17364-16-8

Usage

Uses

Used as a Lipid Biomarker:
1-Palmitoyl-SN-Glycero-3-Phosphocholine is used as a lipid biomarker for stable and unstable heart disease, helping in the diagnosis and monitoring of cardiovascular conditions.
Used in Research on Adipose Tissue Inflammation and Insulin Resistance:
In the field of medical research, 1-Palmitoyl-SN-Glycero-3-Phosphocholine is used to reveal the central role of the adipocyte inflammasome in homocysteine-induced insulin resistance, contributing to a better understanding of the underlying mechanisms of metabolic disorders.
Used in Lipid Extraction and Mass Spectrometry Analysis:
1-Palmitoyl-SN-Glycero-3-Phosphocholine is utilized for lipid extraction and mass spectrometry analysis, enabling researchers to study lipid profiles and their associations with various diseases and biological processes.
Used in Immunology and Inflammation Research:
1-Palmitoyl-SN-Glycero-3-Phosphocholine is used in immunology and inflammation research to investigate its effects on the production of reactive oxygen species (ROS), superoxide dismutase (SOD), endothelial nitric oxide synthase (eNOS), and the secretion of pro-inflammatory cytokines such as IL-6, IL-1β, IL-12, and TNF-α in LPS-stimulated M1 macrophages.
Used in Regulatory T Cell Studies:
In the context of immune regulation, 1-Palmitoyl-SN-Glycero-3-Phosphocholine is used to study its impact on TGF-β1 production and Foxp3 protein levels in Treg cells, which are crucial for maintaining immune tolerance and preventing autoimmunity.
Used in Sepsis and Innate Immune Response Research:
1-Palmitoyl-SN-Glycero-3-Phosphocholine is used in sepsis and innate immune response research to explore its role in enhancing neutrophil function, bacterial clearance, and survival in mouse models of sepsis, providing insights into potential therapeutic approaches for the management of this critical condition.

Biochem/physiol Actions

1-Palmitoyl-sn-glycero-3-phosphocholine may be used as a substrate to identify, differentiate and characterize lysophosphocholine acyl transferases.

InChI:InChI=1/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1

Upstream product

• 7501-44-2 hexadecanoic acid, glycidyl ester 
• 645-84-1 choline phosphate 
• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 14912-92-6 caesium palmitate 
• 605680-01-1 1-palmitoyl-2-(tetrahydropyran-2-yl)-sn-3-glycerophosphocholine 
• 408-35-5 sodium palmitate 
• 112-67-4 n-hexadecanoyl chloride 
• 623-65-4 palmitic anhydride 
• 29603-38-1 1-palmitoyl-2-benzylglycerophosphocholine 
• 17364-18-0 1-palmitoyllysophosphatidylcholine 
• 28319-77-9 L-α-glycerophosphorylcholine 
• 63-89-8 L-α-Dipalmitoylphosphatidylcholine 
• 6753-55-5 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine 
• 525-66-6 propranolol 

Downstream Products

• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 128368-78-5 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine 
• 6931-84-6 lecithin 
• 1039749-81-9 C₅₅H₈₆NO₈PS 
• 57-10-3 1-hexadecylcarboxylic acid 
• 875685-46-4 10-Nitrooleic Acid 
• 294659-11-3 (E)-methyl 10-nitrooctadec-9-enoate 
• 117205-52-4 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine 
• 1372802-60-2 C₇₉H₁₄₃F₄N₅O₁₆P₂S₂ 

Relevant academic research and scientific papers

Lytic reactions of drugs with lipid membranes

Propranolol is shown to undergo lipidation reactions in three types of lipid membrane: (1) synthetic single-component glycerophospholipid liposomes; (2) liposomes formed from complex lipid mixtures extracted from E. coli or liver cells; and (3) in cellulo in Hep G2 cells. Fourteen different lipidated propranolol homologues were identified in extracts from Hep G2 cells cultured in a medium supplemented with propranolol. This isolation of lipidated drug molecules from liver cells demonstrates a new drug reactivity in living systems. Acyl transfer from lipids to the alcoholic group of propranolol was favoured over transfer to the secondary amine. Migration of acyl groups from the alcohol to the amine was diminished. Other drugs that were examined did not form detectable levels of lipidation products, but many of these drugs did affect the lysolipid levels in model membranes. The propensity for a compound to induce lysolipid formation in a model system was found to be a predictor for phospholipidosis activity in cellulo.

Synthetic access to arsenic-containing phosphatidylcholines

We wish to disclose the first synthesis of 1-O-hexadecanoyl-2-O-((15-(dimethylarsinoyl)pentadecanoyl)oxy)-sn-glycero-3-phosphocholine, which belongs to the group of arsenic-containing phosphatidylcholines (AsPCs), recently discovered in herring caviar. The synthesized product will serve as a model compound to study biological and toxicological properties of arsenolipids in food.

Syntheses and antiproliferative activities of novel phosphatidylcholines containing dehydroepiandrosterone moieties

Dehydroepiandrosterone (DHEA) is a natural hormone with many beneficial properties including an anticancer activity. Unfortunately, DHEA is unstable in the body and exhibits cytotoxicity against healthy cells. In this study, a series of new phosphocholines containing DHEA at sn-1 and/or sn-2 positions were prepared. Succinic acid was used as a linker between the active drug and sn-glycero-3-phosphocholine. All the compounds were evaluated in vitro for their antiproliferative activities against four cell lines: Balb/3T3, HL-60, B16, and LNCaP. The results showed that phosphocholines with DHEA at sn-1 and/or sn-2 positions did not have cytotoxic effects on the normal cell line (Balb/3T3). Mixed-chain phospholipids with DHEA and fatty acid residues showed the highest activity against tumor cell lines. The most active compound, 11c, showed a moderate cytotoxic effect against the HL-60 and B16 cell lines.

