New delivery strategies for the old pentavalent antimonial drugs

Expert Opinion on Drug Delivery

Volumn 7, Issue 12, 2010, Pages 1343-1358

  Frézard, Frédéric ^a   Demicheli, Cynthia ^a  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

antimony; cyclodextrin; dogs; immunochemotherapy; leishmaniasis; liposomes; meglumine antimoniate; microparticle; pentavalent antimonials; stibogluconate

Indexed keywords

ANTILEISHMANIAL AGENT; ANTIMONY; CHOLESTEROL; CYCLODEXTRIN; DICETYL PHOSPHATE; DIPALMITOYLPHOSPHATIDYLCHOLINE; GAMMA INTERFERON; GRANULOCYTE MACROPHAGE COLONY STIMULATING FACTOR; LIGAND; LIPOSOME; MEGLUMINE ANTIMONATE; MURAMYL DIPEPTIDE; OCTADECYLAMINE; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLSERINE; POLYMER; PRODRUG; STIBOGLUCONATE SODIUM; TUFTSIN;

BIOCHEMISTRY; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG FORMULATION; DRUG HALF LIFE; DRUG MEGADOSE; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; IMMUNE RESPONSE; LEISHMANIA; LEISHMANIA CHAGASI; LEISHMANIA DONOVANI; LEISHMANIA INFANTUM; LEISHMANIA MAJOR; LEISHMANIASIS; LIPOSOMAL DELIVERY; MACROPHAGE; MACROPHAGE ACTIVATION; MEMBRANE FLUIDITY; MONONUCLEAR PHAGOCYTE; NONHUMAN; REVIEW; SKIN LEISHMANIASIS; SURFACE CHARGE; VISCERAL LEISHMANIASIS;

ADMINISTRATION, ORAL; ADMINISTRATION, TOPICAL; ANIMALS; ANTIMONY SODIUM GLUCONATE; ANTIPROTOZOAL AGENTS; DRUG DELIVERY SYSTEMS; HUMANS; LEISHMANIASIS; LIPOSOMES; MEGLUMINE; ORGANOMETALLIC COMPOUNDS;

EID: 78649958725     PISSN: 17425247     EISSN: None     Source Type: Journal    
DOI: 10.1517/17425247.2010.529897     Document Type: Review

References (99)

