Cationic lipids: Molecular structure/transfection activity relationships and interactions with biomembranes

Topics in Current Chemistry

Volumn 296, Issue , 2010, Pages 51-93

  Koynova, Rumiana ^a,b   Tenchov, Boris ^c  

^a OHIO STATE UNIVERSITY   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c BULGARIAN ACADEMY OF SCIENCES   (Bulgaria)

Author keywords

Cationic lipid; Lipoplex; Nucleic acid; Phase transition; Transfection

Indexed keywords

CATION; LIPID; NUCLEIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GENETIC TRANSFECTION; GENETICS; METABOLISM; SYNTHESIS;

CATIONS; LIPIDS; MOLECULAR STRUCTURE; NUCLEIC ACIDS; TRANSFECTION;

EID: 78649276616     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2010_67     Document Type: Article

References (133)

1. Venter JC, Adams MD, Myers EW et al (2001) The sequence of the human genome. Science 291:1304-1351
2. Flotte TR (2007) Gene therapy: the first two decades and the current state-of-the-art. J Cell Physiol 213:301-305
3. Giacca M (2007) Virus-mediated gene transfer to induce therapeutic angiogenesis: where do we stand? Int J Nanomedicine 2:527-540
4. Hendrie PC, Russell DW (2005) Gene targeting with viral vectors. Mol Ther 12:9-17
5. Felgner PL, Ringold GM (1989) Cationic liposome-mediated transfection. Nature 337:387-388
6. Gao X, Huang L (1991) A novel cationic liposome reagent for efficient transfection of mammalian cells. Biochem Biophys Res Commun 179:280-285
7. Leventis R, Silvius JR (1990) Interactions of mammalian cells with lipid dispersions containing novel metabolizable cationic amphiphiles. Biochim Biophys Acta 1023:124-132
8. Gaucheron J, Wong T, Wong EF et al (2002) Synthesis and properties of novel tetraalkyl cationic lipids. Bioconjug Chem 13:671-675
9. Ghosh YK, Visweswariah SS, Bhattacharya S (2002) Advantage of the ether linkage between the positive charge and the cholesteryl skeleton in cholesterol-based amphiphiles as vectors for gene delivery. Bioconjug Chem 13:378-384
10. Jaaskelainen I, Sternberg B, Monkkonen J et al (1998) Physicochemical and morphological properties of complexes made of cationic liposomes and oligonucleotides. Int J Pharm 167:191-203
11. Lobo BA, Vetro JA, Suich DM et al (2003) Structure/function analysis of peptoid/lipitoid: DNA complexes. J Pharm Sci 92:1905-1918
12. Niculescu-Duvaz D, Heyes J, Springer CJ (2003) Structure-activity relationship in cationic lipid mediated gene transfection. Curr Med Chem 10:1233-1261
13. Song YK, Liu F, Chu SY et al (1997) Characterization of cationic liposome-mediated gene transfer in vivo by intravenous administration. Human Gene Ther 8:1585-1594
14. Subramanian M, Holopainen JM, Paukku T et al (2000) Characterisation of three novel cationic lipids as liposomal complexes with DNA. Biochim Biophys Acta-Biomembranes 1466:289-305
15. Pinnaduwage P, Schmitt L, Huang L (1989) Use of a quaternary ammonium detergent in liposome mediated DNA transfection of mouse L-cells. Biochim Biophys Acta 985:33-37
16. MacDonald RC, Ashley GW, Shida MM et al (1999) Physical and biological properties of cationic triesters of phosphatidylcholine. Biophys J 77:2612-2629
17. MacDonald RC, Rakhmanova VA, Choi KL et al (1999) O- Ethylphosphatidylcholine: a metabolizable cationic phospholipid which is a serum-compatible DNA transfection agent. J Pharm Sci 88:896-904
