Covalent functionalized self-assembled lipo-polymerosome bearing amphotericin B for better management of leishmaniasis and its toxicity evaluation

Molecular Pharmaceutics

Volumn 11, Issue 3, 2014, Pages 951-963

  Gupta, Pramod K ^a   Jaiswal, Anil K ^a   Kumar, Vivek ^a   Verma, Ashwni ^a   Dwivedi, Pankaj ^a   Dube, Anuradha ^a   Mishra, Prabhat R ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

cholesterol; glycol chitosan; lipo polymerosome; molecular organization; stearic acid

Indexed keywords

ALANINE AMINOTRANSFERASE; AMPHOTERICIN B; AMPHOTERICIN B DEOXYCHOLATE; AMPHOTERICIN B LIPID COMPLEX; ASPARTATE AMINOTRANSFERASE; CHITOSAN; COPOLYMER; GAMMA INTERFERON; GLYCOL; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 10; INTERLEUKIN 12; INTERLEUKIN 4; LIPOPOLYMEROSOME; MESSENGER RNA; MONOMER; PLASMA PROTEIN; POLYMER; STEARIC ACID; TRANSFORMING GROWTH FACTOR BETA; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; ANTIPROTOZOAL AGENT; CHITIN; GLYCOLCHITIN; NANOCAPSULE; STEARIC ACID DERIVATIVE;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; ASPARTATE AMINOTRANSFERASE BLOOD LEVEL; CONTROLLED STUDY; DOWN REGULATION; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG FORMULATION; DRUG RELEASE; HUMAN; HUMAN CELL; IMMUNOMODULATION; IN VITRO STUDY; IN VIVO STUDY; LEISHMANIASIS; MALE; MORPHOLOGY; MOUSE; NONHUMAN; PARTICLE SIZE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REAL TIME POLYMERASE CHAIN REACTION; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY; UPREGULATION; ZETA POTENTIAL; ANALOGS AND DERIVATIVES; ANIMAL; APOPTOSIS; CELL CULTURE; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; ENZYME IMMUNOASSAY; GENETICS; HAMSTER; IMMUNOLOGY; LEISHMANIA DONOVANI; MACROPHAGE; MESOCRICETUS; PARASITOLOGY; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; WESTERN BLOTTING;

AMPHOTERICIN B; ANIMALS; ANTIPROTOZOAL AGENTS; APOPTOSIS; BLOTTING, WESTERN; CELL PROLIFERATION; CELLS, CULTURED; CHITIN; CRICETINAE; DRUG DELIVERY SYSTEMS; IMMUNOENZYME TECHNIQUES; IMMUNOMODULATION; LEISHMANIA DONOVANI; LEISHMANIASIS; MACROPHAGES; MALE; MESOCRICETUS; MICE; NANOCAPSULES; POLYMERS; REAL-TIME POLYMERASE CHAIN REACTION; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; RNA, MESSENGER; STEARIC ACIDS;

EID: 84901744013     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400603t     Document Type: Article

References (48)

