Alterations to the structure of Leishmania major induced by N-arylisoquinolines correlate with compound accumulation and disposition

Journal of Medical Microbiology

Volumn 59, Issue 1, 2010, Pages 69-75

  Ponte Sucre, Alicia ^a,b,c   Gulder, Tanja ^a,d   Gulder, Tobias A M ^a,e   Vollmers, Gerina ^a   Bringmann, Gerhard ^a   Moll, Heidrun ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

^c Universidad Central de Venezuela ^*  (United States)

^d SCRIPPS RESEARCH INSTITUTE   (United States)

^e UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; SODIUM CHLORIDE;

ANIMAL EXPERIMENT; ARTICLE; AUTOFLUORESCENCE; CELL DEATH; CONTROLLED STUDY; CORRELATION ANALYSIS; CYTOLYSIS; INTRACELLULAR SPACE; LEISHMANIA MAJOR; MORPHOLOGY; MOUSE; NONHUMAN; PRIORITY JOURNAL; ULTRASTRUCTURE ANALYSIS AND ELECTRON MICROSCOPY;

ISOQUINOLINES; LEISHMANIA MAJOR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 73649110579     PISSN: 00222615     EISSN: None     Source Type: Journal    
DOI: 10.1099/jmm.0.014241-0     Document Type: Article

References (33)

