Evaluation of cationic assemblies constructed with amino acid based lipids for plasmid DNA delivery

Bioconjugate Chemistry

Volumn 19, Issue 5, 2008, Pages 1055-1063

  Obata, Yosuke ^a   Suzuki, Daisuke ^a   Takeoka, Shinji ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; BIOMOLECULES; DNA; EFFICIENCY; GENE EXPRESSION; GENE TRANSFER;

AMINO-ACIDS; CATIONIC HEADGROUPS; CATIONIC LIPIDS; CATIONICS; DNA DELIVERY; EXPRESSION EFFICIENCY; GENES EXPRESSION; L-GLUTAMATE; LIPOPLEXES; PLASMID DNA;

LIPIDS;

1,5 DIHEXADECYL GLUTAMATE; 1,5 DIOCTADECYL GLUTAMATE; 1,5 DITETRADECYL GLUTAMATE; 1,5 DITETRADECYL N ARGINYL GLUTAMATE; 1,5 DITETRADECYL N LYSYL GLUTAMATE; ARGININE; BOVINE SERUM ALBUMIN; GLUTAMIC ACID DERIVATIVE; HISTIDINE; LIPID; LIPOFECTAMINE; LIPOFECTAMINE2000; LIPOPLEX; LUCIFERASE; LYSINE; PLASMID DNA; PLASMID VECTOR;

ANIMAL CELL; ARTICLE; CALORIMETRY; CELL STRAIN COS7; CONTROLLED STUDY; CYTOTOXICITY; ENZYME ACTIVITY; GEL ELECTROPHORESIS; GENE EXPRESSION; GENE TARGETING; GENE TRANSFER; GENETIC TRANSFECTION; LIPID COMPOSITION; LIPOGENESIS; MEMBRANE FUSION; NONHUMAN; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL;

BOVINAE;

EID: 44349177460     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc700416u     Document Type: Article

References (48)

