1 2 dioleoyl sn glycero 3 phosphoethanolamine

Manufactured by Lipoid

Sourced in Germany

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine is a phospholipid that is a major component of biological membranes. It serves as a key structural element in the formation of lipid bilayers.

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Lab products found in correlation

8 protocols using 1 2 dioleoyl sn glycero 3 phosphoethanolamine

Liposomal Delivery of Anticancer Agents

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Raltitrexed (RTX) and paclitaxel were purchased from Selleckchem (Houston, TX, USA) and were dissolved in DMSO immediately before addition to the cell cultures. Cisplatin (cDDP) was obtained from Santa Cruz Biotechnology. All other chemicals were purchased from Sigma–Aldrich S.r.L. (Milan, Italy), except otherwise indicated.
Reagents for liposome formulation: cholesteryl hemisuccinate (CHEMS) purchased from Sigma–Aldrich (St. Louis, MO, USA); 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) and [N-(Cabonyl-methoxypolyethyleneglycol-2000)]-1,2-distearoyl-sn-glycero-3-phosphoethanolamine sodium salt (DSPE_PEG) purchased from Lipoid (Ludwigshafen, Germany). The active peptide [D-Gln⁴]LR and the internal standard (IS) for quantitative analysis, LR-Ala7, were synthesized as previously described [21 (link),22 (link)]. All the other reagents were of analytical grade.

Marverti G., Gozzi G., Maretti E., Lauriola A., Severi L., Sacchetti F., Losi L., Pacifico S., Ferrari S., Ponterini G., Leo E., Costi M.P, & D’Arca D. (2020). A Peptidic Thymidylate-Synthase Inhibitor Loaded on Pegylated Liposomes Enhances the Antitumour Effect of Chemotherapy Drugs in Human Ovarian Cancer Cells. International Journal of Molecular Sciences, 21(12), 4452.

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Lipid-based Nanocarrier Synthesis

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Medium-chain triglycerides (MCTs), 1,2-dioleoyl- sn-glycero-3-phosphoethanolamine (DOPE), 1,2-dioleoyl-sn-glycero-3-trimethylammonium propane (DOTAP), and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-(amino[polyethylene glycol]-2000) (DSPE-PEG) were purchased from Lipoid (Ludwigshafen, Germany). Glycerol and chloroform were obtained from Merck (Rio de Janeiro, Brazil). 4-Methylumbelliferylalpha-l-iduronide was purchased from Glycosynth (Warrington, UK), and TRIzol^® Reagent was purchased from Thermo Fisher Scientific (Waltham, MA, USA). Platinum SYBR Green qPCR SuperMix-UDG kit was obtained from Thermo Fisher Scientific, and High-Capacity cDNA Reverse Transcription Kit was purchased from Thermo Fisher Scientific. All other chemicals were of analytical grades.

Fraga M., de Carvalho T.G., Bidone J., Schuh R.S., Matte U, & Teixeira H.F. (2017). Factors influencing transfection efficiency of pIDUA/nanoemulsion complexes in a mucopolysaccharidosis type I murine model. International Journal of Nanomedicine, 12, 2061-2067.

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Formulation and Evaluation of Lipid-Based Nanocarriers

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1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[amino(polyethyleneglycol)-2000 (DSPE-PEG2000) were supplied by Lipoid GmbH (Ludwigshafen, Germany). Cholesterol hemisuccinate (CHEMS), doxorubicin (DXR), 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) sodium salt, sodium chloride, sodium hydroxide, and Cremophor EL were obtained from Sigma-Aldrich Co. (St. Louis, MO, USA). Paclitaxel (PTX) was supplied by Quiral Quimica do Brasil S.A (Juiz de Fora, Brazil).The human breast adenocarcinoma cell lines MDA-MB-231, MCF-7 and SKBR-3 were purchased from the American Type Culture Collection (Manassas, VA, USA). The different culture media (Dulbecco’s Modified Eagle’s Medium, DMEM; Minimum Essential Medium, MEM and McCoy), fetal bovine serum, penicillin/streptomycin and 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide (MTT) were obtained from Sigma-Aldrich Co. (St. Louis, MO, USA). All other chemicals used in this study were of analytical grade.

Franco M.S., Roque M.C, & Oliveira M.C. (2019). Short and Long-Term Effects of the Exposure of Breast Cancer Cell Lines to Different Ratios of Free or Co-Encapsulated Liposomal Paclitaxel and Doxorubicin. Pharmaceutics, 11(4), 178.

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Lipid-based Nanoparticle Formulation

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NeoPhectin AT containing the cationic cardiolipin 1, 3-Bis-(1,2-bis-tetradecyloxy-propyl-3-dimethylethoxyammoniumbromide)-propane 2-ol was purchased from NeoPharm (Waukegan, IL). 1-Palmitoyl-2-oleoyl-sn-glycero-3 phosphocholine (POPC) and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) were purchased from Lipoid GmbH or Avanti Polar Lipids. Cholesteryl hemisuccinate (CHEMS) and cholesteryl-4-[[2-(4-morpholinyl)ethyl]amino]-4-oxobutanoate (MOCHOL) were produced by Merck & Cie (Shaffhuasen, Switzerland).

