Novel arylimidamides for treatment of visceral leishmaniasis

Antimicrobial Agents and Chemotherapy

Volumn 54, Issue 6, 2010, Pages 2507-2516

  Wang, Michael Zhuo ^a   Zhu, Xiaohua ^b   Srivastava, Anuradha ^c   Liu, Qiang ^d   Sweat, J Mark ^c   Pandharkar, Trupti ^b   Stephens, Chad E ^e   Riccio, Ed ^f   Parman, Toufan ^f   Munde, Manoj ^g   Mandal, Swati ^h   Madhubala, Rentala ^h   Tidwell, Richard R ^a,d   Wilson, W David ^g   Boykin, David W ^g   Hall, James Edwin ^d   Kyle, Dennis E ^c   Werbovetz, Karl A ^b  

^a UNC Hamner Institute for Drug Safety Sciences   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c UNIVERSITY OF SOUTH FLORIDA   (United States)

^d UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^e AUGUSTA STATE UNIVERSITY   (United States)

^f SRI INTERNATIONAL   (United States)

^g GEORGIA STATE UNIVERSITY   (United States)

^h JAWAHARLAL NEHRU UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 BIS[2 (2 PROPOXY) 4 (2 PYRIDYLIMINO)AMINOPHENYL]FURAN; 2,5 BIS[2 ETHOXY 4 (2 PYRIDYLIMINO)AMINOPHENYL]FURAN; ANTIPROTOZOAL AGENT; DB745; DB766; IMIDAMIDE DERIVATIVE; MILTEFOSINE; UNCLASSIFIED DRUG;

ADOLESCENT; AMASTIGOTE; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIPROTOZOAL ACTIVITY; ARTICLE; BONE MARROW; CONTROLLED STUDY; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG DISTRIBUTION; DRUG DOSE ESCALATION; DRUG HALF LIFE; DRUG TISSUE LEVEL; FEMALE; HAMSTER; LEISHMANIA; LEISHMANIA DONOVANI; LEISHMANIA MAJOR; LEISHMANIASIS; LIVER TOXICITY; MALE; MOUSE; MUTAGENICITY; NONHUMAN; PARASITEMIA; PRIORITY JOURNAL; SPLEEN; VISCERAL LEISHMANIASIS;

AMIDINES; ANIMALS; ANTIPROTOZOAL AGENTS; BIOLOGICAL AVAILABILITY; CRICETINAE; DISEASE MODELS, ANIMAL; DRUG DISCOVERY; FEMALE; FURANS; HUMANS; LEISHMANIA DONOVANI; LEISHMANIA MAJOR; LEISHMANIA MEXICANA; LEISHMANIASIS, VISCERAL; LIVER; MESOCRICETUS; MICE; MICE, INBRED BALB C; MICROSOMES, LIVER; MUTAGENICITY TESTS; PARASITEMIA; PARASITIC SENSITIVITY TESTS; SPLEEN; TISSUE DISTRIBUTION;

EID: 77952612936     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00250-10     Document Type: Article

References (36)

