONIASIS; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI; TRYPANOSOMIASIS;

ANIMALS; ANTIPARASITIC AGENTS; ENTAMOEBA HISTOLYTICA; HUMANS; OXIDATION-REDUCTION; OXIDATIVE STRESS; PLASMODIUM FALCIPARUM; REACTIVE OXYGEN SPECIES; TRICHOMONAS VAGINALIS; TRYPANOSOMATINA;

EID: 84862573102     PISSN: 15230864     EISSN: 15577716     Source Type: Journal    
DOI: 10.1089/ars.2011.4436     Document Type: Review

References (164)

1. Adagu IS, Nolder D, Warhurst DC, and Rossignol JF. In vitro activity of nitazoxanide and related compounds against isolates of Giardia intestinalis, Entamoeba histolytica and Trichomonas vaginalis. J Antimicrob Chemother 49: 103-111, 2002. (Pubitemid 34100652)
2. Agarwal A, Srivastava K, Puri SK, and Chauhan PM. Synthesis of 4-pyrido-6-aryl-2-substituted amino pyrimidines as a new class of antimalarial agents. Bioorg Med Chem 13: 6226-6232, 2005. (Pubitemid 41400146)
3. Ahmad R, Srivastava AK, Tripathi RP, Batra S, and Walter RD. Synthesis and biological evaluation of potential modulators of malarial glutathione-S-transferase(s). J Enzym Inhib Med Chem 22: 327-342, 2007. (Pubitemid 47225726)
4. Akoachere M, Buchholz K, Fischer E, Burhenne J, Haefeli WE, Schirmer RH, and Becker K. In vitro assessment of methylene blue on chloroquine-sensitive and -resistant Plasmodium falciparum strains reveals synergistic action with artemisinins. Antimicrob Agents Chemother 49: 4592-4597, 2005. (Pubitemid 41552588)
5. Alarcon de Noya B, Diaz-Bello Z, Colmenares C, Ruiz- Guevara R, Mauriello L, Zavala-Jaspe R, Suarez JA, Abate T, Naranjo L, Paiva M, Rivas L, Castro J, Marques J, Mendoza I, Acquatella H, Torres J, and Noya O. Large urban outbreak of orally acquired acute Chagas disease at a school in Caracas, Venezuela. J Infect Dis 201: 1308-1315, 2010.
6. Alger HM and Williams DL. The disulfide redox system of Schistosoma mansoni and the importance of a multifunctional enzyme, thioredoxin glutathione reductase. Mol Biochem Parasitol 121: 129-139, 2002. (Pubitemid 34457840)
7. Ali V and Nozaki T. Current therapeutics, their problems, and sulfur-containing-amino-acid metabolism as a novel target against infections by "amitochondriate" protozoan parasites. Clin Microbiol Rev 20: 164-187, 2007. (Pubitemid 46167772)
8. Andricopulo AD, Akoachere MB, Krogh R, Nickel C, McLeish MJ, Kenyon GL, Arscott LD, Williams CH, Jr., Davioud- Charvet E, and Becker K. Specific inhibitors of Plasmodium falciparum thioredoxin reductase as potential antimalarial agents. Bioorg Med Chem Lett 16: 2283-2292, 2006. (Pubitemid 43351095)
9. Angelucci F, Sayed AA, Williams DL, Boumis G, Brunori M, Dimastrogiovanni D, Miele AE, Pauly F, and Bellelli A. Inhibition of Schistosoma mansoni thioredoxin-glutathione reductase by auranofin: structural and kinetic aspects. J Biol Chem 284: 28977-28985, 2009.
10. Arias DG, Cabeza MS, Erben ED, Carranza PG, Lujan HD, Tellez Inon MT, Iglesias AA, and Guerrero SA. Functional characterization of methionine sulfoxide reductase A from Trypanosoma spp. Free Radic Biol Med 50: 37-46, 2011.
11. Atamna H and Ginsburg H. Heme degradation in the presence of glutathione. A proposed mechanism to account for the high levels of non-heme iron found in the membranes of hemoglobinopathic red blood cells. J Biol Chem 270: 24876-24883, 1995.
12. Atamna H, Krugliak M, Shalmiev G, Deharo E, Pescarmona G, and Ginsburg H.Mode of antimalarial effect ofmethylene blue and some of its analogues on Plasmodium falciparum in culture and their inhibition of P. vinckei petteri and P. yoelii nigeriensis in vivo. Biochem Pharmacol 51: 693-700, 1996. (Pubitemid 26080142)
13. Mata-Cárdenas BD, Vargas-Villarreal JM. González-Garza MT, and Said-Fernández S. In-vitro high anti-amoebic potency of secnidazole and dimetridazole. Pharm Pharmacol Commun 2: 513-514, 1996. (Pubitemid 28121881)
14. Baiocco P, Colotti G, Franceschini S, and Ilari A. Molecular basis of antimony treatment in leishmaniasis. J Med Chem 52: 2603-2612, 2009.
15. Bandyopadhyay U and Dey S. Antimalarial drugs and molecules inhibiting hemozoin formation. In: Apicomplexan Parasites: Molecular Approaches Toward Targeted Drug Development, edited by Becker K. Weinheim, Germany: Wiley- VCH Verlag & Co. KGaA, 2011, pp. 205-234.
16. BanerjeeAK,Arora N, andMurty US. Structuralmodel of the Plasmodium falciparum thioredoxin reductase: a novel target for antimalarial drugs. J Vector Borne Dis 46: 171-183, 2009.
17. Bansal D, Sehgal R, Chawla Y, Mahajan RC, and Malla N. In vitro activity of antiamoebic drugs against clinical isolates of Entamoeba histolytica and Entamoeba dispar. Ann Clin Microbiol Antimicrob 3: 27, 2004.
