LQB-118, an orally active pterocarpanquinone, induces selective oxidative stress and apoptosis in Leishmania amazonensis

Journal of Antimicrobial Chemotherapy

Volumn 68, Issue 4, 2013, Pages 789-799

  Ribeiro, Grazielle Alves ^a,b,e   Cunha Júnior, Edézio Ferreira ^a   Pinheiro, Roberta Olmo ^a   da Silva, Silvia Amaral Goncalves ^c   Canto Cavalheiro, Marilene Marcuzzo ^a   da Silva, Alcides José Monteiro ^d   Costa, Paulo Roberto R ^d   Netto, Chaquip Daher ^d   Melo, Rossana C N ^b   Almeida Amaral, Elmo Eduardo ^a   Torres Santos, Eduardo Caio ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FEDERAL UNIVERSITY OF JUIZ DE FORA   (Brazil)

^c UNIVERSIDADE DO ESTADO DO RIO DE JANEIRO   (Brazil)

^d FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^e FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

Antiparasitic; Chemotherapy; Quinones

Indexed keywords

ANTIPROTOZOAL AGENT; DICHLORODIHYDROFLUORESCEIN DIACETATE; LQB 118; MILTEFOSINE; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; STAUROSPORINE; UNCLASSIFIED DRUG;

AMASTIGOTE; ANTIPROTOZOAL ACTIVITY; APOPTOSIS; ARTICLE; CONCENTRATION RESPONSE; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DNA FRAGMENTATION; G1 PHASE CELL CYCLE CHECKPOINT; IN VITRO STUDY; LEISHMANIA; MACROPHAGE; MEMBRANE DEPOLARIZATION; MITOCHONDRIAL MEMBRANE POTENTIAL; NICK END LABELING; NONHUMAN; OXIDATIVE STRESS; PHENOTYPE; PROMASTIGOTE; TRANSMISSION ELECTRON MICROSCOPY;

ANTIPROTOZOAL AGENTS; APOPTOSIS; DNA FRAGMENTATION; IN SITU NICK-END LABELING; LEISHMANIA; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICROSCOPY, ELECTRON, TRANSMISSION; NAPHTHOQUINONES; OXIDATIVE STRESS; PTEROCARPANS; REACTIVE OXYGEN SPECIES;

EID: 84875262357     PISSN: 03057453     EISSN: 14602091     Source Type: Journal    
DOI: 10.1093/jac/dks498     Document Type: Article

References (36)

