Novel fluorescent cationic phospholipid, O-4-napthylimido-1-butyl-DOPC, exhibits unusual foam morphology, forms hexagonal and cubic phases in mixtures, and transfects DNA
| Autor: | Robert C. MacDonald, Howard S. Rosenzweig, Michael R. Wasielewski, Li Wang, Rumiana Koynova |
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| Rok vydání: | 2004 |
| Předmět: |
Magnetic Resonance Spectroscopy
Molecular Conformation Phospholipid Imides Transfection Biochemistry Micelle chemistry.chemical_compound X-Ray Diffraction Cardiolipin Organic chemistry Lamellar structure Cationic liposome Molecular Biology Micelles Phospholipids Chemistry Organic Chemistry Cationic polymerization Hexagonal phase DNA Cell Biology Crystallography Liposomes Phosphatidylcholines lipids (amino acids peptides and proteins) Trifluoromethanesulfonate |
| Zdroj: | Chemistry and Physics of Lipids. 129:183-194 |
| ISSN: | 0009-3084 |
| DOI: | 10.1016/j.chemphyslip.2004.01.003 |
| Popis: | The novel cationic triester of phosphatidylcholine, O-4-napthylimido-1-butyl-dioleoylphosphatidylcholine (NB-DOPC), has been synthesized: 1-amino-4-butanol was reacted with napthylic anhydride to form 4-hydroxybutyl-1-napthylamide, which was then reacted with triflic anhydride; the resultant triflate was reacted with dioleoylphosphatidylcholine so as to transfer the napthylimido-butyl group to the unsubstituted phosphate oxygen. The resultant compound is thus not only positively charged, but also has a bulky hydrophobic moiety attached to the headgroup. This novel cationic phospholipid exhibits a peculiar long-living foam-like morphology upon hydration, which could have applications in encapsulation and delivery. It is characterized by high adhesiveness to hydrophobic surfaces. X-ray diffraction showed that it forms a lamellar structure of rather short repeat period, indicative of an unusually small interlamellar separation and low hydration level. It readily incorporates DNA and organizes into lamellar lipoplexes. These DNA-lipid complexes effectively transfect DNA into cells. In an equimolar mixture of this lipid with the anionic dioleoylphosphatidylglycerol lamellar arrays coexist with disordered uncorrelated structures, however, these transform into a bicontinuous cubic phase, Pn3m, upon addition of DNA. When mixed with another anionic lipid, cardiolipin, at a NB-DOPC/ cardiolipin 2:1 molar ratio, it forms the inverted hexagonal phase which is of potential interest for nanotechnology applications. |
| Databáze: | OpenAIRE |
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