Cationic phospholipids forming cubic phases: Lipoplex structure and transfection efficiency

Molecular Pharmaceutics

Volumn 5, Issue 5, 2008, Pages 739-744

  Koynova, Rumiana ^a   Wang, Li ^a   MacDonald, Robert C ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Cationic phospholipid; Cubic phase; Hexagonal; Lamellar; Lipoplex; O alkyl phosphatidylcholine; Transfection

Indexed keywords

1,2 DIERUCOYL SN GLYCERO 3 ETHYLPHOSPHOCHOLINE; 1,2 DIOLEOYL SN GLYCERO 3 HEXYLPHOSPHOCHOLINE; CATION; LIPOPLEX; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; UNCLASSIFIED DRUG;

ARTICLE; DISPERSION; DNA VECTOR; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; LIPID TRANSPORT; LIPOSOMAL DELIVERY; NONVIRAL GENE DELIVERY SYSTEM; NUCLEIC ACID STRUCTURE; PRIORITY JOURNAL;

CATIONS; CELLS, CULTURED; DNA; HUMANS; MACROMOLECULAR SUBSTANCES; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; PARTICLE SIZE; PHASE TRANSITION; PHOSPHATIDYLCHOLINES; PHOSPHOLIPIDS; TEMPERATURE; TRANSFECTION;

EID: 56049093246     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp800011e     Document Type: Article

References (31)