1. World Health Organization. Leishmaniasis. Available from: http:// apps.who.int/tdr/svc/diseases/ leishmaniasis/ [Last accessed on 29 August 2010]
2. Gradoni L, Soteriadou K, Louzir H, et al. Drug regimens for visceral leishmaniasis in Mediterranean countries. Trop Med Int Health 2008;13:1272-6
3. Marsden PD. Pentavalent antimonials: old drugs for new diseases. Rev Soc Bras Med Trop 1985;18:187-98
4. Murray HW, Berman JD, Davies CR, Saravia NG. Advances in leishmaniasis. Lancet 2005;366(9496):1561-77
5. Ashutosh, Sundar S, Goyal N. Molecular mechanisms of antimony resistance in Leishmania. J Med Microbiol 2007;56:143-53
6. Mookerjee Basu J, Mookerjee A, Banerjee R, et al. Inhibition of ABC transporters abolishes antimony resistance in Leishmania infection. Antimicrob Agents Chemother 2008;52:1080-93
7. Laguna F. Treatment of leishmaniasis in HIV-positive patients. Ann Trop Med Parasitol 2003;97(Suppl 1):5135-42
8. Alvar J, Molina R, San Andres M, et al. Canine leishmaniasis: clinical, parasitological and entomological follow-up after chemotherapy. Ann Trop Med Parasitol 1994;88:371-8
9. Noli C, Auxilia ST. Treatment of canine old world visceral leishmaniasis: a systematic review. Vet Dermatol 2005;16:213-32
10. Ridley RG. Drug against parasitic diseases. In: Fairlamb AH, Ridley RG, Vial HJ, editors, UNDP/World Bank/ WHO Special Programme for Research and Training in Tropical Diseases (TDR). Geneva, Switzerland; 2003. p. 13-21
11. Adler-Moore J, Proffitt RT. Effect of tissue penetration on AmBisome efficacy. Curr Opin Investig Drugs 2003;4:179-85
12. Meyerhoff A. U.S. Food and Drug Administration approval of AmBisome (liposomal amphotericin B) for treatment of visceral leishmaniasis. Clin Infect Dis 1999;28:42-8
13. Sundar S, Jha TK, Thakur CP, et al. Oral miltefosine for Indian visceral leishmaniasis. N Engl J Med 2002;347:1739-46
14. Sundar S, Chakravarty J, Agarwal D, et al. Single-dose liposomal amphotericin B for visceral leishmaniasis in India. N Engl J Med 2010;362:504-12
15. Bern C, Adler-Moore J, Berenguer J, et al. Liposomal amphotericin B for the treatment of visceral leishmaniasis. Clin Infect Dis 2006;43:917-24
16. Oliva G, Gradoni L, Ciaramella P, et al. Activity of liposomal amphotericin B (AmBisome) in dogs naturally infected with Leishmania infantum. J Antimicrob Chemother 1995;36:1013-19
17. Manna L, Gravino AE, Picillo E, et al. Leishmania DNA quantification by real-time PCR in naturally infected dogs treated with miltefosine. Ann NY Acad Sci 2008;1149:358-60
18. Manna L, Vitale F, Reale S, et al. Study of efficacy of miltefosine and allopurinol in dogs with leishmaniosis. Vet J 2009;182:441-5
19. Frezard F, Demicheli C, Ribeiro RR. Pentavalent antimonials: new perspectives for old drugs. Molecules 2009;14:2317-36
20. Roberts WL, McMurray WJ, Rainey PM. Characterization of the antimonial antileishmanial agent meglumine antimonate (Glucantime). Antimicrob Agents Chemother 1998;42:1076-82
21. Demicheli C, Figueiredo TL, Carvalho S, et al. Physico-chemical characterization of meglumine antimoniate. Biometals 1999;12:63-6
22. Demicheli C, Ochoa R, Lula IS, et al. Pentavalent organoantimonial derivatives: two simple and efficient synthetic methods for meglumine antimonate. Appl Organomet Chem 2003;17:226-31
23. Frezard F, Martins PS, Barbosa MCM, et al. New insights into the chemical structure and composition of the pentavalent antimonial drugs meglumine antimonate and sodium stibogluconate. J Inorg Biochem 2008;102:656-65
24. Ferreira CS, Pimenta AMC, Demicheli C, Frezard F. Characterization of reactions of antimoniate and meglumine antimoniate with a guanine ribonucleoside at different pH. Biometals 2006;19:573-81
25. Martins PS, Ochoa R, Pimenta AMC, et al. Mode of action of beta-cyclodextrin as an absorption enhancer of the water-soluble drug meglumine antimoniate. Int J Pharm 2006;325:39-47
26. Demicheli C, Santos LS, Ferreira CS, et al. Synthesis and characterization of Sb (V)-adenosine and Sb(V)-guanosine complexes in aqueous solution. Inorganica Chim Acta 2006;359:159-67
27. Goodwin LC, Page JE. A study of the excretion of organic antimonials using a polarographic procedure. Biochem J 1943;22:236-40