18. Bauer H, Fritz-Wolf K, Winzer A, Kuhner S, Little S, Yardley V, Vezin H, Palfey B, Schirmer RH, and Davioud- Charvet E. A fluoro analogue of the menadione derivative 6-[2¢-(3¢-methyl)-1¢,4¢- naphthoquinolyl]hexanoic acid is a suicide substrate of glutathione reductase. Crystal structure of the alkylated human enzyme. J Am Chem Soc 128: 10784- 10794, 2006.
19. Becker K, Kanzok SM, Iozef R, Fischer M, Schirmer RH, and Rahlfs S. Plasmoredoxin, a novel redox-active protein unique for malarial parasites. Eur J Biochem 270: 1057-1064, 2003. (Pubitemid 36384440)
20. Becker K, Rahlfs S, Nickel C, and Schirmer RH. Glutathione- functions and metabolism in the malarial parasite Plasmodium falciparum. Biol Chem 384: 551-566, 2003. (Pubitemid 36609171)
21. Biot C, Bauer H, Schirmer RH, and Davioud-Charvet E. 5- substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials. J Med Chem 47: 5972-5983, 2004. (Pubitemid 39507339)
22. Boiani M, Piacenza L, Hernandez P, Boiani L, Cerecetto H, Gonzalez M, and Denicola A. Mode of action of nifurtimox and N-oxide-containing heterocycles against Trypanosoma cruzi: is oxidative stress involved? Biochem Pharmacol 79: 1736-1745, 2010.
23. Bonse S, Santelli-Rouvier C, Barbe J, and Krauth-Siegel RL. Inhibition of Trypanosoma cruzi trypanothione reductase by acridines: kinetic studies and structure-activity relationships. J Med Chem 42: 5448-5454, 1999. (Pubitemid 30036778)
24. BoseDasgupta S, Das BB, Sengupta S, Ganguly A, Roy A, Dey S, Tripathi G, Dinda B, and Majumder HK. The caspase- independent algorithm of programmed cell death in Leishmania induced by baicalein: the role of LdEndoG, LdFEN-1 and LdTatD as a DNA "degradesome". Cell Death Differ 15: 1629-1640, 2008.
25. Buchholz K, Schirmer RH, Eubel JK, Akoachere MB, Dandekar T, Becker K, and Gromer S. Interactions of methylene blue with human disulfide reductases and their orthologues from Plasmodium falciparum. Antimicrob Agents Chemother 52: 183-191, 2008.
26. Cenas N, Bironaite D, Dickancaite E, Anusevicius Z, Sarlauskas J, and Blanchard JS. Chinifur, a selective inhibitor and "subversive substrate" for Trypanosoma congolense trypanothione reductase. Biochem Biophys Res Commun 204: 224-229, 1994.
27. Chan C, Yin H, Garforth J, McKie JH, Jaouhari R, Speers P, Douglas KT, Rock PJ, Yardley V, Croft SL, and Fairlamb AH. Phenothiazine inhibitors of trypanothione reductase as potential antitrypanosomal and antileishmanial drugs. J Med Chem 41: 148-156, 1998. (Pubitemid 28114356)
28. Chan C, Yin H, McKie JH, Fairlamb AH, and Douglas KT. Peptoid inhibition of trypanothione reductase as a potential antitrypanosomal and antileishmanial drug lead. Amino Acids 22: 297-308, 2002. (Pubitemid 34639589)
29. Chibale K,Haupt H, Kendrick H, Yardley V, Saravanamuthu A, FairlambAH, and Croft SL.Antiprotozoal and cytotoxicity evaluation of sulfonamide and urea analogues of quinacrine. Bioorg Med Chem Lett 11: 2655-2657, 2001. (Pubitemid 32823377)
30. Chong CR and Sullivan DJ, Jr. Inhibition of heme crystal growth by antimalarials and other compounds: implications for drug discovery. Biochem Pharmacol 66: 2201-2212, 2003. (Pubitemid 37377865)
31. Chowdhury S, Mukherjee T, Sengupta S, Chowdhury SR, Mukhopadhyay S, and Majumder HK. Novel betulin derivatives as antileishmanial agents with mode of action targeting type IB DNA topoisomerase. Mol Pharmacol 80: 694-703, 2011.
32. Ciccarelli A, Araujo L, Batlle A, and Lombardo E. Effect of haemin on growth, protein content and the antioxidant defence system in Trypanosoma cruzi. Parasitology 134: 959- 965, 2007.
33. Clark IA and Hunt NH. Evidence for reactive oxygen intermediates causing hemolysis and parasite death in malaria. Infect Immun 39: 1-6, 1983. (Pubitemid 13212489)
34. Cui L and Miao J. Cytotoxic effect of curcumin on malaria parasite Plasmodium falciparum: inhibition of histone acetylation and generation of reactive oxygen species. Antimicrob Agents Chemother 51: 488-494, 2007. (Pubitemid 46185265)
35. Cunha EFFD, Ramalho TC, Mancini DT, Fonsecs EMB, and Oliveira AA. New approaches to the development of antiprotozoan drug candidates: a review of patents. J Braz Chem Soc 21: 1787-1806, 2010.
36. da Silva Junior EN, de Souza MC, Fernandes MC, Menna- Barreto RF, Pinto Mdo C, de Assis Lopes F, de Simone CA, Andrade CK, Pinto AV, Ferreira VF, and de Castro SL. Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones. Bioorg Med Chem 16: 5030-5038, 2008.
37. Dardonville C, Fernandez-Fernandez C, Gibbons SL, Jagerovic N, Nieto L, Ryan G, Kaiser M, and Brun R. Antiprotozoal activity of 1-phenethyl-4- aminopiperidine derivatives. Antimicrob Agents Chemother 53: 3815-3821, 2009.
38. Das R, Roy A, Dutta N, and Majumder HK. Reactive oxygen species and imbalance of calcium homeostasis contributes to curcumin induced programmed cell death in Leishmania donovani. Apoptosis 13: 867-882, 2008.