1. Lobo, B. A.; Vetro, J. A.; Suich, D. M.; Zuckermann, R. N.; Middaugh, C. R. Structure/function analysis of peptoid/lipitoid: DNA complexes. J. Pharm. Sci. 2003, 92, 1905-1918.
2. Gaucheron, J.; Wong, T.; Wong, E. F.; Maurer, N.; Cullis, P. R. Synthesis and properties of novel tetraalkyl cationic lipids. Bioconjugate Chem. 2002, 13, 671-675.
3. Niculescu-Duvaz, D.; Heyes, J.; Springer, C. J. Structure-activity relationship in cationic lipid mediated gene transfection. Curr. Med. Chem. 2003, 10, 1233-1261.
4. Subramanian, M.; Holopainen, J. M.; Paukku, T.; Eriksson, O.; Huhtaniemi, I.; Kinnunen, P. K. J. Characterisation of three novel cationic lipids as liposomal complexes with DNA. Biochim. Biophys. Acta - Biomembranes 2000, 1466, 289-305.
5. Jaaskelainen, I.; Steinberg, B.; Monkkonen, J.; Urtti, A. Physicochemical and morphological properties of complexes made of cationic liposomes and oligonucleotides. Int. J. Pharm. 1998, 167, 191-203.
6. Song, Y. K.; Liu, F.; Chu, S. Y.; Liu, D. X. Characterization of cationic liposome-mediated gene transfer in vivo by intravenous administration. Hum. Gene Ther. 1997, 8, 1585-1594.
7. Ghosh, Y. K.; Visweswariah, S. S.; Bhattacharya, S. Advantage.of the ether linkage between the positive charge and the cholesteryl skeleton in cholesterol-based amphiphiles as vectors for gene delivery. Bioconjugate Chem. 2002, 13, 378-384.
8. Luzzati, V.; Tardieu, A. Lipid Phases - Structure and Structural Transitions. Annu. Rev. Phys. Chem. 1974, 25, 79-94.
9. Seddon, J. M.; Templer, R. H. Polymorphism of lipid-water systems. In Handbook of Biological Physics; Lipowsky, R., Sackmann, E. Eds.; Elsevier Science: Amsterdam, 1995; pp 97-160.
10. Koltover, I.; Salditt, T.; Radler, J. O.; Safinya, C. R. An inverted hexagonal phase of cationic liposome-DNA complexes related to DNA release and delivery. Science 1998, 281, 78-81.
11. Zuhorn, I. S.; Hoekstra, D. On the mechanism of cationic amphiphile-mediated transfection. To fuse or not to fuse: Is that the question? J. Membr. Biol. 2002, 189, 167-179.
12. Smisterova, J.; Wagenaar, A.; Stuart, M. C. A.; Polushkin, E.; ten Brinke, G.; Hulst, R.; Engberts, J. B. F. N.; Hoekstra, D. Molecular shape of the cationic lipid controls the structure of cationic lipid/ dioleylphosphatidylethanolamine-DNA complexes and the efficiency of gene delivery. J. Biol. Chem. 2001, 276, 47615-47622.
13. Simberg, D.; Danino, D.; Talmon, Y.; Minsky, A.; Ferrari, M. E.; Wheeler, C. J.; Barenholz, Y. Phase behavior, DNA ordering, and size instability of cationic lipoplexes - Relevance to optimal transfection activity. J. Biol. Chem. 2001, 276, 47453-47459.
14. Rakhmanova, V. A.; McIntosh, T. J.; MacDonald, R. C. Effects of dioleoylphosphatidylethanolamine on the activity and structure of O-alkyl phosphatidylcholine-DNA transfection complexes. Cell Mol. Biol. Lett. 2000, 5, 51-65.
15. Simberg, D.; Danino, D.; Talmon, Y.; Minsky, A.; Ferrari, M. E.; Wheeler, C. J.; Barenholz, Y. Phase behavior, DNA ordering and size instability of cationic lipoplexes: Relevance to optimal transfection activity. J. Liposome Res. 2003, 13, 86-87.
16. Congiu, A.; Pozzi, D.; Esposito, C.; Castellano, C.; Mossa, G. Correlation between structure and transfection efficiency: A study of DC-Chol-DOPE/DNA complexes. Colloids Surf., B 2004, 36, 43-48.
17. Ross, P. C.; Hensen, M. L.; Supabphol, R.; Hui, S. W. Multilamellar cationic liposomes are efficient vectors for in vitro gene transfer in serum. J. Liposome Res. 1998, 8, 499-520.
18. Wang, L.; Koynova, R.; Parikh, H.; MacDonald, R. C. Transfection activity of binary mixtures of cationic O-substituted phosphatidylcholine derivatives: The hydrophobic core strongly modulates their physical properties and DNA delivery efficacy. Biophys. J. 2006, 91, 3692-3706.
19. Koynova, R.; Wang, L.; Tarahovsky, Y.; MacDonald, R. C. Lipid phase control of DNA delivery. Bioconjugate Chem. 2005, 16, 1335-1339.
20. MacDonald, R. C.; Rakhmanova, V. A.; Choi, K. L.; Rosenzweig, H. S.; Lahiri, M. K. O-ethylphosphatidylcholine: A metabolizable cationic phospholipid which is a serum-compatible DNA transfection agent. J. Pharm. Sci. 1999, 88, 896-904.
21. Rosenzweig, H. S.; Rakhmanova, V. A.; McIntosh, T. J.; MacDonald, R. C. O-alkyl dioleoylphosphatidylcholinium compounds: The effect of varying alkyl chain length on their physical properties and in vitro DNA transfection activity. Bioconjugate Chem 2000, 11, 306-313.
22. Koynova, R.; MacDonald, R. C. Columnar DNA superlattices in lamellar o-ethylphosphatidylcholine lipoplexes: Mechanism of the gel-liquid crystalline lipid phase transition. Nano Lett. 2004, 4, 1475-1479.
23. Koynova, R.; MacDonald, R. C. Mixtures of cationic lipid O-ethylphosphatidylcholine with membrane lipids and DNA: Phase diagrams. Biophys. J. 2003, 85, 2449-2465.
24. Hammersley, A. P.; Svensson, S. O.; Hanfland, M.; Fitch, A. N.; Hausermann, D. Two-dimensional detector software: From real detector to idealised image or two-theta scan. High Pressure Res. 1996, 14, 235-248.
25. Radler, J. O.; Koltover, I.; Salditt, T.; Safinya, C. R. Structure of DNA-cationic liposome complexes: DNA intercalation in multilamellar membranes in distinct interhelical packing regimes. Science 1997, 275, 810-814.
26. Kasper, J. S.; Lonsdale, K. International Tables for X-ray Crystallography; Riedel Publishing Company: Dordrecht, The Netherlands, 1985.
27. Koynova, R.; MacDonald, R. C. Cationic O-ethylphosphatidylcholines and their lipoplexes: Phase behavior aspects, structural organization and morphology. Biochim. Biophys. Acta - Biomembranes 2003, 1613, 39-48.
28. MacDonald, R. C.; Ashley, G. W.; Shida, M. M.; Rakhmanova, V. A.; Tarahovsky, Y. S.; Pantazatos, D. P.; Kennedy, M. T.; Pozharski, E. V.; Baker, K. A.; Jones, R. D.; Rosenzweig, H. S.; Choi, K. L.; Qiu, R. Z.; McIntosh, T. J. Physical and biological properties of cationic triesters of phosphatidylcholine. Biophys. J 1999, 77, 2612-2629.
29. Simberg, D.; Danino, D.; Talmon, Y.; Minsky, A.; Ferrari, M. E.; Wheeler, C. J.; Barenholz, Y. Phase behavior, DNA ordering, and size instability of cationic lipoplexes - Relevance to optimal transfection activity. J. Biol. Chem. 2001, 276, 47453-47459.
30. Koynova, R.; Wang, L.; MacDonald, R. C. An intracellular lamellar - nonlamellar phase transition rationalizes the superior performance of some cationic lipid transfection agents. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 14373-14378.
31. Koynova, R.; Tarahovsky, Y.; Wang, L.; MacDonald. R. C. Lipoplex formulation of superior efficacy exhibits high surface activity and fusogenicity, and readily releases DNA. Biochim. Biophys. Acta - Biomembranes 2007, 1768, 375-386.