77733-28-9

Usage

Uses

Tetradecyl-phosphocholine is a detergent for membrane protein solubilization.

InChI:InChI=1/C19H42NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-18-23-25(21,22)24-19-17-20(2,3)4/h5-19H2,1-4H3

Upstream product

• 75-50-3 trimethylamine 
• 112-72-1 1-Tetradecanol 
• 78561-75-8 2-Tetradecyloxy-[1,3,2]dioxaphospholane 2-oxide 
• 85311-33-7 tetradecyl 2-bromoethyl phosphate 

Relevant academic research and scientific papers

Autotaxin structure-activity relationships revealed through lysophosphatidylcholine analogs

Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) to form the bioactive lipid lysophosphatidic acid (LPA). LPA stimulates cell proliferation, cell survival, and cell migration and is involved in obesity, rheumatoid arthritis, neuropathic pain, atherosclerosis and various cancers, suggesting that ATX inhibitors have broad therapeutic potential. Product feedback inhibition of ATX by LPA has stimulated structure-activity studies focused on LPA analogs. However, LPA displays mixed mode inhibition, indicating that it can bind to both the enzyme and the enzyme-substrate complex. This suggests that LPA may not interact solely with the catalytic site. In this report we have prepared LPC analogs to help map out substrate structure-activity relationships. The structural variances include length and unsaturation of the fatty tail, choline and polar linker presence, acyl versus ether linkage of the hydrocarbon chain, and methylene and nitrogen replacement of the choline oxygen. All LPC analogs were assayed in competition with the synthetic substrate, FS-3, to show the preference ATX has for each alteration. Choline presence and methylene replacement of the choline oxygen were detrimental to ATX recognition. These findings provide insights into the structure of the enzyme in the vicinity of the catalytic site as well as suggesting that ATX produces rate enhancement, at least in part, by substrate destabilization.

Mucosal formulation

A mucosal formulation for administration to mucosal membranes, such as in the mouth, nasal passage, stomach, vagina, etc., is disclosed. The mucosal formulation contains a lipid-pharmaceutical agent complex formed from phospholipids possessing a hydrophobic moiety that orients into a hydrophobic phase and a polar head moiety that orients towards the aqueous phase (i.e., “amphipathic” lipids). When placed in an aqueous medium (e.g., vaginal fluid), the phospholipids form liposomes or other small lipid vesicles (e.g., micelles) that may then be used to deliver pharmaceutical agents into a living organism.

Synthesis and properties of alkyl phosphorylcholine amphiphiles with a linear and an asymmetrically branched alkyl chain

Alkyl phosphorylcholine amphiphiles bearing one linear chain and one asymmetrically branched alkyl chain were successfully synthesized using 2-chloro-2-oxo-1,3,2-dioxaphospholane in tetrahydrofuran or ethyl acetate. 1H and 31PNMR studies revealed that the linear alkyl phosphorylcholines (Cn-PC) provide aqueous micelles in D2O and reverse micelles in CDCl3, while the branched alkyl phosphorylcholines (ISOFOLn-PC) give vesicles in D2O. The critical micelle concentrations (CMCs) of Cn-PC were measured by fluorescence dye solubilization methods: the CMCs of C12-PC, C 14-PC, C16-PC, and C18-PC were 1.6, 0.38, 0.16, and 0.11 mM, respectively, in water at 25 °C. The critical association concentrations (CACs) of ISOFOLn-PC, ISOFOLn-PC, and ISOFOL24-PC were 0.068, 0.005, and 0.077 mM, respectively, in water at 25 °C. The vesicle size of ISOFOLn-PC in aqueous solution was measured by the dynamic light scattering method. The mean diameter of ISOFOLn-PC vesicles was approximately 30 nm and the size distribution was relatively monodisperse. The ISOFOLn-PC vesicles formed were colloidally stable in water over the period of several weeks.

Compound, oleyl-2-pyridinioethyl phosphate having antifungal and antiprotozoal properties

Phospholipids, inclusive of pharmaceutically acceptable salts thereof, of the formula STR1 wherein R1 is a C8-30 aliphatic hydrocarbon residue, R2, R3 and R4 are independently hydrogen or lower alkyl or STR2 represents cyclic ammonio and n is 0 or 1, exhibit inhibitory activity to multiplication of tumor cells and antimycotic (antifungal) and antiprotozoal activities, and are useful for inhibiting multiplication of tumor cells and prolonging the survival time of tumor-bearing warm-blooded animal, for treating or preventing a disease in an animal caused by a mycete (fungus) and for treating or preventing a plant disease.

Synthesis and biological activity of some lysing and fusogenically active phosphocholine derivatives

2-Hexadecylglycerophosphocholine (1) and its 1-O-methyl, 1-O-ethyl and 1-O-benzyl (4) derivatives as well as some n-alkanol phosphocholines were synthetized and tested for haemolytic activity. Most potent (LD50 approximately equal to 5.10(-6) mol/l) were 1 and the hexadecanol and octadecanol phosphocholines (7 and 8). 1, 4 and 7 were tested for fusogenic activity against vegetable protoplasts. When used at sublytic concentrations (0.01 - 0.05 mmol), these compounds were as efficient as polyethylene glycol.