The uptake of pristane (2,6,10,14-tetramethylpentadecane) into phospholipid bilayers as assessed by NMR, DSC, and tritium labeling methods.
Unilamellar dioleoylphosphatidylcholine (DOPC) liposomes (250 microM) incorporated 2 mol% of [3H]pristane at 37 degrees C after addition of 50 microM pristane solubilized with beta-cyclodextrin. Conventional solubilization in dimethyl sulphoxide resulted in much lower uptake. Premixing of perdeuterated pristane with DOPC and dipalmitoylphosphatidylcholine (DPPC) prior to the formation of multilamellar liposomes resulted in homogeneous incorporation of up to 5 mol% pristane at 22 degrees C and 50 degrees C, respectively, as observed by 2H-NMR. Lipid order parameters measured by 31P and 2H-NMR remained unchanged after pristane uptake. Pristane induced the transformation of part of the dioleoylphosphatidylethanolamine (DOPE)/DOPC (3:1, mol/mol) liquid crystalline lamellar phase into an inverse hexagonal phase. 5 mol% pristane in DPPC bilayers decreased the midpoint of the main phase transition temperature of DPPC from 41.5 degrees C to 40.9 degrees C. Upon cooling in the temperature range from 41 degrees C to 36 degrees C, pristane was either displaced from the DPPC bilayer or the mode of incorporation changed. These results may aid in defining the mechanisms whereby pristane, an isoprenoid C19-isoalkane, induces plasmacytomagenesis in mice.
Gawrisch
K
K
Division of Computer Research and Technology, National Institutes of Health, Bethesda, MD 20892.
Janz
S
S
D015060:1,2-Dipalmitoylphosphatidylcholine / Q000737:chemistry; D002152:Calorimetry, Differential Scanning / Q000379:methods; D002273:Carcinogens / Q000737:chemistry*; D008051:Lipid Bilayers; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008954:Models, Biological; D010713:Phosphatidylcholines / Q000737:chemistry*; D010714:Phosphatidylethanolamines / Q000737:chemistry; D010743:Phospholipids / Q000737:chemistry*; D011865:Radioisotope Dilution Technique; D013729:Terpenes / Q000737:chemistry*; D014316:Tritium
D002273:Carcinogens; D008051:Lipid Bilayers; D010713:Phosphatidylcholines; D010714:Phosphatidylethanolamines; D010743:Phospholipids; D013729:Terpenes; D014316:Tritium; D015060:1,2-Dipalmitoylphosphatidylcholine; C009042:pristane; C020888:1,2-dielaidoylphosphatidylethanolamine; C017251:1,2-oleoylphosphatidylcholine