Synthesis and characterization of biodegradable HPMA-oligolysine copolymers for improved gene delivery

Bioconjugate Chemistry

Volumn 21, Issue 1, 2010, Pages 140-150

  Burke, Rob S ^a   Pun, Suzie H ^a  

^a University of Washington   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCOMPATIBILITY; CATIONIC POLYMERIZATION; DNA; GENES; MONOMERS; PEPTIDES;

BIOACTIVE PEPTIDES; CATIONICS; CELL TARGETING; DNA-BINDING; ENDOSOMAL RELEASE; GENE CARRIER; GENE DELIVERY; SYNTHESIS AND CHARACTERIZATIONS; SYNTHETIC GENES; TARGETING PEPTIDES;

GENE TRANSFER;

COPOLYMER; DNA; POLY(N (2 HYDROXYPROPYL)METHACRYLAMIDE; SODIUM CHLORIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; BIODEGRADABILITY; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; GENE TARGETING; HUMAN; HUMAN CELL; POLYMERIZATION;

EID: 74949086064     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc9003662     Document Type: Article

References (50)

1. Bergen, J., and Pun, S. (2005) Peptide-enhanced nucleic acid delivery. MRS Bull. 30, 663-667.
2. Kwon, E., Bergen, J., Park, I., and Pun, S. (2008) Peptide-modified vectors for nucleic acid delivery to neurons. J. Controlled Release 132, 230-235.
3. Martin, M. E., and Rice, K. G. (2007) Peptide-guided gene delivery. AAPS J. 9, E18-E29.
4. O'Brien-Simpson, N. M., Ede, N. J., Brown, L. E., Swan, J., and Jackson, D. C. (1997) Polymerization of unprotected synthetic peptides: A view toward synthetic peptide vaccines. J. Am. Chem. Soc. 119, 1183-1188.
5. Jackson, D. C., O'Brien-Simpson, N., Ede, N. J., and Brown, L. E. (1997) Free radical induced polymerization of synthetic peptides into polymeric immunogens. Vaccine 15, 1697-705.
6. Graham, K. L., Zeng, W. G., Takada, Y., Jackson, D. C., and Coulson, B. S. (2004) Effects on rotavirus cell binding and infection of monomeric and polymeric peptides containing alpha 2 beta 1 and alpha x beta 2 integrin ligand sequences. J. Virol. 78, 11786-11797.
7. Liu, Z. H., Li, M. Y., Cui, D. F., and Fei, J. (2005) Macrobranched cell-penetrating peptide design for gene delivery. J. Controlled Release 102, 699-710.
8. Ding, H., Prodinger, W. M., and Kopecek, J. (2006) Identification of CD21-binding peptides with phage display and investigation of binding properties of HPMA copolymer-peptide conjugates. Bioconjugate Chem. 17, 514-523.
9. Breunig, M., Lungwitz, U., Liebl, R., and Goepferich, A. (2007) Breaking up the correlation between efficacy and toxicity for nonviral gene delivery. Proc. Natl. Acad. Sci. U.S.A. 104, 14454-14459.
10. McKenzie, D. L., Smiley, E., Kwok, K. Y., and Rice, K. G. (2000) Low molecular weight disulfide cross-linking peptides as nonviral gene delivery carriers. Bioconjugate Chem. 11, 901-909.
11. Gosselin, M. A., Guo, W. J., and Lee, R. J. (2001) Efficient gene transfer using reversibly cross-linked low molecular weight polyethylenimine. Bioconjugate Chem. 12, 989-994.
12. Siprashvili, Z., Scholl, F. A., Oliver, S. F., Adams, A., Contag, C. H., Wender, P. A., and Khavari, P. A. (2003) Gene transfer via reversible plasmid condensation with cysteine-flanked, internally spaced arginine-rich peptides. Hum. Gene Ther. 14, 1225-1233.
13. Read, M. L., Singh, S., Ahmed, Z., Stevenson, M., Briggs, S. S., Oupicky, D., Barrett, L. B., Spice, R., Kendall, M., Berry, M., Preece, J. A., Logan, A., and Seymour, L. W. (2005) A versatile reducible polycation-based system for efficient delivery of a broad range of nucleic acids. Nucleic Acids Res. 33, e86.
14. Kloeckner, J., Wagner, E., and Ogris, M. (2006) Degradable gene carriers based on oligomerized polyamines. Eur. J. Pharm. Sci. 29, 414-425.
