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1,2-dioleoyloxy-3-(trimethylammonium)propane

1,2-dioleoyloxy-3-(trimethylammonium)propane is a lipid compound with a quaternary ammonium group and two oleic acid ester moities.
It is commonly used as a cationic lipid in the formulation of liposomes and lipid nanoparticles for drug delivery and gene transfection applications.
PubCompare.ai can help researchers optimize their work with this compound by locating the best protocols from literature, preprints, and patents using AI-driven comparisons to enhance reproducibilty and accuaracy, streamlining the research process.

Most cited protocols related to «1,2-dioleoyloxy-3-(trimethylammonium)propane»

1
In Vitro mRNA Synthesis and LNP Formulation
mRNA was synthesized in vitro by T7 RNA polymerase–mediated transcription, using either uridine 5′-triphosphate or 100% substituted with 1mΨTP, from a linearized DNA template, which incorporates 5′ and 3′ untranslated regions and a polyadenosine tail. For process A, NTPs were included at equimolar concentrations, and the resulting mRNA was purified by 2′-deoxy-T20 oligo affinity chromatography. For process B, NTPs were included at custom molar ratios and purified by ion pair RP-HPLC. After purification, mRNA was buffer-exchanged into 2 mM sodium citrate (pH 6.5), passed through a 0.22-μm filter, and stored at −20°C until use.
LNP formulations were prepared as previously described (48 (link)). Briefly, lipids dissolved in ethanol at a molar ratio of 50:10:38.5:1.5 of ionizable:helper:structural:polyethylene glycol were mixed with acidified mRNA at a ratio of 3:1 mRNA:lipid. Formulations were dialyzed against PBS (pH 7.4) for at least 18 hours, concentrated using Amicon Ultra centrifugal filters (EMD Millipore Corp., Merck KGaA, Darmstadt, Germany), passed through a 0.22-μm filter, and stored at 4°C until use. Particle size was measured by dynamic light scattering and found to be <100 nm; encapsulation was >90%, as measured by the Quant-iT RiboGreen RNA quantitation kit (Thermo Fisher Scientific), and endotoxin was <10 endotoxin units (EU)/ml. mRNA was formulated with DOTAP (Sigma-Aldrich, St. Louis, MO) according to the manufacturer’s recommended protocol.
Nelson J., Sorensen E.W., Mintri S., Rabideau A.E., Zheng W., Besin G., Khatwani N., Su S.V., Miracco E.J., Issa W.J., Hoge S., Stanton M.G, & Joyal J.L. (2020). Impact of mRNA chemistry and manufacturing process on innate immune activation. Science Advances, 6(26), eaaz6893.
Publication 2020
1,2-dioleoyloxy-3-(trimethylammonium)propane bacteriophage T7 RNA polymerase Buffers Chromatography, Affinity Endotoxins Ethanol High-Performance Liquid Chromatographies Lipids Molar Oligonucleotides oxytocin, 1-desamino-(O-Et-Tyr)(2)- polyadenosine Polyethylene Glycols RNA, Messenger Sodium Citrate Tail Transcription, Genetic Uridine Triphosphate
2
Preparation and Characterization of siRNA-Loaded LCP-II Nanoparticles