1. Raper, S. E., Yudkoff, M., Chirmule, N., Gao, G. P., Nunes, F., Haskal, Z. J., Furth, E. E., Propert, K. J., Robinson, M. B., Magosin, S., Simoes, H., Speicher, L., Hughes, J., Tazelaar, J., Wivel, N. A., Wilson, J. M., and Batshaw, M. L. (2002) A pilot study of in vivo liver-directed gene transfer with an adenoviral vector in partial ornithine transcarbamylase deficiency. Hum. Gene Ther. 13, 163-175.
2. Itaka, K., Yamauchi, A., Harada, K., Nakamura, H., Kawaguchi, H., and Kataoka, K. (2003) Polyion complex micelles from plasmid DNA and poly(ethyleneglycol)-poly(L-lysine) block copolymer as serum-tolerable polyplex system: Physicochemical properties of micelles relevant to gene transfection efficiency. Biomaterials 24, 4495-4506.
3. Okuda, T., Kidoaki, S., Ohsaki, M., Koyama, Y., Yoshikawa, K., Niidome, T., and Aoyagi, H. (2003) Time-dependent complex formation of dendritic poly (L-lysine) with plasmid DNA and correlation with in vitro transfection efficiencies. Org. Biomol. Chem. 1, 1270-1273.
4. Yamagata, M., Kawano, T., Shiba, K., Mori, T., Katayama, Y., and Niidome, T. (2007) Structural advantage of dendritic poly(L-lysine) for gene delivery into cells. Bioorg. Med. Chem. 15, 526-32.
5. Gebhart, C. L., Sriadibhatla, S., Vinogradov, S., Lemieux, P., Alakhov, V., and Kabanov, A. V. (2002) Design and formulation of polyplexes based on pluronic-polyethyleneimine conjugates for gene transfer. Bioconjugate Chem. 13, 937-944.
6. Banerjee, P., Weissleder, R., and Bogdanov, A., Jr. (2006) Linear polyethyleneimine grafted to a hyperbranched polyethylene glycol)-like core: A copolymer for gene delivery. Bioconjugate Chem. 17, 125-131.
7. Goula, D., Remy, J. S., Erbacher, P., Wasowicz, M., Levi, G., Abdallah, B., and Demeneix, B. A. (1998) Size, diffusibility and transfection performance of linear PEI/DNA complexes in the mouse central nervous system. Gene Ther. 5, 712-717.
8. Takeuchi, Y., Kurohane, K., Ichikawa, K., Yonezawa, S., Ori, H., Koishi, T., Nango, M., and Oku, N. (2003) Polycation liposome enhances the endocytic uptake of photosensitizer into cells in the presence of serum. Bioconjugate Chem. 14, 790-796.
9. Wong, K., Sun, G., Zhang, X. Q., Dai, H., Liu, Y., He, C. B., and Leong, K. W. (2006) PEI-g-chitosan, a novel gene delivery system with transfection efficiency comparable to polyethylenimine in vitro and after liver administration in vivo. Bioconjugate Chem. 17, 152-158.
10. Chan, P., Kurisawa, M., Chung, J. E., and Yang, Y. Y. (2007) Synthesis and characterization of chitosan-g-poly(ethylene glycol)-folate as a non-viral carrier for tumor-targeted gene delivery. Biomaterials 28, 540-549.
11. Lavertu, M., Méthot, S., Tran-Khanh, N., and Buschmann, M. D. (2007) High efficiency gene transfer using chitosan/DNA nanoparticles with specific combinations of molecular weight and degree of deacetylation. Biomaterials 27, 4815-4824.
12. Cullis, P. R., Wheeler, J. J., Palmer, L., Ossanlou, M., MacLachlan, I., Graham, R. W., Zhang, Y. P., Hope, M. J., and Scherrer, P. (1999) Stabilized plasmid-lipid particles: Construction and characterization. Gene Ther. 6, 271-281.
13. Wheeler, C. J., Felgner, P. L., and Tsai, Y. J. (1996) A novel cationic lipid greatly enhances plasmid DNA delivery and expression in mouse lung. Proc. Natl. Acad. Sci. U.S.A. 93, 11454-11459.
14. Dass, C. R., and Burton, M. A. (2002) A model for evaluating selective delivery of plasmid DNA to tumors via the vasculature. Cancer Biother. Radiopharm. 17, 501-505.
15. Dass, C. R. (2004) Lipoplex-mediated delivery of nucleic acids: Factors affecting in vivo transfection. J. Mol. Med. 82, 579-591.
16. Tachibana, R., Harashima, H., Shinohara, Y., and Kiwada, H. (2001) Quantitative studies on the nuclear transport of plasmid DNA and gene expression employing nonviral vectors. Adv. Drug Delivery Rev. 52, 219-226.
17. Hama, S., Akita, H., Ito, H., Mizuguchi, R., and Hayakawa, H. (2006) Quantitative comparison of intracellular trafficking and nuclear transcription between adenoviral and lipoplex systems. Mol. Ther. 13, 786-794.
18. Nakanishi, M., and Noguchi, A. (2001) Confocal and probe microscopy to study gene transfection mediated by cationic liposomes with a cationic cholesterol derivative. Adv. Drug Delivery Rev. 52, 197-207.
19. Lechardeur, D., and Lukacs, G. L. (2002) Intracellular barriers to non-viral gene transfer. Curr. Gene Ther. 2, 183-194.
20. Zuhorn, I. S., and Hoekstra, D. (2002) On the mechanism of cationic amphiphile-mediated transfection. To fuse or not to fuse: Is that the question? J. Membr. Biol. 189, 167-179.
21. Xu, Y., and Szoka, F. C. (1996) Mechanism of DNA release from cationic liposome/DNA complexes used in cell transfection. Biochemistry 35, 5616-5623.
22. Ishida, T., Kirchmeier, M. J., Moase, E. H., Zalipsky, S., and Allen, T. M. (2001) Targeted delivery and triggered release of liposomal doxorubicin enhanced cytotoxicity against human B lymphoma cells. Biochim. Biophys. Acta 1515, 144-158.
23. Ellens, H., Bentz, J., and Szoka, F. C. (1984) pH-Induced destabilization of phosphatidylethanolamine-containing liposomes, Roles of Bilayer Contact. Biochemistry 23, 1532-1538.
