Silica nanoparticles and polyethyleneimine (PEI)-mediated functionalization: A new method of pei covalent attachment for siRNA delivery applications

Bioconjugate Chemistry

Volumn 24, Issue 12, 2013, Pages 2076-2087

  Buchman, Yekaterina Kapilov ^a   Lellouche, Emmanuel ^a   Zigdon, Sally ^a   Bechor, Moshe ^a   Michaeli, Shulamit ^a   Lellouche, Jean Paul ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CONTROLLED DRUG DELIVERY; DIGITAL STORAGE; GENES; GENETIC ENGINEERING; SILICA NANOPARTICLES; SPECTROSCOPIC ANALYSIS; TARGETED DRUG DELIVERY;

COVALENT ATTACHMENT; DOUBLE-STRANDED RNA; FUNCTIONALIZATIONS; GENE SILENCING; POLY(ETHYLENEIMINE); RNA INTERFERENCE; SEQUENCE-SPECIFIC MANNER; SILICA NANOPARTICLES; SIO 2; SMALL INTERFERING RNA;

RNA;

FLUORESCEIN ISOTHIOCYANATE; NANOPARTICLE; POLYETHYLENEIMINE; SILICON DIOXIDE; SMALL INTERFERING RNA;

ARTICLE; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DISPERSION; DRUG DELIVERY SYSTEM; GENE SILENCING; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROSCOPY; INTERNALIZATION; OSTEOSARCOMA CELL; PHYSICAL CHEMISTRY; SURFACE CHARGE; SURFACE PROPERTY; SURFACE TENSION; THERMOGRAPHY; THERMOGRAVIMETRY; TRANSMISSION ELECTRON MICROSCOPY; X RAY PHOTOELECTRON SPECTROSCOPY;

CELL LINE, TUMOR; DRUG CARRIERS; GENE SILENCING; HUMANS; NANOPARTICLES; POLYETHYLENEIMINE; RNA, SMALL INTERFERING; SILICON DIOXIDE; TRANSFECTION;

EID: 84890833479     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc4004316     Document Type: Article

References (50)