15. Peng, Q., Zhong, Z. L., and Zhuo, R. X. (2008) Disulfide cross-linked polyethylenimines (PEI) prepared via thiolation of low molecular weight PEI as highly efficient gene vectors. Bioconjugate Chem. 19, 499-506.
16. Wadhwa, M. S., Collard, W. T., Adami, R. C., McKenzie, D. L., and Rice, K. G. (1997) Peptide-mediated gene delivery: influence of peptide structure on gene expression. Bioconjugate Chem. 8, 81-8.
17. Fields, C. G., Fields, G. B., Noble, R. L., and Cross, T. A. (1989) Solid-phase peptide-synthesis of N-15-gramicidin-a, N-15-gramicidin-B, and N-15-gramicidin-C and high-performance liquid-chromatographic purification. Int. J. Pept. Protein Res. 33, 298-303.
18. Jiang, X. L., van der Horst, A., van Steenbergen, M. J., Akeroyd, N., van Nostrum, C. F., Schoenmakers, P. J., and Hennink, W. E. (2006) Molar-mass characterization of cationic polymers for gene delivery by aqueous size-exclusion chromatography. Pharm. Res. 23, 595-603.
19. Burke, R. S., and Pun, S. H. (2008) Extracellular barriers to in Vivo PEI and PEGylated PEI polyplex-mediated gene delivery to the liver. Bioconjugate Chem. 19, 693-704.
20. Kopecek, J., and Bazilova, H. (1973) Poly[N-(2-hydroxypropyl) methacrylamide] 0.1. Radical polymerization and copolymerization. Eur. Polym. J. 9, 7-14.
21. Strohalm, J., and Kopecek, J. (1978) Poly[N-(2-hydroxypropyl) methacrylamide] 0.4. Heterogeneous polymerization. Angew. Makromol. Chem. 70, 109-118.
22. Vasey, P. A., Kaye, S. B., Morrison, R., Twelves, C., Wilson, P., Duncan, R., Thomson, A. H., Murray, L. S., Hilditch, T. E., Murray, T., Burtles, S., Fraier, D., Frigerio, E., and Cassidy, J. (1999) Phase I clinical and pharmacokinetic study of PK1 [N-(2-hydroxypropyl)methacrylamide copolymer doxorubicin]: first member of a new class of chemotherapeutic agents-drug-polymer conjugates. Cancer Research Campaign Phase I/II Committee. Clin. Cancer Res. 5, 83-94.
23. Duncan, R., Gac-Breton, S., Keane, R., Musila, R., Sat, Y. N., Satchi, R., and Searle, F. (2001) Polymer-drug conjugates, PDEPT and PELT: basic principles for design and transfer from the laboratory to clinic. J. Controlled Release 74, 135-146.
24. Duncan, R. (2003) The dawning era of polymer therapeutics. Nat. Rev. Drug Discovery 2, 347-360.
25. Rihova, B., and Kubackova, K. (2003) Clinical implications of N-(2-hydroxypropyl)methacrylamide copolymers. Curr. Pharm. Biotechnol. 4, 311-22.
26. Haag, R., and Kratz, F. (2006) Polymer therapeutics: concepts and applications. Angew. Chem., Int. Ed. Engl. 45, 1198-215.
27. Oupicky, D., Konak, C., and Ulbrich, K. (1999) DNA complexes with block and graft copolymers of N-(2-hydroxypropyl) methacrylamide and 2-(trimethylammonio)ethyl methacrylate. J. Biomater. Sci. Polym. Ed. 10, 573-90.
28. Oupicky, D., Konak, C., Dash, P. R., Seymour, L. W., and Ulbrich, K. (1999) Effect of albumin and polyanion on the structure of DNA complexes with polycation containing hydrophilic nonionic block. Bioconjugate Chem. 10, 764-72.
29. Oupicky, D., Konak, C., Ulbrich, K., Wolfert, M. A., and Seymour, L. W. (2000) DNA delivery systems based on complexes of DNA with synthetic polycations and their copolymers. J. Controlled Release 65, 149-71.
30. Radke, W., and Muller, A. H. E. (1992) Copolymerization of methacryloyl-terminated PMMA macromonomers with methylmethacrylate. Makromol. Chem., Macromol. Symp. 545, 583-594.
31. Shinoda, H., Miller, P. J., and Matyjaszewski, K. (2001) Improving the structural control of graft copolymers by combining ATRP with the macromonomer method. Macromolecules 34, 3186-3194.
32. Neugebauer, D., Zhang, Y., and Pakula, T. (2006) Gradient graft copolymers derived from PEO-based macromonomers. J. Polym. Sci., Part A: Polym. Chem. 44, 1347-1356.