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Publication 2011
1,2-dioleoyloxy-3-(trimethylammonium)propane 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-methoxy-poly(ethylene glycol 2000) 1,2-distearoylphosphatidylethanolamine 1,2-oleoylphosphatidylcholine Chloroform Cholesterol Cyclohexane Emulsions Ethanol Lipids Liposomes Molar Pellets, Drug Phosphates polycarbonate Protamines RNA, Small Interfering Surfactants Tissue, Membrane Tromethamine
3
Formulation of RNA-Loaded Lipid Nanoparticles
RNA-loaded LNP formulations were formed using the ethanol dilution method28 (link). The liver-targeted mRNA formulation (mDLNP) was developed and reported in our previous paper27 (link), and the base formulations were prepared as previously described35 (link), 11 . Unless otherwise stated, all lipids with specified molar ratios were dissolved in ethanol and RNA was dissolved in 10 mM citrate buffer (pH 4.0). The two solutions were rapidly mixed at an aqueous to ethanol ratio of 3:1 by volume (3:1, aq.:ethanol, vol:vol) to satisfy a final weight ratio of 40:1 (total lipids:mRNA), then incubated for 10 min at room temperature. To prepare SORT LNP formulations containing anionic SORT lipids (such as 18PA, 14PA and 18BMP), the anionic lipids were dissolved in tetrahydrofuran (THF) first then mixed with other lipid components in ethanol, finally yielding formulations with mRNA buffer (10 mM, pH 3.0) as described above. All formulations were named based on the additional lipids. Taking DOTAP mDLNP as an example, the internal molar ratio of mDLNP was fixed as reported in our published paper with 5A2-SC8/DOPE/Cholesterol/DMG-PEG of 15/15/30/327 (link). DOTAP, as the additional lipid, was dissolved into the above ethanol lipid mixture with specified amount, making the molar ratio of 5A2-SC8/DOPE/Cholesterol/DMG-PEG/DOTAP equal to 15/15/30/3/X, then rapidly mixed with aq. mRNA solutions following the above standard protocol, finally producing SORT LNPs named Y% DOTAP, where Y means the molar percent of DOTAP in total lipids. Formulations with other additional lipids were formed similarly with the above methods (Supplementary Fig. 1 and Table 1). As a representative example, liver targeted SORT LNPs (20% DODAP) could be prepared as follows. A solution of lipids in ethanol was prepared consisting of 7.59 mM 5A2-SC8, 7.59 mM DOPE, 15.18 mM Cholesterol, 1.52 mM DMG-PEG2000, and 7.97 mM DODAP to make the final molar ratio of 19.05/19.05/38.1/3.81/20. To reach a final 40/1 (wt/wt) of total lipids to total RNAs ratio, 1.16 μL lipid solution could be used per μg RNA. For example, to make a final 5 μg RNA formulation, 5.8 μL lipid mixture and 9.2 μL ethanol were mixed first (total 15 μL), then 45 μL mRNA solution was prepared consisting of 5 μg RNA in citrate buffer (10 mM, pH 4.0). The 45 μL mRNA solution was rapidly combined into 15 μL of the ethanol lipid solution to form 20% DODAP SORT LNPs. For Cas9/sgRNA ribonucleoprotein (RNP) encapsulation, 1X PBS was used for formulation and the molar ratio of Cas9 and sgRNA was fixed at 1:3. After SORT LNP formation, the fresh LNP formulations were diluted with 1X PBS to 0.5 ng/μL mRNA (with final ethanol concentration < 5%) for in vitro assays and size detection by Dynamic Light Scattering (DLS, Malvern MicroV model; He-Ne laser, λ = 632 nm). For in vivo experiments, the formulations were dialyzed (Pur-A-Lyzer Midi Dialysis Kits, WMCO 3.5kDa, Sigma-Aldrich) against 1X PBS for 2h, and diluted with PBS to 15 μL/g for intravenous (IV) injections.
Cheng Q., Wei T., Farbiak L., Johnson L.T., Dilliard S.A, & Siegwart D.J. (2020). Selective ORgan Targeting (SORT) nanoparticles for tissue specific mRNA delivery and CRISPR/Cas gene editing. Nature nanotechnology, 15(4), 313-320.
Publication 2020
1,2-dioleoyloxy-3-(trimethylammonium)propane Biological Assay Buffers Cholesterol Citrates Dialysis Ethanol Lipid A Lipids Liver Molar Ribonucleoproteins RNA, Messenger Technique, Dilution tetrahydrofuran
4
Tissue and Single-cell Determination