28. Burguera JL, Burguera M, Petit de Pena Y, et al. Selective determination of antimony(III) and antimony(V) in serum and urine and of total antimony in skin biopsies of patients with cutaneous leishmaniasis treated with meglumine antimoniate. Trace Elem Med 1993;10:66-70
29. Shaked-Mishan P, Ulrich N, Ephros M, et al. Novel intracellular Sb(V) reducing activity correlates with antimony susceptibility in Leishmania donovani. J Biol Chem 2001;276:3971-6
30. Frezard F, Demicheli C, Ferreira CS, Costa MA. Glutathione-induced conversion of pentavalent antimony to trivalent antimony in meglumine antimoniate. Antimicrob Agents Chemother 2001;45:91316
31. Ferreira CS, Martins PS, Demicheli C, et al. Thiol-induced reduction of antimony(V) into antimony(III): a comparative study with trypanothione, cysteinylglycine, cysteine and glutathione. Biometals 2003;16:441-3
32. Yan SC, Li F, Ding KY, et al. Reduction of pentavalent antimony by trypanothione and formation of a binary and ternary complex of antimony(III) and trypanothione. J Biol Inorg Chem 2003;8:689-97
33. Demicheli C, Frezard F, Lecouvey M, Garnier-Suillerot A. Antimony(V) complex formation with adenine nucleosides in aqueous solution. Biochim Biophys Acta 2002;1570:192-8
34. Dzamitika SA, Falcao CA, Oliveira FB, et al. Role of residual Sb(III) in meglumine antimoniate cytotoxicity and MRP1-mediated resistance. Chem Biol Int 2006;160:217-24
35. Ferreira CS, da Rocha ICM, Neto RLM, et al. Influence of the nucleobase on the physicochemical characteristics and biological activities of SbV-ribonucleoside complexes. J Braz Chem Soc 2010;21:1258-65
36. Chulay JD, Fleckenstein L, Smith DH. Pharmacokinetics of antimony during treatment of visceral leishmaniasis with sodium stibogluconate or meglumine antimoniate. Trans R Soc Trop Med Hyg 1988;82:69-72
37. Rees PH, Keating MI, Kager PA, et al. Renal clearance of pentavalent antimony (sodium stibogluconate). Lancet 1980;2(8188):226-9
38. Valladares JE, Alberola J, Esteban M, et al. Disposition of antimony after administration of N-methylglucamine antimoniate to dogs. Vet Rec 1996;138:181-3
39. Ribeiro RR, Ferreira WA, Martins PS, et al. Prolonged absorption of antimony (V) by the oral route from non-inclusion meglumine antimoniate-beta- cyclodextrin conjugates. Biopharm Drug Dispos 2010;31:109-19
40. Alving CR, Swartz GM. Preparation of liposomes for use as drug carriers in the treatment of leishmaniasis. In: Gregoriadis G, editor, Liposome technology. Volume 2. CRC Press: Boca Raton, FL, USA; 1984. p. 55-68
41. Rao LS. Anti-leishmanial pharmaceutical formulation. US4594241; 1986
42. Alving CR. Liposomes as drug carriers in leishmaniasis and malaria. Parasitol Today 1986;2:101-7
43. Baillie AJ, Florence AT, Hume LR, et al. The preparation and properties of niosomes-non-surfactant vesicles. J Pharm Pharmacol 1985;37:863-8
44. Baillie AJ, Coombs GH, Dolan TF, et al. Nonionic surfactant vesicles, niosomes, as a delivery system for the antileishmanial drug sodium stibogluconate. J Pharm Pharmacol 1986;38:502-5
45. Hu C, Rhodes DG. Proniosomes: a novel drug carrier preparation. Int J Pharm 1999;185:23-5
46. Frezard F, Michalick MS, Soares CF, Demicheli C. Novel methods for the encapsulation of meglumine antimoniate in liposomes. Braz J Med Biol Res 2000;33:841-6
47. Frezard F, Demicheli C, Schettini DA, et al. Processo para a preparacao de formulacoes farmaceuticas do antimoniato de meglumina em lipossomas e uso das formulacoes farmaceuticas em animais acometidos com leishmaniose visceral. Brazil Patent Pending PI0405489-0, 2004
48. Demicheli C, Rocha OGF, Schettini DA, et al. Liposomes: physicochemical and pharmacological properties, applications in antimony-based chemotherapy. Quim Nova 2005;28:511-18
49. Schettini DA, Ribeiro RR, Demicheli C, et al. Improved targeting of antimony to the bone marrow of dogs using liposomes of reduced size. Int J Pharm 2006;315:140-7
50. Black CDV, Watson GJ, Ward RJ. The use of pentostam liposomes in the chemotherapy in experimental leishmaniasis. Trans R Soc Trop Med Hyg 1977;71:550-2
51. Alving CR, Steck EA, Chapman WL, et al. Therapy of leishmaniasis: superior efficacies of liposome-encapsulated drugs. Proc Natl Acad Sci USA 1978;75:2959-63
52. New RR, Chance ML, Thomas SC, Peters W. Antileishmanial activity of antimonials entrapped in liposomes. Nature 1978;272:55-6
