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Physical and biological properties of cationic triesters of phosphatidylcholine.

Publication ,  Journal Article
MacDonald, RC; Ashley, GW; Shida, MM; Rakhmanova, VA; Tarahovsky, YS; Pantazatos, DP; Kennedy, MT; Pozharski, EV; Baker, KA; Jones, RD; Qiu, R ...
Published in: Biophys J
November 1999

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.

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Published In

Biophys J

DOI

EISSN

1542-0086

Publication Date

November 1999

Volume

77

Issue

5

Start / End Page

2612 / 2629

Location

United States

Related Subject Headings

  • Water
  • Transition Temperature
  • Transfection
  • Surface Properties
  • Sonication
  • Physical Phenomena
  • Phosphorylcholine
  • Phosphatidylcholines
  • Particle Size
  • Mice
 

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MacDonald, R. C., Ashley, G. W., Shida, M. M., Rakhmanova, V. A., Tarahovsky, Y. S., Pantazatos, D. P., … McIntosh, T. J. (1999). Physical and biological properties of cationic triesters of phosphatidylcholine. Biophys J, 77(5), 2612–2629. https://doi.org/10.1016/S0006-3495(99)77095-5
MacDonald, R. C., G. W. Ashley, M. M. Shida, V. A. Rakhmanova, Y. S. Tarahovsky, D. P. Pantazatos, M. T. Kennedy, et al. “Physical and biological properties of cationic triesters of phosphatidylcholine.Biophys J 77, no. 5 (November 1999): 2612–29. https://doi.org/10.1016/S0006-3495(99)77095-5.
MacDonald RC, Ashley GW, Shida MM, Rakhmanova VA, Tarahovsky YS, Pantazatos DP, et al. Physical and biological properties of cationic triesters of phosphatidylcholine. Biophys J. 1999 Nov;77(5):2612–29.
MacDonald, R. C., et al. “Physical and biological properties of cationic triesters of phosphatidylcholine.Biophys J, vol. 77, no. 5, Nov. 1999, pp. 2612–29. Pubmed, doi:10.1016/S0006-3495(99)77095-5.
MacDonald RC, Ashley GW, Shida MM, Rakhmanova VA, Tarahovsky YS, Pantazatos DP, Kennedy MT, Pozharski EV, Baker KA, Jones RD, Rosenzweig HS, Choi KL, Qiu R, McIntosh TJ. Physical and biological properties of cationic triesters of phosphatidylcholine. Biophys J. 1999 Nov;77(5):2612–2629.
Journal cover image

Published In

Biophys J

DOI

EISSN

1542-0086

Publication Date

November 1999

Volume

77

Issue

5

Start / End Page

2612 / 2629

Location

United States

Related Subject Headings

  • Water
  • Transition Temperature
  • Transfection
  • Surface Properties
  • Sonication
  • Physical Phenomena
  • Phosphorylcholine
  • Phosphatidylcholines
  • Particle Size
  • Mice