1. Dea-Ayuela, M. A.; Rama-Iniguez, S.; Sanchez-Brunete, J. A.; Torrado, J. J.; Alunda, J. M.; Bolas-Fernandez, F. Anti-leishmanial activity of a new formulation of amphotericin B Trop. Med. Int. Health 2004, 9, 981-990
2. Milhaud, J.; Ponsinet, V.; Takashi, M.; Michels, B. Interactions of the drug amphotericin B with phospholipid membranes containing or not ergosterol: new insight into the role of ergosterol Biochim. Biophys. Acta 2002, 1558, 95-108
3. Wasko, P.; Luchowski, R.; Tutaj, K.; Grudzinski, W.; Adamkiewicz, P.; Gruszecki, W. I. Toward understanding of toxic side effects of a polyene antibiotic amphotericin B: fluorescence spectroscopy reveals widespread formation of the specific supramolecular structures of the drug Mol. Pharmaceutics 2012, 9, 1511-1520
4. Larabi, M.; Pages, N.; Pons, F.; Appel, M.; Gulik, A.; Schlatter, J.; Bouvet, S.; Barratt, G. Study of the toxicity of a new lipid complex formulation of amphotericin B J. Antimicrob. Chemother. 2004, 53, 81-88
5. Uchegbu, I. F.; Sadiq, L.; Arastoo, M.; Gray, A. I.; Wang, W.; Waigh, R. D.; Schatzlein, A. G. Quaternary ammonium palmitoyl glycol chitosan-a new polysoap for drug delivery Int. J. Pharm. 2001, 224, 185-199
6. Cho, Y. W.; Park, S. A.; Han, T. H.; Son, D. H.; Park, J. S.; Oh, S. J.; Moon, D. H.; Cho, K. J.; Ahn, C. H.; Byun, Y.; Kim, I. S.; Kwon, I. C.; Kim, S. Y. In vivo tumor targeting and radionuclide imaging with self-assembled nanoparticles: mechanisms, key factors, and their implications Biomaterials 2007, 28, 1236-1247
7. Adams, M. L.; Kwon, G. S. Relative aggregation state and hemolytic activity of amphotericin B encapsulated by poly(ethylene oxide)-block-poly(N- hexyl-L-aspartamide)-acyl conjugate micelles: effects of acyl chain length J. Controlled Release 2003, 87, 23-32
8. Yoshioka, T.; Skalko, N.; Gursel, M.; Gregoriadis, G.; Florence, A. T. A non-ionic surfactant vesicle-in-water-in-oil (v/w/o) system: potential uses in drug and vaccine delivery J. Drug Targeting 1995, 2, 533-539
9. Nam, H. Y.; Kwon, S. M.; Chung, H.; Lee, S. Y.; Kwon, S. H.; Jeon, H.; Kim, Y.; Park, J. H.; Kim, J.; Her, S.; Oh, Y. K.; Kwon, I. C.; Kim, K.; Jeong, S. Y. Cellular uptake mechanism and intracellular fate of hydrophobically modified glycol chitosan nanoparticles J. Controlled Release 2009, 135, 259-267
10. Yoo, H. S.; Lee, J. E.; Chung, H.; Kwon, I. C.; Jeong, S. Y. Self-assembled nanoparticles containing hydrophobically modified glycol chitosan for gene delivery J. Controlled Release 2005, 103, 235-243
11. Park, J. H.; Kwon, S.; Nam, J. O.; Park, R. W.; Chung, H.; Seo, S. B.; Kim, I. S.; Kwon, I. C.; Jeong, S. Y. Self-assembled nanoparticles based on glycol chitosan bearing 5beta-cholanic acid for RGD peptide delivery J. Controlled Release 2004, 95, 579-588
12. Kim, J. H.; Kim, Y. S.; Kim, S.; Park, J. H.; Kim, K.; Choi, K.; Chung, H.; Jeong, S. Y.; Park, R. W.; Kim, I. S.; Kwon, I. C. Hydrophobically modified glycol chitosan nanoparticles as carriers for paclitaxel J. Controlled Release 2006, 111, 228-234
13. Liang, X. F.; Wang, H. J.; Luo, H.; Tian, H.; Zhang, B. B.; Hao, L. J.; Teng, J. I.; Chang, J. Characterization of novel multifunctional cationic polymeric liposomes formed from octadecyl quaternized carboxymethyl chitosan/cholesterol and drug encapsulation Langmuir 2008, 24, 7147-7153
14. Singodia, D.; Verma, A.; Verma, R. K.; Mishra, P. R. Investigations into an alternate approach to target mannose receptors on macrophages using 4-sulfated N-acetyl galactosamine more efficiently in comparison with mannose-decorated liposomes: an application in drug delivery Nanomedicine 2012, 8, 468-477