Synthesis and biological evaluation of novel phosphatidylcholine analogues containing monoterpene acids as potent antiproliferative agents

The synthesis of novel phosphatidylcholines with geranic and citronellic acids in sn-1 and sn-2 positions is described. The structured phospholipids were obtained in high yields (59-87%) and evaluated in vitro for their cytotoxic activity against several cancer cell lines of different origin: MV4-11, A-549, MCF-7, LOVO, LOVO/DX, HepG2 and also towards noncancer cell line BALB/3T3 (normal mice fibroblasts). The phosphatidylcholines modified with monoterpene acid showed a significantly higher antiproliferative activity than free monoterpene acids. The highest activity was observed for the terpene-phospholipids containing the isoprenoid acids in sn-1 position of phosphatidylcholine and palmitic acid in sn-2.

Peptidophospholipids: Synthesis, phospholipase A2 catalyzed hydrolysis, and application to development of phospholipid prodrugs

New phospholipid analogues incorporating sn-2-peptide substituents have been prepared to probe the fundamental structural requirements for phospholipase A2 catalyzed hydrolysis of PLA2-directed synthetic substrates. Two structurally

Synthesis of phosphatidylcholine with conjugated linoleic acid and studies on its cytotoxic activity

Phospholipids with conjugated linoleic acid (CLA), which are potential lipid prodrugs, were synthesised. CLA was obtained by the alkali-isomerisation of linoleic acid and was subsequently used in the synthesis of 1,2-di(conjugated)linoleoyl-sn-glycero-3-phosphocholine in good (82%) yield. 1-Palmitoyl-2-(conjugated)linoleoyl-sn-glycero-3-phosphocholine was obtained by a two-step synthesis in 87% yield. All the compounds were tested in an in vitro cytotoxicity assay against two human cancer cell lines, HL-60 and MCF-7, and a mouse fibroblast cell line, Balb/3T3. The free form of CLA exhibited the highest activity against all cancer cell lines. Results obtained for the Balb/3T3 line proved that phosphatidylcholine derivatives decreased the cytotoxic effect of CLA against healthy cell lines.

Acyl transfer from phosphocholine lipids to melittin

Transfer of fatty acyl groups from membrane phospholipids to melittin, a commonly studied membrane-active peptide, has been observed to occur over extended time periods. Transfer can be detected after 1-2 days and selectively targets amino groups at the N-terminal end of the peptide.

Interfacial kinetic and binding properties of mammalian group IVB phospholipase A2 (cPLA2β) and comparison with the other cPLA2 isoforms

The cytosolic (group IV) phospholipase A2 (cPLA2s) family contains six members. We have prepared recombinant proteins for human α, mouse β, human γ, human δ, human ε, and mouse ζ cPLA2s and have studied their interfacial kinetic and binding properties in vitro. Mouse cPLA2β action on phosphatidylcholine vesicles is activated by anionic phosphoinositides and cardiolipin but displays a requirement for Ca2+ only in the presence of cardiolipin. This activation pattern is explained by the effects of anionic phospholipids and Ca2+ on the interfacial binding of mouse cPLA2β and its C2 domain to vesicles. Ca2+-dependent binding of mouse cPLA 2β to cardiolipin-containing vesicles requires a patch of basic residues near the Ca2+-binding surface loops of the C2 domain, but binding to phosphoinositide-containing vesicles does not depend on any specific cluster of basic residues. Human cPLA2δ also displays Ca 2+- and cardiolipin-enhanced interfacial binding and activity. The lysophospholipase, phospholipase A1, and phospholipase A2 activities of the full set of mammalian cPLA2s were quantified. The relative level of these activities is very different among the isoforms, and human cPLA2δ stands out as having relatively high phospholipase A1 activity. We also tested the susceptibility of all cPLA 2 family members to a panel of previously reported inhibitors of human cPLA2α and analogs of these compounds. This led to the discovery of a potent and selective inhibitor of mouse cPLA2β. These in vitro studies help determine the regulation and function of the cPLA2 family members.

Lysophosphatidylethanolamine is - in contrast to - choline - generated under in vivo conditions exclusively by phospholipase A2 but not by hypochlorous acid

Inflammatory liver diseases are associated with oxidative stress mediated particularly by neutrophilic granulocytes. At inflammatory loci, hypochlorous acid (HOCl) is generated by myeloperoxidase. HOCl reacts with a large variety of molecules and induces

Discrimination of chain positions in mixed short/long-chain glycerophosphocholines by NMR chemical shift variations

The synthesis of a series of (1,2-) mixed short/long-chain glycerophosphocholines has been performed. Starting from glycerophosphorylcholine (GPC), and using regioselective acylation in the presence of dibutyltin oxide, a set of high-purity isomeric mixed-chain phospholipids was obtained. This has allowed the development of a simple NMR method for the structural determination of the isomeric 1(2)-short-2(1)-long- diacylglycerophosphocholines. The method is based on the observation that selected protons in the two series of isomeric phospholipids undergo systematic chemical shift variations Δδ that can be ascribed to the acyl substituents on the glycerol backbone. The observed patterns can be exploited as a simple method for the discrimination of regioisomeric unsymmetrical 1,2-diacylglycerophosphocholines.