24. Wheeler, J. J., Palmer, L., Ossanlou, M., MacLachlan, I., Graham, R. W., Zhang, Y. P., Hope, M. J., Scherrer, P., and Cullis, P. R. (1999) Stabilized plasmid-lipid particles: construction and characterization. Gene Ther. 6, 271-281.
25. Bailey, A. L., and Cullis, P. R. (1997) Membrane fusion with cationic liposomes: Effects of target membrane lipid composition. Biochemistry 36, 1628-34.
26. Bhattacharya, S., and Dileep, P. V. (1999) Synthesis of novel cationic lipids with oxyethylene spacers at the linkages between hydrocarbon chains and pseudoglyceryl backbone. Tetrahedron Lett. 40, 8167-8171.
27. Bajaj, A., Kondaiah, P., and Bhattacharya, S. (2007) Synthesis and gene transfer activities of novel serum compatible cholesterol-based gemini lipids possessing oxyethylene-type Spacers. J. Med. Chem. 50, 2432-2442.
28. Bajaj, A., Kondaiah, P., and Bhattacharya, S. (2007) Synthesis and gene transfer activities of novel serum compatible cholesterol-based Gemini lipids possessing oxyethylene-type spacers. Bioconjugate Chem. 18, 1537-1546.
29. Gaucheron, J., Santaella, C., and Vierling, P. (2001) Highly fluorinated lipospermines for gene transfer: Synthesis and evaluation of their in vitro transfection efficiency. Bioconjugate Chem. 12, 114-128.
30. Sen, J., and Chaudhuri, A. (2005) Design, syntheses, and transfection biology of novel non-cholesterol-based guanidinylated cationic lipids. J. Med. Chem. 48, 812-820.
31. Choi, J. S., Lee, E. J., Jang, H. S., and Park, J. S. (2001) New cationic liposomes for gene transfer into mammalian cells with high efficiency and low toxicity. Bioconjugate Chem. 12, 108-113.
32. Hasegawa, S., Hirashima, N., and Nakanishi, M. (2001) Microtubule involvement in the intracellular dynamics for gene transfection mediated by cationic liposomes. Gene Ther. 8, 1669-1673.
33. Bajaj, A., Paul, B., Indi, S. S., Kondaiah, P., and Bhattacharya, S. (2007) Effect of the Hydrocarbon Chain and Polymethylene Spacer Lengths on Gene Transfection Efficacies of Gemini Lipids Based on Aromatic Backbone. Bioconjugate Chem. 18, 2144-2158.
34. Kim, H. S., Moon, J., Kim, K. S., Choi, M. M., Lee, J. E., Heo, Y., Cho, D. H., Jang, D. O., and Park, Y. S. (2004) Gene-transferring efficiencies of novel diamino catonic lipids with varied hydrocarbon chain. Bioconjugate Chem. 15, 1095-1101.
35. Kim, H. S., Song, I. H., Kim, J. C., Kim, E. J., Jang, D. O., and Park, Y. S. (2006) In vitro and in vivo gene-transferring characteristics of novel cationic lipids, DMKD O, O′-dimyristyl-N-lysyl aspartate) and DMKE (O, O′-dimyristyl-N-lysyl glutamate. J. Controlled Release 115, 234-241.
36. Okamura, Y., Maekawa, I., Teramura, Y., Maruyama, H., Handa, M., Ikeda, Y., and Takeoka, S. (2005) Hemostatic effects of phospholipid vesicles carrying fibrinogen γ-chain dodecapeptide in vitro and in vivo. Bioconjugate Chem. 16, 1589-1596.
37. Takeoka, S. (2005) Production of artificial blood using molecular assembling science. Artif. Blood 13, 136-147.
38. Shimizu, T. (2003) Bottom-up synthesis and norphological control of high-axial-ratio nanostructures through molecular self-assembly. Polym. J. 35, 1-22.
39. Yamada, N., Ariga, K., Naito, M., Matsubara, K., and Koyama, E. (1998) Regulation of β-sheet structures within amyloid-like β-sheet assemblage from tripeptide derivatives. J. Am. Chem. Soc. 120, 12192-12199.
40. Lauf, U., Fahr, A., Westesen, K., and Ulrich, A. S. (2004) Novel lipid nanotubes in dispersions of DMPC. ChemPhysChem 5, 1246-1249.
41. Heyes, J. A., Duvaz, D. N., Cooper, R. G., and Springer, C. J. (2002) Synthesis of novel cationic lipids: Effect of structural modification on the efficacy of gene transfer. J. Med. Chem. 45, 99-114.
42. Rädler, J. O., Koltover, I., Salditt, T., and Safinya, C. R. (1997) Structure of DNA-cationic liposome complexes: DNA intercalation in multi-lamellar membranes in distinct interhelical packing regimes. Science 275, 810-814.
43. Zantl, R., Baicu, L., Artzner, F., Sprenger, I., Rapp, G., and Rädler, J. O. (1999) Thermotropic phase behavior of cationic lipid-DNA complexes compared to binary lipid mixtures. J. Phys. Chem. B 103, 10300-10310.
44. Felgner, P. L., Gadek, T. R., Holm, M., Roman, R., Chan, H. W., Wenz, M., Northrop, J. P., Ringold, G. M., and Danielsen, M. (1987) Lipofectin: a highly efficient, lipid-mediated DNA transfection procedure. Proc. Natl. Acad. Sci. U.S.A. 84, 7413-7417.
45. Floch, V., Audrezet, M. P., Guillaume, C., Gobin, E., Bolen, G. L., Clement, J. C., Yaouanc, J. J., Abbayes, H. D., Mercier, B., Leroy, J. P., Abgrall, J. F., and Ferec, C. (1998) Transgene expression kinetics after transition with cationic phosphonolipids in hematopoietic nonadherent cells. Biochim. Biophys. Acta 1371, 53-70.
46. Floch, V., Loisel, S., Guenin, E., Herve, A. C., Clement, J. C., Yaouanc, J. J., Abbayes, H. D., and Ferec, C. (2000) Cation substitution in cationic phosphonolipids: A new concept to improve transfection activity and decrease cellular toxicity. J. Med. Chem. 43, 4617-4628.
47. Allen, T. M., and Cleland, L. G. (1980) Serum-induced leakage of liposome contents. Biochim. Biophys. Acta 597, 418-426.
48. Leventis, R., and Silvirus, J. R. (1990) Interactions of mammalian cells with lipid dispersion containing metabolizable cationic amphiphiles. Biochim. Biophys. Acta 1023, 124-132.