15. Kansal, S.; Tandon, R.; Dwivedi, P.; Misra, P.; Verma, P. R.; Dube, A.; Mishra, P. R. Development of nanocapsules bearing doxorubicin for macrophage targeting through the phosphatidylserine ligand: a system for intervention in visceral leishmaniasis J. Antimicrob. Chemother. 2012, 67, 2650-2660
16. Nakajima, N.; Ikada, Y. Mechanism of amide formation by carbodiimide for bioconjugation in aqueous media Bioconjugate Chem. 1995, 6, 123-130
17. Asthana, S.; Jaiswal, A. K.; Gupta, P. K.; Pawar, V. K.; Dube, A.; Chourasia, M. K. Immunoadjuvant chemotherapy of visceral leishmaniasis in hamsters using amphotericin B-encapsulated nanoemulsion template-based chitosan nanocapsules Antimicrob. Agents Chemother. 2013, 57, 1714-1722
18. Choi, K. C.; Bang, J. Y.; Kim, P. I.; Kim, C.; Song, C. E. Amphotericin B-incorporated polymeric micelles composed of poly(d,l-lactide-co-glycolide)/ dextran graft copolymer Int. J. Pharm. 2008, 355, 224-230
19. Espada, R.; Valdespina, S.; Alfonso, C.; Rivas, G.; Ballesteros, M. P.; Torrado, J. J. Effect of aggregation state on the toxicity of different amphotericin B preparations Int. J. Pharm. 2008, 361, 64-69
20. Mookerjee Basu, J.; Mookerjee, A.; Banerjee, R.; Saha, M.; Singh, S.; Naskar, K.; Tripathy, G.; Sinha, P. K.; Pandey, K.; Sundar, S.; Bimal, S.; Das, P. K.; Choudhuri, S. K.; Roy, S. Inhibition of ABC transporters abolishes antimony resistance in Leishmania Infection Antimicrob. Agents Chemother. 2008, 52, 1080-1093
21. Gupta, S.; Dube, A.; Vyas, S. P. Antileishmanial efficacy of amphotericin B bearing emulsomes against experimental visceral leishmaniasis J. Drug Targeting 2007, 15, 437-444
22. Park, K.; Kim, J. H.; Nam, Y. S.; Lee, S.; Nam, H. Y.; Kim, K.; Park, J. H.; Kim, I. S.; Choi, K.; Kim, S. Y.; Kwon, I. C. Effect of polymer molecular weight on the tumor targeting characteristics of self-assembled glycol chitosan nanoparticles J. Controlled Release 2007, 122, 305-314
23. Felix, L.; Hernandez, J.; Arguelles-Monal, W. M.; Goycoolea, F. M. Kinetics of gelation and thermal sensitivity of N-isobutyryl chitosan hydrogels Biomacromolecules 2005, 6, 2408-2415
24. Yuan, H.; Lu, L. J.; Du, Y. Z.; Hu, F. Q. Stearic acid-g-chitosan polymeric micelle for oral drug delivery: in vitro transport and in vivo absorption Mol. Pharmaceutics 2011, 8, 225-238
25. Park, K.; Kim, K.; Kwon, I. C.; Kim, S. K.; Lee, S.; Lee, D. Y.; Byun, Y. Preparation and characterization of self-assembled nanoparticles of heparin-deoxycholic acid conjugates Langmuir 2004, 20, 11726-11731
26. Jiang, G. B.; Quan, D.; Liao, K.; Wang, H. Novel polymer micelles prepared from chitosan grafted hydrophobic palmitoyl groups for drug delivery Mol. Pharmaceutics 2006, 3, 152-160
27. Liu, C. G.; Desai, K. G.; Chen, X. G.; Park, H. J. Linolenic acid-modified chitosan for formation of self-assembled nanoparticles J. Agric. Food Chem. 2005, 53, 437-441
28. Gaumet, M.; Vargas, A.; Gurny, R.; Delie, F. Nanoparticles for drug delivery: the need for precision in reporting particle size parameters Eur. J. Pharm. Biopharm. 2008, 69, 1-9
29. Ferdous, A. J.; Stembridge, N. Y.; Singh, M. Role of monensin PLGA polymer nanoparticles and liposomes as potentiator of ricin A immunotoxins in vitro J. Controlled Release 1998, 50, 71-78
30. Jain, J. P.; Kumar, N. Self assembly of amphiphilic (PEG)(3)-PLA copolymer as polymersomes: preparation, characterization, and their evaluation as drug carrier Biomacromolecules 2010, 11, 1027-1035
31. Kucerka, N.; Kiselev, M. A.; Balgavy, P. Determination of bilayer thickness and lipid surface area in unilamellar dimyristoylphosphatidylcholine vesicles from small-angle neutron scattering curves: a comparison of evaluation methods Eur. Biophys. J. 2004, 33, 328-334
