help button home button Biophys. J.
HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrow reprints & permissions
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by MacDonald, R. C.
Right arrow Articles by McIntosh, T. J.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by MacDonald, R. C.
Right arrow Articles by McIntosh, T. J.

Biophys J, November 1999, p. 2612-2629, Vol. 77, No. 5

Physical and Biological Properties of Cationic Triesters of Phosphatidylcholine

Robert C. MacDonald,* Gary W. Ashley, Miho M. Shida, Vera A. Rakhmanova, Yury S. Tarahovsky,# Dennis P. Pantazatos, Michael T. Kennedy, Edvin V. Pozharski, Kent A. Baker, Ramoun D. Jones, Howard S. Rosenzweig, Kenneth L. Choi, Ruozi Qiu, and Thomas J. McIntosh§

 *Department of Biochemistry, Molecular Biology, and Cell Biology, Northwestern University, Evanston, Illinois 60208 USA;  #Institute for Theoretical and Experimental Biophysics, Pushchino 142292, Russia; and  §Department of Cell Biology, Duke University, Durham, North Carolina 27710 USA

The properties of a new class of phospholipids, alkyl phosphocholine triesters, are described. These compounds were prepared from phosphatidylcholines through substitution of the phosphate oxygen by reaction with alkyl trifluoromethylsulfonates. Their unusual behavior is ascribed to their net positive charge and absence of intermolecular hydrogen bonding. The O-ethyl, unsaturated derivatives hydrated to generate large, unilamellar liposomes. The phase transition temperature of the saturated derivatives is very similar to that of the precursor phosphatidylcholine and quite insensitive to ionic strength. The dissociation of single molecules from bilayers is unusually facile, as revealed by the surface activity of aqueous liposome dispersions. Vesicles of cationic phospholipids fused with vesicles of anionic lipids. Liquid crystalline cationic phospholipids such as 1,2-dioleoyl-sn-glycero-3-ethylphosphocholine triflate formed normal lipid bilayers in aqueous phases that interacted with short, linear DNA and supercoiled plasmid DNA to form a sandwich-structured complex in which bilayers were separated by strands of DNA. DNA in a 1:1 (mol) complex with cationic lipid was shielded from the aqueous phase, but was released by neutralizing the cationic charge with anionic lipid. DNA-lipid complexes transfected DNA into cells very effectively. Transfection efficiency depended upon the form of the lipid dispersion used to generate DNA-lipid complexes; in the case of the O-ethyl derivative described here, large vesicle preparations in the liquid crystalline phase were most effective.

Biophys J, November 1999, p. 2612-2629, Vol. 77, No. 5
© 1999 by the Biophysical Society   0006-3495/99/11/2612/18  $2.00


This article has been cited by other articles:


Home page
 Biophys. JHome page
L. Wang, R. Koynova, H. Parikh, and R. C. MacDonald
Transfection Activity of Binary Mixtures of Cationic O-Substituted Phosphatidylcholine Derivatives: The Hydrophobic Core Strongly Modulates Physical Properties and DNA Delivery Efficacy
Biophys. J., November 15, 2006; 91(10): 3692 - 3706.
[Abstract] [Full Text] [PDF]

Home page
 Proc. Natl. Acad. Sci. USAHome page
R. Koynova, L. Wang, and R. C. MacDonald
An intracellular lamellar-nonlamellar phase transition rationalizes the superior performance of some cationic lipid transfection agents
PNAS, September 26, 2006; 103(39): 14373 - 14378.
[Abstract] [Full Text] [PDF]

Home page
 Biophys. JHome page
Y. S. Tarahovsky, R. Koynova, and R. C. MacDonald
DNA Release from Lipoplexes by Anionic Lipids: Correlation with Lipid Mesomorphism, Interfacial Curvature, and Membrane Fusion
Biophys. J., August 1, 2004; 87(2): 1054 - 1064.
[Abstract] [Full Text] [PDF]

Home page
 Biophys. JHome page
E. Goncalves, R. J. Debs, and T. D. Heath
The Effect of Liposome Size on the Final Lipid/DNA Ratio of Cationic Lipoplexes
Biophys. J., March 1, 2004; 86(3): 1554 - 1563.
[Abstract] [Full Text] [PDF]

Home page
 Biophys. JHome page
E. Pozharski and R. C. MacDonald
Lipoplex Thermodynamics: Determination of DNA-Cationic Lipoid Interaction Energies
Biophys. J., December 1, 2003; 85(6): 3969 - 3978.
[Abstract] [Full Text] [PDF]

Home page
 Biophys. JHome page
R. Koynova and R. C. MacDonald
Mixtures of Cationic Lipid O-Ethylphosphatidylcholine with Membrane Lipids and DNA: Phase Diagrams
Biophys. J., October 1, 2003; 85(4): 2449 - 2465.
[Abstract] [Full Text] [PDF]

Home page
 Biophys. JHome page
G. Lei and R. C. MacDonald
Lipid Bilayer Vesicle Fusion: Intermediates Captured by High-Speed Microfluorescence Spectroscopy
Biophys. J., September 1, 2003; 85(3): 1585 - 1599.
[Abstract] [Full Text] [PDF]

Home page
 J. Biol. Chem.Home page
C. M. Wiethoff, M. L. Gill, G. S. Koe, J. G. Koe, and C. R. Middaugh
The Structural Organization of Cationic Lipid-DNA Complexes
J. Biol. Chem., November 15, 2002; 277(47): 44980 - 44987.
[Abstract] [Full Text] [PDF]

Home page
 Biophys. JHome page
E. Pozharski and R. C. MacDonald
Thermodynamics of Cationic Lipid-DNA Complex Formation as Studied by Isothermal Titration Calorimetry
Biophys. J., July 1, 2002; 83(1): 556 - 565.
[Abstract] [Full Text] [PDF]

Home page
 Biophys. JHome page
V. Cherezov, H. Qiu, V. Pector, M. Vandenbranden, J.-M. Ruysschaert, and M. Caffrey
Biophysical and Transfection Studies of the diC14-Amidine/DNA Complex
Biophys. J., June 1, 2002; 82(6): 3105 - 3117.
[Abstract] [Full Text] [PDF]


HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
Copyright © 1999 by the Biophysical Society.