18. Solodin I, Brown CS, Heath TD (1996) Synthesis of phosphotriester cationic phospholipids. Cationic lipids 2. Synlett 5:457-458 (Pubitemid 126426640)
19. Koynova R, MacDonald RC (2003) Cationic O-ethylphosphatidylcholines and their lipo-plexes: phase behavior aspects, structural organization and morphology. Biochim Biophys Acta-Biomembranes 1613:39-48
20. Koynova R, Wang L, MacDonald RC (2008) Cationic phospholipids forming cubic phases: lipoplex structure and transfection efficiency. Mol Pharm 5:739-744
21. Wang L, Koynova R, Parikh H et al (2006) 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 91:3692-3706
22. Lewis RNAH, Winter I, Kriechbaum M et al (2001) Studies of the structure and organization of cationic lipid bilayer membranes: calorimetric, spectroscopic, and X-ray diffraction studies of linear saturated P-O-ethyl phosphatidylcholines. Biophys J 80:1329-1342
23. Winter I, Pabst G, Rappolt M et al (2001) Refined structure of 1, 2-diacyl-P-O-ethylpho-sphatidylcholine bilayer membranes. Chem Phys Lipids 112:137-150
24. Rakhmanova VA, McIntosh TJ, MacDonald RC (2000) Effects of dioleoylphosphatidyletha-nolamine on the activity and structure of O-alkyl phosphatidylcholine-DNA transfection complexes. Cell Mol Biol Lett 5:51-65
25. Rosenzweig HS, Rakhmanova VA, McIntosh TJ et al (2000) O-Alkyl dioleoylphosphatidyl-cholinium compounds: the effect of varying alkyl chain length on their physical properties and in vitro DNA transfection activity. Bioconjug Chem 11:306-313
26. Koynova R, Tenchov B, Wang L et al (2009) Hydrophobic moiety of cationic lipids strongly modulates their transfection activity. Mol Pharm 6:951-958
27. Heyes JA, Niculescu-Duvaz D, Cooper RG et al (2002) Synthesis of novel cationic lipids: effect of structural modification on the efficiency of gene transfer. J Med Chem 45:99-114
28. Karmali PP, Chaudhuri A (2007) Cationic liposomes as non-viral carriers of gene medicines: resolved issues, open questions, and future promises. Med Res Rev 27:696-722
29. Karmali PP, Kumar VV, Chaudhuri A (2004) Design, syntheses and in vitro gene delivery efficacies of novel mono-, di- and trilysinated cationic lipids: a structure-activity investigation. J Med Chem 47:2123-2132
30. Floch V, Loisel S, Guenin E et al (2000) Cation substitution in cationic phosphonolipids: a new concept to improve transfection activity and decrease cellular toxicity. J Med Chem 43:4617-4628
31. Behr JP, Demeneix B, Loeffler JP et al (1989) Efficient gene-transfer into mammalian primary endocrine-cells with lipopolyamine-coated DNA. Proc Natl Acad Sci USA 86:6982-6986
32. Ferrari ME, Nguyen CM, Zelphati O et al (1998) Analytical methods for the characterization of cationic lipid nucleic acid complexes. Hum Gene Ther 9:341-351
33. de Lima MCP, Neves S, Filipe A et al (2003) Cationic liposomes for gene delivery: from biophysics to biological applications. Curr Med Chem 10:1221-1231
34. Wheeler CJ, Felgner PL, Tsai YJ et al (1996) A novel cationic lipid greatly enhances plasmid DNA delivery and expression in mouse lung. Proc Natl Acad Sci USA 93:11454-11459
35. Felgner JH, Kumar R, Sridhar CN et al (1994) Enhanced gene delivery and mechanism studies with a novel series of cationic lipid formulations. J Biol Chem 269:2550-2561
36. Lee ER, Marshall J, Siegel CS et al (1996) Detailed analysis of structures and formulations of cationic lipids for efficient gene transfer to the lung. Hum Gene Ther 7:1701-1717