1. Bandyopadhyay, P., Ghosh, D. K., De, A., Ghosh, K. N., Chaudhuri, P. P., Das, P. & Bhattacharya, A. (1991). Metacyclogenesis of Leishmania spp: species-specific in vitro transformation, complement resistance, and cell surface carbohydrate and protein profiles. J Parasitol 77, 411-446.
2. Bera, A., Singh, S., Nagaraj, R. & Vaidya, T. (2003). Induction of autophagic cell death in Leishmania donovani by antimicrobial peptides. Mol Biochem Parasitol 127, 23-35.
3. Berger, B. J., Fairlamb, A. H., Meiering, S. K. & Schmidt, H. (1993). Cytochrome P450 in trypanosomatids. Biochem Pharmacol 46, 149-157.
4. Bringmann, G. & Pokorny, F. (1995). The naphthylisoquinoline alkaloids. In The Alkaloids, vol. 46, pp. 127-271. Edited by G. A. Cordell. New York: Academic Press.
5. Bringmann, G., François, G., Aké Assi, L. & Schlauer, J. (1998). The alkaloids of Triphyophyllum peltatum (Dioncophyllaceae). Chimia (Aarau) 52, 18-28.
6. Bringmann, G., Hamm, A., Günther, C., Michel, M., Brun, R. & Mudogo, V. (2000). Ancistroealaines A and B, two new bioactive naphthylisoquinolines, and related naphthoic acids from Ancistrocladus ealaensis. J Nat Prod 63, 1465-1470.
7. Bringmann, G., Dreyer, M., Faber, J. H., Dalsgaard, P. W., Staerk, D., Jaroszewski, J. W., Ndangalasi, H., Mbago, F., Brun, R. & other authors (2003a). Ancistrotanzanine A, the first 5,3′-coupled naphthylisoquinoline alkaloid, and two further, 5,8′-linked related compounds from the newly described species Ancistrocladus tanzaniensis. J Nat Prod 66, 1159-1165.
8. Bringmann, G., Hoerr, V., Holzgrabe, U. & Stich, A. (2003b). Antitrypanosomal naphthylisoquinoline alkaloids and related compounds. Pharmazie 58, 343-346.
9. Bringmann, G., Kajahn, I., Pedersen, S. E. H., Faber, J. H., Reichert, M., Gulder, T., Brun, R., Christensen, S. B., Ponte-Sucre, A. & other authors (2006). Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species. J Org Chem 71, 9348-9356.
10. Chappuis, F., Sundar, S., Hailu, A., Ghalib, H., Rijal, S., Peeling, R. W., Alvar, J. & Boelaert, M. (2007). Visceral leishmaniasis: what are the needs for diagnosis, treatment and control? Nat Rev Microbiol 5, 873-882.
11. Croft, S. L. (2008). Kinetoplastida: new therapeutic strategies. Parasite 15, 522-527.
12. Croft, S. L., Seifert, K. & Yardley, V. (2006). Current scenario of drug development for leishmaniasis. Indian J Med Res 123, 399-410.
13. Davis, A. J., Murray, H. W. & Handman, E. (2004). Drugs against leishmaniasis: a synergy of technology and partnerships. Trends Parasitol 20, 73-76.
14. Dodge, M. A., Waller, R. F., Chow, L. M., Zaman, M. M., Cotton, L. M., McConville, M. J. & Wirth, D. F. (2004). Localization and activity of multidrug resistance protein 1 in the secretory pathway of Leishmania parasites. Mol Microbiol 51, 1563-1575.
15. François, G., Timperman, G., Holenz, J., Aké Assi, L., Geuder, T., Maes, L., Dubois, J., Hanocq, M. & Bringmann, G. (1996). Naphthylisoquinoline alkaloids exhibit strong growth-inhibiting activities against Plasmodium falciparum and P. berghei in vitro - structure-activity relationships of dioncophylline C. Ann Trop Med Parasitol 90, 115-123.
16. François, G., Timperman, G., Steenackers, T., Aké Assi, L., Holenz, J. & Bringmann, G. (1997). In vitro inhibition of liver forms of the rodent malaria parasite Plasmodium berghei by naphthylisoquinoline alkaloids - structure-activity relationships of dioncophyllines A and C and ancistrocladine. Parasitol Res 83, 673-679.
17. Granthon, A. C., Braga, M. V., Rodrigues, J. C., Cammerer, S., Lorente, S. O., Gilbert, I. H., Urbina, J. A. & de Souza, W. (2007). Alterations on the growth and ultrastructure of Leishmania chagasi induced by squalene synthase inhibitors. Vet Parasitol 146, 25-34.
18. Krauth-Siegel, R. L., Meiering, S. K. & Schmidt, H. (2003). The parasite-specific trypanothione metabolism of Trypanosoma and Leishmania. Biol Chem 384, 539-549.
19. Lefranc, F., Facchini, V. & Kiss, R. (2007). Proautophagic drugs: a novel means to combat apoptosis-resistant cancers, with a special emphasis on glioblastomas. Oncologist 12, 1395-1403.
20. Menna-Barreto, R. F., Salomão, K., Dantas, A. P., Santa-Rita, R. M., Soares, M. J., Barbosa, H. S. & de Castro, S. L. (2009). Different cell death pathways induced by drugs in Trypanosoma cruzi: an ultrastructural study. Micron 40, 157-168.
21. Miranda, K., Docampo, R., Grillo, O., Franzen, A., Attias, M., Vercesi, A., Plattner, H., Hentschel, J. & de Souza, W. (2004). Dynamics of polymorphism of acidocalcisomes in Leishmania parasites. Histochem Cell Biol 121, 407-418.
22. Misra, P., Khaliq, T., Dixit, A., Sen Gupta, S., Samant, M., Kumari, S., Kumar, A., Kushawaha, P. K., Majumder, H. K. & other authors (2008). Antileishmanial activity mediated by apoptosis and structure-based target study of peganine hydrochloride dihydrate: an approach for rational drug design. J Antimicrob Chemother 62, 998-1002.
23. Moreno, S. N. & Docampo, R. (2003). Calcium regulation in protozoan parasites. Curr Opin Microbiol 6, 359-364.
24. Natera, S., Machuca, C., Padrón-Nieves, M., Romero, A., Diaz, E. & Ponte-Sucre, A. (2007). Proficiency of drug-resistant parasites. Int J Antimicrob Agents 29, 637-642.
25. Ouellette, M., Drummelsmith, J. & Papadopoulou, B. (2004). Leishmaniasis: drugs in the clinic, resistance and new developments. Drug Resist Updat 7, 257-266.
26. Ponte-Sucre, A. (2003). Physiological consequences of drug resistance in Leishmania and their relevance for chemotherapy. Kinetoplastid Biol Dis 2, 14.
27. Ponte-Sucre, A., Faber, J. H., Gulder, T., Kajahn, I., Pedersen, S. E. H., Schultheis, M., Bringmann, G. & Moll, H. (2007). Activity of naphthylisoquinoline alkaloids and synthetic analogs against Leishmania major. Antimicrob Agents Chemother 51, 188-194.
28. Ponte-Sucre, A., Gulder, T., Wegehaupt, A., Albert, C., Rikanović, C., Schaeflein, L., Frank, A., Schultheis, M., Unger, M. & other authors (2009). Structure-activity relationship and studies on the molecular mechanism of leishmanicidal N,C-coupled arylisoquinolinium salts. J Med Chem 52, 626-636.
29. Ramos, H., Valdivieso, E., Gamargo, M., Dagger, F. & Cohen, B. (1996). Amphotericin B kills unicellular Leishmania by forming aqueous pores permeable to small cations and anions. J Membr Biol 152, 65-75.
30. Shaha, C. (2006). Apoptosis in Leishmania species and its relevance to disease pathogenesis. Indian J Med Res 123, 233-244.
31. Sieber, M., Dekant, W., Faber, J. H. & Bringmann, G. (2006). Biotransformation and pharmacokinetics of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A. Xenobiotica 36, 750-762.
32. Sundar, S. & Chakravarty, J. (2008). Paromomycin in the treatment of leishmaniasis. Expert Opin Investig Drugs 17, 787-794.
33. Sundar, S. & Chatterjee, M. (2006). Visceral leishmaniasis - current therapeutic modalities. Indian J Med Res 123, 345-352.