PEI-cellulose nanocrystal hybrids as efficient siRNA delivery agents—Synthesis, physicochemical characterization and in vitro evaluation

Carbohydrate Polymers

Volumn 164, Issue , 2017, Pages 258-267

  Ndong Ntoutoume, Gautier M A ^a   Grassot, Vincent ^b   Brégier, Frédérique ^a   Chabanais, Julien ^b   Petit, Jean Michel ^b   Granet, Robert ^a   Sol, Vincent ^a  

^a UNIVERSITÉ DE LIMOGES   (France)

^b UNIVERSITY OF LIMOGES   (France)

Author keywords

Cellulose nanocrystals; Nanoparticles; PEI; siRNA delivery; Transfected cells

Indexed keywords

CELL DEATH; CELLS; CELLULOSE; CYTOLOGY; GENE EXPRESSION; NANOCRYSTALS; NANOPARTICLES; POLYETHERIMIDES; RNA;

CELLULOSE NANO-CRYSTALS; CELLULOSE NANOCRYSTAL (CNCS); IN-VITRO EVALUATION; IONIC INTERACTION; PHYSICO-CHEMICAL CHARACTERIZATION; REDUCTIVE AMINATION; SIRNA DELIVERY; TRANSFECTED CELLS;

CELLULOSE DERIVATIVES;

CELLULOSE DERIVATIVES; NUCLEIC ACIDS; STAINING; SYNTHESIS;

CELLULOSE; NANOPARTICLE; POLYETHYLENEIMINE; SMALL INTERFERING RNA;

ANIMAL; APOPTOSIS; CHEMISTRY; GENE SILENCING; GENE VECTOR; MOUSE; TUMOR CELL LINE;

ANIMALS; APOPTOSIS; CELL LINE, TUMOR; CELLULOSE; GENE SILENCING; GENETIC VECTORS; MICE; NANOPARTICLES; POLYETHYLENEIMINE; RNA, SMALL INTERFERING;

EID: 85011884889     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2017.02.004     Document Type: Article

References (63)

