Thiazole, oxadiazole, and carboxamide derivatives of artemisinin are highly selective and potent inhibitors of toxoplasma gondii

Journal of Medicinal Chemistry

Volumn 53, Issue 9, 2010, Pages 3594-3601

  Hencken, Christopher P ^a   Jones Brando, Lorraine ^b   Bordón, Claudia ^b   Stohler, Remo ^a   Mott, Bryan T ^a   Yolken, Robert ^b   Posner, Gary H ^a,c   Woodard, Lauren E ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

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

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ARTEMETHER; ARTEMISININ; ARTEMISININ DERIVATIVE; DEHYDROARTEMISININ TRIOXANE DERIVATIVE; OXADIAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; TRIMETHOPRIM; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; HOST CELL; IC 50; IN VITRO STUDY; LYSIS; MICROBIAL GROWTH; MOLECULAR PROBE; NONHUMAN; TOXOPLASMA GONDII;

AMIDES; ANIMALS; ANTIPARASITIC AGENTS; ANTIPROTOZOAL AGENTS; ARTEMISININS; CELL LINE; HUMANS; OXADIAZOLES; PARASITIC SENSITIVITY TESTS; SUBSTRATE SPECIFICITY; THIAZOLES; TOXOPLASMA;

EID: 77952065567     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901857d     Document Type: Article

References (38)