39. Davioud-Charvet E, Delarue S, Biot C, Schwobel B, Boehme CC, Mussigbrodt A, Maes L, Sergheraert C, Grellier P, Schirmer RH, and Becker K. A prodrug form of a Plasmodium falciparum glutathione reductase inhibitor conjugated with a 4-anilinoquinoline. J Med Chem 44: 4268-4276, 2001. (Pubitemid 33095332)
40. Davioud-Charvet E and Lanfranchi D. Subversive substrates of glutathione reductases from plasmodium falciparum- infected red blood cells as antimalarial agents. In: Apicomplexan Parasites: Molecular Approaches Toward Targeted Drug Development, edited by Becker K. Weinheim, Germany: Wiley-VCH Verlag & Co. KGaA, 2011, pp. 375- 396.
41. Davioud-Charvet E, McLeish MJ, Veine DM, Giegel D, Arscott LD, Andricopulo AD, Becker K, Muller S, Schirmer RH, Williams CH, Jr., and Kenyon GL. Mechanism-based inactivation of thioredoxin reductase from Plasmodium falciparum by Mannich bases. Implication for cytotoxicity. Biochemistry 42: 13319-13330, 2003. (Pubitemid 37420684)
42. De Franceschi L, Sada S, Andreoli A, Angheben A, Marocco S, and Bisoffi Z. Sickle cell disease and hyperreactive malarial splenomegaly (HMS) in young immigrants from Africa. Blood 106: 4415-4417, 2005. (Pubitemid 41775959)
43. Delfin DA, Morgan RE, Zhu X, and Werbovetz KA. Redoxactive dinitrodiphenylthioethers against Leishmania: synthesis, structure-activity relationships and mechanism of action studies. Bioorg Med Chem 17: 820-829, 2009.
44. Dey S, Guha M, Alam A, Goyal M, Bindu S, Pal C, Maity P, Mitra K, and Bandyopadhyay U. Malarial infection develops mitochondrial pathology and mitochondrial oxidative stress to promote hepatocyte apoptosis. Free Radic Biol Med 46: 271-281, 2009.
45. Docampo R. Sensitivity of parasites to free radical damage by antiparasitic drugs. Chem Biol Interact 73: 1-27, 1990. (Pubitemid 20041146)
46. Dodean RA, Kelly JX, Peyton D, Gard GL, Riscoe MK, and Winter RW. Synthesis and heme-binding correlation with antimalarial activity of 3,6-bis-(omega-N,N-diethylaminoamyloxy)- 4,5-difluoroxanthone. Bioorg Med Chem 16: 1174-1183, 2008. (Pubitemid 351191783)
47. Edwards DI. Mechanisms of selective toxicity of metronidazole and other nitroimidazole drugs. Br J Vener Dis 56: 285-290, 1980. (Pubitemid 11253444)
48. Egan TJ, Hunter R, Kaschula CH, Marques HM, Misplon A, and Walden J. Structure-function relationships in aminoquinolines: effect of amino and chloro groups on quinolinehematin complex formation, inhibition of beta-hematin formation, and antiplasmodial activity. J Med Chem 43: 283-291, 2000. (Pubitemid 30078160)
49. Elsheikha HM and Sheashaa HA. Epidemiology, pathophysiology, management and outcome of renal dysfunction associated with plasmodia infection. Parasitol Res 101: 1183-1190, 2007. (Pubitemid 47389447)
50. Farber PM, Arscott LD, Williams CH, Jr., Becker K, and Schirmer RH. Recombinant Plasmodium falciparum glutathione reductase is inhibited by the antimalarial dye methylene blue. FEBS Lett 422: 311-314, 1998. (Pubitemid 28075485)
51. Fotie J, Nkengfack AE, Rukunga G, Tolo F, Peter MG, Heydenreich M, and Fomum ZT. In-vivo antimalarial activity of some oxygenated xanthones. Ann Trop Med Parasitol 97: 683-688, 2003. (Pubitemid 37468133)
52. Frearson JA, Wyatt PG, Gilbert IH, and Fairlamb AH. Target assessment for antiparasitic drug discovery. Trends Parasitol 23: 589-595, 2007. (Pubitemid 350161429)
53. Frey PA. Radicals in enzymatic reactions. Curr Opin Chem Biol 1: 347-356, 1997. (Pubitemid 127437161)
54. Friebolin W, Jannack B, Wenzel N, Furrer J, Oeser T, Sanchez CP, Lanzer M, Yardley V, Becker K, and Davioud- Charvet E. Antimalarial dual drugs based on potent inhibitors of glutathione reductase from Plasmodium falciparum. J Med Chem 51: 1260-1277, 2008.
55. Friedman MJ. Oxidant damage mediates variant red cell resistance to malaria. Nature 280: 245-247, 1979. (Pubitemid 9227919)
56. Fung HB and Doan TL. Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther 27: 1859-1884, 2005. (Pubitemid 43293209)
57. Gallo V, Schwarzer E, Rahlfs S, Schirmer RH, van Zwieten R, Roos D, Arese P, and Becker K. Inherited glutathione reductase deficiency and Plasmodium falciparum malaria - a case study. PLoS One 4: e7303, 2009.