53. Rao LS, Hardy JG, Wilson CG. Tissue distribution and fate of free and liposome-encapsulated [125Sb] sodium stibogluconate by gamma scintigraphy. Int J Pharm 1983;17:283-90
54. Heath S, Chance ML, New RR. Quantitative and ultrastructural studies on the uptake of drug loaded liposomes by mononuclear phagocytes infected with Leishmania donovani. Mol Biochem Parasitol 1984;12:49-60
55. Weldon JS, Munnell JF, Hanson WL, Alving CR. Liposomal chemotherapy in visceral leishmaniasis: an ultrastructural study of an intracellular pathway. Z Parasitenkd 1983;69:415-24
56. Valladares JE, Riera C, Gonzalez-Ensenyat P, et al. Long term improvement in the treatment of canine leishmaniosis using antimony liposomal formulation. Vet Parasitol 2001;97:15-21
57. Hunter CA, Dolan TF, Coombs GH, Baillie AJ. Vesicular systems (niosomes and liposomes) for delivery of sodium stibogluconate in experimental murine visceral leishmaniasis. J Pharm Pharmacol 1988;40:161-5
58. Alving CR, Swartz JRGM, Hendricks LD, et al. Liposomes in leishmaniasis: effects of parasite virulence on treatment of experimental leishmaniasis in hamsters. Ann Trop Med Parasitol 1984;78:279-86
59. Alving CR. Delivery of liposome-encapsulated drugs to macrophages. Pharmacol Ther 1983;22:407-24
60. Nieto J, Alvar J, Mullen KC, et al. Pharmacokinetics, toxicities, and efficacies of sodium stibogluconate formulations after intravenous administration in animals. Antimicrob Agents Chemother 2003;47:2781-7
61. Ribeiro RR, Moura EP, Pimentel VM, et al. Reduced tissue parasitic load and infectivity to sand flies in dogs naturally infected by Leishmania (Leishmania) chagasi following treatment with a liposome formulation of meglumine antimoniate. Antimicrob Agents Chemother 2008;52:2564-72
62. Szebeni J. The interaction of liposomes with the complement system. Crit Rev Ther Drug Carrier Syst 1998;15:57-8
63. Pal S, Ravindran R, Ali N. Combination therapy using sodium antimony gluconate in stearylamine-bearing liposomes against established and chronic Leishmania donovani infection in BALB/ c mice. Antimicrob Agents Chemother 2004;38:3591-3
64. Carter KC, Baillie AJ, Alexander J, Dolan TF. The therapeutic effect of sodium stibogluconate in BALB/c mice infected with Leishmania donovani is organ-dependent. J Pharm Pharmacol 1988;40:370-3
65. Carter KC, Dolan TF, Alexander J, et al. Visceral leishmaniasis: drug carrier characteristics and the ability to clear parasites from the liver, spleen and bone marrow in Leishmania donovani infected BALB/c mice. J Pharm Pharmacol 1989;41:87-91
66. Schettini DA, Costa Val AP, Souza LF, et al. Pharmacokinetic and parasitological evaluation of the bone marrow of dogs with visceral leishmaniasis submitted to multiple dose treatment with liposome-encapsulated meglumine antimoniate. Braz J Med Biol Res 2005;38:1879-83
67. Moghimi SM, Patel HM. Serum-mediated recognition of liposomes by phagocytic cells of the reticuloendothelial system-the concept of tissue specificity. Adv Drug Deliv Rev 1998;32:45-60
68. Auger MJ, Ross JA. In: Lewis CE, McGee JOD, editors, The natural immune system: the macrophage. Oxford University Press, New York; 1992;2-74
69. Ahsan F, Rivas IP, Khan MA, Torres Suarez AI. Targeting to macrophages: role of physicochemical properties of particulate carriers-liposomes and microspheres-on the phagocytosis by macrophages. J Control Release 2002;79:29-40
70. Owais M, Gupta CM. Targeted drug delivery to macrophages in parasitic infections. Curr Drug Deliv 2005;2:311-18
71. Das N, Mahato SB, Naskar K, et al. Targeting of urea stibamine encapsulated in liposomes to reticuloendothelial system for the treatment of experimental leishmaniasis. Biochem Med Metab Biol 1990;43:133-9
72. Medda S, Mukherjee S, Das N, et al. Sugar-coated liposomes: a novel delivery system for increased drug efficacy and reduced drug toxicity. Biotechnol Appl Biochem 1993;17:37-47
73. Dutta M, Bandyopadhyay R, Basu MK. Neoglycosylated liposomes as efficient ligands for the evaluation of specific sugar receptors on macrophages in health and in experimental leishmaniasis. Parasitology 1994;109:139-47
74. Tempone AG, Perez D, Rath S, et al. Targeting Leishmania (L.) chagasi amastigotes through macrophage scavenger receptors: the use of drugs entrapped in liposomes containing phosphatidylserine. J Antimicrob Chemother 2004;54:60-8