1. Ferguson, D. J. P. Dubremetz, J. F. The Ultrastructure of Toxoplasma Gondii. In Toxoplasma gondii; 1st ed.; Weiss, L., Kim, K., Eds.; Academic Press: London, 2007; pp 19 -48.
2. Bowie, W. R.; King, A. S.; Werker, D. H.; Isaac-Renton, J. L.; Bell, A.; Eng, S. B.; Marion, S. A. Outbreak of Toxoplasmosis Associated with Municipal Drinking Water Lancet 1997, 350, 173-177
3. Jackson, M. H.; Hutchison, W. M. The Prevalence and Source of Toxoplasma Infection in the Environment Adv. Parasitol. 1989, 28, 55-105
4. Montoya, J. G.; Liesenfeld, O. Toxoplasmosis Lancet 2004, 363, 1965-1976
5. Khan, A.; Jordan, C.; Muccioli, C.; Vallochi, A.; Rizzo, L.; Belfort, R., Jr.; Vitor, R. W. A.; Silveira, C.; Sibley, L. D. Genetic Divergence of Toxoplasma gondii Strains Associated with Ocular Toxoplasmosis, Brazil Emerging Infect. Dis. 2006, 12, 942-949
6. Toxoplasmosis: Epidemiology and Risk Factors; http://www.cdc.gov/ toxoplasmosis/epi.html (accessed Feb 12, 2010).
7. Yolken, R. H.; Bachmann, S.; Rouslanova, I.; Lillehoj, E.; Ford, G.; Torrey, E. F.; Schroeder, J. Antibodies to Toxoplasma gondii in Individuals with First-Episode Schizophrenia Clin. Infect. Dis. 2001, 32, 842-844
8. World Health Organization Fact Sheet No. 297: Cancer; http://www.who.int/mediacentre/factsheets/fs297/en/index.html (accessed Feb 12, 2010).
9. World Health Organization Global Summary of AIDS Epidemic; http://www.who.int/hiv/data/2009-global-summary.gif (accessed Feb 12, 2010).
10. Mayo Foundation for Medical Education and Research. Toxoplasmosis; http://www.mayoclinic.com/print/toxoplasmosis/DS00510/DSECTION=all&METHOD= print (accessed Feb 12, 2010).
11. Vercesi, A. E.; Rodrigues, C. O.; Uyemura, S. A.; Li, Z.; Moreno, S. N. J. Repiration and Oxidative Phosphorylation in the Apicomplexan Parasite Toxoplasma gondii J. Biol. Chem. 1998, 273, 31,040-31,047
12. Saudi, M. N. S.; Gaafar, M. R.; El-Azzouni, M. Z.; Ibrahim, M. A.; Eissa, M. M. Synthesis and Evaluation of Some Pyrimidine Analogs Against Toxoplasmosis Med. Chem. Res. 2008, 17, 541-563
13. Mui, E. J.; Schiehser, G. A.; Milhous, W. K.; Hsu, H.; Roberts, C. W.; Kirisits, M.; Muench, S.; Rice, D.; Dubey, J. P.; Fowble, J. W.; Rathod, P. K.; Queener, S. F.; Liu, S. R.; Jacobus, D. P.; McLeod, R. Novel Triazine JPC-2067-B Inhibits Toxoplasma gondii in Vitro and in Vivo PLoS Neglected Trop. Dis. 2008, 2, 1-13
14. Gangjee, A.; Adair, O. O.; Pagley, M.; Queener, S. F. N9-Substituted 2,4-Diaminoquinazolines: Synthesis and Biological Evaluation of Lipophilic Inhibitors of Pneumocystis carinii and Toxoplasma gondii Dihydrofolate Reductase J. Med. Chem. 2008, 51, 6195-6200
15. Peuchmaur, M.; Sadani, N.; Botté, C.; Maréchal, E.; Vial, H.; Wong, Y. Enhanced Antimalarial Activity of Novel Synthetic Aculeatin Derivatives J. Med. Chem. 2008, 51, 4870-4873
16. Krivogorsky, B.; Grundt, P.; Yolken, R.; Jones-Brando, L. Inhibition of Toxoplasma gondii by Indirubin and Tryptanthrin Analogs Antimicrob. Agents Chemother. 2008, 52, 4466-4469
17. Strobl, J. S.; Seibert, C. W.; Li, Y.; Nagarkatti, R.; Mitchell, S. M.; Rosypal, A. C.; Rathore, D.; Lindsay, D. S. Inhibiton of Toxoplasma gondii and Plasmodium falciparum Infections In Vitro by NSC3852, A Redox Active Antiproliferative and Tumor Cell Differentiation Agent J. Parasitol. 2009, 95, 215-223
18. Walton, J. G. A.; Patterson, S.; Liu, G.; Haraldsen, J. D.; Hollick, J. J.; SlawA. M. Z.; Ward, G. E.; Westwood, N. J. Synthesis and Biological Evaluation of Functionalised Tetrahydro-β-carboline Analogues as Inhibitors of Toxoplasma gondii Invasion Org. Biomol. Chem. 2009, 7, 3049-3060
19. Chimenti, F.; Bizzarri, B.; Bolasco, A.; Secci, D.; Chimenti, P.; Carradori, S.; Granese, A.; Rivanera, D.; Frishberg, N.; Bordón, C.; Jones-Brando, L. Synthesis and Evaluation of 4-Acyl-2-thiazolylhydrazone Derivatives for Anti- Toxoplasma Efficacy In Vitro J. Med. Chem. 2009, 52, 4574-4577