58. Garavito G, Bertani S, Rincon J, Maurel S, Monje MC, Landau I, Valentin A, and Deharo E. Blood schizontocidal activity of methylene blue in combination with antimalarials against Plasmodium falciparum. Parasite 14: 135-140, 2007. (Pubitemid 46996359)
59. Gardner TB and Hill DR. Treatment of giardiasis. Clin Microbiol Rev 14: 114-128, 2001. (Pubitemid 32096209)
60. Gelb MH and Hol WG. Parasitology. Drugs to combat tropical protozoan parasites. Science 297: 343-344, 2002. (Pubitemid 34790750)
61. Gemma S, Campiani G, Butini S, Kukreja G, Coccone SS, Joshi BP, Persico M, Nacci V, Fiorini I, Novellino E, Fattorusso E, Taglialatela-Scafati O, Savini L, Taramelli D, Basilico N, Parapini S, Morace G, Yardley V, Croft S, Coletta M, Marini S, and Fattorusso C. Clotrimazole scaffold as an innovative pharmacophore towards potent antimalarial agents: design, synthesis, and biological and structure-activity relationship studies. J Med Chem 51: 1278-1294, 2008. (Pubitemid 351480389)
62. Gemma S, Campiani G, Butini S, Kukreja G, Joshi BP, Persico M, Catalanotti B, Novellino E, Fattorusso E, Nacci V, Savini L, Taramelli D, Basilico N, Morace G, Yardley V, and Fattorusso C. Design and synthesis of potent antimalarial agents based on clotrimazole scaffold: exploring an innovative pharmacophore. J Med Chem 50: 595-598, 2007. (Pubitemid 46332972)
63. Gilles HM and Hoffman PS. Treatment of intestinal parasitic infections: a review of nitazoxanide. Trends Parasitol 18: 95-97, 2002. (Pubitemid 34164244)
64. Greenwood BM, Fidock DA, Kyle DE, Kappe SH, Alonso PL, Collins FH, and Duffy PE. Malaria: progress, perils, and prospects for eradication. J Clin Invest 118: 1266-1276, 2008. (Pubitemid 351500419)
65. Grellier P, Maroziene A, Nivinskas H, Sarlauskas J, Aliverti A, and Cenas N. Antiplasmodial activity of quinones: roles of aziridinyl substituents and the inhibition of Plasmodium falciparum glutathione reductase. Arch Biochem Biophys 494: 32-39, 2010.
66. Guerin PJ, Olliaro P, Sundar S, Boelaert M, Croft SL, Desjeux P, Wasunna MK, and Bryceson AD. Visceral leishmaniasis: current status of control, diagnosis, and treatment, and a proposed research and development agenda. Lancet Infect Dis 2: 494-501, 2002. (Pubitemid 34826855)
67. Guha M, Kumar S,Choubey V,Maity P, and Bandyopadhyay U. Apoptosis in liver during malaria: role of oxidative stress and implication of mitochondrial pathway. FASEB J 20: 1224-1226, 2006.
68. Hall BS, Wu X, Hu L, and Wilkinson SR. Exploiting the drug-activating properties of a novel trypanosomal nitroreductase. Antimicrob Agents Chemother 54: 1193-1199, 2010.
69. Harwaldt P, Rahlfs S, and Becker K. Glutathione Stransferase of the malarial parasite Plasmodium falciparum: characterization of a potential drug target. Biol Chem 383: 821-830, 2002. (Pubitemid 34649901)
70. Hayat F, Salahuddin A, Umar S, and Azam A. Synthesis, characterization, antiamoebic activity and cytotoxicity of novel series of pyrazoline derivatives bearing quinoline tail. Eur J Med Chem 45: 4669-4675, 2010.
71. Haynes RK, Chan WC, Wong HN, Li KY, Wu WK, Fan KM, Sung HH, Williams ID, Prosperi D, Melato S, Coghi P, and Monti D. Facile oxidation of leucomethylene blue and dihydroflavins by artemisinins: relationship with flavoenzyme function and antimalarial mechanism of action. ChemMedChem 5: 1282-1299, 2010.
72. Henderson GB, Ulrich P, Fairlamb AH, Rosenberg I, Pereira M, Sela M, and Cerami A. "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, 1988.
73. Hirt RP, Muller S, Embley TM, and Coombs GH. The diversity and evolution of thioredoxin reductase: new perspectives. Trends Parasitol 18: 302-308, 2002. (Pubitemid 35257855)
74. Hoffman PS, Sisson G, Croxen MA, Welch K, Harman WD, Cremades N, and Morash MG. Antiparasitic drug nitazoxanide inhibits the pyruvate oxidoreductases of Helicobacter pylori, selected anaerobic bacteria and parasites, and Campylobacter jejuni. Antimicrob Agents Chemother 51: 868-876, 2007. (Pubitemid 46355269)
75. Huynh TT, Huynh VT, Harmon MA, and Phillips MA. Gene knockdown of gamma-glutamylcysteine synthetase by RNAi in the parasitic protozoa Trypanosoma brucei demonstrates that it is an essential enzyme. J Biol Chem 278: 39794-39800, 2003. (Pubitemid 37248541)
76. Ignatushchenko MV, Winter RW, Bachinger HP, Hinrichs DJ, and Riscoe MK. Xanthones as antimalarial agents; studies of a possible mode of action. FEBS Lett 409: 67-73, 1997. (Pubitemid 27248569)
77. Ignatushchenko MV, Winter RW, and Riscoe M. Xanthones as antimalarial agents: stage specificity. Am J Trop Med Hyg 62: 77-81, 2000. (Pubitemid 30180354)
78. Inhoff O, Richards JM, Briet JW, Lowe G, and Krauth-Siegel RL. Coupling of a competitive and an irreversible ligand generates mixed type inhibitors of Trypanosoma cruzi trypanothione reductase. J Med Chem 45: 4524-4530, 2002.
79. Jamonneau V, Bucheton B, Kabore J, Ilboudo H, Camara O, Courtin F, Solano P, Kaba D, Kambire R, Lingue K, Camara M, Baelmans R, Lejon V, and Buscher P. Revisiting the immune trypanolysis test to optimise epidemiological surveillance and control of sleeping sickness in West Africa. PLoS Negl Trop Dis 4: e917, 2010.
