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

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Seuring, Jan ; Reiss, Philipp ; Koert, Ulrich ; Agarwal, Seema:
Synthesis, characterization and properties of a new polymerisable surfactant: 12-Methacryloyl dodecylphosphocholine.
In: Chemistry and Physics of Lipids. Bd. 163 (2010) Heft 4–5 . - S. 367-372.
ISSN 0009-3084
DOI: https://doi.org/10.1016/j.chemphyslip.2010.03.001

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Abstract

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.