For tissue determinations, we assayed tissue lysate using a commercially available kit (Abcam Inc.). For single cell determinations, we transfected alveoli with the probe, GlnK-GFP (Perceval, gift of Dr. G. Yelen, Harvard University)35 (link). We complexed the Perceval plasmid (2.5 µg µl−1) with liposomes (20 µg µl−1, 100-nm pore size; DOTAP, Avanti Lipids) that we suspended in sterile PBS to a final plasmid concentration of 1 µg µl−1. We gave mice intranasal instillations of the plasmid-liposome mixture (50 µl), then 48 h later we imaged Perceval fluorescence in alveoli. For control, we transfected empty vector.
Islam M.N., Das S.R., Emin M.T., Wei M., Sun L., Westphalen K., Rowlands D.J., Quadri S.K., Bhattacharya S, & Bhattacharya J. (2012). Mitochondrial transfer from bone marrow-derived stromal cells to pulmonary alveoli protects against acute lung injury. Nature medicine, 18(5), 759-765.
Publication 2012
1,2-dioleoyloxy-3-(trimethylammonium)propane Cells Cloning Vectors Fluorescence Lipids Liposomes Mus Plasmids Sterility, Reproductive Tissues Tooth Socket
5
Formulation of RNA-Loaded Lipid Nanoparticles
RNA-loaded LNP formulations were formed using the ethanol dilution method28 (link). The liver-targeted mRNA formulation (mDLNP) was developed and reported in our previous paper27 (link), and the base formulations were prepared as previously described35 (link), 11 . Unless otherwise stated, all lipids with specified molar ratios were dissolved in ethanol and RNA was dissolved in 10 mM citrate buffer (pH 4.0). The two solutions were rapidly mixed at an aqueous to ethanol ratio of 3:1 by volume (3:1, aq.:ethanol, vol:vol) to satisfy a final weight ratio of 40:1 (total lipids:mRNA), then incubated for 10 min at room temperature. To prepare SORT LNP formulations containing anionic SORT lipids (such as 18PA, 14PA and 18BMP), the anionic lipids were dissolved in tetrahydrofuran (THF) first then mixed with other lipid components in ethanol, finally yielding formulations with mRNA buffer (10 mM, pH 3.0) as described above. All formulations were named based on the additional lipids. Taking DOTAP mDLNP as an example, the internal molar ratio of mDLNP was fixed as reported in our published paper with 5A2-SC8/DOPE/Cholesterol/DMG-PEG of 15/15/30/327 (link). DOTAP, as the additional lipid, was dissolved into the above ethanol lipid mixture with specified amount, making the molar ratio of 5A2-SC8/DOPE/Cholesterol/DMG-PEG/DOTAP equal to 15/15/30/3/X, then rapidly mixed with aq. mRNA solutions following the above standard protocol, finally producing SORT LNPs named Y% DOTAP, where Y means the molar percent of DOTAP in total lipids. Formulations with other additional lipids were formed similarly with the above methods (Supplementary Fig. 1 and Table 1). As a representative example, liver targeted SORT LNPs (20% DODAP) could be prepared as follows. A solution of lipids in ethanol was prepared consisting of 7.59 mM 5A2-SC8, 7.59 mM DOPE, 15.18 mM Cholesterol, 1.52 mM DMG-PEG2000, and 7.97 mM DODAP to make the final molar ratio of 19.05/19.05/38.1/3.81/20. To reach a final 40/1 (wt/wt) of total lipids to total RNAs ratio, 1.16 μL lipid solution could be used per μg RNA. For example, to make a final 5 μg RNA formulation, 5.8 μL lipid mixture and 9.2 μL ethanol were mixed first (total 15 μL), then 45 μL mRNA solution was prepared consisting of 5 μg RNA in citrate buffer (10 mM, pH 4.0). The 45 μL mRNA solution was rapidly combined into 15 μL of the ethanol lipid solution to form 20% DODAP SORT LNPs. For Cas9/sgRNA ribonucleoprotein (RNP) encapsulation, 1X PBS was used for formulation and the molar ratio of Cas9 and sgRNA was fixed at 1:3. After SORT LNP formation, the fresh LNP formulations were diluted with 1X PBS to 0.5 ng/μL mRNA (with final ethanol concentration < 5%) for in vitro assays and size detection by Dynamic Light Scattering (DLS, Malvern MicroV model; He-Ne laser, λ = 632 nm). For in vivo experiments, the formulations were dialyzed (Pur-A-Lyzer Midi Dialysis Kits, WMCO 3.5kDa, Sigma-Aldrich) against 1X PBS for 2h, and diluted with PBS to 15 μL/g for intravenous (IV) injections.
Cheng Q., Wei T., Farbiak L., Johnson L.T., Dilliard S.A, & Siegwart D.J. (2020). Selective ORgan Targeting (SORT) nanoparticles for tissue specific mRNA delivery and CRISPR/Cas gene editing. Nature nanotechnology, 15(4), 313-320.
Publication 2020
1,2-dioleoyloxy-3-(trimethylammonium)propane Biological Assay Buffers Cholesterol Citrates Dialysis Ethanol Lipid A Lipids Liver Molar Ribonucleoproteins RNA, Messenger Technique, Dilution tetrahydrofuran