37. Kearns MD, Donkor AM, Savva M (2008) Structure-transfection activity studies of nove cationic cholesterol-based amphiphiles. Mol Pharm 5:128-139
38. Bajaj A, Mishra SK, Kondaiah P et al (2008) Effect of the headgroup variation on the gene transfer properties of cholesterol based cationic lipids possessing ether linkage. Biochim Biophys Acta-Biomembranes 1778:1222-1236
39. Soltan MK, Ghonaim HM, El Sadek M et al (2009) Design and synthesis of N-4, N-9-disubstituted spermines for non-viral siRNA delivery - structure-activity relationship studies of transfection efficiency versus toxicity. Pharm Res 26:286-295
40. Ghosh YK, Visweswariah SS, Bhattacharya S (2000) Nature of linkage between the cationic headgroup and cholesteryl skeleton controls gene transfection efficiency. FEBS Lett 473:341-344
41. Rajesh M, Sen J, Srujan M et al (2007) Dramatic influence of the orientation of linker between hydrophilic and hydrophobic lipid moiety in liposomal gene delivery. J Am Chem Soc 129:11408-11420
42. Ghosh YK, Visweswariah SS, Bhattacharya S (2002) Advantage of the ether linkage between the positive charge and the cholesteryl skeleton in cholesterol-based amphiphiles as vectors for gene delivery. Bioconjug Chem 13:378-384
43. Obata Y, Saito S, Takeda N et al (2009) Plasmid DNA-encapsulating liposomes: effect of a spacer between the cationic head group and hydrophobic moieties of the lipids on gene expression efficiency. Biochim Biophys Acta-Biomembranes 1788:1148-1158
44. Horobin RW, Weissig V (2005) A QSAR-modeling perspective on cationic transfection lipids. 1. Predicting efficiency and understanding mechanisms. J Gene Med 7:1023-1034
45. Liu D, Qiao D, Li Z et al (2008) Structure-function relationship research of glycerol backbone-based cationic lipids for gene delivery. Chem Biol Drug Des 71:336-344
46. Koynova R, Tenchov B (2009) Cationic phospholipids - structure/ transfection activity relationships. Soft Matter 5:3187-3200
47. Tenchov BG, Wang L, Koynova R et al (2008) Modulation of a membrane lipid lamellar- nonlamellar phase transition by cationic lipids: a measure for transfection efficiency. Bio-chim Biophys Acta-Biomembranes 1778:2405-2412
48. Das A, Niven R (2001) Use of perfluorocarbon (Fluorinert) to enhance reporter gene expression following intratracheal instillation into the lungs of Balb/c mice: implications for nebulized delivery of plasmids. J Pharm Sci 90:1336-1344
49. Faneca H, Cabrita AS, Simoes S et al (2007) Evaluation of the antitumoral effect mediated by IL-12 and HSV-tk genes when delivered by a novel lipid-based system. Biochim Biophys Acta-Biomembranes 1768:1093-1102
50. Faneca H, Faustino A, de Lima MCP (2008) Synergistic antitumoral effect of vinblastine and HSV-Tk/GCV gene therapy mediated by albumin-associated cationic liposomes. J Control Release 126:175-184
51. Faneca H, Simoes S, de Lima MCP (2004) Association of albumin or protamine to lipo-plexes: enhancement of transfection and resistance to serum. J Gene Med 6:681-692
52. Gorman CM, Aikawa M, Fox B et al (1997) Efficient in vivo delivery of DNA to pulmonary cells using the novel lipid EDMPC. Gene Ther 4:983-992
53. McDonald RJ, Liggitt HD, Roche L et al (1998) Aerosol delivery of lipid: DNA complexes to lungs of rhesus monkeys. Pharm Res 15:671-679
