Add time:07/30/2019         Source:sciencedirect.com

Available methodology was adapted to synthesize a labeled diether analog of 2-phosphatidylcholine (1,3-di-O-9'-cis-[9',10'(n)-3H]octadecenylglycero-2-phosphocholine ([3H)DOE-2-PC). Unilamellar liposomes prepared by sonication from this phospholipid were injected into rats and, 4 h later, 65–78% of injected label was recovered in the liver. Thereafter, liver radioactivity disappeared with a half-life of 2–3 days. The radioactivity lost from the liver was recovered in the feces and in bile. Analysis of liver radioactivity showed that at all time intervals examined (4 h to 3 days after injection), 90% of the label remained as phospholipid. These findings provide evidence that this structural isomer is not readily metabolized, but is fairly rapidly eliminated from the liver. Of the 10% recovered as neutral lipid, 70% comigrated with diacylglycerol and 30% with triacylglycerol. Similar results were obtained when human hepatoma G2 cells in culture were incubated with [3H]DOE-2-PC liposomes. Following incubation of liposomes with liver homogenates, up to 10% conversion of [3H]DOE-2-PC to neutral lipid occurred at pH 4.6, but not at pH 7.4. These data show that conversion of [3H]DOE-2-PC to dialkenylglycerol is catalyzed by a lysosomal enzyme. In separate experiments with cultured cells, sonicated dispersions of DOE-2-PC were mixed with high-density apolipoprotein and were shown to enhance markedly cellular cholesterol efflux. This novel diether phospholipid fulfills some of the criteria required of liposomes for their ability to remove cholesterol from the periphery as well as for drug delivery to the liver i.e., stability in the circulation, marked hepatic uptake, slow metabolism, and elimination from the body.

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