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1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium

Cat No.:V50407 Purity: ≥98%
1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol (sodium) is a component of liposomes used for drug delivery.
1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium
1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium Chemical Structure CAS No.: 200880-42-8
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
500mg
Other Sizes

Other Forms of 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium:

  • (Rac)-1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium
  • 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol-d70 sodium
  • 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol (DSPG)
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Product Description
1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol (sodium) is a component of liposomes used for drug delivery.
1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium (CAS#: 200880-42-8) is a phospholipid used as a component of liposomes for drug delivery. It is a sodium salt of the phosphatidylglycerol lipid with two stearoyl (C18:0) fatty acid chains attached to the glycerol backbone. The compound has a molecular formula of C42H82NaO10P and a molecular weight of 801.06. The IUPAC name is sodium (R)-2,3-bis(stearoyloxy)propyl (2,3-dihydroxypropyl) phosphate. 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium is commonly used in the formulation of liposomal drug delivery systems, where it contributes to liposome stability, drug encapsulation, and targeting. Its negative charge and saturated fatty acid chains make it valuable for preparing stable liposomes for preclinical and clinical applications.
Biological Activity I Assay Protocols (From Reference)
Targets
1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium does not have a specific protein target but functions as a structural lipid in liposomal formulations. As a phosphatidylglycerol, it is an anionic phospholipid that contributes to the negative surface charge of liposomes, which can affect their interactions with cells, proteins, and the immune system. The two saturated stearoyl chains provide rigidity and stability to the lipid bilayer, influencing membrane fluidity, phase transition temperature, and permeability. Phosphatidylglycerols are minor components of biological membranes but are important in mitochondrial membranes and bacterial membranes. In liposomal drug delivery, the compound is often used in combination with other phospholipids (e.g., phosphatidylcholines) and cholesterol to form stable, drug-loaded liposomes. Its negative charge can help reduce liposome aggregation and improve circulation time.
ln Vitro
In vitro, 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium is used in the preparation of liposomes for drug delivery studies. Liposomes containing this lipid are characterized for size, zeta potential, encapsulation efficiency, and drug release kinetics. The compound's negative charge contributes to the zeta potential of liposomes, which affects their stability and interactions with cells. In cellular uptake studies, liposomes containing the compound are incubated with various cell lines, and uptake is quantified using fluorescently labeled lipids or encapsulated fluorescent markers. The compound's effects on liposome stability in biological fluids (e.g., serum) are evaluated by measuring drug leakage and particle size changes over time. Its inclusion in liposomal formulations can influence the rate of drug release, making it a valuable component for designing controlled-release drug delivery systems. The compound is also used in studies of lipid-protein interactions and membrane biophysics.
ln Vivo
In vivo, 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium is used as a component of liposomal drug delivery systems for preclinical studies. Liposomes containing this lipid are administered to rodents to evaluate the pharmacokinetics, biodistribution, and efficacy of encapsulated drugs. The negative charge and saturated fatty acid chains of the lipid contribute to the stability and circulation time of liposomes. Liposomes formulated with this lipid are often taken up by the reticuloendothelial system (RES), primarily in the liver and spleen. The lipid itself is metabolized by phospholipases to release stearic acid and lysophosphatidylglycerol, which enter fatty acid and phospholipid metabolic pathways. The compound's in vivo behavior is formulation-dependent, and its role is to provide the structural matrix for drug delivery rather than to exert direct pharmacological effects.
Enzyme Assay
The in vitro assays using 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium typically involve liposome preparation and characterization. Liposomes are prepared by dissolving the lipid (often in combination with other lipids such as phosphatidylcholine and cholesterol) in organic solvent (e.g., chloroform), evaporating the solvent to form a lipid film, and hydrating the film with aqueous buffer containing the drug to be encapsulated. The resulting liposomes are extruded through polycarbonate membranes to achieve uniform size. Liposome size is measured by dynamic light scattering (DLS), and zeta potential is measured by electrophoretic light scattering. Encapsulation efficiency is determined by separating free drug from liposome-encapsulated drug using size exclusion chromatography or ultracentrifugation, followed by drug quantification by HPLC or UV-Vis spectroscopy. Drug release kinetics are assessed by dialysis or by measuring drug concentration in the release medium over time. Liposome stability in serum is evaluated by monitoring size and drug leakage. All experiments are performed with appropriate controls (liposomes without the compound) and under controlled conditions.
Cell Assay
For in vitro cellular assays, liposomes containing 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium are incubated with cultured cells (e.g., cancer cell lines, macrophages) at varying lipid concentrations. Cellular uptake is assessed using fluorescently labeled lipids or encapsulated fluorescent markers (e.g., calcein, doxorubicin) by flow cytometry or confocal microscopy. Cytotoxicity of empty liposomes and drug-loaded liposomes is evaluated using MTT or CellTiter-Glo assays. For drug delivery studies, the efficacy of encapsulated chemotherapeutic agents is compared to free drug controls. The compound's effects on cellular membrane properties and lipid raft organization are studied using fluorescent probes and imaging techniques. All experiments include appropriate controls (empty liposomes, free drug) and are performed in triplicate.
Animal Protocol
For in vivo studies, liposomes containing 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium are typically administered to rodents via intravenous injection. The liposomes may be used to deliver chemotherapeutic agents, nucleic acids, or imaging agents. Pharmacokinetic studies involve collecting blood samples at various time points and measuring drug or lipid concentrations by HPLC or LC-MS/MS. Biodistribution studies involve harvesting organs (liver, spleen, kidney, lung, tumor) and measuring drug or lipid content. In tumor models, the antitumor efficacy of drug-loaded liposomes is assessed by measuring tumor growth inhibition and survival. The stability of liposomes in circulation is evaluated by measuring the leakage of encapsulated markers. All animal procedures are conducted in accordance with institutional guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium as a lipid component are typically characterized in the context of the liposomal formulation. When administered as liposomes, the lipid components are taken up by the reticuloendothelial system (RES), primarily in the liver and spleen. The compound is metabolized by phospholipases to release stearic acid and lysophosphatidylglycerol, which enter fatty acid and phospholipid metabolic pathways. The half-life of liposomal lipids in circulation ranges from hours to days, depending on the formulation, particle size, and surface modifications (e.g., PEGylation). The compound's distribution and elimination are influenced by its lipophilic nature and its incorporation into lipid bilayers. Detailed PK data for this specific lipid are limited, as it is primarily used as a formulation component rather than a therapeutic agent. However, its behavior is expected to be similar to other phosphatidylglycerols used in liposomal formulations.
Toxicity/Toxicokinetics
Toxicology data for 1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium are primarily evaluated in the context of liposomal formulations. As a naturally occurring phospholipid, it is generally considered biocompatible and has low toxicity. In acute toxicity studies of liposomal formulations, the compound is well-tolerated at doses used for drug delivery. At high doses, liposomal lipids may cause mild inflammatory responses or RES saturation, but these effects are typically reversible. The compound itself is not genotoxic or carcinogenic. In repeated-dose studies, liposomal formulations containing this phospholipid show no significant organ toxicity or hematological abnormalities at therapeutic doses. The safety profile of the compound is consistent with other phospholipids used in FDA-approved liposomal drug products (e.g., Doxil, Ambisome). The compound is for research use only and is not approved as a therapeutic agent, though it may be used in liposomal formulations for preclinical studies.
References

