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1-Stearoyl-2-docosahexaenoyl-sn-glyerco-3-phosphocholine (SDPC; DHA-PC; 18:0/22:6 PC)

Cat No.:V84017 Purity: ≥98%
1-Stearoyl-2-docosahexaenoyl-sn-glyerco-3-phosphocholine (SDPC; DHA-PC; 18:0/22:6 PC)
1-Stearoyl-2-docosahexaenoyl-sn-glyerco-3-phosphocholine (SDPC; DHA-PC; 18:0/22:6 PC) Chemical Structure CAS No.: 59403-52-0
Product category: PPAR
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
1-Stearoyl-2-docosahexaenoyl-sn-glyerco-3-phosphocholine (SDPC; DHA-PC) is a new generation omega-3 lipid that contains an ester bond to DHA at the sn-2 position of the phospholipid. 1-Stearoyl-2-docosahexaenoyl-sn-glyerco-3-phosphocholine exerts anti-angiogenic effects through activation of PPARγ. 1-Stearoyl-2-docosahexaenoyl-sn-glyerco-3-phosphocholine significantly reduces proliferation, migration, and tube formation of human umbilical vein endothelial cells. 1-Stearoyl-2-docosahexaenoyl-sn-glyerco-3-phosphocholine has the potential for anti-tumor angiogenesis research.
1-Stearoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine (SDPC; DHA-PC; 18:0/22:6 PC) is a new generation omega-3 lipid that contains an ester bond linking docosahexaenoic acid (DHA) at the sn-2 position of the phospholipid. It exerts anti-angiogenic effects through activation of PPARγ. The compound significantly reduces proliferation, migration, and tube formation of human umbilical vein endothelial cells (HUVECs). It has a molecular weight of 834.16 and formula C48H84NO8P. It is intended for research use only.
Biological Activity I Assay Protocols (From Reference)
Targets
PPARγ
SDPC targets PPARγ (peroxisome proliferator-activated receptor gamma), a nuclear receptor that regulates lipid metabolism, glucose homeostasis, and inflammation. As a PPARγ activator, SDPC exerts anti-angiogenic effects. The compound's structure features an ester bond linking DHA at the sn-2 position of the phospholipid. By activating PPARγ, it modulates gene expression involved in angiogenesis and endothelial cell function.
ln Vitro
In vitro studies demonstrate that SDPC significantly reduces the proliferation, migration, and tube formation of human umbilical vein endothelial cells (HUVECs). It exerts anti-angiogenic effects through activation of PPARγ. In MTT assays, SDPC inhibits HUVEC proliferation with an IC50 of 331.8 μg/mL at 48 hours. Wound-healing assays confirm its inhibitory effects on cell migration. These activities make it a valuable tool for angiogenesis research.
ln Vivo
In vivo activity of SDPC is inferred from its anti-angiogenic mechanism as a PPARγ activator. By inhibiting endothelial cell proliferation, migration, and tube formation, the compound may reduce pathological angiogenesis in vivo. Detailed in vivo efficacy data from animal models, including tumor angiogenesis and retinopathy models, are not extensively documented in the available literature.
Enzyme Assay
The in vitro receptor binding assay for SDPC involves measuring its activation of PPARγ. Transcriptional reporter assays using PPARγ-responsive luciferase constructs transfected into cells are commonly employed. Cells are treated with SDPC at various concentrations, and luciferase activity is measured to assess PPARγ activation. Standard protocols include appropriate positive controls such as rosiglitazone and vehicle controls.
Cell Assay
In vitro cell-based assays for SDPC are conducted using human umbilical vein endothelial cells (HUVECs). Cells are treated with the compound at various concentrations, and proliferation is measured using MTT or CCK-8 assays. Cell migration is assessed using wound-healing or transwell assays. Tube formation is evaluated on Matrigel-coated plates. PPARγ activation is confirmed by measuring downstream target gene expression by qPCR. Cytotoxicity is evaluated using standard cell viability assays.
Animal Protocol
In vivo animal studies for SDPC would typically be conducted using mouse models of angiogenesis-dependent diseases such as cancer, retinopathy, or wound healing. Animals would be administered the compound via appropriate routes, and angiogenesis would be assessed by measuring vessel density, tumor growth, or wound closure. PPARγ activation in tissues would be confirmed. However, detailed protocols and efficacy data are not available from the search results.
ADME/Pharmacokinetics
Pharmacokinetic properties of SDPC include a molecular weight of 834.16 and a molecular formula of C48H84NO8P. As a phospholipid containing DHA at the sn-2 position, it is a new generation omega-3 lipid. Detailed pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution are not extensively documented in the available literature. The compound is intended for research use only.
Toxicity/Toxicokinetics
Toxicity information for SDPC is limited. As a naturally occurring phospholipid, it is generally considered to have low toxicity. Standard safety precautions for handling research chemicals should be followed. The compound is designated for research use only and is not for human therapeutic applications. No detailed toxicity data are available from the search results.
References

[1].DHA-enriched phosphatidylcholine suppressed angiogenesis by activating PPARγ and modulating the VEGFR2/Ras/ERK pathway in human umbilical vein endothelial cells. Food Sci Biotechnol. 2021 Oct 27;30(12):1543-1553.

Additional Infomation
1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol-3-phosphocholine is a phosphatidylcholine 40:6, wherein the acyl groups at positions 1 and 2 are octadecanoyl and (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl, respectively. It is a mouse metabolite. Its function is related to octadecanoic acid and all-cis-docosahexaenoic acid (4,7,10,13,16,19-hexaenoic acid).
SDPC (DHA-PC; 18:0/22:6 PC) is a new generation omega-3 lipid with DHA at the sn-2 position. It exerts anti-angiogenic effects through PPARγ activation. It inhibits HUVEC proliferation (IC50 331.8 μg/mL), migration, and tube formation. It has MW 834.16 and formula C48H84NO8P. It is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C48H84NO8P
Molecular Weight
834.16
Exact Mass
833.593
CAS #
59403-52-0
PubChem CID
24778876
Appearance
Typically exists as solid at room temperature
LogP
11.56
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
42
Heavy Atom Count
58
Complexity
1210
Defined Atom Stereocenter Count
1
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC
InChi Key
FAUYAENFVCNTAL-PFFNLMTBSA-N
InChi Code
InChI=1S/C48H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-39-41-48(51)57-46(45-56-58(52,53)55-43-42-49(3,4)5)44-54-47(50)40-38-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,24-25,29,31,35,37,46H,6-7,9,11-13,15,17-19,21,23,26-28,30,32-34,36,38-45H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,31-29-,37-35-/t46-/m1/s1
Chemical Name
[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxy-3-octadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl 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

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)
Typically soluble in DMSO (e.g. 10 mM)
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 1.1988 mL 5.9941 mL 11.9881 mL
5 mM 0.2398 mL 1.1988 mL 2.3976 mL
10 mM 0.1199 mL 0.5994 mL 1.1988 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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An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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  • The answer appears in the Volume (to add to vial) box
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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