Development and characterization of chitosan-PEG-TAT nanoparticles for the intracellular delivery of siRNA

International Journal of Nanomedicine

Volumn 8, Issue , 2013, Pages 2041-2052

  Malhotra, Meenakshi ^a   Tomaro Duchesneau, Catherine ^a   Saha, Shyamali ^a   Kahouli, Imen ^a   Prakash, Satya ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Chemical conjugation; In vitro; Peptide; Polymer; Synthesis; Transfection

Indexed keywords

CHITOSAN; CROSS LINKING REAGENT; MACROGOL; MALEIMIDE; N HYDROXYSUCCINIMIDE; NANOPARTICLE; SMALL INTERFERING RNA; TRANSACTIVATOR PROTEIN;

AMIDATION; ANIMAL CELL; ARTICLE; CANCER GENE THERAPY; CELL TRANSPORT; CHEMICAL STRUCTURE; COLORIMETRY; COMPLEX FORMATION; CONTROLLED STUDY; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM COMPARISON; DRUG FORMULATION; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; GENETIC TRANSFECTION; IN VITRO STUDY; MOLECULAR INTERACTION; MOLECULAR WEIGHT; MOUSE; NANOPHARMACEUTICS; NEUROBLASTOMA CELL; NONHUMAN; PARTICLE SIZE; PH; PROCESS OPTIMIZATION; SURFACE CHARGE; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL;

CHEMICAL CONJUGATION; IN-VITRO; PEPTIDE; POLYMER; SYNTHESIS; TRANSFECTION;

ANIMALS; CELL LINE, TUMOR; CELL SURVIVAL; CHITOSAN; DITHIONITROBENZOIC ACID; DRUG DELIVERY SYSTEMS; HYDROGEN-ION CONCENTRATION; MICE; NANOPARTICLES; PARTICLE SIZE; POLYETHYLENE GLYCOLS; RNA, SMALL INTERFERING; TAT GENE PRODUCTS, HUMAN IMMUNODEFICIENCY VIRUS; TRANSFECTION;

EID: 84878170578     PISSN: 11769114     EISSN: 11782013     Source Type: Journal    
DOI: 10.2147/IJN.S43683     Document Type: Article

References (63)