80. Jockers-Scherubl MC, Schirmer RH, and Krauth-Siegel RL. Trypanothione reductase from Trypanosoma cruzi. Catalytic properties of the enzyme and inhibition studies with trypanocidal compounds. Eur J Biochem 180: 267-272, 1989. (Pubitemid 19088813)
81. Kanzok SM, Rahlfs S, Becker K, and Schirmer RH. Thioredoxin, thioredoxin reductase, and thioredoxin peroxidase of malaria parasite Plasmodium falciparum. Methods Enzymol 347: 370-381, 2002. (Pubitemid 34233290)
82. Kanzok SM, Schirmer RH, Turbachova I, Iozef R, and Becker K. The thioredoxin system of the malaria parasite Plasmodium falciparum. Glutathione reduction revisited. J Biol Chem 275: 40180-40186, 2000. (Pubitemid 32064647)
83. Kawazu S, Komaki K, Tsuji N, Kawai S, Ikenoue N, Hatabu T, Ishikawa H, Matsumoto Y, Himeno K, and Kano S. Molecular characterization of a 2-Cys peroxiredoxin from the human malaria parasite Plasmodium falciparum. Mol Biochem Parasitol 116: 73-79, 2001. (Pubitemid 32706428)
84. Kehr S, Jortzik E, Delahunty C, Yates JR, Rahlfs S, and Becker K. Protein s-glutathionylation in malaria parasites. Antioxid Redox Signal 15: 2855-2865, 2011.
85. Keiser J, Stich A, and Burri C. New drugs for the treatment of human African trypanosomiasis: research and development. Trends Parasitol 17: 42-49, 2001.
86. Khan MO, Austin SE, Chan C, Yin H, Marks D, Vaghjiani SN, Kendrick H, Yardley V, Croft SL, and Douglas KT. Use of an additional hydrophobic binding site, the Z site, in the rational drug design of a new class of stronger trypanothione reductase inhibitor, quaternary alkylammonium phenothiazines. J Med Chem 43: 3148-3156, 2000. (Pubitemid 30627549)
87. Khaw M and Panosian CB. Human antiprotozoal therapy: past, present, and future. Clin Microbiol Rev 8: 427-439, 1995.
88. Koliwer-Brandl H, Gbem TT, Waespy M, Reichert O, Mandel P, Drebitz E, Dietz F, and Kelm S. Biochemical characterization of trans-sialidase TS1 variants from Trypanosoma congolense. BMC Biochem 12: 39, 2011.
89. Kotecka BM, Barlin GB, Edstein MD, and Rieckmann KH. New quinoline di-Mannich base compounds with greater antimalarial activity than chloroquine, amodiaquine, or pyronaridine. Antimicrob Agents Chemother 41: 1369-1374, 1997. (Pubitemid 27231444)
90. Krauth-Siegel RL, Bauer H, and Schirmer RH. Dithiol proteins as guardians of the intracellular redox milieu in parasites: old and new drug targets in trypanosomes and malaria-causing plasmodia. Angew Chem Int Ed Engl 44: 690-715, 2005. (Pubitemid 40203977)
91. Krauth-Siegel RL, Meiering SK, and Schmidt H. The parasite- specific trypanothione metabolism of trypanosoma and leishmania. Biol Chem 384: 539-549, 2003. (Pubitemid 36609170)
92. Krnajski Z, Gilberger TW, Walter RD, Cowman AF, and Muller S. Thioredoxin reductase is essential for the survival of Plasmodium falciparum erythrocytic stages. J Biol Chem 277: 25970-25975, 2002. (Pubitemid 34967078)
93. Krnajski Z, Walter RD, and Muller S. Isolation and functional analysis of two thioredoxin peroxidases (peroxiredoxins) from Plasmodium falciparum. Mol Biochem Parasitol 113: 303-308, 2001. (Pubitemid 32274303)
94. Kumar S, Das SK, Dey S, Maity P, Guha M, Choubey V, Panda G, and Bandyopadhyay U. Antiplasmodial activity of [(aryl)arylsulfanylmethyl]Pyridine. Antimicrob Agents Chemother 52: 705-715, 2008. (Pubitemid 351170847)
95. Kumar S, Guha M, Choubey V, Maity P, and Bandyopadhyay U. Antimalarial drugs inhibiting hemozoin (beta-hematin) formation: a mechanistic update. Life Sci 80: 813-828, 2007. (Pubitemid 46149853)
96. Kuntz AN, Davioud-Charvet E, Sayed AA, Califf LL, Dessolin J, Arner ES, and Williams DL. Thioredoxin glutathione reductase from Schistosoma mansoni: an essential parasite enzyme and a key drug target. PLoS Med 4: e206, 2007.
97. Lee B, Bauer H, Melchers J, Ruppert T, Rattray L, Yardley V, Davioud-Charvet E, and Krauth-Siegel RL. Irreversible inactivation of trypanothione reductase by unsaturated Mannich bases: a divinyl ketone as key intermediate. J Med Chem 48: 7400-7410, 2005. (Pubitemid 41743653)
98. Legorreta-Herrera M, Retana-Ugalde R, Ventura-Gallegos JL, and Narvaez V. Pyrimethamine induces oxidative stress in Plasmodium yoelii 17XL-infected mice: a novel immunomodulatory mechanism of action for an old antimalarial drug? Exp Parasitol 126: 381-388, 2010.
99. Leitsch D, Kolarich D, Wilson IB, Altmann F, and Duchene M. Nitroimidazole action in Entamoeba histolytica: a central role for thioredoxin reductase. PLoS Biol 5: e211, 2007.
100. Li R, Kenyon GL, Cohen FE, Chen X, Gong B, Dominguez JN, Davidson E, Kurzban G, Miller RE, Nuzum EO, et al. In vitro antimalarial activity of chalcones and their derivatives. J Med Chem 38: 5031-5037, 1995. (Pubitemid 26012258)
101. Li Z, Fennie MW, Ganem B, Hancock MT, Kobaslija M, Rattendi D, Bacchi CJ, and O'Sullivan MC. Polyamines with N- (3-phenylpropyl) substituents are effective competitive inhibitors of trypanothione reductase and trypanocidal agents. Bioorg Med Chem Lett 11: 251-254, 2001. (Pubitemid 32099652)
102. Liebau E, Bergmann B, Campbell AM, Teesdale-Spittle P, Brophy PM, Luersen K, and Walter RD. The glutathione Stransferase from Plasmodium falciparum. Mol Biochem Parasitol 124: 85-90, 2002.
103. Liu H, Walker LA, Nanayakkara NP, and Doerksen RJ. Methemoglobinemia caused by 8-aminoquinoline drugs: DFT calculations suggest an analogy to H4B's role in nitric oxide synthase. J Am Chem Soc 133: 1172-1175, 2011.
