Malaria-infected mice live until at least day 30 after a new artemisinin-derived thioacetal thiocarbonate combined with mefloquine are administered together in a single, low, oral dose

Journal of Medicinal Chemistry

Volumn 55, Issue 17, 2012, Pages 7892-7899

  Jacobine, Alexander M ^a   Mazzone, Jennifer R ^a   Slack, Rachel D ^a   Tripathi, Abhai K ^b   Sullivan, David J ^b   Posner, Gary H ^a,b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b JOHNS HOPKINS BLOOMBERG SCHOOL OF PUBLIC HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; DIHYDROARTEMISININ; MEFLOQUINE; THIOACETAL BENZIMIDAZOLE AMIDE; THIOACETAL CARBONATE; THIOACETAL THIOCARBONATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; MALE; MOUSE; NONHUMAN; PARASITE IDENTIFICATION; PARASITEMIA; PLASMODIUM BERGHEI INFECTION; SINGLE DRUG DOSE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SURVIVAL TIME;

ACETALS; ADMINISTRATION, ORAL; ANIMALS; ANTIMALARIALS; ARTEMISININS; MAGNETIC RESONANCE SPECTROSCOPY; MALARIA; MEFLOQUINE; MICE; MICE, INBRED C57BL; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 84866317492     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3009986     Document Type: Article

References (55)

1. World Malaria Report 2011; World Health Organization: Geneva, Switzerland, 2011.
2. Delves, M.; Plouffe, D.; Scheurer, C.; Meister, S.; Wittlin, S.; Winzeler, E. A.; Sinden, R. E.; Leroy, D. The activities of current antimalarial drugs on the life cycle stages of Plasmodium: a comparative study with human and rodent parasites PLoS Med. 2012, 9, e1001169 10.1371/journal.pmed.1001169
3. Murray, C. J. L.; Rosenfeld, L. C.; Lim, S. S.; Andrews, K. G.; Foreman, K. J.; Hqqaring, D.; Fullman, N.; Naghavi, M.; Lozano, R.; Lopez, A. D. Global malaria mortality between 1980 and 2010: a systematic analysis Lancet 2012, 379, 413-431
4. Gulland, A. Death toll from Malaria is double the WHO estimate, study finds Brit. Med. J. 2012, 344, 895
5. Thera, M. A.; Plowe, C. V. Vaccines for malaria: how close are we? Annu. Rev. Med. 2012, 63, 345-357
6. Nussenzweig, V.; Good, M. F.; Hill, A. V. S. Mixed results for a malaria vaccine Nature Med. 2011, 17, 1560-1561
7. Olliaro, P. L.; Boland, P. B. Clinical Public Health Implications of Antimalarial Drug Resistance. In Antimalarial Chemotherapy: Mechanisms of Action, Resistance, and New Directions in Drug Discovery; Rosenthal, P. J., Ed.; Humana Press: Totowa, NJ, 2001; pp 65-84.
8. Burgess, S. J.; Selzer, A.; Kelly, J. X.; Smilkstein, M. J.; Riscoe, M. K.; Peyton, D. H. A chloroquine-like molecule designed to reverse resistance in Plasmodium falciparum J. Med. Chem. 2006, 49, 5623-5625 (Pubitemid 44373193)
9. Guidelines for Treatment of Malaria; World Health Organization: Geneva, Switzerland, 2006.
10. Slack, R. D.; Jacobine, A. M.; Posner, G. H. Antimalarial peroxides: advances in drug discovery and design Med. Chem. Commun. 2012, 3, 281-297
11. Tilley, L.; Charman, S. A.; Vennerstrom, J. L. Semisynthetic Artemisinin and Synthetic Peroxide Antimalarials. RSC Drug Discovery Series; Neglected Diseases and Drug Discovery; Royal Society of Chemistry: London, 2012; Vol. 14, 33-64.