54. Noone PG, Hohneker KW, Zhou ZQ et al (2000) Safety and biological efficacy of a lipid- CFTR complex for gene transfer in the nasal epithelium of adult patients with cystic fibrosis. Mol Ther 1:105-114
55. Hyvonen Z, Plotniece A, Riene I et al (2000) Novel cationic amphiphilic 1,4-dihydropyr-idine derivatives for DNA delivery. Biochim Biophys Acta-Biomembranes 1509:451-466
56. Yingyongnarongkul BE, Radchatawedchakoon W, Krajarng A et al (2009) High transfection efficiency and low toxicity cationic lipids with aminoglycerol-diamine conjugate. Bioorg Med Chem 17:176-188
57. Zhu L, Lu Y, Miller DD et al (2008) Structural and formulation factors influencing pyridi-nium lipid-based gene transfer. Bioconjug Chem 19:2499-2512
58. VanDerWoude I, Wagenaar A, Meekel AAP et al (1997) Novel pyridinium surfactants for efficient, nontoxic in vitro gene delivery. Proc Natl Acad Sci USA 94:1160-1165
59. Heyes J, Palmer L, Bremner K et al (2005) Cationic lipid saturation influences intracellular delivery of encapsulated nucleic acids. J Control Release 107:276-287
60. Aberle AM, Bennett MJ, Malone RW et al (1996) The counterion influence on cationic lipid-mediated transfection of plasmid DNA. Biochim Biophys Acta-Lipids Lipid Metabolism 1299:281-283
61. Koynova R, Brankov J, Tenchov B (1997) Modulation of lipid phase behavior by kosmo-tropic and chaotropic solutes - experiment and thermodynamic theory. Eur Biophys J Biophys Lett 25:261-274
62. Boukhnikachvili T, AguerreChariol O, Airiau M et al (1997) Structure of in-serum transfect-ing DNA-cationic lipid complexes. FEBS Lett 409:188-194
63. Lasic DD, Strey H, Stuart MCA et al (1997) The structure of DNA-liposome complexes. J Am Chem Soc 119:832-833
64. Radler JO, Koltover I, Salditt T et al (1997) Structure of DNA-cationic liposome complexes: DNA intercalation in multilamellar membranes in distinct interhelical packing regimes. Science 275:810-814
65. Bruinsma R (1998) Electrostatics of DNA cationic lipid complexes: isoelectric instability. Eur Phys J B 4:75-88
66. Hirsch-Lerner D, Barenholz Y (1999) Hydration of lipoplexes commonly used in gene delivery: follow-up by laurdan fluorescence changes and quantification by differential scanning calorimetry. Biochim Biophys Acta-Biomembranes 1461:47-57
67. Kennedy MT, Pozharski EV, Rakhmanova VA et al (2000) Factors governing the assembly of cationic phospholipid-DNA complexes. Biophys J 78:1620-1633
68. Pozharski EV, MacDonald RC (2007) Single lipoplex study of cationic lipoid-DNA, self-assembled complexes. Mol Pharm 4:962-974
69. Koynova R, MacDonald RC (2007) Natural lipid extracts and biomembrane-mimicking lipid compositions are disposed to form nonlamellar phases, and they release DNA from lipo-plexes most efficiently. Biochim Biophys Acta-Biomembranes 1768:2373-2382
70. Zelphati O, Nguyen C, Ferrari M et al (1998) Stable and monodisperse lipoplex formulations for gene delivery. Gene Ther 5:1272-1282
71. Takeuchi K, Ishihara M, Kawaura C et al (1996) Effect of zeta potential of cationic liposomes containing cationic cholesterol derivatives on gene transfection. FEBS Lett 397:207-209
72. Almofti MR, Harashima H, Shinohara Y et al (2003) Lipoplex size determines lipofection efficiency with or without serum. Mol Membr Biol 20:35-43
73. Ross PC, Hui SW (1999) Lipoplex size is a major determinant of in vitro lipofection efficiency. Gene Ther 6:651-659
