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DODAP

Cat No.:V74054 Purity: ≥98%
DODAP is a cationic lipid.
DODAP
DODAP Chemical Structure CAS No.: 127512-29-2
Product category: Liposome
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
100mg
Other Sizes
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Product Description
DODAP is a cationic lipid. The ionizable lipid DODAP is the lipid component of liposomes. DODAP can be used for encapsulation of siRNA, delivery of immunostimulatory and chemotherapeutic active molecules in vitro and in vivo, etc.
DODAP (1,2-Dioleoyl-3-dimethylammonium-propane) (CAS#: 127512-29-2) is an ionizable cationic lipid with a pKa of 5.59 in a TNS binding assay. It has low cytotoxicity and high transfection efficiency and can be used to synthesize liposomes and encapsulate biologically active molecules such as mRNA, siRNA, and plasmid DNA. The molecular formula is C41H77NO4 and the molecular weight is 648.05.
Biological Activity I Assay Protocols (From Reference)
Targets
DODAP does not have a specific receptor target. As an ionizable cationic lipid, its primary function is to facilitate the encapsulation and intracellular delivery of nucleic acids by forming lipid nanoparticles that enable endosomal escape. It remains largely neutral at physiological pH and becomes protonated under acidic conditions, such as those encountered during endosomal trafficking.
ln Vitro
In vitro, DODAP-based LNPs delivered luciferase mRNA to HEK293T cells for 24 hours, though luciferase expression was lower than MC3-LNPs, indicating reduced transfection efficiency. DODAP has been used to encapsulate siRNA, immunostimulatory oligodeoxynucleotides, antisense oligonucleotides, and chemotherapeutic agents.
ln Vivo
In vivo, DODAP-containing liposomes are used for the delivery of siRNA, immunostimulatory agents, antisense oligonucleotides, and chemotherapeutic agents. The ionizable nature of DODAP (pKa 5.59) allows for pH-dependent charge, facilitating endosomal escape after cellular uptake.
Enzyme Assay
In vitro liposome formation with DODAP involves dissolving the lipid with other components (e.g., DSPC, cholesterol, PEG-lipid) in ethanol, then mixing with aqueous buffer containing the nucleic acid cargo at controlled pH. The resulting LNPs are characterized for size, polydispersity, and encapsulation efficiency. The pKa is determined using a TNS (2-(p-toluidino)naphthalene-6-sulfonic acid) binding assay. DODAP is slightly soluble in chloroform and methanol.
Cell Assay
Cellular transfection efficiency of DODAP formulations is assessed in cell lines such as HEK293T. Cells are treated with LNPs encapsulating reporter genes (luciferase or GFP mRNA), and expression is measured after 24 hours. Cytotoxicity is evaluated using standard assays such as MTT or CellTiter-Glo.
Animal Protocol
In vivo studies involve intravenous administration of DODAP-based LNPs in mice. Tissue distribution, gene expression levels (for mRNA/siRNA cargo), and pharmacokinetic parameters are assessed. DODAP formulations have been evaluated for the delivery of therapeutic nucleic acids in preclinical models.
ADME/Pharmacokinetics
DODAP is an ionizable cationic lipid with low cytotoxicity. Its pKa of 5.59 allows the lipid to be positively charged at acidic pH (enabling endosomal escape) and neutral at physiological pH (reducing toxicity). Pharmacokinetic properties depend on the LNP formulation.
Toxicity/Toxicokinetics
DODAP exhibits low cytotoxicity compared to permanently cationic lipids. The ionizable nature of DODAP reduces non-specific membrane disruption and toxicity at physiological pH, while enabling endosomal escape in acidic compartments. Standard safety precautions for handling lipids should be followed.
References

[1]. Ionization and structural properties of mRNA lipid nanoparticles influence expression in intramuscular and intravascular administration. Commun Biol. 2021 Aug 11;4(1):956.

[2]. Importance of the liposomal cationic lipid content and type in tumor vascular targeting: physicochemical characterization and in vitro studies using human primary and transformed endothelial cells. Endothelium. 2008;15(4):189-201.

[3]. Targeted liposomal delivery of TLR9 ligands activates spontaneous antitumor immunity in an autochthonous cancer model. J Immunol. 2009;183(2):1091-1098.

[4]. Biotinylated cyclen-contained cationic lipids as non-viral gene delivery vectors. Chem Biol Drug Des. 2013;82(4):376-383.

[5]. Transferrin receptor-targeted liposomes encapsulating anti-BCR-ABL siRNA or asODN for chronic myeloid leukemia treatment. Bioconjug Chem. 2010 Jan;21(1):157-68.

Additional Infomation
DODAP (also known as 18:1 DAP) is used as a component in liposomes for encapsulating siRNA, immunostimulatory oligodeoxynucleotides, antisense oligonucleotides, and chemotherapeutic agents. Its ionizable property makes it a valuable tool for nucleic acid delivery research. It has been used in studies for tumor vascular targeting and targeted liposomal delivery.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C41H77NO4
Molecular Weight
648.05
Exact Mass
647.585
CAS #
127512-29-2
PubChem CID
9895790
Appearance
Colorless to light yellow liquid
Density
0.916g/cm3
Boiling Point
670.148ºC at 760 mmHg
Flash Point
359.092ºC
Vapour Pressure
0mmHg at 25°C
Index of Refraction
1.476
LogP
12.078
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
37
Heavy Atom Count
46
Complexity
717
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCC/C=C\CCCCCCCC(OCC(OC(CCCCCCC/C=C/CCCCCCCC)=O)CN(C)C)=O
InChi Key
NYDLOCKCVISJKK-WRBBJXAJSA-N
InChi Code
InChI=1S/C41H77NO4/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-40(43)45-38-39(37-42(3)4)46-41(44)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-2/h19-22,39H,5-18,23-38H2,1-4H3/b21-19-,22-20-
Chemical Name
[3-(dimethylamino)-2-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
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)
DMSO: 100 mg/mL (154.31 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.86 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (3.86 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (3.86 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.5431 mL 7.7155 mL 15.4309 mL
5 mM 0.3086 mL 1.5431 mL 3.0862 mL
10 mM 0.1543 mL 0.7715 mL 1.5431 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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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)
  • Click the “Calculate” button
  • 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)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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