1. Bumcrot, D., Manoharan, M., Koteliansky, V., and Sah, D. W. Y. (2006) RNAi therapeutics: a potential new class of pharmaceutical drugs Nat. Chem. Biol. 2, 711-719
2. Vaishnaw, A., Gollob, J., Gamba-Vitalo, C., Hutabarat, R., Sah, D., Meyers, R., de Fougerolles, T., and Maraganore, J. (2010) A status report on RNAi therapeutics Silence 1, 14
3. Merdan, T., Kopecìek, J., and Kissel, T. (2002) Prospects for cationic polymers in gene and oligonucleotide therapy against cancer Adv. Drug Delivery Rev. 54, 715-758
4. Boyer, C., Teo, J., Phillips, P., Erlich, R. B., Sagnella, S., Sharbeen, G., Dwarte, T., Duong, H. T. T., Goldstein, D., Davis, T. P., Kavallaris, M., and McCarroll, J. (2013) Effective delivery of siRNA into cancer cells and tumors using well-defined biodegradable cationic star polymers Mol. Pharmaceutics 10, 2435-2444
5. Cho, H. Y., Averick, S. E., Paredes, E., Wegner, K., Averick, A., Jurga, S., Das, S. R., and Matyjaszewski, K. (2013) Star polymers with a cationic core prepared by ATRP for cellular nucleic acids delivery Biomacromolecules 14, 1262-1267
6. Nakase, I., Tanaka, G., and Futaki, S. (2013) Cell-penetrating peptides (CPPs) as a vector for the delivery of siRNAs into cells Mol. Biosyst. 9, 855-861
7. van Asbeck, A. H., Beyerle, A., McNeill, H., Bovee-Geurts, P. H. M., Lindberg, S., Verdurmen, W. P. R., Hällbrink, M., Langel, Ü., Heidenreich, O., and Brock, R. (2013) Molecular Parameters of siRNA-cell penetrating peptide nanocomplexes for efficient cellular delivery ACS Nano 7, 3797-3807
8. Schroeder, A., Levins, C. G., Cortez, C., Langer, R., and Anderson, D. G. (2010) Lipid-based nanotherapeutics for siRNA delivery J. Intern. Med. 267, 9-21
9. Gomes-da-Silva, L. C., Fonseca, N. A., Moura, V., Pedroso de Lima, M. C., Simões, S., and Moreira, J. N. (2012) Lipid-based nanoparticles for siRNA delivery in cancer therapy: paradigms and challenges Acc. Chem. Res. 45, 1163-1171
10. Godinho, B. M. D. C., Ogier, J. R., Darcy, R., Odriscoll, C. M., and Cryan, J. F. (2013) Self-assembling moified β-cyclodextrin nanoparticles as neuronal siRNA delivery vectors: focus on Huntington's disease Mol. Pharmaceutics 10, 640-649
11. McCarthy, J., O'Neill, M. J., Bourre, L., Walsh, D., Quinlan, A., Hurley, G., Ogier, J., Shanahan, F., Melgar, S., Darcy, R., and O'Driscoll, C. M. (2013) Gene silencing of TNF-alpha in a murine model of acute colitis using a modified cyclodextrin delivery system J. Controlled Release 168, 28-34
12. Biswas, S., Deshpande, P. P., Navarro, G., Dodwadkar, N. S., and Torchilin, V. P. (2013) Lipid modified triblock PAMAM-based nanocarriers for siRNA drug co-delivery Biomaterials 34, 1289-1301
13. Liu, J., Gu, C., Cabigas, E. B., Pendergrass, K. D., Brown, M. E., Luo, Y., and Davis, M. E. (2013) Functionalized dendrimer-based delivery of angiotensin type 1 receptor siRNA for preserving cardiac function following infarction Biomaterials 34, 3729-3736
14. Boyer, C., Priyanto, P., Davis, T. P., Pissuwan, D., Bulmus, V., Kavallaris, M., Teoh, W. Y., Amal, R., Carroll, M., Woodward, R., and St Pierre, T. (2010) Anti-fouling magnetic nanoparticles for siRNA delivery J. Mater. Chem. 20, 255-265
15. Chen, C., Mei, H., Shi, W., Deng, J., Zhang, B., Guo, T., Wang, H., and Hu, Y. (2013) EGFP-EGF1-conjugated PLGA nanoparticles for targeted delivery of siRNA into injured brain microvascular endothelial cells for efficient RNA interference PLoS One 8, e60860
16. Chen, C.-J., Wang, J.-C., Zhao, E.-Y., Gao, L.-Y., Feng, Q., Liu, X.-Y., Zhao, Z.-X., Ma, X.-F., Hou, W.-J., Zhang, L.-R., Lu, W.-L., and Zhang, Q. (2013) Self-assembly cationic nanoparticles based on cholesterol-grafted bioreducible poly(amidoamine) for siRNA delivery Biomaterials 34, 5303-5316