74. Zhang JS, Huang L (2003) Cationic liposome-protamine-DNA complexes for gene delivery. Methods Enzymol 373:332-342
75. Rejman J, Oberle V, Zuhorn IS et al (2004) Size-dependent internalization of particles via the pathways of clathrin-and caveolae-mediated endocytosis. Biochem J 377:159-169
76. Hoekstra D, Rejman J, Wasungu L et al (2007) Gene delivery by cationic lipids: in and out of an endosome. Biochem Soc Trans 35:68-71
77. Lechardeur D, Verkman AS, Lukacs GL (2005) Intracellular routing of plasmid DNA during non-viral gene transfer. Adv Drug Deliv Rev 57:755-767
78. Prasad TK, Rangaraj N, Rao NM (2005) Quantitative aspects of endocytic activity in lipid-mediated transfections. FEBS Lett 579:2635-2642
79. Elouahabi A, Ruysschaert JM (2005) Formation and intracellular trafficking of lipoplexes and polyplexes. Mol Ther 11:336-347
80. Tyagi P, Wu PC, Chancellor M et al (2006) Recent advances in intravesical drug/gene delivery. Mol Pharm 3:369-379
81. Koynova R, Tarahovsky Y, Wang L et al (2007) Lipoplex formulation of superior efficacy exhibits high surface activity and fusogenicity, and readily releases DNA. Biochim Biophys Acta-Biomembranes 1768:375-386
82. Salditt T, Koltover I, Radler JO et al (1997) Two-dimensional smectic ordering of linear DNA chains in self-assembled DNA-cationic liposome mixtures. Phys Rev Lett 79:2582-2585
83. Artzner F, Zantl R, Rapp G et al (1998) Observation of a rectangular columnar phase in condensed lamellar cationic lipid-DNA complexes. Phys Rev Lett 81:5015-5018
84. Koynova R, MacDonald RC (2004) Columnar DNA superlattices in lamellar o-ethylpho-sphatidylcholine lipoplexes: mechanism of the gel-liquid crystalline lipid phase transition. Nano Lett 4:1475-1479
85. Congiu A, Pozzi D, Esposito C et al (2004) Correlation between structure and transfection efficiency: a study of DC-Chol-DOPE/DNA complexes. Coll Surf B Biointerfaces 36:43-48
86. Koltover I, Salditt T, Radler JO et al (1998) An inverted hexagonal phase of cationic liposome-DNA complexes related to DNA release and delivery. Science 281:78-81
87. Smisterova J, Wagenaar A, Stuart MCA et al (2001) Molecular shape of the cationic lipid controls the structure of cationic lipid/ dioleylphosphatidylethanolamine-DNA complexes and the efficiency of gene delivery. J Biol Chem 276:47615-47622
88. Francescangeli O, Pisani M, Stanic V et al (2004) Evidence of an inverted hexagonal phase in self-assembled phospholipid-DNA-metal complexes. Europhys Lett 67:669-675
89. Caracciolo G, Caminiti R (2005) Do DC-Chol/DOPE-DNA complexes really form an inverted hexagonal phase? Chem Phys Lett 411:327-332
90. Caracciolo G, Pozzi D, Caminiti R et al (2003) Structural characterization of a new lipid/DNA complex showing a selective transfection efficiency in ovarian cancer cells. Eur Phys J E 10:331-336
91. Lin AJ, Slack NL, Ahmad A et al (2003) Three-dimensional imaging of lipid gene-carriers: membrane charge density controls universal transfection behavior in lamellar cationic liposome-DNA complexes. Biophys J 84:3307-3316
92. Ross PC, Hensen ML, Supabphol R et al (1998) Multilamellar cationic liposomes are efficient vectors for in vitro gene transfer in serum. J Liposome Res 8:499-520
93. Simberg D, Danino D, Talmon Y et al (2003) Phase behavior, DNA ordering and size instability of cationic lipoplexes: relevance to optimal transfection activity. J Liposome Res 13:86-87
