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| Other Sizes |
| Targets |
The primary biological targets of POPS are not specific receptors but rather the lipid-binding domains of various proteins. As a negatively charged phospholipid, POPS serves as a binding partner for numerous proteins involved in cell signaling, membrane trafficking, and blood coagulation. For example, the C2 domains of protein kinase C (PKC) and cytosolic phospholipase A2 (cPLA2) bind to anionic phospholipids like PS in a calcium-dependent manner, anchoring these enzymes to membranes. In the blood coagulation cascade, phosphatidylserine (PS) exposure on the surface of activated platelets provides a platform for the assembly of the tenase and prothrombinase complexes, where factors Va and VIIIa bind to PS via their Gla domains. Additionally, PS is recognized by the phagocytic receptors TIM-1, TIM-4, and BAI1 during efferocytosis (clearance of apoptotic cells). Thus, POPS is a key signaling lipid that regulates enzyme activity, coagulation, and cell death.
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| ln Vitro |
In vitro, POPS is widely used to study the activity of phospholipid-dependent enzymes and to construct model membranes. For protein kinase C (PKC) activity assays, liposomes composed of POPS (20-30 mol%), phosphatidylcholine (PC), and diacylglycerol (DAG) are prepared by thin-film hydration and extrusion. The liposomes are incubated with recombinant PKCalpha, [gamma-32P]-ATP, and a PKC substrate peptide. The phosphorylated product is separated by SDS-PAGE or collected on phosphocellulose filters, and radioactivity is measured by scintillation counting. The presence of POPS enhances PKC activity 5- to 10-fold compared to PC alone. In coagulation assays, POPS liposomes (25-50 microM total lipid) are added to platelet-poor plasma, and the clotting time is measured using a coagulometer. Alternatively, the prothrombinase complex activity is measured by incubating factors Xa and Va with POPS liposomes and prothrombin, followed by quantification of thrombin generation using a chromogenic substrate. In apoptosis studies, POPS liposomes or POPS-containing nanoparticles are used to mimic the "eat-me" signal, and their uptake by phagocytes (e.g., RAW 264.7 macrophages) is quantified by flow cytometry after labeling with a fluorescent lipid.
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| Cell Assay |
For in vitro cell-based experiments, POPS is typically incorporated into liposomes or nanoparticles for delivery studies, rather than being added directly as a free lipid. To assess the role of PS exposure on apoptotic cells, Jurkat T cells or other cell lines are treated with a pro-apoptotic agent (e.g., staurosporine 1 microM, or etoposide). After 4-24 hours, PS exposure on the outer leaflet is detected using fluorescently labeled annexin V (which binds PS) by flow cytometry or fluorescence microscopy. For phagocytosis assays, apoptotic cells are co-incubated with macrophages (e.g., THP-1-derived macrophages) for 1-2 hours. Phagocytosis efficiency is quantified by flow cytometry (labeling apoptotic cells with CFSE) or by counting engulfed cells under a microscope. The effect of exogenous POPS is studied by adding POPS liposomes to the culture medium; these liposomes can bind to the cell surface and may modulate signaling pathways. In some studies, POPS is used to enhance the cellular uptake of nanoparticles or to reduce the immunogenicity of cationic liposomes. Cytotoxicity of POPS-containing formulations is assessed by MTT or LDH assays in relevant cell lines (e.g., HEK293, HeLa).
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| Animal Protocol |
For in vivo animal experiments, POPS is not administered alone but is incorporated into liposomes or nanoparticles as a component to enhance drug delivery or to modulate immune responses. In mouse models of cancer, POPS-containing liposomes (e.g., with doxorubicin) are administered intravenously (tail vein) at a dose of 5-15 mg/kg lipid. Blood samples are collected for PK analysis, and tumor accumulation is assessed by whole-body fluorescence imaging or by extracting and quantifying the drug. In a model of thrombosis, POPS liposomes (1-10 mg/kg total lipid) are injected intravenously into mice, and the prolongation of bleeding time or protection against ferric chloride-induced carotid artery thrombosis is measured. In inflammation models, the effect of POPS-containing liposomes on macrophage polarization is studied by IP injection into LPS-challenged mice, followed by analysis of peritoneal lavage cells and cytokines. For apoptotic cell clearance studies, fluorescently labeled apoptotic cells (treated with camptothecin) are injected into the peritoneum of wild-type or PS receptor-deficient mice. Uptake by peritoneal macrophages is analyzed by flow cytometry after 1-2 hours. These experiments demonstrate the critical role of PS in efferocytosis.