1. Fawell S, Seery J, Daikh Y, et al. Tat mediated delivery of heterologous proteins into cells. Proc Natl Acad Sci U S A. 1994;91(2):664-668.
2. Vives E, Brodin P, Lebleu B. A truncated HIV-1 Tat protein basic domain rapidly translocates through the plasma membrane and accumulates in the cell nucleus. J Biol Chem. 1997;272(25):16010-16017.
3. Richard J, Melikov K, Vives E, et al. Cell-penetrating peptides. A reevaluation of the mechanism of cellular uptake. J Biol Chem. 2003;278(1): 585-590.
4. Futaki S. Oligoarginine vectors for intracellular delivery: design and cellular-uptake mechanisms. Biopolymers. 2006;84(3):241-249.
5. Torchilin VP, Mohan R, Weissig V, Levchenko TS. TAT peptide on the surface of liposomes affords their efficient intracellular delivery even at low temperature and in the presence of metabolic inhibitors. Proc Natl Acad Sci U S A. 2001;98(15):8786-8791.
6. Weeks KM, Ampe C, Schultz SC, Steitz TA, Crothers DM. Fragments of the HIV-1 Tat protein specifically bind TAR RNA. Science. 1990; 249(4974):1281-1285.
7. Ruben S, Perkins A, Purcell R, et al. Structural and functional characterization of human immunodeficiency virus tat protein. J Virol. 1989; 63(1):1-8.
8. Rudolph C, Plank C, Lousier J, Schillinger U, Muller RH, Rosenecker J. Oligomers of the arginine-rich motif of the HIV-1 TAT protein are capable of transferring plasmid DNA into cells. J Biol Chem. 2003;278(13): 11411-11418.
9. Hashida H, Miyamoto M, Cho Y, et al. Fusion of HIV-1 Tat protein transduction domain to poly-lysine as a new DNA delivery tool. Br J Cancer. 2004;90(6):1252-1258.
10. Hyndman L, Lemoine JL, Huang L, Porteous DJ, Boyd AC, Nan X. HIV-1 Tat protein transduction domain peptide facilitates gene transfer in combination with cationic liposomes. J Control Release. 2004;99(3):435-444.
11. Turner JJ, Jones S, Fabani MM, Ivanova G, Arzumanov AA, Gait MJ. RNA targeting with peptide conjugates of oligonucleotides, siRNA and PNA. Blood Cells Mol Dis. 2007;38(1):1-7.
12. Schwarze SR, Ho A, Vocero-Akbani A, Dowdy SF. In-vivo protein transduction: delivery of a biologically active protein into the mouse. Science. 1999;285(5433):1569-1572.
13. Santra S, Yang H, Stanley JT, et al. Rapid and effective labeling of brain tissue using TAT-conjugated CdS:Mn/ZnS quantum dots. Chem Commun (Camb). 2005;7(25):3144-3146.
14. Bondì ML, Di Gesù R, Craparo EF. Lipid nanoparticles for drug targeting to the brain. Methods Enzymol. 2012;508:229-251.
15. Boado RJ, Pardridge WM. The Trojan horse liposome technology for nonviral gene transfer across the blood-brain barrier. J Drug Deliv. 2011;2011:296151.
16. Jones AR, Shusta EV. Blood-brain barrier transport of therapeutics via receptor-mediation. Pharm Res. 2007;24(9):1759-1771.
17. Sharma HS, Castellani RJ, Smith MA, Sharma A. The blood-brain barrier in Alzheimer's disease: novel therapeutic targets and nanodrug delivery. Int Rev Neurobiol. 2012;102:47-90.
18. Sharma G, Modgil A, Sun C, Singh J. Grafting of cell-penetrating peptide to receptor-targeted liposomes improves their transfection efficiency and transport across blood-brain barrier model. J Pharm Sci. 2012;101(7):2468-2478.
19. Dehouck MP, Jolliet-Riant P, Brée F, Fruchart JC, Cecchelli R, Tillement JP. Drug transfer across the blood-brain barrier: correlation between in-vitro and in-vivo models. J Neurochem. 1992;58(5):1790-1797.
20. Paolino D, Cosco D, Molinaro R, Celia C, Fresta M. Supramolecular devices to improve the treatment of brain diseases. Drug Discov Today. 2011;16(7/8):311-324.
21. Alexis F, Lo SL, Wang S. Covalent attachment of low molecular weight Poly(ethylene imine) improves Tat peptide mediated gene delivery. Adv Mater. 2006;18(16):2174-2178.