17. Heinemann, D., Schomaker, M., Kalies, S., Schieck, M., Carlson, R., Escobar, H. M., Ripken, T., Meyer, H., and Heisterkamp, A. (2013) Gold nanoparticle mediated laser transfection for efficient siRNA mediated gene knock down PLoS One 8, e58604
18. Jagani, H. V., Josyula, V. R., Palanimuthu, V. R., Hariharapura, R. C., and Gang, S. S. (2013) Improvement of therapeutic efficacy of PLGA nanoformulation of siRNA targeting anti-apoptotic Bcl-2 through chitosan coating Eur. J. Pharm. Sci. 48, 611-618
19. Vicennati, P., Giuliano, A., Ortaggi, G., and Masotti, A. (2008) Polyethylenimine in medicinal chemistry Curr. Med. Chem. 15, 2826-2839
20. Guenther, M., Lipka, J., Malek, A., Gutsch, D., Kreyling, W., and Aigner, A. (2011) Polyethylenimines for RNAi-mediated gene targeting in vivo and siRNA delivery to the lung Eur. J. Pharm. Biopharm. 77, 438-449
21. Nimesh, S. (2012) Polyethylenimine as a promising vector for targeted siRNA delivery Curr. Clin. Pharmacol. 7, 121-130
22. Aravindan, L., Bicknell, K. A., Brooks, G., Khutoryanskiy, V. V., and Williams, A. C. A comparison of thiolated and disulfide-crosslinked polyethylenimine for nonviral gene delivery. Macromol. Biosci. 2013; Epub ahead of print.
23. Tian, H., Li, F., Chen, J., Huang, Y., and Chen, X. (2012) N-isopropylacrylamide-modified polyethylenimines as effective gene carriers Macromol. Biosci. 12, 1680-1688
24. Cheng, W., Yang, C., Hedrick, J. L., Williams, D. F., Yang, Y. Y., and Ashton-Rickardt, P. G. (2013) Delivery of a granzyme B inhibitor gene using carbamate-mannose modified PEI protects against cytotoxic lymphocyte killing Biomaterials 34, 3697-3705
25. Lo, Y.-L., Sung, K.-H., Chiu, C.-C., and Wang, L.-F. (2013) Chemically conjugating polyethylenimine with chondroitin sulfate to promote CD44-mediated endocytosis for gene delivery Mol. Pharmaceutics 10, 664-676
26. Tripathi, S. K., Singh, V. P., Gupta, K. C., and Kumar, P. (2013) Hydrophobic and membrane permeable polyethylenimine nanoparticles efficiently deliver nucleic acids in vitro and in vivo J. Mater. Chem. B 1, 2515-2524
27. Wen, S., Zheng, F., Shen, M., and Shi, X. (2013) Surface modification and PEGylation of branched polyethyleneimine for improved biocompatibility J. Appl. Polym. Sci. 128, 3807-3813
28. Badruddoza, A. Z. M., Rahman, M. T., Ghosh, S., Hossain, M. Z., Shi, J., Hidajat, K., and Uddin, M. S. (2013) β-Cyclodextrin conjugated magnetic, fluorescent silica core-shell nanoparticles for biomedical applications Carbohydr. Polym. 95, 449-457
29. Kong, L., Mume, E., Triani, G., and Smith, S. V. (2013) Optimizing radiolabeling amine-functionalized silica nanoparticles using SarAr-NCS for applications in imaging and radiotherapy Langmuir 29, 5609-5616
30. Sharma, P., Bengtsson, N. E., Walter, G. A., Sohn, H.-B., Zhou, G., Iwakuma, N., Zeng, H., Grobmyer, S. R., Scott, E. W., and Moudgil, B. M. (2012) Gadolinium-doped silica nanoparticles encapsulating indocyanine green for near infrared and magnetic resonance imaging Small 8, 2856-2868
31. Singh, A. K., Hahn, M. A., Gutwein, L. G., Rule, M. C., Knapik, J. A., Moudgil, B. M., Grobmyer, S. R., and Brown, S. C. (2012) Multi-dye theranostic nanoparticle platform for bioimaging and cancer therapy Int. J. Nanomed. 7, 2739-2750
32. Zhang, X., Yang, P., Dai, Y., Ma, P. a., Li, X., Cheng, Z., Hou, Z., Kang, X., Li, C., and Lin, J. (2013) Multifunctional up-converting nanocomposites with smart polymer brushes gated mesopores for cell imaging and thermo/pHdual-responsive drug controlled release Adv. Funct. Mater. 23, 4067-4078
