Acetal linked oligoethylenimines for use as pH-sensitive gene carriers

Bioconjugate Chemistry

Volumn 19, Issue 8, 2008, Pages 1625-1634

  Knorr, Veronika ^a,b   Russ, Verena ^a,b   Allmendinger, Lars ^a   Ogris, Manfred ^a,b   Wagner, Ernst ^a,b  

^a UNIVERSITY OF MUNICH   (Germany)

^b Center for NanoScience

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BIOCOMPATIBILITY; CELL CULTURE; EFFICIENCY; GENE EXPRESSION; PH; PH SENSORS;

CROSSLINKER; GENE CARRIER; METHOXY; METHOXYBENZALDEHYDE; NONVIRAL; PH SENSITIVE; POLYPLEXES; SENSITIVE GENES; STABLE POLYMERS; SYNTHESISED;

GENE TRANSFER;

AZIRIDINE DERIVATIVE; OLIGOETHYLENIMINE 1,1 BIS(2 ACRYLOYLOXY ETHOXY) [4 METHOXYPHENYL]METHANE; OLIGOETHYLENIMINE 2,2 BIS(N MALEIMIDOETHYLOXY)PROPANE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOCOMPATIBILITY; DRUG HALF LIFE; DRUG SYNTHESIS; FEMALE; GENE TRANSFER; GENE VECTOR; HYDROLYSIS; LIVER HISTOLOGY; MOUSE; NONHUMAN; NONVIRAL GENE DELIVERY SYSTEM; PH; PLASMID; TOXICITY;

MUS;

EID: 50249125911     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc8001858     Document Type: Article

References (39)

