4217-84-9

Basic information

• Product Name: L-A-GLYCERYLPHOSPHORYLCHOLINE(GPC)
• Synonyms: L-A-GLYCERYLPHOSPHORYLCHOLINE(GPC);2-[[(S)-2,3-Dihydroxypropyl]oxy(oxylato)phosphinyloxy]-N,N,N-trimethylethanaminium;D-Glycero-3-phosphocholine;D-Glycerol 3-phosphorylcholine;D-Glycerolphosphocholine;D-Glycerophosphocholine;D-Glycerophosphorylcholin
• CAS NO: 4217-84-9
• Molecular Formula: C₈H₂₀NO₆P
• Molecular Weight: 257.22
• Mol File: 4217-84-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly, Sonicated)
• Stability: Hygroscopic
• CAS DataBase Reference: L-A-GLYCERYLPHOSPHORYLCHOLINE(GPC)(CAS DataBase Reference)
• NIST Chemistry Reference: L-A-GLYCERYLPHOSPHORYLCHOLINE(GPC)(4217-84-9)
• EPA Substance Registry System: L-A-GLYCERYLPHOSPHORYLCHOLINE(GPC)(4217-84-9)

Safety Data

• Hazardous Substances Data: 4217-84-9(Hazardous Substances Data)

Usage

Uses

α-Glycerylphosphorylcholine is a parasympathomimetic acetylcholine precursor which may have potential for the treatment of Alzheimer''s disease and other dementias.

Upstream product

• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 3436-45-1 1,2-Diheptanoyl-3-L-α-phosphatidylcholine 
• 1299486-12-6 C₁₃H₂₆N₄O₅P⁽¹⁺⁾ 
• 960075-50-7 L-α-glycerophosphorylcholine chloride 
• 75-50-3 trimethylamine 

Relevant articles and documents

Diplasmenylcholine-folate liposomes: An efficient vehicle for intracellular drug delivery

Most pharmaceutical and gene therapy applications of targeted liposomes presently suffer from inefficient contents delivery to the cytoplasm of target cells. We report a plasma-stable liposome, composed of synthetic, naturally occurring diplasmenylcholine (1,2-di-O-(Z-1′-hexadecenyl)-sn-glycero-3-phosphocholine; DPPlsC), that rapidly and efficiently releases its contents at endosomal pHs. Acid-catalyzed hydrolysis of these liposomes produces glycerophosphocholine and fatty aldehydes, leading to greatly enhanced liposome permeability (t50% release ? 1-4 h between pH 4.5-5.5) when > 20% of the vinyl ether lipid has been hydrolyzed. Plasma stability of nonhydrolyzed 9:1 DPPlsC/dihydrocholesterol liposomes exceeds 48 h at 37°C, pH 7.4 in 50% serum; pure DPPlsC liposomes remain stable in 10% serum under the same conditions. Fluorescence assays of KB cells treated with 99.5:0.5 DPPlsC/DSPE-PEG3350-folate liposomes containing encapsulated propidium iodide (PI) indicate that 83% of the PI escapes the endosomal compartment within 8 h to produce intensely stained nucleii. The IC50 value of 1-β-arabinofuranosylcytosine (Ara-C) encapsulated in DPPlsC/DSPE-PEG3350-folate liposomes is 0.49 μM in KB cell cultures, a approx. 6000-fold enhancement in cytotoxicity compared with free drug (2.8 mM). Empty DPPlsC/DSPE-PEG3350-folate liposomes had no effect on DNA synthesis, indicating that DPPlsC and its degradation products are benign to cell function at these lipid concentrations. Our results suggest that concurrent application of selective targeting and membrane translocation mechanisms in drug carriers can significantly increase their efficacy. Most pharmaceutical and gene therapy applications of targeted liposomes presently suffer from inefficient contents delivery to the cytoplasm of target cells. We report a plasma-stable liposome, composed of synthetic, naturally occurring diplasmenylcholine (1,2-di-O-(Z-1'-hexadecenyl)-sn- glycero-3-phosphocholine; DPPIsC), that rapidly and efficiently releases its contents at endosomal pHs. Acid-catalyzed hydrolysis of these liposomes produces glycerophosphocholine and fatty aldehydes, leading to greatly enhanced liposome permeability (t(50% release) ? 1-4 h between pH 4.5-5.5) when >20% of the vinyl ether lipid has been hydrolyzed. Plasma stability of nonhydrolyzed 9:1 DPPlsC/dihydrocholesterol liposomes exceeds 48 h at 37°C, pH 7.4 in 50% serum; pure DPPlsC liposomes remain stable in 10% serum under the same conditions. Fluorescence assays of KB cells treated with 99.5:0.5 DPPlsC/DSPE-PEG3350-folate liposomes containing encapsulated propidium iodide (PI) indicate that 83% of the PI escapes the endosomal compartment within 8 h to produce intensely stained nucleii. The IC50 value of 1-β- arabinofuranosylcytosine (Ara-C) encapsulated in DPPlsC/DSPE-PEG3350-folate liposomes is 0.49 μM in KB cell cultures, a ~6000-fold enhancement in cytotoxicity compared with free drug (2.8 mM). Empty DPPlsC/DSPE-PEG3350- folate liposomes had no effect on DNA synthesis, indicating that DPPlsC and its degradation products are benign to cell function at these lipid concentrations. Our results suggest that concurrent application of selective targeting and membrane translocation mechanisms in drug carriers can significantly increase their efficacy.

Fluorogenic probes to monitor cytosolic phospholipase A2 activity

Arachidonic acid derivatives equipped with either one or two fluorescent groups attached to the tip of the alkyl chains were synthesized and shown to function as inhibitor and substrate probes of cPLA2. The inhibitor probe was demonstrated to p

SYNTHESIS OF PHOSPHORIC ESTERS

The present invention relates to a process for the preparation of phosphoric esters, and to selected compounds.