1. Akinc, A., Thomas, M., Klibanov, A.M., Langer, R., Exploring polyethylenimine-mediated DNA transfection and the proton sponge hypothesis. The Journal of Gene Medicine 7 (2005), 657–663.
2. Azizi Samir, M.A.S., Alloin, F., Dufresne, A., Review of recent research into cellulosic whiskers, their properties and their application in nanocomposite field. Biomacromolecules 6 (2005), 612–626.
3. Barazzouk, S., Daneault, C., Amino acid and peptide immobilization on oxidized nanocellulose: Spectroscopic characterization. Nanomaterials 2 (2012), 187–205.
4. Boyer, C., Teo, J., Phillips, P., Erlich, R.B., Sagnella, S., Sharbeen, G., et al. Effective delivery of siRNA into cancer cells and tumors using well-defined biodegradable cationic star polymers. Molecular Pharmaceutics 10 (2013), 2435–2444.
5. Buchman, Y.K., Lellouche, E., Zigdon, S., Bechor, M., Michaeli, S., Lellouche, J.-P., Silica nanoparticles and polyethyleneimine (PEI)-mediated functionalization: A new method of PEI covalent attachment for siRNA delivery applications. Bioconjugate Chemistry 24 (2013), 2076–2087.
6. Cao, S.-L., Li, X.-H., Lou, W.-Y., Zong, M.-H., Preparation of a novel magnetic cellulose nanocrystal and its efficient use for enzyme immobilization. Journal of Material Chemistry B 2 (2014), 5522–5530.
7. Casto, D.O., Tabary, N., Martel, B., Gandini, A., Belgacem, B., Effect of different carboxylic acids in cyclodextrin functionalization of cellulose nanocrystals for prolonged release of carvacrol. Materials Science and Engineering C 69 (2016), 1018–1025.
8. Chauhan, P., Hadad, C., Sartorelli, A., Zarattini, M., Herreros-López, A., Mba, M., et al. Nanocrystalline cellulose-porphyrin hybrids: Synthesis, supramolecular properties, and singlet-oxygen production. Chemical Communications 49 (2013), 8525–8527.
9. Colombo, L., Zoia, L., Violatto, M.B., Previdi, S., Talamini, L., Sitia, L., et al. Organ distribution and bone tropism of cellulose nanocrystals in living mice. Biomacromolecules 16 (2015), 2862–2871.
10. Credou, J., Berthelot, T., Cellulose: From biocompatible to bioactive material. Journal of Materials Chemistry B 2 (2014), 4767–4788.
11. Dong, S., Roman, M., Fluorescently labeled cellulose nanocrystals for bioimaging applications. Journal of the American Chemical Society 129 (2007), 13810–13811.
12. Dong, S., Cho, H.J., Lee, Y.W., Roman, M., Synthesis and cellular uptake of folic acid-conjugated cellulose nanocrystal for cancer targeting. Biomacromolecules 15 (2014), 1560–1567.
13. Draz, M.S., Fang, B.A., Zhang, P., Hu, Z., Gu, S., Weng, K.C., et al. Nanoparticle-mediated systemic delivery of siRNA for treatment of cancers and viral infections. Theranostics 4 (2014), 872–892.
14. Drogat, N., Granet, R., Sol, V., Memmi, A., Saad, N., Klein Koerkamp, C., et al. Antimicrobial silver nanoparticles generated on cellulose nanocrystals. Journal of Nanoparticle Research 13 (2011), 1557–1562.
15. Drogat, N., Granet, R., Le Morvan, C., Bégaud-Grimaud, G., Krausz, P., Sol, V., Chlorin-PEI-labeled cellulose nanocrystals: Synthesis, characterization and potential application in PDT. Bioorganic & Medicinal Chemistry Letters 22 (2012), 3648–3652.
16. Feese, E., Sadeghifar, H., Gracz, H.S., Argyropoulos, D.S., Ghiladi, R.A., Photobactericidal porphyrin-cellulose nanocrystals: Synthesis, characterization, and antimicrobial properties. Biomacromolecules 12 (2011), 3528–3539.
17. Fredon, E., Granet, R., Zerrouki, R., Krausz, P., Saulnier, L., Thilbault, J.F., et al. Hydrophobic films from maize bran hemicelluloses. Carbohydrate Polymers 49 (2002), 1–12.
18. Ge, X., Feng, J., Chen, S., Zhang, C., Ouyang, Y., Liu, Z., et al. Biscarbamate cross-linked low molecular weight polyethylenimine polycation as an efficient intra-cellular delivery cargo for cancer therapy. Journal of Nanobiotechnology, 12, 2014, 13.
19. Grate, J.W., Mo, K.-F., Shin, Y., Vasdekis, A., Warner, M.G., Kelly, R.T., et al. Alexa fluor-labeled fluorescent cellulose nanocrystals for bioimaging solid cellulose in spatially structured microenvironments. Bioconjugate Chemistry 26 (2015), 593–601.
20. Gratton, S.E.A., Ropp, P.A., Pohlhaus, P.D., Luft, J.C., Madden, V.J., Napier, M.E., et al. The effect of particle design on cellular internalization pathways. Proceedings of the National Academy of Sciences of the United States of America 105 (2008), 11613–11618.
