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| Targets |
1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine does not possess a specific pharmacological target as a standalone molecule. Its function is structural and biophysical—it serves as a lipid component in biological membranes and in synthetic lipid-based delivery systems. In liposome and lipid nanoparticle formulations, DOPE acts as a helper lipid that promotes membrane destabilization and fusion with cellular membranes, enhancing the intracellular delivery of encapsulated therapeutics. The compound's ability to form inverted hexagonal phases facilitates membrane fusion and endosomal escape, which is critical for efficient delivery of nucleic acids and other macromolecules. DOPE does not interact with specific receptors or signaling pathways; its effects are mediated through its physicochemical properties as a phospholipid.
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| ln Vitro |
In this investigation, every single siRNA was encapsulated in LNP (cationic tray-A: PEG2000-DMPE: DOPE molar percentage of 47.8: 5.18: 47.1) [1]. The knockdown (KD) effect is exhibited by macrophages and DCs, while fusion is observed in DOPE that contains liposomes. Instead,Monocytes, neutrophils, plasmacytoid DCs, and B cells are not inhibited by LNP/siRNA, but it dramatically reduces the expression of CD45 protein, causing a 30% reduction in macrophage and DC activity [1]. Human giant cell eroded cells and DCs, as well as cells, may use LNP as a siRNA suspension system [1].
The in vitro activity of DOPE is evaluated primarily in the context of lipid-based drug delivery systems. DOPE is incorporated into liposomes or lipid nanoparticles, and its effects on membrane fusion, cargo delivery, and transfection efficiency are assessed. In cell-based assays, DOPE-containing formulations are evaluated for their ability to deliver nucleic acids (DNA, siRNA, mRNA) or other therapeutics into cells. The compound's ability to enhance transfection efficiency is assessed by measuring the expression of reporter genes (for DNA or mRNA) or the knockdown of target genes (for siRNA). DOPE's membrane fusion properties can be studied using liposome fusion assays, where the mixing of lipids or contents between liposomes is monitored by fluorescence. |
| ln Vivo |
In vivo activity of DOPE is realized through lipid-based drug delivery systems that incorporate this phospholipid. DOPE-containing liposomes or lipid nanoparticles are used to deliver therapeutics, including nucleic acids, chemotherapeutics, and imaging agents, to target tissues in animal models. The compound's ability to enhance membrane fusion and endosomal escape contributes to the efficacy of these delivery systems. DOPE is a common component in FDA-approved lipid nanoparticle formulations for nucleic acid delivery, including siRNA and mRNA therapeutics. Specific in vivo data for DOPE alone are not typically reported, as its activity is always evaluated in the context of a complete formulation.
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| Enzyme Assay |
Characterization of DOPE involves standard analytical techniques for phospholipids. Purity is typically assessed by HPLC or TLC, with the compound available at ≥98% purity. Nuclear magnetic resonance (NMR) spectroscopy (¹H and ³¹P) confirms the chemical structure, while mass spectrometry (MS) provides accurate molecular weight confirmation. The compound's fatty acid composition can be confirmed by gas chromatography. The compound is typically stored frozen to maintain stability. Its molecular weight is 744.05 and its molecular formula is C41H78NO8P. DOPE is a white to light yellow powder or lump at room temperature. It is heat sensitive and should be stored in a freezer.
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| Cell Assay |
Cell-based studies with DOPE are typically conducted in the context of lipid-based delivery systems. DOPE-containing liposomes or lipid nanoparticles are formulated with therapeutic cargo and evaluated in cell lines for delivery efficiency. Cells are treated with the formulation, and the following endpoints are assessed: cellular uptake (by flow cytometry or fluorescence microscopy), transfection efficiency (by reporter gene expression or gene knockdown), and cytotoxicity (by MTT or CellTiter-Glo). The contribution of DOPE to the formulation's activity is assessed by comparing formulations with and without DOPE or by varying the DOPE content.