12. Wells, T. N. C. Natural products as starting points for future anti-malarial therapies: going back to our roots? Malaria J. 2011, 10, 1-12
13. Eastman, R. T.; Fidock, D. A. Artemisinin-based combination therapies: a vital tool in efforts to eliminate malaria Nat. Rev. Microbiol. 2009, 7, 864-874
14. Charman, S. A.; Arbe-Barnes, S; Bathurst, I. C.; Brun, R.; Campbell, M.; Charman, W. N.; Chiu, F. C. K.; Chollet, J.; Craft, J. C.; Creek, D. J.; Dong, Y.; Matile, H.; Maurer, M.; Morizzi, J.; Nguyen, T.; Papastogiannidis, P.; Scheurer, C.; Shackleford, D. M.; Sriraghavan, K.; Stingelin, L.; Tang, Y.; Urwyler, H.; Wang, X.; White, K. L.; Wittlin, S.; Zhou, L.; Vennerstrom, J. L. Synthetic ozonide drug candidate OZ439 offers new hope for a single-dose cure of uncomplicated malaria Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 4400-4405
15. O'Neill, P. M. The therapeutic potential of semi-synthetic artemisinin and synthetic endoperoxide antimalarial agents Expert Opin. Invest. Drugs 2005, 14, 1117-1128 (Pubitemid 41246167)
16. Yavo, W.; Faye, B.; Kuete, T.; Djohan, V.; Oga, S. A.; Kassi, R. R.; Diatta, M.; Ama, M. V.; Tine, R.; Ndiaye, J.-L.; Evi, J.-B.; Same-Ekobo, A.; Faye, O.; Koné, M. Multicentric assessment of the efficacy and tolerability of dihydroartemisinin-piperaquine compared to artemether- lumefantrine in the treatment of uncomplicated Plasmodium falciparum malaria in sub-Saharan Africa Malaria J. 2011, 10, 198-205
17. Macedo de Oliveira, A.; Chavez, J.; Ponce de Leon, G.; Durand, S.; Arrospide, N.; Roberts, J.; Cabezas, C.; Marquiño, W. Efficacy and effectiveness of mefloquine and artesunate combination therapy for uncomplicated Plasmodium falciparum malaria in the Peruvian Amazon Am. J. Trop. Med. Hyg. 2011, 85, 573-578
18. Sagara, I.; Diallo, A.; Kone, M.; Coulibaly, M.; Diawara, S. I.; Guindo, O.; Maiga, H.; Niambele, M. B.; Sissoko, M.; Dicko, A.; Djimde, A.; Doumbo, O. K. A randomized trial of artesunate-mefloquine versus artemether-lumefantrine for treatment of uncomplicated Plasmodium falciparum malaria in Mali Am. J. Trop. Med. Hyg. 2008, 79, 655-661
19. Rueangweerayut, R.; Phyo, A. P.; Uthaisin, C.; Poravuth, Y.; Binh, T. Q.; Tinto, H.; Pénali, L. K.; Valecha, N.; Tien, N. T.; Abdulla, S.; Borghini-Fuhrer, I.; Duparc, S.; Shin, C.-K.; Fleckenstein, L. Pyronaridine-artesunate versus mefloquine plus artesunate for malaria N. Engl. J. Med. 2012, 366, 1298-1309
20. Kurth, F.; Bélard, S.; Basra, A.; Ramharter, M. Pyronaridine-artesunate combination therapy for the treatment of malaria Curr. Opin. Infect. Dis. 2011, 24, 564-569
21. Sagara, I.; Diallo, A.; Kone, M.; Coulibaly, M.; Diawara, S. I.; Guindo, O.; Maiga, H.; Diambele, M. B.; Sissoko, M.; Dicko, A.; Djimde, A.; Doumbo, O. K. A randomized trial of aresunate-mefloquine versus artemether-lumefantrine for treatment of uncomplicated Plasmodium falciparum malaria in Mali Am. J. Trop. Med. Hyg. 2008, 79, 655-661
22. Cohen, J. L.; Yavuz, E.; Morris, A.; Arkedis, J.; Sabot, O. Do malaria patients adhere to over-the-counter artemisinin combination therapy for malaria? evidence from an intervention study in Uganda Malaria J. 2012, 11, 83-93
23. Lawford, H.; Zurovac, D.; O'Reilly, L.; Hoibak, S.; Cowley, A.; Munga, S.; Vulule, J.; Juma, E.; Snow, R. W; Allan, R. Adherence to prescribed artemisinin-based combination therapy in Garissa and Bunyala districts, Kenya Malaria J. 2011, 10, 281-288
24. O'Brien, C.; Philipp, H. P.; Passi, N.; Fidock, D. A. Recent clinical and molecular insights into emerging artemisinin resistance in Plasmodium falicaparum Curr. Opin. Infect. Dis. 2011, 24, 570-577
25. Ferrer, P.; Tripathi, A. K.; Clark, M. A.; Hand, C. C.; Rienhoff, H. Y., Jr.; Sullivan, D. J. Antimalarial iron chelator, FBS0701, shows asexual and gametocyte Plasmodium falciparum activity and single oral dose cure in murine malaria model PLoS One 2012, 7, e37171
26. Tun, T.; Tint, H. S.; Lin, K.; Kyaw, T. T.; Myint, M. K.; Khaing, W.; Tun, Z W. Efficacy of oral single dose therapy with artemisinin-naphthoquine phosphate in uncomplicated falciparum malaria Acta Tropica 2009, 111, 275-278