21. Habibi, Y., Lucia, L.A., Rojas, O.J., Cellulose nanocrystals: Chemistry, self assembly, and applications. Chemical Reviews 110 (2010), 3479–3500.
22. Habibi, Y., Key advances in the chemical modification of nanocelluloses. Chemical Society Reviews 43 (2014), 1519–1542.
23. Han, L., Zhao, J., Zhang, X., Cao, W., Hu, X., Zou, G., et al. Enhanced siRNA delivery and silencing gold-chitosan nanosystem with surface charge-reversal polymer assembly and good biocompatibility. ACS Nano 6 (2012), 7340–7351.
24. Han, J., Cai, J., Borjihan, W., Ganbold, T., Rana, T.M., Baigude, H., Preparation of novel curdlan nanoparticles for intracellular siRNA delivery. Carbohydrate Polymers 117 (2015), 324–330.
25. Harrington, H.A., Ho, K.L., Ghosh, S., Tung, K.C., Construction and analysis of a modular model of caspase activation in apoptosis. Theoretical Biology and Medical Modelling, 5, 2008, 10.1186/1742-4682-5-26.
26. Hemraz, U.D., Campbell, K.A., Burdick, J.S., Ckless, K., Boluk, Y., Sunasee, R., Cationic poly (2-aminoethylmethacrylate) and poly(N-(2-aminoethymethacrylamide) modified cellulose nanocrystals: Synthesis, characterization, and cytotoxicity. Biomacromolecules 16 (2015), 319–325.
27. Hu, Y., Xu, B.-H., Xu, J.-J., Shou, D., Gao, J.-Q., Synthesis of mannosylated Polyethylenimine and its potential application as cell-targeting non-viral vector for gene therapy. Polymers 6 (2014), 2573–2587.
28. Hu, H., Yuang, W., Liu, F.-S., Cheng, G., Xu, F.-J., Ma, J., Redox-responsive polycation-functionalized cotton cellulose nanocrystals for effective cancer treatment. ACS Applied Materials & Interfaces 7 (2015), 8942–8951.
29. Huang, J.-L., Li, C.-J., Gray, D.G., Cellulose nanocrystals incorporating fluorescent methylcoumarin groups. ACS Sustainable Chemistry & Engineering 1 (2013), 1160–1164.
30. Jana, P., Sarkar, K., Mitra, T., Chatterjee, A., Gnanamani, A., Chakraborti, G., et al. Synthesis of a carboxymethylated guar gum grafted polyethyleneimine copolymer as an efficient gene vehicle. RSC Advances 6 (2016), 13730–13741.
31. Jian, G., Park, K., Kim, J., Kim, K.S., Oh, E.J., Kang, H., et al. Hyaluronic acid-polyethyleneimine conjugate for target specific intracellular delivery of siRNA. Biopolymers 89 (2008), 635–642.
32. Kapilov-Buchman, Y., Lellouche, E., Michaeli, S., Lellouche, J.P., Unique surface modification of silica nanoparticles with Polyethyleneimine (PEI) for siRNA delivery using cerium cation coordination chemistry. Bioconjugate Chemistry 26 (2015), 880–889.
33. Lavrik, I.N., Systems biology of death receptor networks: Live and let die. Cell Death and Disease, 5, 2014, e1259, 10.1038/cddis.2014.160.
34. Layek, B., Lipp, L., Singh, J., Cell penetrating peptide conjugated chitosan for enhanced delivery of nucleic acid. International Journal of Molecular Sciences 16 (2015), 28912–28930.
35. Lin, N., Dufresne, A., Supramolecular hydrogels from in situ host-guest inclusion between chemically modified cellulose nanocrystals and cyclodextrin. Biomacromolecules 14 (2013), 871–880.
36. Lin, X., Zhao, N., Yan, P., Hu, H., Xu, F.J., The shape and size effects of polycation functionalized silica nanoparticles on gene transfection. Acta Biomaterialia 11 (2015), 381–392.
37. Liu, X., Mo, Y., Liu, X., Go, R., Zhang, Y., Xue, W., et al. Synthesis, characterisation and preliminary investigation of the haemocompatibility of polyethyleneimine-grafted carboxymethyl chitosan for gene delivery. Materials Science and Engineering C 62 (2016), 173–182.
38. Mahmoud, K.A., Mena, J.A., Male, K.B., Hrapovic, S., Kamen, A., Luong, J.H.T., Effect of surface charge on the cellular uptake and cytotoxicity of fluorescent labeled cellulose nanocrystals. ACS Applied Materials & Interfaces 2 (2010), 2924–2932.
39. McCarthy, J., O'Neill, M.J., Bourre, L., Walsh, D., Quinlan, A., Hurley, G., et al. Gene silencing of TNF-alpha in a murine model of acute colitis using a modified cyclodextrin delivery system. Journal of Controlled Release 168 (2013), 28–34.
40. Nam, J.-P., Nah, J.-W., Target gene delivery from targeting ligand conjugated chitosan-PEI copolymer for cancer therapy. Carbohydrate Polymers 135 (2016), 153–161.
41. Ndong Ntoutoume, G.M.A., Granet, R., Mbakidi, J.-P., Brégier, F., Léger, D.Y., Fidanzi-Dugas, C., et al. Development of curcumin-cyclodextrin/cellulose nanocrystals complexes: New anticancer drug delivery systems. Bioorganic & Medicinal Chemistry Letters 26 (2016), 941–945.