Most recents protocols related to «1,2-dioleoyloxy-3-(trimethylammonium)propane»

1
Lipid Nanoparticle Formulation for siRNA Delivery

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Publication 2023
1,2-dioleoyloxy-3-(trimethylammonium)propane Cations Centrifugation DNA Chips Ethanol Lipid A Lipids Molar Nucleic Acids RNA, Small Interfering
2
Preparation of Lipid Nanoparticles for siRNA Delivery

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Publication 2023
1,2-dioleoyloxy-3-(trimethylammonium)propane Cholesterol Freezing Isotonic Solutions Lipid Droplet Molar N-palmitoylsphingosine Nitrogen Nucleic Acids Phosphates RNA, Small Interfering Solvents Sterility, Reproductive Sucrose tert-Butyl Alcohol
3
Ethanol-Injection Liposomal Formulations
Several liposomal formulations were fabricated using ethanol injection method as previously performed (Nikoofal-Sahlabadi et al. 2018 (link)). The lipid phase consisted of variable molar ratios of the cationic lipid DOTAP, and/or other neutral lipids including DOPE, HSPC, DSPE-mPEG2000, the MMP-2 cleavable mPEG2000-peptide-DOPE, cholesterol and the antioxidant α-tocopherol (Table 1). The total lipid concentration of each formulation was set to 50 mM. Briefly, lipids were dissolved in chloroform and mixed at different molar ratios in a round-bottom flask, as shown in Table 1. The organic solvent was then evaporated by a rotary evaporator (Heidolph, Germany), followed by a 2 h freeze-drying process using the VD-800F lyophilizer (Taitech, Koshigaya, Japan) to remove any residue of the organic solvent in the prepared thin layer lipid film. Next, the lipid film was dissolved in warm absolute ethyl alcohol (65 °C) and injected with pre-heated ammonium sulfate solution (250 mM, 65 °C) at 1:9 v/v ratio. The liposomal formulations were incubated at 65 °C for 1 h while shaking on a vortex shaker. This was followed by a 5 min sonication using a bath sonicator (Bandelin electronic GmbH & Co. KG, Berlin, Germany). The resultant large multilamellar vesicles (MLVs) were then extruded (11×) using the thermobarrel extruder (Avestin, Inc., Ottava, Canada) through 200 nm, 100 nm, and 50 nm polycarbonate filters (Whatman, Maidstone, UK). The final products were dialyzed (cellulose membrane, 12–14 kDa MWCO, MilliporeSigma, Burlington, MA, USA) against dextrose histidine buffer (10 mM, pH 6.5) to remove free ammonium sulfate. To Dox encapsulation, the amount of 1 mg Dox per 12 µmol total lipid from Dox solution was loaded into liposomes after incubation at 65 °C for 1 h, and cooled to room temperature. Free Dox were finally removed by dialysis (cellulose membrane, 12–14 kDa MWCO, MilliporeSigma, Burlington, MA, USA) against dextrose histidine buffer (10 mM, pH 6.5).
The ultimate prepared liposomal formulations were sterilized using 0.22 µm syringe filters and stored at 2–8 °C. Liposomes characterization is explained in detail in the SI.
Askarizadeh A., Mashreghi M., Mirhadi E., Mirzavi F., Shargh V.H., Badiee A., Alavizadeh S.H., Arabi L, & Jaafari M.R. (2023). Doxorubicin-loaded liposomes surface engineered with the matrix metalloproteinase-2 cleavable polyethylene glycol conjugate for cancer therapy. Cancer Nanotechnology, 14(1), 18.
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Publication 2023
1,2-dioleoyloxy-3-(trimethylammonium)propane 1,2-distearoylphosphatidylethanolamine Absolute Alcohol alpha-Tocopherol Antioxidants Bath Buffers Cations Cellulose Chloroform Cholesterol Dialysis Ethanol Glucose Histidine Lipids Liposomes MMP2 protein, human Molar Peptides polycarbonate Solvents Sulfate, Ammonium Syringes Tissue, Membrane
4
Formulation and Characterization of Cubosomal Nanoparticles
The standard CNPs (SCNPs) were prepared using the Bottom-up method. Briefly, 5.33 mg/mL of MO (Danisco A/S, Denmark) were dissolved in ethanol and dispersed in an aqueous phase at a ratio of 1:3 v/v.38 (link) Dextran (Pharmacosmos, Denmark) and Kolliphor® P407 (BASF, Germany) (4.32 mg/mL and 173 μg/mL, respectively) were previously dissolved in MilliQ water. The resulting formulation was mixed for 15 minutes by moderate magnetic stirring.
For the preparation of the cationic and chitosan-coated cubosomal nanoparticles liquid formulations, several proportions of lipid mixtures were prepared by the thin lipid film hydration method to evaluate their influence on the physicochemical properties of the resulting cubosomes. Briefly, the lipid mixtures were composed of 70:25:5, 60:30:10, 50:35:15 and 40:40:20%MOL of MO, CHO (Sigma-Aldrich, USA) and charged lipids (DOTAP or DOPS, cationic and anionic lipids, respectively) (Lipoid GmbH, Germany). The lipids were introduced into a round-bottomed opaque flask and dissolved by a mixture of organic solvents (dichloromethane:methanol 50:50 v/v). Except for the blank formulations, the PP (Biochem Partner, China) was previously dissolved in the organic solvent-lipid mixture.
The organic solvents were removed within 20 minutes using a Rotavapor R-205 (Büchi Labortechnik, Flawil, Switzerland) at 60°C to produce a thin lipid film at the internal surface of the round-bottom flask. The pressure was set at 250 mmHg for 10 minutes and 150 mmHg for the next 10 minutes.
Finally, the Bottom-up method was used to generate the CNPs. This process relies on the lipid film dissolution by ethanol and, then, by the precipitation of the cubosomes by adding of an excess of an aqueous phase. In this work, Kolliphor® P407 (10% w/w of lipid mixture) was dissolved in MilliQ water to stabilize the colloidal system.
A further coating step of the anionic CNPs with chitosan followed this procedure to produce the chitosan-coated CNPs (ChCNPs) liquid formulation, this procedure was followed by a further step of coating the anionic CNPs with chitosan low molecular weight (50–190 kDa, 75–85% deacetylated, Sigma-Aldrich, USA). A solution of 10% w/v of chitosan was prepared in 1% v/v acetic acid solution. Then, this solution was added drop by drop under vigorous magnetic stirring for 10 minutes in the previously formed anionic liquid formulation to obtain a final product with 0.1% w/v of chitosan. So, the anionic CNPs were positively charged thanks to the chitosan coating.
Deruyver L., Rigaut C., Gomez-Perez A., Lambert P., Haut B, & Goole J. (2023). In vitro Evaluation of Paliperidone Palmitate Loaded Cubosomes Effective for Nasal-to-Brain Delivery. International Journal of Nanomedicine, 18, 1085-1106.
Publication 2023
1,2-dioleoyloxy-3-(trimethylammonium)propane Acetic Acid Cations Chitosan Dextran Droxidopa Ethanol Lipid A Lipids Methanol Methylene Chloride Pressure Solvents
5
Cationic Lipid Nanoparticle Synthesis Protocol

