Phosphatidyl choline lipids

FIG. 8 The ITIES modified with a monolayer of phospholipid. The insert shows the structure of synthetic saturated phosphatidyl choline lipid. (From Ref. 26.)... 

FIG. 13 Structure of the synthetic conjugated phosphatidyl choline lipid, 2-(3-(di-phenylhexatrienyl)propanoyl)-l-hexadecanoyl-glycero-3-phosphocholine (DPHC). 

Small sonicated unilamellar vesicles were prepared from egg phosphatidyl choline (Lipid Products, Surrey, England) in a solution containing 2 X 10 5-M NaCl and 0.1-M glucose by sonication in a bath sonicator (Laboratory Supply Company, Hicksville, NY) until a clear dispersion was obtained. After vesicle preparation, small aliqouts of alamethicin in methanol (10 mL) were added to 1.8 mL of vesicle-containing solution. The final lipid concentration was 1 mg/mL and the final polypeptide concentration was 150 (xg/mL. The polypeptide to lipid ratio was about 1 20. The Donnan potentials across the membrane were established as follows (8). 

Fig. 6 Structures of phosphatidyl choline lipids (a) isomer la (b) parallel (Tl) and perpendicular (T2) chain conformations (c) isomer lb (d) snperposed DLPC blue) and DMPC (red) isomer la optimized stmctnres...

Goursot A, Mineva T, Krishnamurty S, Salahub D (2009) Structural analysis of phosphatidyl choline lipids and glycerol precursOTS. Can J Chem 87 1261... 

Phosphatidylcholine is an important component of cell membranes but cell mem branes are more than simply lipid bilayers Although their composition varies with their source a typical membrane contains about equal amounts of lipid and protein and the amount of cholesterol m the lipid fraction can approximate that of phosphatidylcholine The lipid fraction is responsible for the structure of the membrane Phosphatidyl choline provides the bilayer that is the barrier between what is inside the cell and what IS outside Cholesterol intermingles with the phosphatidylcholine to confer an extra measure of rigidity to the membrane... 

Crowe and Crowe [3.39] proved that it is sufficient for certain liposomes, e. g. egg phosphatidyl-choline (DPPC), to be vitrified by trehalose or dextran during freezing and freeze drying. In trehalose the retention rate was almost 100 %, and in dextran more than 80 %. This did not apply to egg PC-liposomes Dextran as CPA alone led to an almost total loss of the CF-indicator, but addition of dextran into a trehalose solution (Fig. 3.20) also reduced the retention rate of CF substantially, e. g. from 90 % in a pure trehalose to approx. 45 % if trehalose and dextran were in equal amounts in the solution. Since T of dextran is approx. -10 °C and Tg- of trehalose is -30 to -32 °C, dextran should form a glass phase at much higher temperatures than trehalose. Therefore the stabilization of egg- PC with trehalose cannot be related with the vitrification. Crowe showd with IR spectroscopy that egg-PC freeze dried with 2 g trehalose/g lipid had almost the identical spectrographic characteristics as the hydrous lipid Trehalose molecules replaced the water molecules, and hydrogen... 

Another factor affecting the lifetime of a membrane fluorophore probe is its proximity to the surface. The lifetimes of the DPH, DPH-phosphatidyl-choline (DPH-PC), and trimethylammonium-DPH (TMA-DPH) probes decrease in the order DPH > DPH-PC > TMA-DPH, as the probe locates nearer to the surface of the lipid bilayer.(7) The same is found for the anthroyl-stearate probes.(8) More recently, it has been shown that with TMA-DPH, the lifetime appears to be fairly sensitive to the differences in lipid bilayer packing induced by differing degrees of unsaturation in the phospholipid fatty acyl chains.(9) This aspect of the use of TMA-DPH and possibly other probes remains to be further exploited. 

The preformed vesicle (PFV) approach involves incubation of liposomes containing a cationic lipid and a PEG coating with polynucleotides in the presence of ethanol. Typically, LUV composed of distearoyl-phosphatidyl-choline (DSPC), cholesterol (Choi), l-0-(2 -(oi-methoxy-polyethylene-glycol)... 

Encapsulation efficiencies are listed as a function of ethanol concentration for distearoyl-phosphatidyl-choline/choles-terol/l,2-dioleoyl-3-dimethylammoniumpropane large unilamellar vesicle (LUVs). The initial oligonucleotide-to-lipid ratio was 0.034 mol/mol (0.3mg/mg). The LUVs used for these experiments were 99 22 nm in size. The encapsulation values are given as mean SD. 