104. Loftus B, Anderson I, Davies R, Alsmark UC, Samuelson J, Amedeo P, Roncaglia P, Berriman M, Hirt RP, Mann BJ, Nozaki T, Suh B, Pop M, Duchene M, Ackers J, Tannich E, Leippe M, Hofer M, Bruchhaus I, Willhoeft U, Bhattacharya A, Chillingworth T, Churcher C, Hance Z, Harris B, Harris D, Jagels K, Moule S, Mungall K, Ormond D, Squares R, Whitehead S, Quail MA, Rabbinowitsch E, Norbertczak H, Price C, Wang Z, Guillen N, Gilchrist C, Stroup SE, Bhattacharya S, Lohia A, Foster PG, Sicheritz-Ponten T, Weber C, Singh U, Mukherjee C, El-Sayed NM, Petri WA, Jr., Clark CG, Embley TM, Barrell B, Fraser CM, and Hall N. The genome of the protist parasite Entamoeba histolytica. Nature 433: 865-868, 2005. (Pubitemid 40314894)
105. Massimine KM, McIntosh MT, Doan LT, Atreya CE, Gromer S, Sirawaraporn W, Elliott DA, Joiner KA, Schirmer RH, and Anderson KS. Eosin B as a novel antimalarial agent for drug-resistant Plasmodium falciparum. Antimicrob Agents Chemother 50: 3132-3141, 2006. (Pubitemid 44403775)
106. Meunier B and Robert A. Heme as trigger and target for trioxane-containing antimalarial drugs. Acc Chem Res 43: 1444-1451, 2010.
107. Miller MA, McGowan SE, Gantt KR, Champion M, Novick SL, Andersen KA, Bacchi CJ, Yarlett N, Britigan BE, and Wilson ME. Inducible resistance to oxidant stress in the protozoan Leishmania chagasi. J Biol Chem 275: 33883-33889, 2000.
108. Mkoji GM, Smith JM, and Prichard RK. Antioxidant systems in Schistosoma mansoni: correlation between susceptibility to oxidant killing and the levels of scavengers of hydrogen peroxide and oxygen free radicals. Int J Parasitol 18: 661-666, 1988.
109. Mookerjee Basu J, Mookerjee A, Sen P, Bhaumik S, Banerjee S, Naskar K, Choudhuri SK, Saha B, Raha S, and Roy S. Sodium antimony gluconate induces generation of reactive oxygen species and nitric oxide via phosphoinositide 3- kinase and mitogen-activated protein kinase activation in Leishmania donovani-infected macrophages. Antimicrob Agents Chemother 50: 1788-1797, 2006.
110. Muller S. Thioredoxin reductase and glutathione synthesis in Plasmodium falciparum. Redox Rep 8: 251-255, 2003. (Pubitemid 38035582)
111. Muller S, Liebau E, Walter RD, and Krauth-Siegel RL. Thiol-based redox metabolism of protozoan parasites. Trends Parasitol 19: 320-328, 2003. (Pubitemid 36829189)
112. Muller T, Johann L, Jannack B, Bruckner M, Lanfranchi DA, Bauer H, Sanchez C, Yardley V, Deregnaucourt C, Schrevel J, Lanzer M, Schirmer RH, and Davioud-Charvet E. A glutathione reductase-catalyzed cascade of redox reactions to bioactivate potent antimalarial 1,4-naphthoquinones - a new strategy to combat malarial parasites. J Am Chem Soc 133: 11557-11571, 2011.
113. Newton CR and Krishna S. Severe falciparum malaria in children: current understanding of pathophysiology and supportive treatment. Pharmacol Ther 79: 1-53, 1998. (Pubitemid 28318261)
114. O'Neill PM, Mukhtar A, Stocks PA, Randle LE, Hindley S, Ward SA, Storr RC, Bickley JF, O'Neil IA, Maggs JL, Hughes RH, Winstanley PA, Bray PG, and Park BK. Isoquine and related amodiaquine analogues: a new generation of improved 4-aminoquinoline antimalarials. J Med Chem 46: 4933-4945, 2003. (Pubitemid 37352033)
115. Oke TT, Moskovitz J, and Williams DL. Characterization of the methionine sulfoxide reductases of Schistosoma mansoni. J Parasitol 95: 1421-1428, 2009.
116. Olds GR and Dasarathy S. Recent advances in schistosomiasis. Curr Infect Dis Rep 3: 59-67, 2001.
117. Oza SL, Ariyanayagam MR, and Fairlamb AH. Characterization of recombinant glutathionylspermidine synthetase/ amidase from Crithidia fasciculata. Biochem J 364: 679-686, 2002. (Pubitemid 34680843)
118. Perez-Pineiro R, Burgos A, Jones DC, Andrew LC, Rodriguez H, Suarez M, Fairlamb AH, and Wishart DS. Development of a novel virtual screening cascade protocol to identify potential trypanothione reductase inhibitors. J Med Chem 52: 1670-1680, 2009.
119. Perry MR, Wyllie S, Prajapati VK, Feldmann J, Sundar S, Boelaert M, and Fairlamb AH. Visceral leishmaniasis and arsenic: an ancient poison contributing to antimonial treatment failure in the Indian subcontinent? PLoS Negl Trop Dis 5: e1227, 2011.
120. Ponasik JA, Strickland C, Faerman C, Savvides S, Karplus PA, and Ganem B. Kukoamine A and other hydrophobic acylpolyamines: potent and selective inhibitors of Crithidia fasciculata trypanothione reductase. Biochem J 311 (Pt 2): 371-375, 1995.
121. Raether W and Hanel H. Nitroheterocyclic drugs with broad spectrum activity. Parasitol Res 90 Supp 1: S19-S39, 2003. (Pubitemid 36831290)
122. Rahlfs S, Fischer M, and Becker K. Plasmodium falciparum possesses a classical glutaredoxin and a second, glutaredoxin-like protein with a PICOT homology domain. J Biol Chem 276: 37133-37140, 2001.
