Phosphatidylethanolamine Series

Phosphatidylethanolamine is the second most abundant phospholipid in mammalian cells. It accounts for about 15-25% of the total lipids in mammalian cells; it is enriched in the inner leaflet of membranes and is especially abundant in the inner mitochondrial membrane. Phosphatidylethanolamine is a non-bilayer formed phospholipid containing small polar heads proportional to the diameter of its fatty acid chain. The intrinsic biophysical properties of this cone-shaped lipid induce the formation of hexagonal phases within the membrane and, in so doing, promotes membrane fusion and fission events, protein integration into membranes, and conformational changes in protein structure.

Figure 1. Diagram of phosphatidylethanolamine structure ^[1]. The spheres represent different atoms present in the phospholipid structure tan: carbon, red: oxygen, orange: phosphate, and blue: nitrogen (hydrogen atoms are not represented).

Structure of phosphatidylethanolamine

Phosphatidylethanolamine is composed of glycerol, two fatty acids and phosphoric acid, where the ethanolamine is attached to the phosphoric acid group. The glycerol molecules in phosphatidylethanolamine esterify at the sn-1 and sn-2 positions to form acid chain fatty acids with 16 to 20 carbon atoms. The fatty acids esterified in the sn-1 hydroxyl are generally saturated (without double bonds) with maximum lengths of 18 carbon atoms, while the chains linked in the sn-2 position are longer and with one or more unsaturation (double bonds).

Figure 2. General phosphatidylethanolamine structure ^[1].

Common phosphatidylethanolamine series

Phosphatidylethanolamine series are important excipients for nucleic acid delivery. Common phosphatidylethanolamine series are listed below.

• DOPE

1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) is a neutral phospholipid and displays sensitivity towards pH change and has been used in the preparation of liposome. DOPE tends to adopt an inverted hexagonal H(II) phase, which destabilizes endosomal membranes and facilitates endosomal escape of lipid nanoparticles. In addition, DOPE can be used in combination with cationic phospholipids to improve the efficiency of nucleic acid transfection studies.

Figure 3. The structure of DOPE.

• DSPE

1,2-Distearoyl-sn-glycero-3-phosphoethanolamine (DSPE) is a derivative of phosphatidylethanolamine with (18:0) stearic acid acyl chains. DSPE has been widely used in the field of nucleic acid delivery because of its emulsifying and solubilizing properties. Modification of DSPE can also give it the ability to release and target specific cells under specific conditions.

Figure 4. The structure of DSPE.

What we offer

Alfa Chemistry supplies a wide range of phosphatidylethanolamine products for companies researching vaccines. If you cannot find the product you need, please contact us. We also offer product customization according to customer's detailed requirements.

Reference

1. Calzada, E.; et al. Phosphatidylethanolamine metabolism in health and disease. International Review of Cell and Molecular Biology. 2016, 321: 29-88.

Our products and services are for research use only and cannot be used for any clinical purposes.

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