42. Nimesh, S., Polyethylenimine as a promising vector for targeted siRNA delivery. Current Clinical Pharmacology 7 (2012), 121–130.
43. Pecot, C.V., Calin, G.A., Coleman, R.L., Lopez-Berestein, G., Sood, A.K., RNA interference in the clinic: Challenges and future directions. Nature Reviews Cancer 11 (2011), 59–67.
44. Qi, L., Wu, L., Zheng, S., Wang, Y., Fu, H., Cui, D., Cell-penetrating magnetic nanoparticles for highly efficient delivery and intracellular imaging of siRNA. Biomacromolecules 13 (2012), 2723–2730.
45. Roman, M., Toxicity of cellulose nanocrystals: A review. Industrial Biotechnology 11 (2015), 25–33.
46. Sadeghifar, H., Filpponen, I., Clarke, S.P., Brougham, D.F., Argyropoulos, D.S., Production of cellulose nanocrystals using hydrobromic acid and click reactions on their surface. Journal of Materials Science 46 (2011), 7344–7355.
47. Salvesen, G.S., Walsh, C.M., Functions of caspase 8: The identified and the mysterious. Seminars in Immunology 26 (2014), 246–252.
48. Sarkar, K., Debnath, M., Kundu, P.P., Preparation of low toxic chitosan-graft-polyethyleneimine copolymer for gene carrier. Carbohydrate Polymers 92 (2013), 2048–2057.
49. Shi, Z., Tang, J., Chen, L., Yan, C., Tanvir, S., Anderson, W.A., et al. Enhanced colloidal stability and antibacterial performance of silver nanoparticles/cellulose nanocrystal hydrids. Journal of Materials Chemistry B 3 (2015), 603–611.
50. Singh, R.S., Kaur, N., Kennedy, J.F., Pullulan and pullulan derivatives as promising biomolecules for drug and gene targeting. Carbohydrate Polymers 123 (2015), 190–207.
51. Sirviö, J.A., Visanko, M., Laitinen, O., Ämmälä, A., Liimatainen, H., Amino-modified cellulose nanocrystals with adjustable hydrophobicity from combined regioselective oxidation and reductive amination. Carbohydrate Polymers 136 (2016), 581–587.
52. Socrates, G., Hydration study of acetaldehyde and propionaldehyde. The Journal of Organic Chemistry 34 (1969), 2958–2961.
53. Tripathi, S.K., Singh, V.P., Gupta, K.C., Kumar, P., Hydrophobic and membrane permeable polyethylenimine nanoparticles efficiently deliver nucleic acids in vitro and in vivo. Journal of Materials Chemistry B 1 (2013), 2515–2524.
54. Van Asbeck, A.H., Beyerle, A., McNeill, H., Bovee-Geurts, P.H.M., Lindberg, S., Verdurmen, W.P.R., et al. Molecular parameters of siRNA-cell penetrating peptide nanocomplexes for efficient cellular delivery. ACS Nano 7 (2013), 3797–3807.
55. Verma, I.M., Somia, N., Gene therapy – promises, problems and prospects. Nature 389 (1997), 239–242.
56. Visanko, M., Liimatainen, H., Sirviö, J.A., Heiskanen, J.P., Niinimäki, J., Hormi, O., Amphiphilic cellulose nanocrystals from acid-free oxidative treatment: Physicochemical characteristics and use as an oil-water stabilizer. Biomacromolecules 15 (2014), 2769–2775.
57. Wang, Y., Gu, H., Core-shell-type magnetic mesoporous silica nanocomposites for bioimaging and therapeutic agent delivery. Advanced Materials 27 (2015), 576–585.
58. Wang, X., Zhu, L., Hou, X., Wang, L., Yin, S., Polyethyleneimine mediated magnetic nanoparticles for combined intracellular imaging, siRNA delivery and anti-tumor therapy. RSC Advances 5 (2015), 101569–101581.
59. Wang, L., Wu, W., Wang, J., Wang, J., Tong, X., Hu, Q., et al. Highly efficient Gab2 siRNA delivery to ovarian cancer cells mediated by chitosan-polyethyleneimine nanoparticles. Journal of Materials Chemistry B 4 (2016), 273–281.
60. Wu, Y., Wang, W., Chen, Y., Huang, K., Shuai, X., Chen, Q., et al. The investigation of polymer-siRNA nanoparticle for gene therapy of gastric cancer in vitro. International Journal of Nanomedicine 5 (2010), 129–136.
61. Yang, Y., Liu, F., Liu, X., Xing, B., NIR light controlled photorelease of siRNA and its targeted intracellular delivery based on upconversion nanoparticles. Nanoscale 5 (2013), 231–238.
62. Zhang, M., Gao, Y., Caja, K., Zhao, B., Kim, J.A., Non-viral nanoparticles delivers small interfering RNA to macrophages in vitro and in vivo. PloS One, 10, 2015, 10.1371/journal.pone.0118472.
63. Zuckerman, J.E., Choi, C.H.J., Han, H., Davis, M.E., Polycation-siRNA nanoparticles can disassemble at the kidney glomerular basement membrane. PNAS 109 (2012), 3137–3142.