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Publication 2023
1,2-dioleoyloxy-3-(trimethylammonium)propane Bath Cations Emulsions Lipid Nanoparticles Methylene Chloride Polylactic Acid-Polyglycolic Acid Copolymer Polymers Sulfate, Protamine

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Dotap by Avanti Polar Lipids
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DOTAP is a cationic lipid commonly used in the formulation of liposomes and other lipid-based delivery systems. It is designed to facilitate the delivery of various payloads, including nucleic acids, proteins, and small molecules, to target cells or tissues.
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Dotap liposomal transfection reagent by Roche
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DOTAP is a cationic lipid used in the preparation of lipid-based transfection reagents. It facilitates the delivery of nucleic acids, such as DNA and RNA, into cells for various research applications.
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More about "1,2-dioleoyloxy-3-(trimethylammonium)propane"

1,2-Dioleoyloxy-3-(trimethylammonium)propane (DOTAP) is a cationic lipid compound commonly used in the formulation of liposomes and lipid nanoparticles for drug delivery and gene transfection applications.
This lipid molecule features a quaternary ammonium group and two oleic acid ester moities, making it an effective carrier for negatively charged nucleic acids.
DOTAP is closely related to other cationic lipids like Cholesterol and Lipofectamine 2000, which are also widely used in liposome and nanoparticle-based delivery systems.
These lipid-based carriers can encapsulate and protect fragile payloads like plasmid DNA, mRNA, and siRNA, facilitating their cellular uptake and enhancing transfection efficiency.
When formulating DOTAP-based delivery systems, researchers often combine it with neutral lipids like Cholesterol to modulate the surface charge and improve stability.
The inclusion of serum components like FBS (Fetal Bovine Serum) or Opti-MEM media can also impact the performance of these lipid-based formulations.
PubCompare.ai is an AI-driven platform that can help researchers optimize their work with DOTAP and similar compounds.
By locating the best protocols from literature, preprints, and patents, the tool can enhance the reproducibility and accuracy of your research, streamlining the process and saving time.
This can be particularly useful when navigating the complexities of liposome and nanoparticle engineering for drug delivery and gene transfection applications.