Synthesis, characterization and properties of a new polymerisable surfactant: 12-Methacryloyl dodecylphosphocholine

A new polymerizable surfactant, 12-methacryloyl dodecylphosphocholine (MDPC), has been synthesized using a three-step procedure in moderate yield. Phase transitions were characterized by DSC and phase behavior in water was determined by surface tension and polarizing microscopy. MDPC showed typical surfactant behavior and self-aggregated to micelles above a distinct concentration. The critical micelle concentration (CMC) of MDPC was determined to be 5 × 10−4 mol/L. MDPC showed mesomorphic properties between 75 and 86 °C as studied by differential scanning calorimetry (DSC). The formation of black lipid membranes was further investigated. The methacrylate functionalized MDPC could form a bilayer membrane (BLM) although it was very unstable (collapsed after 10–30 s). However, it was possible to form stable BLMs in mixture with non-polymerizable two chain phospholipids, i.e. asolectin and diphytanoyl phosphatidylcholine (DPhPC). Stable bilayers could be obtained up to a MDPC content of 50 mol%. Gramicidin A was incorporated into MDPC/DPhPC membranes and exhibited ion-channel activity shown by single channel conductivity measurements.