94. Legendre JY, Szoka FC (1992) Delivery of plasmid DNA into mammalian-cell lines using Ph-sensitive liposomes - comparison with cationic liposomes. Pharm Res 9:1235-1242
95. Zabner J, Fasbender AJ, Moninger T et al (1995) Cellular and molecular barriers to gene-transfer by a cationic lipid. J Biol Chem 270:18997-19007
96. Zhou XH, Huang L (1994) DNA transfection mediated by cationic liposomes containing lipopolylysine - characterization and mechanism of action. Biochim Biophys Acta-Biomem-branes 1189:195-203
97. Ashley GW, Shida MM, Qiu R et al (1996) Phosphatidylcholinium compounds: a new class of cationic phospholipids with transfection activin and unusual physical properties (abstract). Biophys J 70:88-A
98. Tarahovsky YS, Koynova R, MacDonald RC (2004) DNA release from lipoplexes by anionic lipids: correlation with lipid mesomorphism, interfacial curvature, and membrane fusion. Biophys J 87:1054-1064
99. Xu YH, Szoka FC (1996) Mechanism of DNA release from cationic liposome/DNA complexes used in cell transfection. Biochemistry 35:5616-5623
100. Zelphati O, Szoka FC (1996) Mechanism of oligonucleotide release from cationic liposomes. Proc Natl Acad Sci USA 93:11493-11498
101. Koynova R, Tenchov B (2009) Phase transitions of lipids. In: Begley TP (ed) Wiley encyclopedia of chemical biology. Wiley, Hoboken, NJ, pp 601-615
102. Seddon JM, Templer RH (1995) Polymorphism of lipid-water systems. In: Lipowsky R, Sackmann E (eds) Handbook of biological physics. Elsevier Science, Amsterdam, pp 97-160
103. Hafez IM, Maurer N, Cullis PR (2001) On the mechanism whereby cationic lipids promote intracellular delivery of polynucleic acids. Gene Ther 8:1188-1196
104. Koynova R, MacDonald RC (2003) Mixtures of cationic lipid O-ethylphosphatidylcholine with membrane lipids and DNA: phase diagrams. Biophys J 85:2449-2465
105. Lewis RNAH, McElhaney RN (2000) Surface charge markedly attenuates the nonlamellar phase-forming propensities of lipid bilayer membranes: calorimetric and P-31-nuclear magnetic resonance studies of mixtures of cationic, anionic, and zwitterionic lipids. Biophys J 79:1455-1464
106. Tarahovsky YS, Arsenault AL, MacDonald RC et al (2000) Electrostatic control of phos-pholipid polymorphism. Biophys J 79:3193-3200
107. Kleinschmidt JH, Tamm LK (2002) Structural transitions in short-chain lipid assemblies studied by P-31-NMR spectroscopy. Biophys J 83:994-1003
108. Koynova R, MacDonald RC (2005) Lipid transfer between cationic vesicles and lipid-DNA lipoplexes. Effect of serum. Biochim Biophys Acta-Biomembranes 1714:63-70
109. Simoes S, Pires P, Duzgunes N et al (1999) Cationic liposomes as gene transfer vectors: barriers to successful application in gene therapy. Curr Opin Mol Ther 1:147-157
110. Sen GL, Blau HM (2005) Argonaute 2/RISC resides in sites of mammalian mRNA decay known as cytoplasmic bodies. Nat Cell Biol 7:633-636
111. Lu JJ, Langer R, Chen JZ (2009) A novel mechanism is involved in cationic lipid-mediated functional siRNA delivery. Mol Pharm 6:763-771
112. Koynova R, Wang L, MacDonald RC (2006) An intracellular lamellar - nonlamellar phase transition rationalizes the superior performance of some cationic lipid transfection agents. Proc Natl Acad Sci USA 103:14373-14378
113. Lipid Data Bank (2000) http://www.lipidat.ul.ie/
114. Anderson DM, Gruner SM, Leibler S (1988) Geometrical aspects of the frustration in the cubic phases of lyotropic liquid-crystals. Proc Natl Acad Sci USA 85:5364-5368
