Synthesis of a single-tailed cationic lipid and investigation of its transfection

Journal of Controlled Release

Volumn 62, Issue 3, 1999, Pages 345-358

  Tang, Fuxing ^a   Hughes, Jeffrey A ^a  

^a UNIVERSITY OF FLORIDA   (United States)

Author keywords

Gene delivery; Liposome; Plasmid DNA; Single tailed

Indexed keywords

LIPID; LIPOSOME; PLASMID DNA; PLASMID VECTOR;

ANIMAL CELL; ARTICLE; BIODEGRADATION; CELL CULTURE; CHO CELL; CONTROLLED STUDY; CYTOTOXICITY; DRUG ABSORPTION; FLOW CYTOMETRY; IN VITRO STUDY; LIPOGENESIS; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; CATIONS; CELLS, CULTURED; CETRIMONIUM COMPOUNDS; CRICETINAE; DNA; DRUG DESIGN; FEMALE; LIPIDS; LIPOSOMES; ORNITHINE; OVARY; PLASMIDS; TIME FACTORS; TRANSFECTION;

EID: 0032828009     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-3659(99)00158-3     Document Type: Article

References (28)

1. Felgner P.L., Gadek T.R., Holm M., Roman R., Chan H.W., Wenz M., Northrop J.P., Ringold G.M., Danielsen M. Lipofection: a highly efficient, lipid-mediated DNA-transfection procedure. Proc. Natl. Acad. Sci. USA. 84:(21):1987;7413-7417.
2. Gao X., Huang L. Cationic liposome-mediated gene transfer. Gene Ther. 2:(10):1995;710-722.
3. Lee R.J., Huang L. Lipidic vector systems for gene transfer. Crit. Rev. Ther. Drug Carrier Syst. 14:(2):1997;173-206.
4. Mahato R.I., Takakura Y., Hashida M. Nonviral vectors for in vivo gene delivery: physicochemical and pharmacokinetic considerations. Crit. Rev. Ther. Drug Carrier Syst. 14:(2):1997;133-172.
5. Rolland A.P. From genes to gene medicines: recent advances in nonviral gene delivery. Crit. Rev. Ther. Drug Carrier Syst. 15:(2):1998;143-198.
6. Pinnaduwage P., Schmitt L., Huang L. Use of a quaternary ammonium detergent in liposome mediated DNA transfection of mouse L-cells. Biochim. Biophys. Acta. 985:(1):1989;33-37.
7. Farhood H., Bottega R., Epand R.M., Huang L. Effect of cationic cholesterol derivatives on gene transfer and protein kinase C activity. Biochim. Biophys. Acta. 1111:(2):1992;239-246.
8. Leventis R., Silvius J.R. Interactions of mammalian cells with lipid dispersions containing novel metabolizable cationic amphiphiles. Biochim. Biophys. Acta. 1023:(1):1990;124-132.
9. Aberle A.M., Tablin F., Zhu J., Walker N.J., Gruenert D.C., Nantz M.H. A novel tetraester construct that reduces cationic lipid-associated cytotoxicity. Implications for the onset of cytotoxicity. Biochemistry. 37:(18):1998;6533-6540.
10. Felgner J.H., Kumar R., Sridhar C.N., Wheeler C.J., Tsai Y.J., Border R., Ramsey P., Martin M., Felgner P.L. Enhanced gene delivery and mechanism studies with a novel series of cationic lipid formulations. J. Biol. Chem. 269:(4):1994;2550-2561.
11. Tang F., Hughes J.A. Introduction of a disulfide bond into a cationic lipid enhances transgene expression of plasmid DNA. Biochem. Biophys. Res. Commun. 242:(1):1998;141-145.
12. Hassner A., Alexanian V. Direct room temperature esterification of carboxylic acids. Tetrahedron Letters. 46:1978;4475-4478.
13. Behr J.P., Demeneix B., Loeffler J.P., Perez-Mutul J. Efficient gene transfer into mammalian primary endocrine cells with lipopolyamine-coated DNA. Proc. Natl. Acad. Sci. USA. 86:(18):1989;6982-6986.
14. Vigneron J.P., Oudrhiri N., Fauquet M., Vergely L., Bradley J.C., Basseville M., Lehn P., Lehn J.M. Guanidinium-cholesterol cationic lipids: efficient vectors for the transfection of eukaryotic cells. Proc. Natl. Acad. Sci. USA. 93:(18):1996;9682-9686.
15. Lichtenfels R., Biddison W.E., Schulz H., Vogt A.B., Martin R. CARE-LASS (calcein-release-assay), an improved fluorescence-based test system to measure cytotoxic T lymphocyte activity. J. Immunol. Methods. 172:(2):1994;227-239.
16. Legendre J.Y., Szoka F.C. Jr. Delivery of plasmid DNA into mammalian cell lines using pH-sensitive liposomes: comparison with cationic liposomes. Pharm. Res. 9:(10):1992;1235-1242.
17. Zabner J., Fasbender A.J., Moninger T., Poellinger K.A., Welsh M.J. Cellular and molecular barriers to gene transfer by a cationic lipid. J. Biol. Chem. 270:(32):1995;18997-19007.
18. Tseng W.C., Haselton F.R., Giorgio T.D. Transfection by cationic liposomes using simultaneous single cell measurements of plasmid delivery and transgene expression. J. Biol. Chem. 272:(41):1997;25641-25647.
19. Yang J.P., Huang L. Time-dependent maturation of cationic liposome-DNA complex for serum resistance. Gene Ther. 5:(3):1998;380-387.
20. Escriou V., Ciolina C., Helbling-Leclerc A., Wils P., Scherman D. Cationic lipid-mediated gene transfer: analysis of cellular uptake and nuclear import of plasmid DNA. Cell Biol. Toxicol. 14:(2):1998;95-104.
21. McMurry J. Organic Chemistry. 1988;900 Brooks/Cole Publishing Company, California.
22. Zuidam N.J., Barenholz Y. Electrostatic parameters of cationic liposomes commonly used for gene delivery as determined by 4-heptadecyl-7-hydroxycoumarin [published erratum appears in Biochem. Biophys. Acta 1998;1372(1):151]. Biochim. Biophys. Acta. 1329:(2):1997;211-222.
23. Zuidam N.J., Barenholz Y. Electrostatic and structural properties of complexes involving plasmid DNA and cationic lipids commonly used for gene delivery. Biochim. Biophys. Acta. 1368:(1):1998;115-128.
24. Xu Y., Szoka F.C. Jr. Mechanism of DNA release from cationic liposome/DNA complexes used in cell transfection. Biochemistry. 35:(18):1996;5616-5623.
25. Lasic D.D. Liposomes in Gene Delivery. 1997;CRC, New York.
26. Gao X., Huang L. A novel cationic liposome reagent for efficient transfection of mammalian cells. Biochem. Biophys. Res. Commun. 179:(1):1991;280-285.
27. Lasch J. Interaction of detergents with lipid vesicles. Biochim. Biophys. Acta. 1241:(2):1995;269-292.
28. Escriou V., Ciolina C., Lacroix F., Byk G., Scherman D., Wils P. Cationic lipid-mediated gene transfer: effect of serum on cellular uptake and intracellular fate of lipopolyamine/DNA complexes. Biochim. Biophys. Acta. 1368:(2):1998;276-288.