123. Rahlfs S, Schirmer RH, and Becker K. The thioredoxin system of Plasmodium falciparum and other parasites. Cell Mol Life Sci 59: 1024-1041, 2002. (Pubitemid 34734634)
124. Rassi A, Jr., Rassi A, and Marin-Neto JA. Chagas disease. Lancet 375: 1388-1402, 2010.
125. Rodrigues JR, Lourenco D, and Gamboa N. Disturbance in hemoglobin metabolism and in vivo antimalarial activity of azole antimycotics. Rev InstMed Trop SaoPaulo 53: 25-29, 2011.
126. Roldan MD,Perez-Reinado E, Castillo F, and Moreno-Vivian C. Reduction of polynitroaromatic compounds: the bacterial nitroreductases. FEMS Microbiol Rev 32: 474-500, 2008. (Pubitemid 351538747)
127. Roy A, Ganguly A, BoseDasgupta S, Das BB, Pal C, Jaisankar P, and Majumder HK. Mitochondria-dependent reactive oxygen species-mediated programmed cell death induced by 3,3′-diindolylmethane through inhibition of F0F1-ATP synthase in unicellular protozoan parasite Leishmania donovani. Mol Pharmacol 74: 1292-1307, 2008.
128. Royer RE, Deck LM, Campos NM, Hunsaker LA, and Vander Jagt DL. Biologically active derivatives of gossypol: synthesis and antimalarial activities of peri-acylated gossylic nitriles. J Med Chem 29: 1799-1801, 1986. (Pubitemid 16018218)
129. Saleheen D, Ali SA, Ashfaq K, Siddiqui AA, Agha A, and Yasinzai MM. Latent activity of curcumin against leishmaniasis in vitro. Biol Pharm Bull 25: 386-389, 2002. (Pubitemid 39663296)
130. Salinas AE and Wong MG. Glutathione S-transferases - a review. Curr Med Chem 6: 279-309, 1999. (Pubitemid 29226114)
131. Sarma GN, Savvides SN, Becker K, Schirmer M, Schirmer RH, and Karplus PA. Glutathione reductase of the malarial parasite Plasmodium falciparum: crystal structure and inhibitor development. J Mol Biol 328: 893-907, 2003. (Pubitemid 36506894)
132. Savvides SN, Scheiwein M, Bohme CC, Arteel GE, Karplus PA, Becker K, and Schirmer RH. Crystal structure of the antioxidant enzyme glutathione reductase inactivated by peroxynitrite. J Biol Chem 277: 2779-2784, 2002. (Pubitemid 34953308)
133. Sayed AA, Cook SK, and Williams DL. Redox balance mechanisms in Schistosoma mansoni rely on peroxiredoxins and albumin and implicate peroxiredoxins as novel drug targets. J Biol Chem 281: 17001-17010, 2006.
134. Schirmer RH, Coulibaly B, Stich A, Scheiwein M, Merkle H, Eubel J, Becker K, Becher H, Muller O, Zich T, Schiek W, and Kouyate B. Methylene blue as an antimalarial agent. Redox Rep 8: 272-275, 2003. (Pubitemid 38035586)
135. Seeber F, Aliverti A, and Zanetti G. The plant-type ferredoxin- NADP + reductase/ferredoxin redox system as a possible drug target against apicomplexan human parasites. Curr Pharm Des 11: 3159-3172, 2005. (Pubitemid 41149931)
136. Sen N, Banerjee B, Das BB, Ganguly A, Sen T, Pramanik S, Mukhopadhyay S, and Majumder HK. Apoptosis is induced in leishmanial cells by a novel protein kinase inhibitor withaferin A and is facilitated by apoptotic topoisomerase IDNA complex. Cell Death Differ 14: 358-367, 2007. (Pubitemid 46092238)
137. Sen N, Das BB, Ganguly A, Mukherjee T, Tripathi G, Bandyopadhyay S, Rakshit S, Sen T, and Majumder HK. Camptothecin induced mitochondrial dysfunction leading to programmed cell death in unicellular hemoflagellate Leishmania donovani. Cell Death Differ 11: 924-936, 2004. (Pubitemid 39139751)
138. Sharma N, Shukla AK, Das M, and Dubey VK. Evaluation of plumbagin and its derivative as potential modulators of redox thiol metabolism of Leishmania parasite. Parasitol Res 2011 [Epub ahead of print]: DOI: 10.1007/s00436-011- 2498-x.
139. Shukla AK, Patra S, and Dubey VK. Evaluation of selected antitumor agents as subversive substrate and potential inhibitor of trypanothione reductase: an alternative approach for chemotherapy of Leishmaniasis. Mol Cell Biochem 352: 261-270, 2011.
140. Simeonov A, Jadhav A, Sayed AA, Wang Y, Nelson ME, Thomas CJ, Inglese J, Williams DL, and Austin CP. Quantitative high-throughput screen identifies inhibitors of the Schistosoma mansoni redox cascade. PLoS Negl Trop Dis 2: e127, 2008.
141. Singh C, Hassam M, Naikade NK, Verma VP, Singh AS, and Puri SK. Synthesis and antimalarial assessment of a new series of orally active amino-functionalized spiro 1,2,4- trioxanes. J Med Chem 53: 7587-7598, 2010.
142. Singh C, Srivastav NC, and Puri SK. In vivo active antimalarial isonitriles. Bioorg Med Chem Lett 12: 2277-2279, 2002. (Pubitemid 34879848)
143. Smith HK and Bradley M. Comparison of resin and solution screening methodologies in combinatorial chemistry and the identification of a 100nM inhibitor of trypanothione reductase. J Comb Chem 1: 326-332, 1999.
144. Spinks D, Shanks EJ, Cleghorn LA, McElroy S, Jones D, James D, Fairlamb AH, Frearson JA, Wyatt PG, and Gilbert IH. Investigation of trypanothione reductase as a drug target in Trypanosoma brucei. ChemMedChem 4: 2060-2069, 2009.