115. Shearman GC, Ces O, Templer RH et al (2006) Inverse lyotropic phases of lipids and membrane curvature. J Phys Condens Matter 18:S1105-S1124
116. Templer RH, Seddon JM, Duesing PM et al (1998) Modeling the phase behavior of the inverse hexagonal and inverse bicontinuous cubic phases in 2:1 fatty acid phosphatidylcho-line mixtures. J Phys Chem B 102:7262-7271
117. Siegel DP (2005) Bicontinuous Liquid Crystals. In: Lynch ML, Spicer PT (eds) Bicontinuous liquid crystals. Taylor & Francis Group, CRC Press, Boca Raton, pp 59-98, Chap 4
118. Siegel DP, Epand RM (1997) The mechanism of lamellar-to-inverted hexagonal phase transitions in phosphatidylethanolamine: implications for membrane fusion mechanisms. Biophys J 73:3089-3111
119. Yang L, Huang HW (2002) Observation of a membrane fusion intermediate structure. Science 297:1877-1879
120. Farhood H, Serbina N, Huang L (1995) The role of dioleoyl phosphatidylethanolamine in cationic liposome-mediated gene-transfer. Biochim Biophys Acta-Biomembranes 1235:289-295
121. Zuhorn IS, Oberle V, Visser WH et al (2002) Phase behavior of cationic amphiphiles and their mixtures with helper lipid influences lipoplex shape, DNA translocation, and transfec-tion efficiency. Biophys J 83:2096-2108
122. Fletcher S, Ahmad A, Price WS et al (2008) Biophysical properties of CDAN/DOPE-analogue lipoplexes account for enhanced gene delivery. Chembiochem 9:455-463
123. Hong KL, Zheng WW, Baker A et al (1997) Stabilization of cationic liposome-plasmid DNA complexes by polyamines and poly(ethylene glycol)-phospholipid conjugates for efficient in vivo gene delivery. FEBS Lett 400:233-237
124. Liu Y, Mounkes LC, Liggitt HD et al (1997) Factors influencing the efficiency of cationic liposome-mediated intravenous gene delivery. Nat Biotechnol 15:167-173
125. Smith JG, Wedeking T, Vernachio JH et al (1998) Characterization and in vivo testing of a heterogeneous cationic lipid-DNA formulation. Pharm Res 15:1356-1363
126. Sternberg B, Hong KL, Zheng WW et al (1998) Ultrastructural characterization of cationic liposome-DNA complexes showing enhanced stability in serum and high transfection activity in vivo. Biochim Biophys Acta-Biomembranes 1375:23-35
127. Wang JK, Guo X, Xu YH et al (1998) Synthesis and characterization of long chain alkyl acyl carnitine esters. Potentially biodegradable cationic lipids for use in gene delivery. J Med Chem 41:2207-2215
128. Regelin AE, Fankhaenel S, Gurtesch L et al (2000) Biophysical and lipofection studies of DOTAP analogs. Biochim Biophys Acta-Biomembranes 1464:151-164
129. Jiao J (2008) Polyoxyethylated nonionic surfactants and their applications in topical ocular drug delivery. Adv Drug Deliv Rev 60:1663-1673
130. Wang L, MacDonald RC (2004) New strategy for transfection: mixtures of medium-chain and long-chain cationic lipids synergistically enhance transfection. Gene Ther 11:1358-1362
131. Koynova R, Wang L, Tarahovsky Y et al (2005) Lipid phase control of DNA delivery. Bioconjug Chem 16:1335-1339
132. Koynova R, Wang L, MacDonald RC (2007) Synergy in lipofection by cationic lipid mixtures: superior activity at the gel-liquid crystalline phase transition. J Phys Chem B 111:7786-7795
133. Wagner E, Culmsee C, Boeckle S (2005) Targeting of polyplexes: toward synthetic virus vector systems. Adv Genet 53:333-354