33. Xia, T., Kovochich, M., Liong, M., Meng, H., Kabehie, S., George, S., Zink, J. I., and Nel, A. E. (2009) Polyethyleneimine coating enhances the cellular uptake of mesoporous silica nanoparticles and allows safe delivery of siRNA and DNA cnstructs ACS Nano 3, 3273-3286
34. Li, X., Xie, Q. R., Zhang, J., Xia, W., and Gu, H. (2011) The packaging of siRNA within the mesoporous structure of silica nanoparticles Biomaterials 32, 9546-9556
35. Davies, W. G., Hardisty, E. W., Nevell, T. P., and Peters, R. H. (1970) The addition of alcohols to vinyl sulphones and sulphonamides J. Chem. Soc. B Phys. Org. 998-1004
36. Davies, W. G., Hardisty, E. W., Nevell, T. P., and Peters, R. H. (1970) The addition of amines to vinyl sulphones and sulphonamides J. Chem. Soc. B Phys. Org. 0, 1004-1007
37. Imai, Y., Asamidori, Y., Inoue, T., and Ueda, M. (1981) Synthesis of polysulfone-sulfides by polyadditions of dithiols to divinyl sulfones J. Polym. Sci., Part A: Polym. Chem. 19, 583-590
38. Green-Sadan, T., Kuttner, Y., Lublin-Tennenbaum, T., Kinor, N., Boguslavsky, Y., Margel, S., and Yadid, G. (2005) Glial cell line-derived neurotrophic factor-conjugated nanoparticles suppress acquisition of cocaine self-administration in rats Exp. Neurol. 194, 97-105
39. Ziv, O., Avtalion, R. R., and Margel, S. (2008) Immunogenicity of bioactive magnetic nanoparticles: Natural and acquired antibodies J. Biomed. Mater. Res. A 85A, 1011-1021
40. Sarin, V. K., Kent, S. B. H., Tam, J. P., and Merrifield, R. B. (1981) Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction Anal. Biochem. 117, 147-157
41. Ring, R. N., Tesoro, G. C., and Moore, D. R. (1967) Kinetics of the addition of alcohols to activated vinyl compounds J. Org. Chem. 32, 1091-1094
42. Zhuravlev, L. T. (2000) The surface chemistry of amorphous silica. Zhuravlev model Colloids Surf., A 173, 1-38
43. Abdollahi, M. and Rouhani, M. (2012) Hydrophilic polymer/fumed silica hybrid nanoparticles synthesized via surface-initiated redox polymerization J. Polym. Res. 19, 1-10
44. Kumar, V., Misra, N., Paul, J., Bhardwaj, Y. K., Goel, N. K., Francis, S., Sarma, K. S. S., and Varshney, L. (2013) Organic/inorganic nanocomposite coating of bisphenol A diglycidyl ether diacrylate containing silica nanoparticles via electron beam curing process Prog. Org. Coat. 76, 1119-1126
45. 4 nanocrystals in a silica matrix with infrared spectroscopy and electron paramagnetic resonance J. Mol. Struct. 560, 87-93
46. Coates, J., (2000) Interpretation of Infrared Spectra, A Practical Approach. Encyclopedia of Analytical Chemistry (Meyers, R. A., Eds.) Vol. 2, Wiley Online Library, Chichester.
47. Ha, S.-W., Camalier, C. E., Beck, G. R., Jr, and Lee, J.-K. (2009) New method to prepare very stable and biocompatible fluorescent silica nanoparticles Chem. Commun. 2881-2883
48. Comiskey, G. A., Malefyt, A. P., Walton, S. P., Chen, C., and Baker, G. L. Surface functionalized silica nanoparticles for active transfection of siRNA, PMSE Prepr. 2012.
49. Suwalski, A., Dabboue, H., Delalande, A., Bensamoun, S. F., Canon, F., Midoux, P., Saillant, G., Klatzmann, D., Salvetat, J.-P., and Pichon, C. (2010) Accelerated Achilles tendon healing by PDGF gene delivery with mesoporous silica nanoparticles Biomaterials. 31, 5237-5245
50. Zintchenko, A., Philipp, A., Dehshahri, A., and Wagner, E. (2008) Simple modifications of branched PEI lead to highly efficient siRNA carriers with Low toxicity Bioconjugate Chem. 19, 1448-1455