27. Younis, Y.; Douelle, F.; Feng, T.-S.; González Cabrera, D.; Le Manach, C.; Nchinda, A. T.; Duffy, S.; White, K. L.; Shackleford, D. M.; Morizzi, J.; Mannila, J.; Katneni, K.; Bhamidipati, R.; Zabiulla, K. M.; Joseph, J. T.; Bashyam, S.; Waterson, D.; Witty, M. J.; Hardick, D.; Wittlin, S.; Avery, V.; Charman, S. A.; Chibale, K. 3,5-Diaryl-2-aminopyridines as a novel class of orally active antimalarials demonstrating single dose cure in mice and clinical candidate potential J. Med. Chem. 2012, 55, 3479-3487
28. Benjamin, J.; Morre, B.; Lee, S. T.; Senn, M.; Griffin, S.; Lautu, D.; Salman, S.; Siba, P.; Mueller, I.; Davis, T. M. E. Artemisinin-naphthoquine combination therapy for uncomplicated pediatric malaria: a tolerability, safety, and preliminary efficacy study Antimicrob. Agents Chemother. 2012, 56, 2465-2471
29. Batty, K. T.; Salman, S.; Moore, B. R.; Benjamin, J.; Lee, S. T.; Page-Sharp, M.; Pitus, N.; Ilett, K. F.; Mueller, I.; Hombhanje, F. W.; Siba, P.; Davis, T. M. E. Artemisinin-napthoquine combination therapy for uncomplicated pediatric malaria: a pharmacokinetic study Antimicrob. Agents Chemother. 2012, 56, 2472-2484
30. Slack, R. D.; Mott, B. T.; Woodard, L. E.; Tripathi, A.; Sullivan, D.; Nenortas, E; Girdwood, S. C. T.; Shapiro, T. A.; Posner, G. H. Malaria-infected mice are completely cured by one 6 mg/kg oral dose of new monomeric trioxane sulfide combined with mefloquine J. Med. Chem. 2012, 55, 291-296
31. Moon, D. K.; Tripathi, A.; Sullivan, D.; Siegler, M. A.; Parkin, S.; Posner, G. H. A single, low, oral dose of a 5-carbon-linked trioxane dimer orthoester plus mefloquine cures malaria-infected mice Bioorg. Med. Chem. Lett. 2011, 21, 2773-2775
32. García-álvares, I.; Groult, H.; Casas, J.; Barreda-Manso, M. A.; Yanguas-Casás, N.; Nieto-Sampedro, M.; Romero-Ramírez, L.; Fernández-Mayoralas, A. Synthesis of antimitotic thioglycosides: in vitro and in vivo evaluation of their anticancer activity J. Med. Chem. 2011, 54, 6949-6955
33. Fanton, J.; Camps, F; Castillo, J. A.; Guérard-Hélaine, C.; Lemaire, M.; Charmantray, F.; Hecquet, L. Enzymatic and organocatalyzed asymmetric aldolization reactions for the synthesis of thiosugar scaffolds Eur. J. Org. Chem. 2012, 203-210
34. Hibino, H.; Nishiuchi, Y. 4-Methoxybenzyloxymethyl group, a racemization-resistant protecting group for cysteine in Fmoc solid phase peptide synthesis Org. Lett. 2012, 14, 1926-1929
35. Posner, G. H.; Cumming, J. N.; Woo, S.-H.; Ploypradith, P.; Xie, S.; Shapiro, T. A. Orally active antimalarial 3-substituted trioxanes: new synthetic methodology and biological evaluation J. Med. Chem. 1998, 41, 940-951 (Pubitemid 28146249)
36. Chadwick, J.; Mercer, A. E.; Park, B. K.; Cosstick, R.; O'Neill, P. M. Synthesis and biological evaluation of extraordinarily potent C-10 carba artemisinin dimers against P. falciparum malaria parasites and HL-60 cancer cells Bioorg. Med. Chem. 2009, 17, 1325-1338
37. Venugopalan, B.; Karnik, P. J.; Bapat, C. P.; Chatterjee, D. K.; Iver, N.; Lepcha, D. Antimalarial activity of new ether and thioethers of dihydroartemisinin Eur. J. Med. Chem. 1995, 30, 697-706
38. Lee, S.; Oh, S. A simple synthesis of C-10 substituted deoxoartemisinin and 9- epi -deoxoartemisinin with various organozinc reagents Tetrahedron Lett. 2002, 43, 2891-2894 (Pubitemid 34286481)
39. Oh, S.; Jeong, I. H.; Shin, W.-S.; Lee, S. Growth inhibition activity of thioacetal artemisinin derivatives against human umbilical vein endothelial cells Bioorg. Med. Chem. Lett. 2003, 13, 3665-3668 (Pubitemid 37206482)
40. Lee, S.; Oh, S.; Park, G.-M.; Kim, T.-S.; Ryu, J.-S.; Choi, H.-K. Antimalarial activity of thiophenyl- and benzenesulfonyl-artemisinin Korean J. Parasitol. 2005, 43, 123-126
41. Oh, S.; Jeong, I. H.; Ahn, C. M.; Shin, W.-S.; Lee, S. Synthesis and antiangiogenic activity of thioacetal artemisinin derivatives Bioorg. Med. Chem. 2004, 12, 3783-3790 (Pubitemid 38798239)
42. Satchell, D. P. N.; Satchell, R. S. Mechanisms of hydrolysis of thioacetals Chem. Soc. Rev. 1990, 19, 55-81
43. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4 th ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2007; pp 501-503.