22. Boussif O, Lezoualch F, Zanta MA, et al. A versatile vector for gene and oligonucleotide transfer into cells in culture and in-vivo: polyethylenimine. Proc Natl Acad Sci U S A. 1995;92(16):7297-7301.
23. Godbey WT, Wu KK, Mikos AG. Poly(ethylenimine) and its role in gene delivery. J Control Rel. 1999;60(2/3):149-160.
24. Putnam D, Gentry CA, Pack DW, Langer R. Polymer-based gene delivery with low cytotoxicity by a unique balance of side-chain termini. Proc Natl Acad Sci U S A. 2001;98(3):1200-1205.
25. Tang GP, Guo HY, Alexis F, et al. Low molecular weight polyethylenimines linked by β-cyclodextrin for gene transfer into the nervous system. J Gene Med. 2006;8(6):736-744.
26. Walkey CD, Olsen JB, Guo H, Emili A, Chan WC. Nanoparticle size and surface chemistry determine serum protein adsorption and macrophage uptake. J Am Chem Soc. 2012;134(4):2139-2147.
27. Sung SJ, Min SH, Cho KY, et al. Effect of polyethylene glycol on gene delivery of polyethylenimine. J Biol Pharm Bull. 2003;26(4): 492-500.
28. Suh J, Choy K, Lai SK, et al. PEGylation of nanoparticles improves their cytoplasmic transport. Int J Nanomedicine. 2007;2(4): 735-741.
29. Chan P, Kurisawa M, Chung JE, Yang YY. Synthesis and characterization of chitosan-g-poly(ethylene glycol)-folate as a non-viral carrier for tumor-targeted gene delivery. Biomaterials. 2007;28(3): 540-549.
30. Malhotra M, Lane C, Tomaro-Duchesneau C, Saha S, Prakash S. A novel method for synthesizing PEGylated chitosan nanoparticles: strategy, preparation and in-vitro analysis. Int J Nanomedicine. 2011;6:485-494.
31. Kean T, Thanou M. Biodegradation, biodistribution and toxicity of chitosan. Adv Drug Deliv Rev. 2010;62(1):3-11.
32. Yamamoto H, Amaike M. Biodegradation of cross-linked chitosan gels by a microorganism. Macromolecules. 1997;30(13):3936-3937.
33. Tomihata K, Ikada Y. In-vitro and in-vivo degradation of films of chitin and its deacetylated derivatives. Biomaterials. 1997;18(7):567-575.
34. Liu L, Bai Y, Zhu D, et al. Evaluation of the impact of arginine-chitosan/DNA nanoparticles on human naive CD4+ T cells. J Biomed Mater Res A. 2011;96(1):170-176.
35. Risbud MV, Bhonde RR. Polyacrylamide-chitosan hydrogels: in-vitro biocompatibility and sustained antibiotic release studies. Drug Deliv. 2000;7(2):69-75.
36. Shahidi F, Synowiecki J. Isolation and characterization of nutrients and value-added products from snow crab (Chionoecetes opilio) and shrimp (Pandalus borealis) processing discards. J Agric Food Chem. 1991;39(8):1527-1532.
37. Bernkop-Schnurch A. Chitosan and its derivatives: potential excipients for peroral peptide delivery systems. Int J Pharm. 2000;194(1):1-13.
38. Illum L, Jabbal-Gill I, Hinchcliffe M, Fisher AN, Davis SS. Chitosan as a novel nasal delivery system for vaccines. Adv Drug Deliv Rev. 2001;51(1/3):81-96.
39. Guang Liu W, De Yao K. Chitosan and its derivatives - a promising non-viral vector for gene transfection. J Control Release. 2002;83(1): 1-11.
40. Madihally SV, Matthew HW. Porous chitosan scaffolds for tissue engineering. Biomaterials. 1999;20(12):1133-1142.
41. Chellat F, Grandjean-Laquerriere A, Le Naour R, et al. Metalloproteinase and cytokine production by THP-1 macrophages following exposure to chitosan-DNA nanoparticles. Biomaterials. 2005;26(9):961-970.
42. Turan K, Nagata K. Chitosan-DNA nanoparticles: the effect of cell type and hydrolysis of chitosan on in-vitro DNA transfection. Pharm Dev Technol. 2006;11(4):503-512.
43. Gao Y, Xu Z, Chen S, Gu W, Chen L, Li Y. Arginine-chitosan/DNA self-assemble nanoparticles for gene delivery: In-vitro characteristics and transfection efficiency. Int J Pharm. 2008;359(1/2):241-246.