Figure 2 Encapsulation as a function of ethanol concentration. Oligonucleotides were added to distearoyl-phosphatidyl-choline/cholesterol/l-0-(2 -(co-methoxy-poly-ethylene-glycol)succinoyl)-2-iV-myristoyl-sphingosine /1,2-dioleoyl-3-dimethylam-monium propane liposomes in varying concentrations of ethanol at an initial oligonucleotide-to-lipid ratio of 0.24mg/mg. Abbreviations AS, antisense oligonucleotide %EtOH(v/v), percentage of ethanol in volume/volume.

Recently, this method was adapted to label two commercially available liposomal formulations doxorubicin encapsulated in polyethylene glycol (PEG)-coated liposomes (Caelyx /Doxil ) (14) and daunorubicin encapsulated in small distearoyl-phosphatidyl-choline/cholesterol liposomes (Daunoxome ) (15). Although no DTPA was encapsulated in these liposomes, the labeling efficiency was typically between 70% and 80% and the radiolabeled preparations were stable in vivo during the time course of the experiment (four hours). Most likely, the lipophilic In-oxine avidly associates with the lipid bilayer and encapsulation of DTPA might not be necessary when the experimental observation period does not exceed four to six hours. 

Practically all available iodinated extracellular X-ray contrast agents have been encapsulated into liposomes using different lipids and methods of preparation. Table 1 gives a short and intentionally incomplete overview of some of the approaches. The first liposomal contrast agent preparation that was tested in humans contained diatrizoate [48]. The injected dose was up to 0.5 ml kg k The preparation was effective even in plain radiography where lesions down to 0.8-1.0 cm could be detected in patients. However, adverse events such as fever and hyperthermia, which occurred in 30% of the patients, limited further use. We have incorporated iopromide into MLVs that were prepared from phosphatidyl choline (PC), cholesterol and stearic acid at a molar ratio of 4 5 1 using the ethanol-evaporation technique [44]. The liposomes can be stored freeze-dried and they are reconstituted before use by... 

A series of iomeprol-containing liposomes were evaluated in animals by Petersein et al. [62] and in healthy volunteers by Spinazzi et al. [63,64]. BR2 and BR21 are liposomes made of phosphatidyl choline (PC),dipalmitoyl phospatidic acid (DPPA) and cholesterol at a molar ratio of 2 1 (PC -i- DPPA/cholesterol) with an iodine content of 260 mg mL (BR2) and 320 mg mL" (BR21), respectively, and a size of 0.4 pm. BR2 contains 40 mg lipid mL and BR21 20 mg mL L In rabbits, BR2 tended to provide a higher and more persistent CT enhancement than BR21. 

Several studies have evaluated the effects of oral di(2-ethylhexyl) adipate on various aspects of hepatic lipid metabolism. Feeding di(2-ethylhexyl) adipate (2% of diet) to male Wistar rats for seven days resulted in increased hepatic fatty acid-binding protein as well as in increased microsomal stearoyl-CoA desaturation activity (Kawashima et al., 1983a,b). Feeding the compound at this dose for 14 days resulted in increased levels of hepatic phospholipids and a decline in phosphatidyl-choline phosphatidylethanolamine ratio (Yanagita et al., 1987). Feeding di(2-ethyl-hexyl) adipate (2% of diet) to male NZB mice for five days resulted in induction of fatty acid translocase, fatty acid transporter protein and fatty acid binding protein in the liver (Motojima et al., 1998). 

Palmitic acid is conjugated to glucuronic acid to form a reticuloendothelial system-avoiding liposome delivery system (79). Phospholipids such as phosphatidyl choline or phosphatidyl ethanolamine are used as constituents of lipid complexes or... 

The vesicles were shown to be rich in lipids with at laest 1.5 times more total lipid, phospholipid, cholesterol and glycolipid per unit protein than in whole chondrocytes. The ratio of cholesterol to PL was 1.7 times greater in vesicles than in chondrocytes and vesicles which contained twice the cellular amount of phosphatidyl serine and sphingomyelin102, 46S) and which are depleted in phosphatidyl choline. It is of note that the principal PL in vesicles was phosphatidyl serine which has been shown to have a strong affinity for calcium ions, especially in the presence of phosphate96). 

This lamellar phase is formed of alternate sheets of lipid and water. The lipidic sheets containing the lecithin and the cholesterol are made of two superposed layers of oriented molecules. Each of these two monolayers is mixed and consists of lecithin and cholesterol molecules arranged side by side with their paraffinic ends turned toward the inside of the sheet and their polar groups (phosphatidyl choline group for lecithin and hydroxyl group for the cholesterol) outward—i.e., toward the adjacent sheet of water. This constitution of each of the two mono-layers forming the lipidic sheet is in conformity with the conclusion arising from the study of mixed monolayers of cholesterol and lecithin spread on the free surface of water (1). 

Materials. Lipids and Protein. The sources of synthetic N-palmitoyl and N-stearoyldihydrosphingosyl lactosides, phosphatidyl choline (egg), cholesterol, and rabbit y-globulin have been described (7). 

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