Polymerized Phosphatidylcholine Vesicles. Synthesis and Characterization

Article abstract of DOI:10.1021/ja00367a023

The synthesis and characterization of photopolymerized vesicles derived from bis<12-(methacryloyloxy)dodecanoyl>-L-α-phosphatidylcholine (3) 1-<12-(methacryloyloxy)dodecanoyl>-2-palmitoyl-L-α-phosphatidylcholine (4), and 1-palmitoyl-2-<12-(methacryloyloxy)dodecanoyl>-L-α-phosphatidylcholine (5) are described.Ultrasonic irradiation of 3, 4, 5, 20percent 3 + 80percent 4, and 20percent 3 + 80percent 5 in water at 50 deg C yields opalescent to optically clear dispersions.Electron microscopy, entrapment of <14C>sucrose, and permeability measurements provide strong evidence for closed multilamellar vesicles having diameters ranging between 350 and 1400 Angstroem.Fourier transform 1H NMR spectra of the aqueous dispersions as well as IR spectra of chloroform extracts establish that no significant lipid decomposition occurs during vesicle preparation.Direct UV irradiation (254 nm) produces polymerized analogues of similar size and shape which (1) entrap <14C>sucrose, (2) show reduced permeability, and (3) exhibit enchanced stability.