33. Lang, J. L. (1960) Retardation of polymerization in substituted styrenes by chelated nitrophenols. J. Chem. Eng. Data 5, 53-56.
34. Motyakin, M. V., Wasserman, A. M., Stott, P. E., and Zaikov, G. E. (2004) Inhibitor radicals in styrene polymerization. J. Appl. Polym. Sci. 91, 1599-1603.
35. Tsutsumi, K., Okamoto, Y., and Tsukahara, Y. (1994) Radical polymerization behavior of macromonomers 0.3. Effect of macromonomer concentration. Polymer 35, 2205-2209.
36. Paulusse, J. M. J., Amir, R. J., Evans, R. A., and Hawker, C. J. (2009) Free radical polymers with tunable and selective bio- and chemical degradability. J. Am. Chem. Soc. 131, 9805-9812.
37. Ogris, M., Steinlein, P., Kursa, M., Mechtler, K., Kircheis, R., and Wagner, E. (1998) The size of DNA/transferrin-PEI complexes is an important factor for gene expression in cultured cells. Gene Ther. 5, 1425-1433.
38. Ruponen, M., Yla-Herttuala, S., and Urtti, A. (1999) Interactions of polymeric and liposomal gene delivery systems with extracellular glycosaminoglycans: physicochemical and transfection studies. Biochim. Biophys. Acta Biomembr. 1415, 331-341.
39. Moret, I., Peris, J. E., Guillem, V. M., Benet, M., Revert, F., Dasi, F., Crespo, A., and Alino, S. F. (2001) Stability of PEIDNA and DOTAP-DNA complexes: effect of alkaline pH, heparin and serum. J. Controlled Release 76, 169-181.
40. Schaffer, D. V., Fidelman, N. A., Dan, N., and Lauffenburger, D. A. (2000) Vector unpacking as a potential barrier for receptor-mediated polyplex gene delivery. Biotechnol. Bioeng. 67, 598-606.
41. Holmgren, A. (1989) Thioredoxin and glutaredoxin systems. J. Biol. Chem. 264, 13963-13966.
42. Arunachalam, B., Phan, U. T., Geuze, H. J., and Cresswell, P. (2000) Enzymatic reduction of disulfide bonds in lysosomes: Characterization of a Gamma-interferon-inducible lysosomal thiol reductase (GILT). Proc. Natl. Acad. Sci. U.S.A. 97, 745-750.
43. Yang, J., Chen, H., Vlahov, I. R., Cheng, J. X., and Low, P. S. (2006) Evaluation of disulfide reduction during receptor-mediated endocytosis by using FRET imaging. Proc. Natl. Acad. Sci. U.S.A. 103, 13872-13877.
44. Mishra, S., Webster, P., and Davis, M. E. (2004) PEGylation significantly affects cellular uptake and intracellular trafficking of non-viral gene delivery particles. Eur. J. Cell Biol. 83, 97-111.
45. Kursa, M., Walker, G. F., Roessler, V., Ogris, M., Roedl, W., Kircheis, R., and Wagner, E. (2003) Novel shielded transferrin-polyethylene glycol-polyethylenimine/DNA complexes for systemic tumor-targeted gene transfer. Bioconjugate Chem. 14, 222-231.
46. Boussif, O., Lezoualch, F., Zanta, M. A., Mergny, M. D., Scherman, D., Demeneix, B., and Behr, J. P. (1995) A versatile vector for gene and oligonucleotide transfer into cells in culture and in-vivo - polyethylenimine. Proc. Natl. Acad. Sci. U.S.A. 92, 7297-7301.
47. Sonawane, N. D., Szoka, F. C., and Verkman, A. S. (2003) Chloride accumulation and swelling in endosomes enhances DNA transfer by polyamine-DNA polyplexes. J. Biol. Chem. 278, 44826-44831.
48. Akinc, A., Thomas, M., Klibanov, A. M., and Langer, R. (2005) Exploring polyethylenimine-mediated DNA transfection and the proton sponge hypothesis. J. Gene Med. 7, 657-663.
49. Cheng, H., Zhu, J. L., Zeng, X., Jing, Y., Zhang, X. Z., and Zhuo, R. X. (2009) Targeted gene delivery mediated by folate-polyethylenimine-block- poly(ethylene glycol) with receptor selectivity. Bioconjugate Chem. 20, 481-487.
50. Hunter, A. C. (2006) Molecular hurdles in polyfectin design and mechanistic background to polycation induced cytotoxicity. Adv. Drug Delivery Rev. 58, 1523-31.