20. Hencken, C. P.; Kalinda, A. S.; D'Angelo, J. G. The Anti-infective and Anti-cancer Properties of Artemisinin and its Derivatives Ann. Rev. Med. Chem. 2009, 44, 359-378
21. Krishna, S.; Bustamante, L.; Haynes, R. K.; Staines, H. M. Artemisinins: Their Growing Importance in Medicine Trends Pharmacol. Sci. 2008, 29, 520-527
22. O'Neill, P. M; Rawe, S. L.; Borstnik, K.; Miller, A; Ward, S. A.; Bray, P. G.; Davies, J.; Oh, C. H.; Posner, G. H. Enantiomeric 1,2,4-Trioxanes Display Equivalent in Vitro Antimalarial Activity Versus Plasmodium falciparum Malaria Parasites: Implications for the Molecular Mechanism of Action of the Artemisinins ChemBioChem 2005, 6, 2048-2054
23. O'Neill, P. M.; Posner, G. H. A Medicinal Chemistry Perspective on Artemisinin and Related Endoperoxides J. Med. Chem. 2004, 47, 2945-2964
24. D'Angelo, J. G.; Bordón, C.; Posner, G. H.; Yolken, R. H.; Jones-Brando, L. Artemisinin Derivatives Inhibit Toxoplasma gondii in Vitro at Multiple Steps in the Lytic Cycle J. Antimicrob. Chem. 2009, 63, 146-150
25. Nagamune, K.; Beatty, W. L.; Sibley, D. L. Artemisinin Induces Calcium-dependent Protein Secretion in the Protozoan Parasite Toxoplasma gondii Eukaryotic Cell 2007, 6, 2147-2156
26. Kawase, O.; Nishikawa, Y.; Bannai, H.; Zhang, H.; Zhang, G.; JS.; Lee, E.; Xuan, X. Proteomic Analysis of Calcium-Dependent Secretion in Toxoplasma gondii Proteomics 2007, 7, 3718-3725
27. Nagamune, K.; Moreno, S. N. J.; Sibley, D. L. Artemisinin-Resistant Mutants of Toxoplasma gondii Have Altered Calcium Homeostasis Antimicrob. Agents Chemother. 2007, 51, 3816-3823
28. 2+-dependent ATPase Activity in Toxoplasma gondii Cell Struct. Funct. 2001, 26, 49-60
29. Karegoudar, P.; Karthikeyan, M. S.; Prasad, D. J.; Mahalinga, M.; Holla, B. S.; Kumari, N. S. Synthesis of Some Novel 2,4-Disubstituted Thiazoles as Possible Antimicrobial Agents Eur. J. Med. Chem. 2008, 43, 261-267
30. Hemphill, A.; Mueller, J.; Esposito, M. Nitazoxanide, A Broad Spectrum Thiazolide Anti-infective Agent for the Treatment of Gastrointestinal Infections Expert Opin. Pharmacother. 2006, 7, 953-964
31. Karade, H. N.; Acharya, B. N.; Sathe, M.; Kaushik, M. P. Design, Synthesis and Antimalarial Evaluation of Thiazole-Derived Amino Acids Med. Chem. Res. 2008, 17, 19-29
32. Delbecq, F.; Cordonnier, G.; Pommery, N.; Barbry, D.; Henichart, J. New Heteroarylbenzenesulphonamides as Matrix Metalloproteinase Inhibitors Bioorg. Med. Chem. Lett. 2004, 14, 1119-1121
33. Brando, L. V.; Posner, G. H.; D'Angelo, J. G.; Yolken, R. H.; Hencken, C. P.; Woodard, L. Artemisinin derivatives. PCT Int. Appl. WO 2008127381, 2008.
34. Hamzé, A.; Hernandez, J.; Fulcrand, P.; Martinez, J. Synthesis of Various 3-Substituted 1,2,4-Oxadiazole-Containing Chiral β3 and α-Amino Acids from Fmoc-Protected Aspartic Acid J. Org. Chem. 2003, 68, 7316-7321
35. Gangloff, A. R.; Litvak, J.; Shelton, E. J.; Sperandio, D.; Wang, V. R.; Rice, K. D. Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst Tetrahedron Lett. 2001, 42, 1441-1443
36. Huynh, M.-H.; Rabenau, K. E.; Harper, J. M.; Beatty, W. L.; Sibley, L. D.; Carruthers, V. B. Rapid invasion of host cells by Toxoplasma requires secretion of the MIC2-M2AP adhesive protein complex EMBO J. 2003, 22, 2082-2090
37. Bordón, C.; Hencken, C. P.; Posner, G. H.; Yolken, R. H.; Jones-Brando, L. Unpublished results.
38. Silverman, J. A.; Hayes, M. L.; Luft, B. J.; Joiner, K. A. Characterization of anti- Toxoplasma activity of SDZ 215-918, a cyclosporin derivative lacking immunosuppressive and peptidyl-prolyl-isomerase-inhibiting activity: possible role of a P glycoprotein in Toxoplasma physiology Antimicrob. Agents Chemother. 1997, 41, 1859-1866