32. Kilicarslan, M.; Baykara, T. The effect of the drug/polymer ratio on the properties of the verapamil HCl loaded microspheres Int. J. Pharm. 2003, 252, 99-109
33. Kucerka, N.; Marquardt, D.; Harroun, T. A.; Nieh, M. P.; Wassall, S. R.; de Jong, D. H.; Schafer, L. V.; Marrink, S. J.; Katsaras, J. Cholesterol in bilayers with PUFA chains: doping with DMPC or POPC results in sterol reorientation and membrane-domain formation Biochemistry 2010, 49, 7485-7493
34. Adams, M. L.; Andes, D. R.; Kwon, G. S. Amphotericin B encapsulated in micelles based on poly(ethylene oxide)-block-poly(L-amino acid) derivatives exerts reduced in vitro hemolysis but maintains potent in vivo antifungal activity Biomacromolecules 2003, 4, 750-757
35. Berry, M. R.; Likar, M. D. Statistical assessment of dissolution and drug release profile similarity using a model-dependent approach J. Pharm. Biomed. Anal. 2007, 45, 194-200
36. Costa, P.; Sousa Lobo, J. M. Modeling and comparison of dissolution profiles Eur. J. Pharm. Sci. 2001, 13, 123-133
37. Dash, S.; Murthy, P. N.; Nath, L.; Chowdhury, P. Kinetic modeling on drug release from controlled drug delivery systems Acta Pol. Pharm. 2010, 67, 217-223
38. Thevenot, J.; Troutier, A. L.; David, L.; Delair, T.; Ladaviere, C. Steric stabilization of lipid/polymer particle assemblies by poly(ethylene glycol)-lipids Biomacromolecules 2007, 8, 3651-3660
39. Huang, W.; Zhang, Z.; Han, X.; Tang, J.; Wang, J.; Dong, S.; Wang, E. Ion channel behavior of amphotericin B in sterol-free and cholesterol-or ergosterol-containing supported phosphatidylcholine bilayer model membranes investigated by electrochemistry and spectroscopy Biophys. J. 2002, 83, 3245-3255
40. Barwicz, J.; Christian, S.; Gruda, I. Effects of the aggregation state of amphotericin B on its toxicity to mice Antimicrob. Agents Chemother. 1992, 36, 2310-2315
41. Charvalos, E.; Tzatzarakis, M. N.; Van Bambeke, F.; Tulkens, P. M.; Tsatsakis, A. M.; Tzanakakis, G. N.; Mingeot-Leclercq, M. P. Water-soluble amphotericin B-polyvinylpyrrolidone complexes with maintained antifungal activity against Candida spp. and Aspergillus spp. and reduced haemolytic and cytotoxic effects J. Antimicrob. Chemother. 2006, 57, 236-244
42. Legrand, P.; Romero, E. A.; Cohen, B. E.; Bolard, J. Effects of aggregation and solvent on the toxicity of amphotericin B to human erythrocytes Antimicrob. Agents Chemother. 1992, 36, 2518-2522
43. Adams, M. L.; Kwon, G. S. The effects of acyl chain length on the micelle properties of poly(ethylene oxide)-block-poly(N-hexyl-L-aspartamide)-acyl conjugates J. Biomater. Sci., Polym. Ed. 2002, 13, 991-1006
44. Yardley, V.; Croft, S. L. A comparison of the activities of three amphotericin B lipid formulations against experimental visceral and cutaneous leishmaniasis Int. J. Antimicrob. Agents 2000, 13, 243-248
45. Canali, M. M.; Porporatto, C.; Aoki, M. P.; Bianco, I. D.; Correa, S. G. Signals elicited at the intestinal epithelium upon chitosan feeding contribute to immunomodulatory activity and biocompatibility of the polysaccharide Vaccine 2010, 28, 5718-5724
46. Choi, M.; Cho, M.; Han, B. S.; Hong, J.; Jeong, J.; Park, S.; Cho, M. H.; Kim, K.; Cho, W. S. Chitosan nanoparticles show rapid extrapulmonary tissue distribution and excretion with mild pulmonary inflammation to mice Toxicol. Lett. 2010, 199, 144-152
47. Melby, P. C.; Tryon, V. V.; Chandrasekar, B.; Freeman, G. L. Cloning of Syrian hamster (Mesocricetus auratus) cytokine cDNAs and analysis of cytokine mRNA expression in experimental visceral leishmaniasis Infect. Immun. 1998, 66, 2135-2142
48. Sundar, S.; Chakravarty, J.; Agarwal, D.; Rai, M.; Murray, H. W. Single-dose liposomal amphotericin B for visceral leishmaniasis in India N. Engl. J. Med. 2010, 362, 504-512