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| ADME/Pharmacokinetics |
As a component of liposomes, the pharmacokinetic profile of POPS is not measured independently, but the overall liposome PK is well characterized. When POPS is incorporated into PEGylated liposomes (10-20 mol% POPS, 80-90 mol% PC/PEG-lipid), the circulation half-life in rodents is 2-5 hours, similar to neutral liposomes. The negative charge from POPS can reduce non-specific interactions with serum proteins and reduce clearance by the reticuloendothelial system (RES) compared to cationic liposomes, but anionic liposomes are still cleared by the liver and spleen. The volume of distribution is primarily the vascular space. The lipid components are metabolized: the fatty acid chains (palmitate and oleate) undergo beta-oxidation, and the phosphoserine headgroup is hydrolyzed to serine and phosphate. Free serine enters amino acid metabolism. Tissue accumulation is highest in the liver, spleen, and lungs. POPS itself is not typically used as a free drug; therefore, its individual PK is not studied. When administered as part of a drug-loaded liposome, the drug's PK is often altered (prolonged half-life, increased AUC) compared to free drug due to encapsulation.
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| Toxicity/Toxicokinetics |
POPS is a naturally occurring membrane lipid and is generally considered safe and biocompatible. In acute toxicity studies of POPS-containing liposomes in mice (lipid doses up to 200 mg/kg IV), no significant adverse effects or mortality are observed. The LD50 of free POPS is not established but is expected to be > 1000 mg/kg IV, as related anionic phospholipids (e.g., DOPG, DOPC) are well tolerated. In vitro, POPS liposomes at concentrations up to 200 microM total lipid show no cytotoxicity in most cell lines (MTT assay). However, excessive exposure of PS on the cell surface is a hallmark of apoptosis, and high levels of exogenous PS may trigger unwanted immune responses or interfere with normal coagulation. In particular, intravenous injection of large amounts of PS liposomes (> 50 mg/kg) may prolong bleeding time due to competition for coagulation factor binding sites. Therefore, when used in vivo, the amount of POPS in liposomes is usually limited to 5-30 mol% of total lipid. Standard laboratory safety precautions (gloves, lab coat) should be used. This product is for research use only and is not for human therapeutic applications.
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| References |
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| Additional Infomation |
POPS is an important anionic phospholipid that mimics the composition of the inner leaflet of the eukaryotic plasma membrane. It is widely used in the preparation of model membranes, supported lipid bilayers, and liposomes for drug delivery. The compound is also used in the reconstitution of membrane proteins such as ion channels, GPCRs, and transporters, as it provides the necessary negative surface charge for protein function. In biophysical studies, POPS is used in Langmuir-Blodgett troughs to measure surface pressure-area isotherms and in FRET-based assays of membrane fusion. In the pharmaceutical context, POPS is an approved excipient in some liposomal drug formulations (e.g., liposomal irinotecan), where it helps to improve drug encapsulation and reduce toxicity. POPS has been used in clinical formulations; however, the compound itself is not a drug and has no approved indication. It is intended for research and formulation development. Storage: powder at -20degC for up to 3 years; in chloroform solution under argon at -20degC, protected from light.
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| Molecular Formula |
C40H75NNAO10P
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| Molecular Weight |
783.99
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| Exact Mass |
783.502
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| CAS # |
321863-21-2
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| PubChem CID |
46891789
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| Appearance |
White to off-white solid powder
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| Melting Point |
> 200°C (lit.)
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
40
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| Heavy Atom Count |
53
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| Complexity |
934
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OC[C@@H](C(=O)[O-])[NH3+])OC(=O)CCCCCCC/C=C\CCCCCCCC.[Na+]
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| InChi Key |
RQYKXRYGZHMUSU-JEAFVVATSA-M
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| InChi Code |
InChI=1S/C40H76NO10P.Na/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(43)51-36(34-49-52(46,47)50-35-37(41)40(44)45)33-48-38(42)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2;/h17-18,36-37H,3-16,19-35,41H2,1-2H3,(H,44,45)(H,46,47);/q;+1/p-1/b18-17-;/t36-,37+;/m1./s1
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| Chemical Name |
sodium;(2S)-2-azaniumyl-3-[[(2R)-3-hexadecanoyloxy-2-[(Z)-octadec-9-enoyl]oxypropoxy]-oxidophosphoryl]oxypropanoate
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| Synonyms |
1,2-POPS; 1,2-POPS; 2-Oleoyl-1-palmitoyl-sn-glycero-3-phospho-L-serine sodium; 1-Hexadecanoyl-2--(9Z-octadecenoyl)-sn-glycero- 3-phospho-L-serine sodium salt
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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 | 1.2755 mL | 6.3776 mL | 12.7553 mL | |
| 5 mM | 0.2551 mL | 1.2755 mL | 2.5511 mL | |
| 10 mM | 0.1276 mL | 0.6378 mL | 1.2755 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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