4235-95-4Relevant articles and documents
Synthesis of phosphatidylcholine: An improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine
Ichihara, Ken'ichi,Iwasaki, Hitomi,Ueda, Kaori,Takizawa, Ryoko,Naito, Hideko,Tomosugi, Mitsuhiro
, p. 94 - 99 (2005)
An improved safe method that does not contaminate the environment with cadmium chloride, a toxic heavy metal salt, was developed for the synthesis of phosphatidylcholine (PC). PC was synthesized from sn-glycero-3-phosphocholine (GPC) and fatty acid in one step under mild conditions without the use of cadmium chloride. GPC was prepared from egg yolk PC and adsorbed by kieselguhr in a Teflon vessel. The GPC on kieselguhr was acylated with fatty acid in the presence of two reagents, dicyclohexylcarbodiimide for synthesis of fatty acid anhydride and 4-dimethylaminopyridine as an acylating catalyst, at 30°C overnight. The PC thus produced was purified by silica gel column chromatography. The yield of dioleoyl PC was 90% based on the starting material, GPC.
cis-trans Isomerization of monounsaturated fatty acid residues in phospholipids by thiyl radicals
Chatgilialoglu, Chryssostomos,Ferreri, Carla,Ballestri, Marco,Mulazzani, Quinto G.,Landi, Laura
, p. 4593 - 4601 (2007/10/03)
Thiyl radicals reversibly attack the double bonds of methyl oleate and dioleoyl phosphatidyl choline (DOPC), thus producing methyl elaidate and the corresponding phospholipids containing trans-fatty acid residues in high yield. These processes are radical chain reactions with relatively long chain lengths. The rate constant for the β-elimination of a thiyl radical from the adduct radical has been estimated to be 6 x 106 s-1 at ambient temperature. The cis-trans isomerization of fatty acid residues in DOPC vesicles (multilamellar vesicles and large unilamellar vesicles made by the extrusion technique) by a thiyl radical, generated from biologically relevant thiols, has also been studied in detail. The presence of 0.2 mM oxygen does not influence the effectiveness of cis-trans isomerization in both homogeneous solution and lipid vesicles. This process, which does not cause lipid degradation but permanent modification of the membrane constituents, ultimately influences the barrier properties and functions of biological membranes.
The development of improved cationic lipids for gene transfer into cystic fibrosis airway epithelial cells
Harris,Marshall,Lee,Siegel,Mcneilly,Yew,Nietupski,Nichols,Cherry,Wan,Jiang,Lane,Rowe,Scheule,Smith,Cheng
, p. 289 - 292 (2007/10/03)
In an effort to improve the efficiency of cationic lipid mediated gene transfer, over 90 novel cationic lipids of diverse structural types were synthesized and evaluated in vitro. Four cationic lipids derived from phospholipids were examined. The most promising cationic lipid formulations were tested in vivo by intranasal or transtracheal instillation into the lungs of BALB/c mice. The most active formulations gave CAT reporter gene expression levels which are greater than 500 fold over that which could be attained using free DNA alone. Certain cationic lipid formulations have been shown to facilitate substantial expression of the CFTR (cystic fibrosis transmembrane conductance regulator) gene in vitro as determined by the SPQ and Ussing Chamber assays.