145. Stuart K, Brun R, Croft S, Fairlamb A, Gurtler RE, McKerrow J, Reed S, and Tarleton R. Kinetoplastids: related protozoan pathogens, different diseases. J Clin Invest 118: 1301-1310, 2008. (Pubitemid 351500422)
146. Stump B, Eberle C, Kaiser M, Brun R, Krauth-Siegel RL, and Diederich F. Diaryl sulfide-based inhibitors of trypanothione reductase: inhibition potency, revised binding mode and antiprotozoal activities. Org Biomol Chem 6: 3935-3947, 2008.
147. Thornalley PJ, Strath M, and Wilson RJ. Antimalarial activity in vitro of the glyoxalase I inhibitor diester, S-pbromobenzylglutathione diethyl ester. Biochem Pharmacol 47: 418-420, 1994. (Pubitemid 24050902)
148. Trivedi V, Chand P, Srivastava K, Puri SK, Maulik PR, and Bandyopadhyay U. Clotrimazole inhibits hemoperoxidase of Plasmodium falciparum and induces oxidative stress. Proposed antimalarial mechanism of clotrimazole. J Biol Chem 280: 41129-41136, 2005. (Pubitemid 41832165)
149. Tsumori Y, Ndounga M, Sunahara T, Hayashida N, Inoue M, Nakazawa S, Casimiro P, Isozumi R, Uemura H, Tanabe K, Kaneko O, and Culleton R. Plasmodium falciparum: differential selection of drug resistance alleles in contiguous urban and peri-urban areas of Brazzaville, Republic of Congo. PLoS One 6: e23430, 2011.
150. Turrens JF. Oxidative stress and antioxidant defenses: a target for the treatment of diseases caused by parasitic protozoa. Mol Aspects Med 25: 211-220, 2004.
151. van Hal SJ, Stark DJ, Fotedar R, Marriott D, Ellis JT, and Harkness JL. Amoebiasis: current status in Australia. Med J Aust 186: 412-416, 2007.
152. VennerstromJL, EllisWY, Ager AL, Jr., Andersen SL, Gerena L, and Milhous WK. Bisquinolines. 1. N,N-bis(7-chloroquinolin- 4-yl)alkanediamines with potential against chloroquine- resistant malaria. J Med Chem 35: 2129-2134, 1992.
153. VieitesM, Smircich P, Parajon-Costa B, Rodriguez J, Galaz V, Olea-Azar C, Otero L, Aguirre G, Cerecetto H, Gonzalez M, Gomez-BarrioA,Garat B, andGambinoD.Potent in vitro anti- Trypanosoma cruzi activity of pyridine-2-thiol N-oxide metal complexes having an inhibitory effect on parasite-specific fumarate reductase. J Biol Inorg Chem 13: 723-735, 2008.
154. Viode C, Bettache N, Cenas N, Krauth-Siegel RL, Chauviere G, Bakalara N, and Perie J. Enzymatic reduction studies of nitroheterocycles. Biochem Pharmacol 57: 549-557, 1999. (Pubitemid 29073333)
155. Wagner JT,LudemannH,FarberPM,LottspeichF, andKrauth- Siegel RL. Glutamate dehydrogenase, the marker protein of Plasmodium falciparum - cloning, expression and characterization of the malarial enzyme. Eur J Biochem 258: 813-819, 1998. (Pubitemid 28557950)
156. Walton JG, Jones DC, Kiuru P, Durie AJ, Westwood NJ, and Fairlamb AH. Synthesis and evaluation of indatralinebased inhibitors for trypanothione reductase. ChemMed- Chem 6: 321-328, 2011.
157. Westrop GD, Georg I, and Coombs GH. The mercaptopyruvate sulfurtransferase of Trichomonas vaginalis links cysteine catabolism to the production of thioredoxin persulfide. J Biol Chem 284: 33485-33494, 2009.
158. White NJ. Antimalarial drug resistance. J Clin Invest 113: 1084-1092, 2004. (Pubitemid 38544090)
159. Wilkinson SR, Taylor MC, Horn D, Kelly JM, and Cheeseman I. A mechanism for cross-resistance to nifurtimox and benznidazole in trypanosomes. Proc Natl Acad Sci U S A 105: 5022-5027, 2008. (Pubitemid 351738503)
160. Williams CH, Arscott LD, Muller S, Lennon BW, Ludwig ML, Wang PF, Veine DM, Becker K, and Schirmer RH. Thioredoxin reductase two modes of catalysis have evolved. Eur J Biochem 267: 6110-6117, 2000.
161. Wright AD, Wang H, Gurrath M, Konig GM, Kocak G, Neumann G, Loria P, Foley M, and Tilley L. Inhibition of heme detoxification processes underlies the antimalarial activity of terpene isonitrile compounds from marine sponges. J Med Chem 44: 873-885, 2001. (Pubitemid 32861612)
162. XuKelly J,WinterR,RiscoeM, and PeytonDH.Aspectroscopic investigation of the binding interactions between 4,5-dihydroxyxanthone and heme. J Inorg Biochem86: 617-625, 2001.
163. Yeo M, Acosta N, Llewellyn M, Sanchez H, Adamson S, Miles GA, Lopez E, Gonzalez N, Patterson JS, Gaunt MW, de Arias AR, and Miles MA. Origins of Chagas disease: Didelphis species are natural hosts of Trypanosoma cruzi I and armadillos hosts of Trypanosoma cruzi II, including hybrids. Int J Parasitol 35: 225-233, 2005. (Pubitemid 40248717)
164. Yeo M, Mauricio IL, Messenger LA, Lewis MD, Llewellyn MS, Acosta N, Bhattacharyya T, Diosque P, Carrasco HJ, and Miles MA. Multilocus sequence typing (MLST) for lineage assignment and high resolution diversity studies in Trypanosoma cruzi. PLoS Negl Trop Dis 5: e1049, 2011.