1. Ames, B. N., J. McCann, and E. Yamasaki. 1975. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test. Mutat. Res. 31:347-364.
2. Antoine, J. C., E. Prina, C. Jouanne, and P. Bongrand. 1990. Parasitophorous vacuoles of Leishmania amazonensis-infected macrophages maintain an acidic pH. Infect. Immun. 58:779-787.
3. Avdeef, A. 2001. Physicochemical profiling (solubility, permeability and charge state). Curr. Top. Med. Chem. 1:277-351.
4. Basselin, M., H. Denise, G. H. Coombs, and M. P. Barrett. 2002. Resistance to pentamidine in Leishmania mexicana involves exclusion of the drug from the mitochondrion. Antimicrob. Agents Chemother. 46:3731-3738.
5. + pump in plasma-membrane vesicles from Trypanosoma brucei; selective inhibition by pentamidine. Biochem. J. 296(Pt. 3):759-763.
6. Chappuis, F., S. Sundar, A. Hailu, H. Ghalib, S. Rijal, R. W. Peeling, J. Alvar, and M. Boelaert. 2007. Visceral leishmaniasis: what are the needs for diagnosis, treatment and control? Nat. Rev. Microbiol. 5:873-882.
7. Croft, S. L., and R. P. Brazil. 1982. Effect of pentamidine isethionate on the ultrastructure and morphology of Leishmania mexicana amazonensis in vitro. Ann. Trop. Med. Parasitol. 76:37-43.
8. Delfin, D. A., R. E. Morgan, X. Zhu, and K. A. Werbovetz. 2009. Redox-active dinitrodiphenylthioethers against Leishmania: synthesis, structure-activity relationships and mechanism of action studies. Bioorg. Med. Chem. 17:820-829.
9. Glaser, T. A., J. E. Baatz, G. P. Kreishman, and A. J. Mukkada. 1988. pH homeostasis in Leishmania donovani amastigotes and promastigotes. Proc. Natl. Acad. Sci. U. S. A. 85:7602-7606.
10. Kumar, D., A. Kulshrestha, R. Singh, and P. Salotra. 2009. In vitro susceptibility of field Isolates of Leishmania donovani to miltefosine and amphotericin B: correlation with sodium antimony gluconate susceptibility and implications for treatment in areas of endemicity. Antimicrob. Agents Chemother. 53:835-838.
11. Mandal, S., M. Maharjan, S. Ganguly, M. Chatterjee, S. Singh, F. Buckner, and R. Madhubala. 2009. High-throughput screening of amastigotes of Leishmania donovani clinical isolates against drugs using a colorimetric β-lactamase assay. Indian J. Exp. Biol. 47:475-479.
12. Mandal, S., M. Maharjan, S. Singh, M. Chatterjee, and R. Madhubala. 2010. Assessing aquaglyceroporin gene status and expression profile in antimony-susceptible and -resistant clinical isolates of Leishmania donovani from India. J. Antimicrob. Chemother. 65:496-507.
13. Mathis, A. M., A. S. Bridges, M. A. Ismail, A. Kumar, I. Francesconi, M. Anbazhagan, Q. Hu, F. A. Tanious, T. Wenzler, J. Saulter, W. D. Wilson, R. Brun, D. W. Boykin, R. R. Tidwell, and J. E. Hall. 2007. Diphenyl furans and aza analogs: effects of structural modification on in vitro activity, DNA binding, and accumulation and distribution in trypanosomes. Antimicrob. Agents Chemother. 51:2801-2810.
14. Melby, P. C., B. Chandrasekar, W. Zhao, and J. E. Coe. 2001. The hamster as a model of human visceral leishmaniasis: progressive disease and impaired generation of nitric oxide in the face of a prominent Th1-like cytokine response. J. Immunol. 166:1912-1920.
15. Melby, P. C., Y. Z. Yang, J. Cheng, and W. Zhao. 1998. Regional differences in the cellular immune response to experimental cutaneous or visceral infection with Leishmania donovani. Infect. Immun. 66:18-27.
16. Moreno, S. N. 1996. Pentamidine is an uncoupler of oxidative phosphorylation in rat liver mitochondria. Arch. Biochem. Biophys. 326:15-20.
17. Mortelmans, K., and E. Zeiger. 2000. The Ames Salmonella/microsome mutagenicity assay. Mutat. Res. 455:29-60.
18. Olliaro, P. L., P. J. Guerin, S. Gerstl, A. A. Haaskjold, J. A. Rottingen, and S. Sundar. 2005. Treatment options for visceral leishmaniasis: a systematic review of clinical studies done in India, 1980-2004. Lancet Infect. Dis. 5:763-774.