44. Ma, J.; Katz, E.; Kyle, D. E.; Ziffer, H. Syntheses and antimalarial activities of 10-substituted deoxoartemisinins J. Med. Chem. 2000, 43, 4228-4232
45. Klayman, D. L. Qinghaosu (artemisinin): an antimalarial drug from China Science 1985, 228, 1049-1055 (Pubitemid 15227365)
46. Rautio, J.; Kumpulainen, H.; Heimbach, T.; Oliyai, R.; Oh, D.; Järvinen, T.; Savolainen, J. Prodrugs: design and clinical applications Nat. Rev. Drug Discovery 2008, 7, 255-270 (Pubitemid 351324639)
47. Ueda, Y.; Wong, H.; Matiskella, J. D.; Mikkilineni, A. B.; Farina, V.; Fairchild, C.; Rose, W. C.; Mamber, S. W.; Long, B. H.; Kerns, E. H.; Casazza, A. M.; Vyas, D. M. Synthesis and antitumor evaluation of 2′- oxycarbonylpaclitaxels (paclitaxel-2′-carbonates) Bioorg. Med. Chem. Lett. 1994, 4, 1861-1864 (Pubitemid 24248792)
48. Nicolaou, K. C.; Riemer, C.; Kerr, M. A.; Rideout, D.; Wrasidlo, W. Design, synthesis and biological activity of protaxols Nature 1993, 364, 464-466 (Pubitemid 23263221)
49. Skinner-Adams, T. S.; Davis, T. M.; Manning, L. S.; Johnston, W. A. The efficacy of benzimidazole drugs against Plasmodium falciparum in vitro Trans. R. Soc. Trop. Med. Hyg. 1997, 91, 580-594
50. Berger, O.; Kaniti, A.; Tran van Ba, C.; Vial, H.; Ward, S. A.; Biagini, G. A.; Bray, P. G.; O'Neill, P. M. Synthesis and antimalarial activities of a diverse set of triazole-containing furamidine analogues ChemMedChem 2011, 6, 2094-2108
51. Saify, Z. S.; Azim, M. K.; Ahmad, W.; Nisa, M.; Goldberg, D. E.; Hussain, S. A.; Akhtar, S.; Akram, A.; Arayne, A.; Oksman, A.; Khan, I. A. New benzimidazole derivatives as antiplasmodial agents and plasmepsin inhibitors: synthesis and analysis of structure-activity relationships Bioorg. Med. Chem. Lett. 2012, 22, 1282-1286
52. Taudon, N.; Margout, D.; Wein, S.; Calas, M.; Vial, H. J.; Bressole, F. M. M. Quantitative analysis of a bis-thiazolium antimalarial compound, SAR97276, in mouse plasma and red blood cell samples, using liquid chromatography mass spectrometry J. Pharm. Biomed. Anal. 2008, 46, 148-156 (Pubitemid 350216341)
53. Ban, K.; Duffy, S.; Khakham, Y.; Avery, V. M.; Hughes, A.; Montagnat, O.; Katneni, K.; Ryan, E.; Baell, J. B. 3-Alkyl-1,2,4-triazine dimers with potent antimalarial activity Bioorg. Med. Chem. Lett. 2010, 20, 6024-6029
54. Woodard, L. E.; Chang, W.; Chen, X.; Liu, J. O.; Shapiro, T. A.; Posner, G. H. Malaria-infected mice live until at least day 30 after a new monomeric trioxane combined with mefloquine are administered together in a single low oral dose J. Med. Chem. 2009, 52, 7458-7462
55. Jung, M.; Lee, S. Stability of acetal and non acetal-type analogs of artemisinin in simulated stomach acid Bioorg. Med. Chem. Lett. 1998, 8, 1003-1006 (Pubitemid 28216273)