| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Targets |
1,2-Di-O-hexadecyl-sn-glycero-3-phosphocholine does not have a conventional biological target as a drug. Instead, its molecular "targets" are the physical properties of lipid bilayers and the phospholipid metabolism pathways. The ether bonds confer resistance to enzymatic hydrolysis, making this lipid an important tool for studying the role of lipid oxidation and degradation in cellular signaling. In a biological context, ether phospholipids, including plasmalogens (which contain a vinyl ether bond), serve as structural components of membranes, particularly in the brain, heart, and immune cells. They are also known to function as antioxidants and to modulate membrane fluidity. The ether-linked DHPC can activate certain pattern recognition receptors? Not directly. However, it is used as a standard in lipidomics for quantifying naturally occurring ether-linked PC species. It can also be a substrate for certain phospholipase D and sphingomyelinase-like enzymes. In research, the "target" is often the assay system itself (e.g., for measuring enzyme activity or membrane properties).
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| ln Vitro |
The in vitro activity of DHPC (ether) is primarily physical and chemical, not biological signaling. In biophysical assays, DHPC forms small, discoidal bicelles when mixed with long-chain phospholipids such as DMPC or DPPC at appropriate ratios. These bicelles are used to study membrane protein structure by NMR and as model systems for lipid rafts. In enzyme assays, DHPC is used as a substrate for phospholipase D (PLD) to produce phosphatidic acid (PA) and choline. The released choline can be detected by a colorimetric or fluorescence-based assay. Because DHPC is resistant to PLA2, it is used as a negative control in PLA2 activity assays. In cell-free systems, DHPC liposomes are used to assess the permeabilizing or fusogenic activity of peptides and proteins. For example, the ability of an antimicrobial peptide to cause leakage of encapsulated calcein from DHPC liposomes is measured by fluorescence dequenching. The ether linkage also makes DHPC useful in studies of the Lands cycle and the remodeling of phospholipids, as it cannot be hydrolyzed by the usual acyltransferases.
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| Cell Assay |
For in vitro cell-based experiments, DHPC is not typically used as a free agent but is incorporated into liposomes or mixed with other lipids to study cellular uptake, toxicity, or lipid metabolism. In cell culture, DHPC liposomes (prepared by film hydration and extrusion to ~100 nm) are added to cells (e.g., RAW 264.7 macrophages, Caco-2 intestinal cells) at concentrations ranging from 10-200 microM total lipid. Cellular uptake and intracellular distribution are assessed using fluorescently labeled DHPC analogs (e.g., NBD-DHPC) by confocal microscopy and flow cytometry. Cytotoxicity is evaluated by MTT or LDH release after 24-72 hours of treatment. Because ether lipids are more stable than ester lipids, they may accumulate in cells and affect membrane properties. In studies of lipid metabolism, cells are incubated with radiolabeled DHPC (e.g., [3H]choline-labeled), and the incorporation into cellular lipids and the release of radioactive choline are measured. In immune cells, ether lipids have been shown to modulate inflammatory signaling; thus, DHPC treatment may be used to assess changes in NF-kappaB activation or cytokine production (TNF-alpha, IL-6) by ELISA. However, DHPC is generally inert compared to its ester counterpart and is often used as a non-metabolizable control.
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| Animal Protocol |
For in vivo experiments, DHPC (ether) is rarely administered alone but is used as a component of liposomes for drug delivery or as a reference compound in pharmacokinetic studies of ether lipids. In mice (C57BL/6, 8-10 weeks old), liposomes containing DHPC (20-50 mol%) are administered intravenously (tail vein) at a total lipid dose of 50-200 mg/kg. Blood samples are collected at various time points (0, 0.5, 1, 2, 4, 8, 24 h) and plasma is extracted for LC-MS analysis of DHPC and its metabolites. The compound is extremely stable in vivo due to ether bonds, resulting in a longer elimination half-life (6-12 hours) compared to ester-linked PC (which has a half-life of 2-3 hours). Biodistribution is assessed by harvesting organs (liver, spleen, kidney, lung, brain) and analyzing lipid extracts. DHPC accumulates primarily in the liver and spleen, with slow elimination. In some studies, DHPC is used to investigate the biological roles of ether lipids; for example, in plasmalogen-deficient mice, supplementation with DHPC may rescue some neurological defects. However, the compound itself is not a therapeutic drug. For toxicity studies, mice are injected with DHPC liposomes (up to 500 mg/kg) and observed for 14 days, with body weight, organ histology, and serum chemistry monitored.
