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DSPE-succinic acid

Alias: DSPE-succinic acid; 248253-94-3; NSC671619; SCHEMBL22788417; NSC-671619;
Cat No.:V73448 Purity: ≥98%
DSPE-succinic acid is a phospholipid with a carboxylic acid terminal end.
DSPE-succinic acid
DSPE-succinic acid Chemical Structure CAS No.: 248253-94-3
Product category: Liposome
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
500mg
Other Sizes
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Product Description
DSPE-succinic acid is a phospholipid with a carboxylic acid terminal end. Its carboxylic acid moiety can react with amines to form stable amide bonds. DSPE-succinic acid may be utilized to prepare nanoparticles or liposomes that serve as nanocarriers for active molecules.
DSPE-succinic acid (CAS#: 248253-94-3) is a phospholipid compound consisting of 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (DSPE) conjugated to a succinic acid moiety. It has a molecular formula of C45H86NO11P and a molecular weight of 848.14. The molecule features two 18-carbon lipid tails and a phosphate group joined by a glycerol backbone, with a carboxylic acid group at the terminal end of the succinic acid linker. This amphiphilic molecule can self-assemble in water to form lipid bilayers. DSPE-succinic acid is used to prepare nanoparticles or liposomes for drug delivery applications.
Biological Activity I Assay Protocols (From Reference)
Targets
As a lipid excipient, DSPE-succinic acid does not have a specific biological receptor target. Its primary function is as a structural component of liposomes and nanoparticles. The carboxylic acid moiety provides a reactive handle for conjugation to amine-containing molecules (e.g., proteins, peptides, targeting ligands) in the presence of an activating agent such as EDC or HATU, forming a stable amide linkage. This allows for the functionalization of liposomes for targeted drug delivery.
ln Vitro
In vitro, DSPE-succinic acid is used in the preparation of nanoparticles or liposomes for drug delivery. The carboxylic acid group can be used to conjugate targeting ligands or therapeutic agents, enabling the creation of functionalized nanocarriers. The compound's ability to form stable lipid bilayers makes it a valuable component for encapsulating and delivering therapeutics such as mRNA or DNA vaccines.
ln Vivo
In vivo, DSPE-succinic acid-containing liposomes and nanoparticles are used for drug delivery applications. The functionalized nanoparticles can be used to deliver therapeutics to specific tissues or cells. The compound itself is an excipient and does not have intrinsic biological activity, but it enables the creation of targeted and effective drug delivery systems.
Enzyme Assay
In vitro assays for DSPE-succinic acid typically involve characterizing the formation and functionalization of liposomes or nanoparticles. Liposomes are prepared by dissolving the lipid components in organic solvent, followed by solvent removal and hydration. The successful incorporation of DSPE-succinic acid and the availability of the carboxylic acid group for conjugation can be verified using methods such as dynamic light scattering (DLS) for size and zeta potential, and by using colorimetric assays to quantify carboxylic acid groups.
Cell Assay
In vitro cellular assays for DSPE-succinic acid are typically performed as part of drug delivery studies. Cells are treated with liposomes or nanoparticles formulated with the lipid, and their uptake, cytotoxicity, and therapeutic efficacy are assessed. The carboxylic acid group can be used to conjugate fluorescent probes or targeting ligands to track cellular uptake and targeting efficiency.
Animal Protocol
In vivo animal studies for DSPE-succinic acid-containing formulations typically involve the administration of the nanoparticles to rodent models to assess their pharmacokinetics, biodistribution, and therapeutic efficacy. The formulations can be used to deliver a variety of therapeutic agents, including nucleic acids and small molecule drugs.
ADME/Pharmacokinetics
DSPE-succinic acid has a molecular weight of 848.14 and a molecular formula of C45H86NO11P. It is soluble in DMF at 3.33 mg/mL (3.93 mM) with ultrasonic warming to 60°C. The compound is typically stored at -20°C. Detailed pharmacokinetic parameters are not applicable as the compound is an excipient.
Toxicity/Toxicokinetics
There is no specific toxicity data reported for DSPE-succinic acid in the available literature. As a research chemical, it should be handled with standard safety precautions. Phospholipids are generally considered biocompatible and low in toxicity. The compound is not approved for human therapeutic use.
References

[1]. Antitumor effect of folate-targeted liposomal doxorubicin in KB tumor-bearing mice after intravenous administration. J Drug Target. 2011 Jan;19(1):14-24.

Additional Infomation
The role of folate-targeted liposomal doxorubicin (FTL-Dox) in folate receptor (FR)-overexpressing tumors in vitro has been well characterized, particularly in human KB cancer cells. However, studies evaluating the in vivo efficacy of FTL-Dox in a KB mouse xenograft model are scarce. This study investigated the antitumor activity of intravenously administered FTL-Dox in KB-bearing tumor-bearing mice. We synthesized a folate ligand composed of folate-polyethylene glycol-distearate phosphatidylethanolamine (FA-PEG-DSPE) and used polyethylene glycol (PEG) of varying molecular weights. To design the optimal FTL-Dox formulation for therapeutic studies, we prepared multiple FTLs and characterized their in vitro targeting and in vivo tissue biodistribution. Mice received a single intravenous injection of free doxorubicin, untargeted PEGylated liposomal doxorubicin (PL-Dox), or FTL-Dox, respectively. Although FTL was cleared from the circulatory system more rapidly, FTL and PL accumulated similarly in tumor tissues. Mice treated with FTL-Dox 20 mg/kg showed slightly higher tumor growth inhibition than mice treated with PL-Dox 20 mg/kg, and their lifespan was extended by nearly 50% (P = 0.0121; log-rank test). We conclude that systemically administered FTLs have the potential to enhance in vivo anticancer drug delivery; however, to realize the benefits of tumor-targeted therapy, it may be necessary to block the clearance of FTLs by normal tissues expressing FRs. [1]
DSPE-succinic acid is a phospholipid with a carboxylic acid moiety, used to prepare nanoparticles or liposomes for drug delivery. It has a molecular formula of C45H86NO11P and a molecular weight of 848.14. The carboxylic acid group allows for conjugation to amine-containing molecules, enabling the creation of functionalized drug delivery systems.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C45H86NO11P
Molecular Weight
848.138216495514
Exact Mass
847.593
CAS #
248253-94-3
PubChem CID
54608655
Appearance
Typically exists as White to off-white solid at room temperature
LogP
14.4
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
47
Heavy Atom Count
58
Complexity
1040
Defined Atom Stereocenter Count
1
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCNC(=O)CCC(=O)O)OC(=O)CCCCCCCCCCCCCCCCC
InChi Key
YHASCFOFGLKNAQ-VQJSHJPSSA-N
InChi Code
InChI=1S/C45H86NO11P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-44(50)54-39-41(40-56-58(52,53)55-38-37-46-42(47)35-36-43(48)49)57-45(51)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h41H,3-40H2,1-2H3,(H,46,47)(H,48,49)(H,52,53)/t41-/m1/s1
Chemical Name
4-[2-[[(2R)-2,3-di(octadecanoyloxy)propoxy]-hydroxyphosphoryl]oxyethylamino]-4-oxobutanoic acid
Synonyms
DSPE-succinic acid; 248253-94-3; NSC671619; SCHEMBL22788417; NSC-671619;
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)
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
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 1.1791 mL 5.8953 mL 11.7905 mL
5 mM 0.2358 mL 1.1791 mL 2.3581 mL
10 mM 0.1179 mL 0.5895 mL 1.1791 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?
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  • 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:
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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
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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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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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