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.
Physical and biological properties of cationic triesters of phosphatidylcholine.
R. Macdonald,G. Ashley,M. Shida,V. Rakhmanova,Y. Tarahovsky,D. Pantazatos,M. T. Kennedy,Edvin V. Pozharski,K. A. Baker,Ramoun D. Jones,H. S. Rosenzweig,Kenneth L. Choi,Ruozi Qiu,T. McIntosh
Published 1999 in Biophysical Journal
ABSTRACT
PUBLICATION RECORD
- Publication year
1999
- Venue
Biophysical Journal
- Publication date
1999-11-01
- Fields of study
Biology, Medicine, Chemistry
- Identifiers
- External record
- Source metadata
Semantic Scholar, PubMed
CITATION MAP
EXTRACTION MAP
CLAIMS
CONCEPTS
- alkyl phosphocholine triesters
A class of phospholipid derivatives bearing an alkyl phosphocholine triester headgroup.
Aliases: cationic triesters of phosphatidylcholine
박진우 (dztg5apj7m) extraction뀨 (7c402c1b98) reviewB (s683577b42) reviewKiller Whale (322360f1c1) review - alkyl trifluoromethylsulfonates
Alkylating reagents used to replace phosphate oxygen during triester synthesis.
Aliases: alkyl triflates
박진우 (dztg5apj7m) extraction뀨 (7c402c1b98) reviewB (s683577b42) reviewKiller Whale (322360f1c1) review - cationic phospholipids
Phospholipid molecules carrying a net positive charge in their headgroup region.
Aliases: cationic lipid
박진우 (dztg5apj7m) extraction뀨 (7c402c1b98) reviewB (s683577b42) reviewKiller Whale (322360f1c1) review - dna-lipid complexes
Assemblies formed when cationic lipid bilayers interact with DNA strands or plasmids.
Aliases: lipoplexes
박진우 (dztg5apj7m) extraction뀨 (7c402c1b98) reviewB (s683577b42) reviewKiller Whale (322360f1c1) review - large unilamellar liposomes
Single-bilayer vesicles formed by hydrating selected lipid derivatives in aqueous solution.
Aliases: LUVs
박진우 (dztg5apj7m) extraction뀨 (7c402c1b98) reviewB (s683577b42) reviewKiller Whale (322360f1c1) review - liquid crystalline phase
A fluid bilayer state of lipid assemblies used here to characterize vesicle dispersions.
Aliases: Lalpha phase
박진우 (dztg5apj7m) extraction뀨 (7c402c1b98) reviewB (s683577b42) reviewKiller Whale (322360f1c1) review - phosphatidylcholines
The parent phospholipids used as starting materials for making the triester derivatives.
Aliases: PCs
박진우 (dztg5apj7m) extraction뀨 (7c402c1b98) reviewB (s683577b42) reviewKiller Whale (322360f1c1) review
REFERENCES
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