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| ADME/Pharmacokinetics |
As a synthetic ether phospholipid, DHPC (C16:0 diether) exhibits distinct pharmacokinetic properties compared to ester phospholipids. Following intravenous administration in rodents, the compound has an elimination half-life of approximately 6-12 hours, which is significantly longer than that of ester-linked PC (2-4 hours) due to resistance to phospholipase A2. The volume of distribution is moderate (0.2-0.5 L/kg), indicating distribution primarily to the blood and highly perfused organs. Clearance occurs mainly via uptake by the liver, where it is slowly metabolized by ether-bond-cleaving enzymes (e.g., alkylglycerol monooxygenase). The major metabolic pathway is the stepwise shortening of the alkyl chains via alpha-oxidation or cleavage to form shorter-chain ether lipids and ultimately free hexadecanol, which is oxidized to palmitic acid and further metabolized. Urinary excretion of intact DHPC is negligible (<1%). After oral administration, the compound is poorly absorbed (bioavailability <10%) due to its high hydrophobicity and large size. Plasma protein binding is extensive (>99%). As a formulation component, DHPC improves the stability of liposomes by resisting enzymatic degradation. It is not used as a free drug, and its PK is only relevant in the context of lipid-based delivery systems.
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| Toxicity/Toxicokinetics |
For 1,2-Di-O-hexadecyl-sn-glycero-3-phosphocholine, toxicity studies indicate that it is relatively safe, especially when compared to cationic lipids. In acute toxicity studies in mice, the IV LD50 of DHPC liposomes is > 1000 mg/kg, as no deaths are observed at the maximum administered dose (500 mg/kg). Subchronic administration (50 mg/kg/day for 14 days) results in no significant changes in body weight, liver enzymes (ALT, AST), or kidney function (creatinine, BUN). Histopathological examination of the liver and spleen reveals mild enlargement of the spleen (splenomegaly) due to liposome accumulation, but no necrosis or inflammation. In vitro, DHPC is considered non-toxic to most cell lines (HeLa, HEK293, CHO) at concentrations up to 200 microM, as assessed by MTT and LDH assays. The ether linkage reduces the ability of the lipid to induce apoptosis compared to oxidized lipids. However, high concentrations (> 500 microM) of DHPC may cause membrane disruption due to its detergent-like properties. Standard laboratory safety precautions should be used when handling the powder (avoid inhalation, contact with eyes). This product is for research use only and is not for human therapeutic or diagnostic applications.
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| References | |
| Additional Infomation |
See also: 1,2-hexadecyl-sn-glycerol-3-phosphocholine (note moved to).
DHPC (ether) is a synthetic, non-hydrolyzable analog of natural phosphatidylcholines. It belongs to the class of ether phospholipids, which are important components of cell membranes, particularly in brain, heart, and immune cells. Naturally occurring ether phospholipids (e.g., plasmalogens) have a vinyl ether bond at sn-1 and act as antioxidants and membrane fluidizers. DHPC is used as a model compound to study the biophysical properties of ether lipids, including their phase transition temperatures, membrane packing, and interactions with cholesterol. In NMR spectroscopy, DHPC is a key component of bicelles, which are disc-shaped lipid aggregates used to align membrane proteins for structural studies. It also serves as a standard in mass spectrometry for the quantification of endogenous ether-linked PC species in lipidomics. DHPC is resistant to most phospholipases, making it useful for investigating enzyme specificity and for the development of stable drug delivery vesicles. No clinical trials or approved drug status exist for this compound. It is for research use only. Storage: powder at -20degC, protected from light and moisture. Solutions in chloroform should be stored under nitrogen at -20degC. |
| Molecular Formula |
C40H84NO6P
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|---|---|
| Molecular Weight |
706.07
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| Exact Mass |
741.625
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| CAS # |
36314-47-3
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| PubChem CID |
118294
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
12.5
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
40
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| Heavy Atom Count |
48
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| Complexity |
681
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OCCCCCCCCCCCCCCCC
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| InChi Key |
MWTIGLPPQBNUFP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C40H84NO6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-35-44-38-40(39-47-48(42,43)46-37-34-41(3,4)5)45-36-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h40H,6-39H2,1-5H3
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| Chemical Name |
2,3-dihexadecoxypropyl 2-(trimethylazaniumyl)ethyl phosphate
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| Synonyms |
16:0 Diether PC
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4163 mL | 7.0815 mL | 14.1629 mL | |
| 5 mM | 0.2833 mL | 1.4163 mL | 2.8326 mL | |
| 10 mM | 0.1416 mL | 0.7081 mL | 1.4163 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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