[1]. Negatively-charged Liposome Nanoparticles Can Prevent Dyslipidemia and Atherosclerosis Progression in the Rabbit Model. Curr Vasc Pharmacol. 2022;20(1):69-76.

Additional Infomation
1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium is a phospholipid used as a component of liposomes for drug delivery. Its negative charge and saturated fatty acid chains contribute to liposome stability, drug encapsulation, and delivery. The compound is commonly used in the formulation of liposomal drug delivery systems for preclinical research, including the delivery of chemotherapeutic agents, nucleic acids, and imaging agents. It is a research-grade reagent and is not approved for human use as a therapeutic agent. However, liposomal formulations containing this lipid may be used in preclinical studies to evaluate the efficacy and safety of encapsulated drugs. The compound's role in membrane biology and drug delivery research makes it a valuable tool for pharmaceutical scientists and researchers developing lipid-based drug delivery systems.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C42H82O10P-.NA+
Molecular Weight
801.05808
Exact Mass
800.554
CAS #
200880-42-8
Related CAS #
(Rac)-1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol sodium;124011-52-5;1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol-d70 sodium;326495-47-0;1,2-Distearoyl-sn-Glycero-3-Phosphatidylglycerol;217939-97-4
PubChem CID
46891829
Appearance
White to off-white solid powder
Boiling Point
480.0 °C
Melting Point
90.27 °C
LogP
11.889
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
44
Heavy Atom Count
54
Complexity
865
Defined Atom Stereocenter Count
1
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC(CO)O)OC(=O)CCCCCCCCCCCCCCCCC.[Na+]
InChi Key
YNQYZBDRJZVSJE-QTOMIGAPSA-M
InChi Code
InChI=1S/C42H83O10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h39-40,43-44H,3-38H2,1-2H3,(H,47,48);/q;+1/p-1/t39?,40-;/m1./s1
Chemical Name
sodium;2,3-dihydroxypropyl [(2R)-2,3-di(octadecanoyloxy)propyl] phosphate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO :< 1 mg/mL
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2483 mL 6.2417 mL 12.4835 mL
5 mM 0.2497 mL 1.2483 mL 2.4967 mL
10 mM 0.1248 mL 0.6242 mL 1.2483 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.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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