2929-07-9Relevant articles and documents
Sterol-modified phospholipids: Cholesterol and phospholipid chimeras with improved biomembrane properties
Huang, Zhaohua,Szoka Jr., Francis C.
experimental part, p. 15702 - 15712 (2009/03/12)
We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37°C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.
Homologues and isomers of noladin ether, a putative novel endocannabinoid: Interaction with rat cannabinoid CB1 receptors
Appendino, Giovanni,Ligresti, Alessia,Minassi, Alberto,Daddario, Nives,Bisogno, Tiziana,Di Marzo, Vincenzo
, p. 43 - 46 (2007/10/03)
Two regioisomers and 13 analogues of the putative endocannabinoid noladin ether (2-arachidonyl glyceryl ether, 2-AGE, 1) were synthesized and tested for their interaction with CB1 receptors in rat brain membranes. The results showed that a C-20 tetra-unsaturated moiety is necessary for high affinity, and that a series of alkyl glyceryl ethers of potential occurrence in brain tissues have less affinity than 2-AGE for CB1 receptors.
The Synthesis of Some Ethers and Mixed Ether Esters of Glycerol
Joll, Cynthia A.,Mortimer, Bok-Cheng,Redgrave, Trevor G.,Stick, Robert V.
, p. 1445 - 1448 (2007/10/02)
The syntheses of various monoethers of glycerol, the derived diesters and two triethers are reported.As well, one of the chiral ether diesters of glycerol has been prepared in both optically active forms.
