120964-49-0

Usage

Uses

1-O-Hexadecyl-2-O-methyl-sn-glycerol inhibits protein kinase C activity in human neutrophils.

Upstream product

• 122822-33-7 3-O-hexadecyl-2-O-methyl-1-O-(p-tolylsulfonyl)-sn-glycerol 
• 122822-35-9 3-O-hexadecyl-2-O-methyl-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 36653-82-4 1-Hexadecanol 
• 89496-73-1 4-(n-hexadecyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 92471-46-0 (R)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-ol 
• 74-88-4 methyl iodide 
• 10550-58-0 (R)-3-(hexadecyloxy)-1,2-propanediol 
• 119879-84-4 3-O-hexadecyl-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 119944-30-8 3‐hexadecyloxy‐2R‐hydroxyl propyl‐1‐p‐toluene sulphonate 
• 156737-69-8 3-O-Hexadecyl-1-O-(4-methoxyphenyl)-sn-glycerol 
• 112-82-3 hexadecanyl bromide 
• 156737-70-1 3-O-Hexadecyl-2-O-methyl-1-O-(4-methoxyphenyl)-sn-glycerol 

Relevant academic research and scientific papers

Method for preventing cancer metastasis

The present invention relates to the use of a specific family of glycerolipid compounds of formula (I) described in the detailed description or the manufacture of a medicament for the prevention or for the treatment of cancer metastasis.

A phosphatidylinositol 3,4,5-trisphosphate analogue with low serum protein-binding affinity

Phosphatidylinositol 3,4,5-trisphosphate (PIP3) plays an important role in the regulation of diverse physiological functions. Recent evidence indicates that PIP3 is cell permeant, and can be added exogenously to modulate cellular responses. However, like many other phospholipids, PIP3 binds serum proteins with high affinity, resulting in rapid deactivation of this lipid second messenger. Our study indicates that bovine serum albumin (BSA) at concentrations as low as 10 μg/mL abrogated the biological activity of dipalmitoyl-PIP3. This nonspecific interaction with serum proteins hampers the use of PIP3 in biological studies where serum is needed. We report here an ether-linked PIP3 analogue, 1-O-(1-O-hexadecyl-2-O-methyl-sn-glycero-3-phosphoryl)-myoinositol 3,4,5-trisphosphate (C16Me-PIP3), which displays low serum protein-binding affinity while retaining the biological function of PIP3. The affinity of C16Me-PIP3 with BSA was two orders of magnitude lower than that of its dipalmitoyl-counterpart. Biochemical data indicate that C16Me-PIP3 was able to stimulate Ca2+ influx in T cells in the presence of moderate levels (up to 1 mg/mL) of BSA. Thus, C16Me-PIP3 may provide a useful tool to study the physiological function of phosphoinositide (PI) 3-kinase in vivo.

Regiospecific Opening of Glycidyl Derivatives Mediated by Boron Trifluoride. Asymmetric Synthesis of Ether-Linked Phospholipids

A short, chiral synthesis of unnatural, cytotoxic ether-linked phospholipids is reported in which the key step is the very high regio- and stereospecific nucleophilic opening of the p-toluenesulfonate (1a, 1b) or tert-butyldiphenylsilyl ether (6a, 6b) derivatives of (R)- or (S)-glycidol with 1-hexadecanol using boron trifluoride etherate as catalyst.The enantiomeric excess of the ring-opened products was >94percent, as judged by 1H NMR and chiral HPLC analysis of the Mosher ester derivatives, indicating that ring opening of 1 and 6 proceeds without significant loss of optical purity.The synthetic strategy of using optically active glycidyl derivatives as the precursor of the glycerol backbone permits the desired enantiomers of 1(3)-O-2-O-methylphosphocholines (5a, 5b) to be generated in good yield and high optical purity from the ring-opened intermediates (2, 7) in three steps without the use of protecting groups.