19. Pacheco, M. G., C. F. da Silva, E. M. de Souza, M. M. Batista, P. B. da Silva, A. Kumar, C. E. Stephens, D. W. Boykin, and N. Soeiro Mde. 2009. Trypanosoma cruzi: activity of heterocyclic cationic molecules in vitro. Exp. Parasitol. 123:73-80.
20. Paul, M., R. Durand, Y. Boulard, T. Fusai, C. Fernandez, D. Rivollet, M. Deniau, and A. Astier. 1998. Physicochemical characteristics of pentamidine-loaded polymethacrylate nanoparticles: implication in the intracellular drug release in Leishmania major infected mice. J. Drug Target. 5:481-490. (Pubitemid 28499682)
21. Pearson, R. D., and A. Q. Sousa. 1996. Clinical spectrum of leishmaniasis. Clin. Infect. Dis. 22:1-13.
22. Rosypal, A. C., J. E. Hall, S. Bakunova, D. A. Patrick, S. Bakunov, C. E. Stephens, A. Kumar, D. W. Boykin, and R. R. Tidwell. 2007. In vitro activity of dicationic compounds against a North American foxhound isolate of Leishmania infantum. Vet. Parasitol. 145:207-216.
23. Rosypal, A. C., K. A. Werbovetz, M. Salem, C. E. Stephens, A. Kumar, D. W. Boykin, J. E. Hall, and R. R. Tidwell. 2008. Inhibition by dications of in vitro growth of Leishmania major and Leishmania tropica: causative agents of old world cutaneous leishmaniasis. J. Parasitol. 94:743-749.
24. Silva, C. F., M. B. Meuser, E. M. De Souza, M. N. Meirelles, C. E. Stephens, P. Som, D. W. Boykin, and M. N. Soeiro. 2007. Cellular effects of reversed amidines on Trypanosoma cruzi. Antimicrob. Agents Chemother. 51:3803-3809.
25. Stauber, L. A., E. M. Franchino, and J. Grun. 1958. An eight-day method for screening compounds against Leishmania donovani in the golden hamster. J. Eukaryot. Microbiol. 5:269-273.
26. Stephens, C. E., R. Brun, M. M. Salem, K. A. Werbovetz, F. Tanious, W. D. Wilson, and D. W. Boykin. 2003. The activity of diguanidino and "reversed" diamidino 2,5-diarylfurans versus Trypanosoma cruzi and Leishmania donovani. Bioorg. Med. Chem. Lett. 13:2065-2069.
27. Stephens, C. E., F. Tanious, S. Kim, W. D. Wilson, W. A. Schell, J. R. Perfect, S. G. Franzblau, and D. W. Boykin. 2001. Diguanidino and "reversed" diamidino 2,5-diarylfurans as antimicrobial agents. J. Med. Chem. 44:1741-1748.
28. Sturk, L. M., J. L. Brock, C. R. Bagnell, J. E. Hall, and R. R. Tidwell. 2004. Distribution and quantitation of the anti-trypanosomal diamidine 2,5-bis(4-amidinophenyl)furan (DB75) and its N-methoxy prodrug DB289 in murine brain tissue. Acta Trop. 91:131-143.
29. Sundar, S., T. K. Jha, C. P. Thakur, J. Engel, H. Sindermann, C. Fischer, K. Junge, A. Bryceson, and J. Berman. 2002. Oral miltefosine for Indian visceral leishmaniasis. N. Engl. J. Med. 347:1739-1746.
30. Sundar, S., H. Mehta, A. V. Suresh, S. P. Singh, M. Rai, and H. W. Murray. 2004. Amphotericin B treatment for Indian visceral leishmaniasis: conventional versus lipid formulations. Clin. Infect. Dis. 38:377-383.
31. Troutman, M. D., and D. R. Thakker. 2003. Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm. Res. 20:1210-1224.
32. +, pentamidine and WR-6026 on mitochondrial membrane potential in situ. Biochem. J. 284(Pt. 2):463-467.
33. Wang, M. Z., J. Y. Saulter, E. Usuki, Y. L. Cheung, M. Hall, A. S. Bridges, G. Loewen, O. T. Parkinson, C. E. Stephens, J. L. Allen, D. C. Zeldin, D. W. Boykin, R. R. Tidwell, A. Parkinson, M. F. Paine, and J. E. Hall. 2006. CYP4F enzymes are the major enzymes in human liver microsomes that catalyze the O-demethylation of the antiparasitic prodrug DB289 [2,5-bis(4-amidinophenyl) furan-bis-O-methylamidoxime]. Drug Metab. Dispos. 34:1985-1994.
34. Werbovetz, K. 2006. Diamidines as antitrypanosomal, antileishmanial and antimalarial agents. Curr. Opin. Invest. Drugs 7:147-157.
35. WHO. Leishmaniasis: the global trend. WHO, Geneva, Switzerland. http: //www.who.int/neglected-diseases/integrated-media-leishmaniasis/en/index.html.
36. Yeates, C. 2002. Sitamaquine (GlaxoSmithKline/Walter Reed Army Institute). Curr. Opin. Invest. Drugs 3:1446-1452.