1. Boussif, O., Lezoualc'h, 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.
2. Zou, S. M., Erbacher, P., Remy, J. S., and Behr, J. P. (2000) Systemic linear polyethylenimine (L-PEI)-mediated gene delivery in the mouse. J. Gene Med. 2, 128-134.
3. Moghimi, S. M., Symonds, P., Murray, J. C., Hunter, A. C., Debska, G., and Szewczyk, A. (2005) A two-stage poly(ethylenimine)-mediated cytotoxicity: implications for gene transfer/therapy. Mol. Ther. 11, 990-995.
4. Chollet, P., Favrot, M. C., Hurbin, A., and Coll, J. L. (2002) Side-effects of a systemic injection of linear polyethylenimine-DNA complexes. J. Gene Med. 4, 84-91.
5. Gosselin, M. A., Guo, W., and Lee, R. J. (2001) Efficient gene transfer using reversibly cross-linked low molecular weight polyethylenimine. Bioconjugate Chem. 12, 989-994.
6. Kloeckner, J., Wagner, E., and Ogris, M. (2006) Degradable gene carriers based on oligomerized polyamines. Eur. J. Pharm. Sci. 29, 414-425.
7. 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.
8. Lee, Y., Mo, H., Koo, H., Park, J. Y., Cho, M. Y., Jin, G. W., and Park, J. S. (2007) Visualization of the degradation of a disulfide polymer, linear poly(ethylenimine sulfide), for gene delivery. Bioconjugate Chem. 18, 13-18.
9. Christensen, L. V., Chang, C. W., Kim, W. J., Kim, S. W., Zhong, Z., Lin, C., Engbersen, J. F., and Feijen, J. (2006) Reducible poly(amido ethylenimine)s designed for triggered intracellular gene delivery. Bioconjugate Chem. 17, 1233-1240.
10. Thomas, M., Ge, Q., Lu, J. J., Chen, J., and Klibanov, A. M. (2005) Cross-linked small polyethylenimines: while still nontoxic, deliver DNA efficiently to mammalian cells in vitro and in vivo. Pharm. Res. 22, 373-380.
11. Forrest, M. L., Koerber, J. T., and Pack, D. W. (2003) A degradable polyethylenimine derivative with low toxicity for highly efficient gene delivery. Bioconjugate Chem. 14, 934-940.
12. Russ, V., Elfberg, H., Thoma, C., Kloeckner, J., Ogris, M., and Wagner, E. (2008) Novel degradable oligoethylenimine acrylate ester-based pseudodendrimers for in vitro and in vivo gene transfer. Gene Ther. 15, 18-29.
13. Kim, Y. H., Park, J. H., Lee, M., Kim, Y. H., Park, T. G., and Kim, S. W. (2005) Polyethylenimine with acid-labile linkages as a biodegradable gene carrier. J. Controlled Release 103, 209-219.
14. Wang, J., Mao, H. Q., and Leong, K. W. (2001) A novel biodegradable gene carrier based on polyphosphoester. J. Am. Chem. Soc. 123, 9480-9481.
15. Zhao, Z., Wang, J., Mao, H. Q., and Leong, K. W. (2003) Polyphosphoesters in drug and gene delivery. Adv. Drug Delivery Rev. 55, 483-499.
16. Murthy, N., Thng, Y. X., Schuck, S., Xu, M. C., and Frechet, J. M. (2002) A novel strategy for encapsulation and release of proteins: hydrogels and microgels with acid-labile acetal cross-linkers. J. Am. Chem. Soc. 124, 12398-12399.
17. Paramonov, S. E., Bachelder, E. M., Beaudette, T. T., Standley, S. M., Lee, C. C., Dashe, J., and Frechet, J. M. (2008) Fully Acid-degradable biocompatible polyacetal microparticles for drug delivery. Bioconjugate Chem. 19, 911-919.
18. Srinivasachar, K., and Neville, D. M., Jr. (1989) New protein cross-Unking reagents that are cleaved by mild acid. Biochemistry 28, 2501-2509.
19. Chan, Y., Bulmus, V., Zareie, M. H., Byrne, F. L., Barner, L., and Kavallaris, M. (2006) Acid-cleavable polymeric coreshell particles for delivery of hydrophobic drugs. J. Controlled Release 115, 197-207.
20. Brissault, B., Kichler, A., Guis, C., Leborgne, C., Danos, O., and Cheradame, H. (2003) Synthesis of linear polyethylenimine derivatives for DNA transfection. Bioconjugate Chem. 14, 581-587.
21. Plank, C., Zatloukal, K., Cotten, M., Mechtler, K., and Wagner, E. (1992) Gene transfer into hepatocytes using asialoglycoprotein receptor mediated endocytosis of DNA complexed with an artificial tetra-antennary galactose ligand. Bioconjugate Chem. 3, 533-539.
22. Kloeckner, J., Bruzzano, S., Ogris, M., and Wagner, E. (2006) Gene carriers based on hexanediol diacrylate linked oligoethylenimine: effect of chemical structure of polymer on biological properties. Bioconjugate Chem. 17, 1339-1345.
23. Kircheis, R., Kichler, A., Wallner, G., Kursa, M., Ogris, M., Felzmann, T., Buchberger, M., and Wagner, E. (1997) Coupling of cell-binding ligands to polyethylenimine for targeted gene delivery. Gene Ther. 4, 409-418.
24. Boeckle, S., von Gersdorff, K., van der Piepen, S., Culmsee, C., Wagner, E., and Ogris, M. (2004) Purification of polyethylenimine polyplexes highlights the role of free polycations in gene transfer. J. Gene Med. 6, 1102-1111.
25. de Wolf, H. K., Luten, J., Snel, C. J., Oussoren, C., Hennink, W. E., and Storm, G. (2005)In vivo tumor transfection mediated by polyplexes based on biodegradable poly(DMAEA)-phosphazene. J. Controlled Release.
26. Kulkarni, R. P., Mishra, S., Fraser, S. E., and Davis, M. E. (2005) Single cell kinetics of intracellular, nonviral, nucleic acid delivery vehicle acidification and trafficking. Bioconjugate Chem. 16, 986-994.
27. Guo, X., and Szoka, F. C., Jr. (2003) Chemical approaches to triggerable lipid vesicles for drug and gene delivery. Acc. Chem. Res. 36, 335-341.
28. Heller, J., Barr, J., Ng, S. Y., Abdellauoi, K. S., and Gurny, R. (2002) Poly(ortho esters): synthesis, characterization, properties and uses. Adv. Drug Delivery Rev. 54, 1015-1039.
29. Murthy, N., Campbell, J., Fausto, N., Hoffman, A. S., and Stayton, P. S. (2003) Bioinspired pH-responsive polymers for the intracellular delivery of biomolecular drugs. Bioconjugate Chem. 14, 412-419.
30. Li, W., Huang, Z., MacKay, J. A., Grube, S., and Szoka, F. C., Jr. (2005) Low-pH-sensitive poly(ethylene glycol) (PEG)-stabilized plasmid nanolipoparticles: effects of PEG chain length, lipid composition and assembly conditions on gene delivery. J. Gene Med. 7, 67-79.
31. Knorr, V., Allmendinger, L., Walker, G. F., Paintner, F. F., and Wagner, E. (2007) An acetal-based PEGylation reagent for pH-sensitive shielding of DNA polyplexes. Bioconjugate Chem. 18, 1218-1225.
32. Saito, G., Swanson, J. A., and Lee, K. D. (2003) Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities. Adv. Drug Delivery Rev. 55, 199-215.
33. Lim, Y. B., Kim, S. M., Suh, H., and Park, J. S. (2002) Biodegradable, endosome disruptive, and cationic network-type polymer as a highly efficient and nontoxic gene delivery carrier. Bioconjugate Chem. 13, 952-957.
34. 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.
35. Wightman, L., Kircheis, R., Rossler, V., Carotta, S., Ruzicka, R., Kursa, M., and Wagner, E. (2001) Different behavior of branched and linear polyethylenimine for gene delivery in vitro and in vivo. J Gene Med. 3, 362-372.
36. Sonawane, N. D., Szoka, F. C., Jr., and Verkman, A. S. (2003) Chloride accumulation and swelling in endosomes enhances DNA transfer by polyamine-DNA polyplexes. J. Biol. Chem. 278, 44826-44831.
37. Rozema, D. B., Lewis, D. L., Wakefield, D. H., Wong, S. C., Klein, J. J., Roesch, P. L., Bertin, S. L., Reppen, T. W., Chu, Q., Blokhin, A. V., Hagstrom, J. E., and Wolff, J. A. (2007) Dynamic PolyConjugates for targeted in vivo delivery of siRNA to hepatocytes. Proc. Natl. Acad. Sci. U.S.A. 104, 12982-12987.
38. Meyer, M., Philipp, A., Oskuee, R., Schmidt, C., and Wagner, E. (2008) Breathing life into polycations: functionalization with pH-responsive endosomolytic peptides and polyethylene glycol enables siRNA delivery. J. Am. Chem. Soc. 130, 3272-3273.
39. Walker, G. F., Fella, C., Pelisek, J., Fahrmeir, J., Boeckle, S., Ogris, M., and Wagner, E. (2005) Toward synthetic viruses: endosomal pH-triggered deshielding of targeted polyplexes greatly enhances gene transfer in vitro and in vivo. Mol. Ther. 11, 418-425.