1. Kerr JF, Wyllie AH, Currie AR. Apoptosis: a basic biological phenomenon with wide-ranging implications in tissue kinetics. Br J Cancer 1972; 26: 239-57.
2. Deponte M. Programmed cell death in protists. Biochim Biophys Acta 2008; 1783: 1396-405.
3. Hengartner MO. The biochemistry of apoptosis. Nature 2000; 407: 770-6.
4. Shaha C. Apoptosis in Leishmania species and its relevance to disease pathogenesis. Indian J Med Res 2006; 123: 233-44.
5. Desjeux P. Leishmaniasis: current situation and new perspectives. Comp Immunol Microbiol Infect Dis 2004; 27: 305-18.
6. Verma NK, Dey CS. Possible mechanism of miltefosine-mediated death of Leishmania donovani. Antimicrob Agents Chemother 2004; 48: 3010-5.
7. Lee N, Bertholet S, Debrabant A et al. Programmed cell death in the unicellular protozoan parasite Leishmania. Cell Death Differ 2002; 9: 53-64.
8. Sen N, Das BB, Ganguly A et al. Camptothecin induced mitochondrial dysfunction leading to programmed cell death in unicellular hemoflagellate Leishmania donovani. Cell Death Differ 2004; 11: 924-36.
9. Dutta A, Bandyopadhyay S, Mandal C et al. Aloe vera leaf exudate induces a caspase-independent cell death in Leishmania donovani promastigotes. J Med Microbiol 2007; 56: 629-36.
10. Sen R, Bandyopadhyay S, Dutta A et al. Artemisinin triggers induction of cell-cycle arrest and apoptosis in Leishmania donovani promastigotes. J Med Microbiol 2007; 56: 1213-8.
11. Dutta A, Ghoshal A, Mandal D et al. Racemoside A, an anti-leishmanial, water-soluble, natural steroidal saponin, induces programmed cell death in Leishmania donovani. J Med Microbiol 2007; 56: 1196-204.
12. Sen N, Banerjee B, Das BB et al. Apoptosis is induced in leishmanial cells by a novel protein kinase inhibitor withaferin A and is facilitatedby apoptotic topoisomerase I-DNA complex. Cell Death Differ 2007; 14: 358-67.
13. Das R, Roy A, Dutta N et al. Reactive oxygen species and imbalance of calcium homeostasis contributes to curcumin induced programmed cell death in Leishmania donovani. Apoptosis 2008; 13: 867-82.
14. Arnoult D, Akarid K, Grodet A et al. On the evolution of programmed cell death: apoptosis of the unicellular eukaryote Leishmania major involves cysteine proteinase activation and mitochondrion permeabilization. Cell Death Differ 2002; 9: 65-81.
15. Zangger H, Mottram JC, Fasel N. Cell death in Leishmania induced by stress and differentiation: programmed cell death or necrosis? Cell Death Differ 2002; 9: 1126-39.
16. Debrabant A, Lee N, Bertholet S et al. Programmed cell death in trypanosomatids and other unicellular organisms. Int J Parasitol 2003; 33: 257-67.
17. Jimenez-Ruiz A, Alzate JF, Macleod ET et al. Apoptotic markers in protozoan parasites. Parasit Vectors 2010; 3: 104.
18. Fidalgo LM, Gille L. Mitochondria and trypanosomatids: targets and drugs. Pharm Res 2011; 28: 2758-700.
19. Mukherjee P, Majee SB, Ghosh S et al. Apoptosis-like death in Leishmania donovani promastigotes induced by diospyrin and its ethanolamine derivative. Int J Antimicrob Agents 2009; 34: 596-601.
20. da Silva AJM, Netto CD, Pacienza-Lima W et al. Antitumoral, antileishmanial and antimalarial activity of pentacyclic 1,4-naphthoquinone derivatives. J Braz Chem Soc 2009; 20: 176-82.
21. Netto CD, da Silva AJ, Salustiano EJ et al. New pterocarpanquinones: synthesis, antineoplasic activity on cultured human malignant cell lines and TNF-a modulation in human PBMC cells. Bioorg Med Chem 2010; 18: 1610-6.
22. da Silva AJ, Buarque CD, Brito FV et al. Synthesis and preliminary pharmacological evaluation of new (+/2) 1,4-naphthoquinones structurally related to lapachol. Bioorg Med Chem 2002; 10: 2731-8.
23. da Cunha-Junior EF, Pacienza-Lima W, Ribeiro GA et al. Effectiveness of the local or oral delivery of the novel naphthopterocarpanquinone LQB-118 against cutaneous leishmaniasis. J Antimicrob Chemother 2011; 66: 1555-9.
24. Netto CD, Santos ES, Castro CP et al. (+/2)-3,4-Dihydroxy-8,9-methylenedioxypterocarpan and derivatives: cytotoxic effect on human leukemia cell lines. Eur J Med Chem 2009; 44: 920-5.
25. Fonseca-Silva F, Inacio JD, Canto-Cavalheiro MM et al. Reactive oxygen species production and mitochondrial dysfunction contribute to quercetin induced death in Leishmania amazonensis. PLoS One 2011; 6: e14666.
26. Menna-Barreto RF, Goncalves RL, Costa EM et al. The effects on Trypanosoma cruzi of novel synthetic naphthoquinones are mediated by mitochondrial dysfunction. Free Radic Biol Med 2009; 47: 644-53.
27. Reers M, Smiley ST, Mottola-Hartshorn C et al. Mitochondrial membrane potential monitored by JC-1 dye. Methods Enzymol 1995; 260: 406-17.
28. Handa K, Sato S. Generation of free radicals of quinone group-containing anti-cancer chemicals in NADPH-microsome system as evidenced by initiation of sulfite oxidation. Gann 1975; 66: 43-7.
29. Green DR, Reed JC. Mitochondria and apoptosis. Science 1998; 281: 1309-12.
30. Halliwell B, Gutteridge JM. Role of free radicals and catalytic metal ions in human disease: an overview. Methods Enzymol 1990; 186: 1-85.
31. Roy A, Ganguly A, Bosedasgupta S et al. 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 2008; 74: 1292-307.
32. van Hellemond JJ, Opperdoes FR, Tielens AG. The extraordinary mitochondrion and unusual citric acid cycle in Trypanosoma brucei. Biochem Soc Trans 2005; 33: 967-71.
33. Fry M, Pudney M. Site of action of the antimalarial hydroxynaphthoquinone, 2-[trans-4-(4'-chlorophenyl) cyclohexyl]-3-hyd roxy-1,4-naphthoquinone (566C80). BiochemPharmacol 1992; 43: 1545-3.
34. Srivastava IK, Rottenberg H, Vaidya AB. Atovaquone, a broad spectrum antiparasitic drug, collapses mitochondrial membrane potential in a malarial parasite. J Biol Chem 1997; 272: 3961-6.
35. Sen N, Das BB, Ganguly A et al. Leishmania donovani: intracellular ATP level regulates apoptosis-like death in luteolin induced dyskinetoplastid cells. Exp Parasitol 2006; 114: 204-14.
36. Maia RC, Vasconcelos FC, de Sá Bacelar T et al. LQB-118, a pterocarpanquinone structurally related to lapachol [2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone]: a novel class of agent with high apoptotic effect in chronic myeloid leukemia cells. Invest New Drugs 2011; 29: 1143-55.