44. Kadiyala I, Loo Y, Roy K, Rice J, Leong KW. Transport of chitosan-DNA nanoparticles in human intestinal M-cell model versus normal intestinal enterocytes. Eur J Pharm Sci. 2010;39(1/3):103-109.
45. Katas H, Alpar HO. Development and characterization of chitosan nanoparticles for siRNA delivery. J Control Release. 2006;115(2): 216-225.
46. Lee MK, Chun SK, Choi WJ, et al. The use of chitosan as a condensing agent to enhance emulsion mediated gene transfer. Biomaterials. 2005; 26(14):2147-2156.
47. Howard KA, Rahbek UL, Liu X, et al. RNA interference in-vitro and in-vivo using a novel chitosan/siRNA nanoparticle system. Mol Ther. 2006;14(4):476-484.
48. Xie W, Liu J, Qiu M, Yuan J, Xu A. Design, synthesis and biological activity of cell-penetrating peptide-modified octreotide analogs. J Pept Sci. 2010;16(2):105-109.
49. Malhotra M, Kulamarva A, Sebak S, et al. Ultrafine chitosan nanoparticles as an efficient nucleic acid delivery system targeting neuronal cells. Drug Dev Ind Pharm. 2009;35(6):719-726.
50. Anthonsen MW, Smidsrød O. Hydrogen ion titration of chitosans with varying degrees of N-acetylation by monitoring induced 1H-NMR chemical shifts. Carbohydr Polym. 1995;26(4):303-305.
51. Malhotra M, Tomaro-Duchesneau C, Prakash S. Synthesis of TAT peptide-tagged PEGylated chitosan nanoparticles for siRNA delivery targeting neurodegenerative diseases. Biomaterials. 2013;34(4): 1270-1280.
52. Iqbal J, Shahnaz G, Dünnhaupt S, Müller C, Hintzen F, Bernkop-Schnürch A. Preactivated thiomers as mucoadhesive polymers for drug delivery. Biomaterials. 2012;33(5):1528-1535.
53. Luangtana-Anan M, Limmatvapirat S, Nunthanid J, Chalongsuk R, Yamamoto K. Polyethylene glycol on stability of chitosan microparticulate carrier for protein. AAPS Pharm Sci Tech. 2010; 11(3):1376-1382.
54. Gan Q, Wang T, Cochrane C, McCarron P. Modulation of surface charge, particle size and morphological properties of chitosan-TPP nanoparticles intended for gene delivery. Colloids Surf B Biointerfaces. 2005;44(2/3):65-73.
55. Xu H, Yan F, Monson EE, Kopelman R. Room-temperature preparation and characterization of poly (ethylene glycol)-coated silica nanoparticles for biomedical applications. J Biomed Mater Res. 2003;66A(4):870-879.
56. Mao S, Neu M, Germershaus O, et al. Influence of polyethylene glycol chain length on the physicochemical and biological properties of poly(ethylene imine)-graft-poly(ethylene glycol) block copolymer/ SiRNA polyplexes. Bioconjug Chem. 2006;17(5):1209-1218.
57. Hak S, Helgesen E, Hektoen HH, et al. The effect of nanoparticle polyethylene glycol surface density on ligand-directed tumor targeting studied in-vivo by dual modality imaging. ACS Nano. 2012;6(6): 5648-5658.
58. Ishida T, Kiwada H. Accelerated blood clearance (ABC) phenomenon upon repeated injection of PEGylated liposomes. Int J Pharm. 2008;354(1/2):56-62.
59. Ishihara T, Maeda T, Sakamoto H, et al. Evasion of the accelerated blood clearance phenomenon by coating of nanoparticles with various hydrophilic polymers. Biomacromolecules. 2010;11(10):2700-2706.
60. Sherman MR, Williams LD, Sobczyk MA, Michaels SJ, Saifer MG. Role of the methoxy group in immune responses to mPEG-protein conjugates. Bioconjug Chem. 2012;23(3):485-499.
61. Jokerst JV, Lobovkina T, Zare RN, Gambhir SS. PEGylated nanoparticles for imaging and therapy. Nanomedicine (Lond). 2011;6(4):715-728.
62. Wang AZ, Langer R, Farokhzad OC. Nanoparticle delivery of cancer drugs. Annu Rev Med. 2012;63:186-198.
63. Malhotra M, Prakash S. Targeted drug delivery across blood-brain-barrier using cell penetrating peptides tagged nanoparticles. Curr Nanosci. 2011;7(1):81-93.