75. Bar-Shavit Z, Stabinsky Y, Fridkin M, Goldman R. Tuftsin-macrophage interaction: specific binding and augmentation of phagocytosis. J Cell Physiol 1979;100:55-62
76. Najjar VA. Biological and biochemical characteristics of the tetrapeptide tuftsin, Thr-Lys-Pro-Arg. Adv Exp Med Biol 1979;121:131-47
77. Agrawal A, Gupta C. Tuftsin-bearing liposomes in treatment of macrophage-based infections. Adv Drug Deliv Rev 2000;41:135-46
78. Guru PY, Agrawal AK, Singha UK, et al. Drug targeting in Leishmania donovani infections using tuftsin-bearing liposomes as drug vehicles. FEBS Lett 1989;245:204-8
79. Dey T, Anam K, Afrin F, Ali N. Antileishmanial activities of sterylamine-bering liposomes. Antimicrob Agents Chemother 2000;44:1739-42
80. El-On J. Current status and perspectives of the immunotherapy of leishmaniasis. Isr Med Assoc J 2009;11:623-
81. Murray HW, Berman JD, Wright SD. Immunochemotherapy for intracellular Leishmania donovani infection: gamma interferon plus pentavalent antimony. J Infect Dis 1988;157:973-8
82. Santos JB, de Jesus AR, Machado PR, et al. Antimony plus recombinant human granulocyte-macrophage colonystimulating factor applied topically in low doses enhances healing of cutaneous Leishmaniasis ulcers: a randomized, double-blind, placebo-controlled study. J Infect Dis 2004;190:1793-6
83. Adinolfi LE, Bonventre PF, Pas MV, Eppstein DA. Synergistic effect of glucantime and a liposome-encapsulated muramyl dipeptide analog in therapy of experimental visceral leishmaniasis. Infect Immun 1985;48:409-16
84. Haidaris CG, Bonventre PF. Efficacy of combined immunostimulation and chemotherapy in experimental visceral Leishmaniasis. Am J Trop Med Hyg 1983;32:286-95
85. Machado-Pinto J, Pinto J, da Costa CA, et al. Immunochemotherapy for cutaneous leishmaniasis: a controlled trial using killed Leishmania (Leishmania) amazonensis vaccine plus antimonial. Int J Dermatol 2002;41:73-8
86. Everlien H, Hockertz S. Combined liposomal immuno- and chemotherapy of visceral leishmaniasis. Arzneimittelforschung 1999;49:954-61
87. Chapman WL, Hanson WL, Alving CR, Hendricks LD. Antileishmanial activity of liposome-encapsulated meglumine antimonate in the dog. Am J Vet Res 1984;45:1028-30
88. Valladares JE, Riera C, Gonzalez-Ensenyat P, et al. Long term improvement in the treatment of canine leishmaniosis using antimony liposomal formulation. Vet Parasitol 2001;97:15-21
89. New RRC, Chance ML, Heath S. The treatment of experimental cutaneous leishmaniasis with liposome-entrapped Pentostam. Parasitology 1981;83:519-27
90. Croft SL, Neal RA, Rao LS. Liposomes and other drug delivery systems in the treatment of leishmaniasis. In: Hart DT, editor, Leishmaniasis: the current status and new strategies for control. Plenum Press /Nato Scient. Affairs Div., New York and London; 1989. p.783-92
91. Baillie AJ, Coombs GH, Dolan TF, et al. Biodegradable microspheres: polyacryl starch microparticles as a delivery system for the antileishmanial drug, sodium stibogluconate. J Pharm Pharmacol 1987;39:832-5
92. Roberts WL, Hariprashad J, Rainey PM, Murray HW. Pentavalent antimony-mannan conjugate therapy of experimental visceral leishmaniasis. Am J Trop Med Hyg 1996;55:444-6
93. Irie T, Uekama K. Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J Pharm Sci 1997;86:147-62
94. Hirayama F, Uekama K. Cyclodextrin-based controlled drug release system. Adv Drug Deliv Rev 1999;36:125-41
95. Demicheli C, Ochoa R, Silva JBB, et al. Oral delivery of meglumine antimoniate-beta-cyclodextrin complex for treatment of leishmaniasis. Antimicrob Agents Chemother 2004;48:100-3
96. Frezard F, Martins PS, Bahia APCO, et al. Enhanced oral delivery of antimony from meglumine antimoniate/ beta-cyclodextrin nanoassemblies. Int J Pharm 2008;347:102-8
97. Solomon M, Baum S, Barzilai A, et al. Treatment of cutaneous leishmaniasis with intralesional sodium stibogluconate. J Eur Acad Dermatol Venereol 2009;23:1189-92
98. Costa JM, Barrios LA, Netto EM, Marsden PD. Topical pentostam in an attempt to produce more rapid healing of skin ulcers due to Leishmania braziliensis braziliensis. Rev Soc Bras Med Trop 1986;19:199-200
99. Price reductions for drugs for leishmaniasis. May 2007. Available from: archive/200705/msg00062.php [Accessed on 29 August 2010]