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| Animal Protocol |
In vivo studies with DOPE are performed using lipid-based delivery systems that incorporate this phospholipid. DOPE-containing liposomes or lipid nanoparticles are administered to animal models via various routes (e.g., intravenous, intramuscular, subcutaneous), and the following endpoints are assessed: biodistribution (by imaging or tissue analysis), therapeutic efficacy (by disease outcome measures), and toxicity (by clinical chemistry and histopathology). DOPE is a common component in approved lipid nanoparticle formulations for nucleic acid delivery.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of DOPE are typically evaluated in the context of lipid nanoparticle formulations rather than as a free compound. The phospholipid's contribution to the overall pharmacokinetics of the formulation—including circulation half-life, biodistribution, and clearance—is assessed in preclinical studies. DOPE is generally considered biocompatible and biodegradable, with the lipid being metabolized through normal lipid metabolic pathways.
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| Toxicity/Toxicokinetics |
As a phospholipid, DOPE is generally considered to have low toxicity and is biocompatible. It is a naturally occurring lipid that is a component of biological membranes. DOPE is approved for use in pharmaceutical formulations, including FDA-approved lipid nanoparticle products for nucleic acid delivery. However, as with all research chemicals, standard laboratory safety precautions should be followed when handling the compound.
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| References |
[1]. Uemura Y, et al. The efficiency of lipid nanoparticles with an original cationic lipid as a siRNA delivery system for macrophages and dendritic cells.Pharm Dev Technol. 2019 Mar;24(3):263-268.
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| Additional Infomation |
1,2-Di-[(9Z)-octadecenoyl]-sn-glycerol-3-phosphate ethanolamine is a 1,2-diacyl-sn-glycerol-3-phosphate ethanolamine, wherein the acyl substituents at positions 1 and 2 are both (9Z)-octadecenoyl. It is a mouse metabolite functionally associated with oleic acid. PE (18:1(9Z)/18:1(9Z)) is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain).
DOPE is a naturally occurring phospholipid widely used in the formulation of liposomes and lipid nanoparticles for drug delivery applications. It is a key component of lipid-based delivery systems for nucleic acids, chemotherapeutics, and imaging agents. DOPE is included in FDA-approved lipid nanoparticle formulations for siRNA and mRNA therapeutics. It is not a drug itself but a pharmaceutical excipient. Synonyms include Dioleoyl phosphatidylethanolamine and 1,2-DOPE. The compound is available from multiple chemical suppliers. |
| Molecular Formula |
C₄₁H₇₈NO₈P
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| Molecular Weight |
744.03
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| Exact Mass |
743.546
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| CAS # |
4004-05-1
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| PubChem CID |
9546757
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| Appearance |
White to light yellow solid powder
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| Density |
1.008g/cm3
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| Boiling Point |
759.2±70.0 °C at 760 mmHg
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| Melting Point |
200 °C
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| Flash Point |
413.0±35.7 °C
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| Vapour Pressure |
0.0±5.5 mmHg at 25°C
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| Index of Refraction |
1.484
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| LogP |
14.79
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
41
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| Heavy Atom Count |
51
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| Complexity |
897
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| Defined Atom Stereocenter Count |
1
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| SMILES |
P(=O)(O[H])(OC([H])([H])C([H])([H])N([H])[H])OC([H])([H])C([H])(C([H])([H])OC(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(/[H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O)OC(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(/[H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
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| InChi Key |
MWRBNPKJOOWZPW-NYVOMTAGSA-N
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| InChi Code |
InChI=1S/C41H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39H,3-16,21-38,42H2,1-2H3,(H,45,46)/b19-17-,20-18-/t39-/m1/s1
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| Chemical Name |
[(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
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| Synonyms |
1,2Dioleoylsnglycero3phosphoethanolamine; 1,2 Dioleoyl sn glycero 3 phosphoethanolamine
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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) |
Ethanol : ~10 mg/mL (~13.44 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2 mg/mL (2.69 mM) (saturation unknown) in 10% EtOH + 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 20.0 mg/mL clear EtOH 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 mg/mL (2.69 mM) in 10% EtOH + 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 20.0 mg/mL clear EtOH 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. View More
Solubility in Formulation 3: ≥ 2 mg/mL (2.69 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3440 mL | 6.7202 mL | 13.4403 mL | |
| 5 mM | 0.2688 mL | 1.3440 mL | 2.6881 mL | |
| 10 mM | 0.1344 mL | 0.6720 mL | 1.3440 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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