Rodrigueza W.V., Woolliscroft M.J., Ebrahim A.S., Forgey R., McGovren P.J., Endert G., Wagner A., Holewa D., Aboukameel A., Gill R.D., Bisgaier C.L., Messmann R.A., Whitehead C.E., Izbicka E., Streeper R., Wick M.C., Stiegler G., Stein C.A., Monsma D., Webb C., Sooch M.P., Panzner S., Mohammad R., Goodwin N.C, & Al-Katib A. (2014). Development and antitumor activity of a BCL-2 targeted single-stranded DNA oligonucleotide. Cancer Chemotherapy and Pharmacology, 74(1), 151-166.

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Liposomal Doxorubicin Synthesis and Characterization

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Black Phosphorus (bulk) was purchased from Ossila Ltd., Sheffield, UK (Product Code M2106C1). All chemicals were purchased from Sigma-Aldrich, Gillingham, UK. 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine, (Lipoid PC 16:0/16:0 (DPPC), 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine, (DOPE Lipoid 565600), and [N-(Carbonyl-methoxy polyethylene glycol-2000)-1,2-distearoyl-sn-glycero-3-phosphoethano[amine, sodium salt]] (DSPE-PEG2000 Lipoid 588200) were generous gifts from Lipoid GmbH (Ludwigshafen, Germany). 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine and 1-stearoyl-2-hydroxy-sn-glycero-3-phosphocholine (MSPC) were purchased from Avanti Polar Lipid (Alabaster, AL, USA). Doxorubicin hydrochloride (Dox·HCl) was obtained from Biosynth Ltd., Compton, UK (Product Code: AD15377). Roswell Park Memorial Institute (RPMI) 1640 Medium, Dulbecco’s PBS (1x), penicillin–streptomycin solution liquid (10,000 units/mL), glutamine supplement (200 mM), and 0.25% trypsin/EDTA were purchased from ThermoFisher Scientific, Winsford, UK. Heat-inactivated foetal bovine serum (FBS) (11580516) was obtained from Gibco Life Technologies, Paisley, UK.

Das C., Martín C., Habermann S., Walker H.R., Iqbal J., Elies J., Jones H.S., Reina G, & Ruiz A. (2023). Co-Loading of Black Phosphorus Nanoflakes and Doxorubicin in Lysolipid Temperature-Sensitive Liposomes for Combination Therapy in Prostate Cancer. International Journal of Molecular Sciences, 25(1), 115.

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Lipid Nanoparticle Formulation and miRNA Encapsulation

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1,2-dioleoyl-3-trimethylammonium-propane (DOTAP), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC) and N-(carbonyl-methoxypolyethyleneglycol-2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine (DSPE-mPEG₂₀₀₀) were kindly provided by Lipoid GmbH (Ludwigshafen, Germany). Cholesterol was purchased from Carl Roth GmbH+Co KG (Karlsruhe, Germany), 1,2-dimyristoyl-rac-glycero-3-methoxypolyethylene glycol-2000 (DMG-PEG₂₀₀₀) from Avanti Polar Lipids (Alabaster, USA) and 9-Heptadecanyl 8-{(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino}octanoate (SM-102) from Cayman Chemical Co. (Ann Arbor, USA). Methanol (MeOH) HPLC ultra gradient grade as well as Ethanol (EtOH) HPLC gradient grade were purchased from Carl Roth GmbH+Co KG (Karlsruhe, Germany). Trifluoroacetic acid (TFA) 99% Extra Pure was purchased from Acros Organics | Thermo Fisher Scientific GmbH (Dreieich, Germany). For buffer preparation, purified water of an Arium pro system from Sartorius AG (Göttingen, Germany), HEPES and Sucrose from Carl Roth GmbH+Co KG (Karlsruhe, Germany) were used. Hydrochloric acid for film preparation was purchased from Carl Roth GmbH+Co KG (Karlsruhe, Germany). hsa-miR-100-5p (mature sequence: 5´-AACCCGUAGAUCCGAACUUGUG-3′) from Thermo Fisher Scientific GmbH (Dreieich, Germany) was used for loading LNPs with RNA.

Bender V., Fuchs L, & Süss R. (2024). RP-HPLC-CAD method for the rapid analysis of lipids used in lipid nanoparticles derived from dual centrifugation. International Journal of Pharmaceutics: X, 7, 100255.

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Lipid-based Nanoparticles for siRNA Delivery

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The lipids 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP) and egg phosphatidylcholine (EPC) were purchased from Lipoid (Ludwigshafen, Germany) to manufacture LNCs and LPXs. 1,2-distearoyl-sn-glycero-3phosphoethanolamine-N-[amino(polyethylene glycol)-2000] [DSPE-PEG(2000)] was purchased from Avanti Polar Lipids, Inc. (Alabama, USA) and used to produce LNCs with stealth properties to prevent opsonisation and improve therapeutic efficiency of siRNA. Discussion regarding the lipid composition and chemical structures of the lipids used in our study can be found in Fig. S1 (Supplementary Material). Ethanol was obtained from Labsynth (São Paulo, Brazil) and used to disperse the lipids and DSPE-PEG(2000) following the dehydration process with molecular sieves (3 Å beads). The Sylgard® 184 Silicone Elastomer Kit for the fabrication of microfluidic devices was purchased from Dow Corning (Auburn, MI, United States). Deionised water was obtained from Samtec Biotechnology (São Paulo, Brazil). Ambion® Silencer® GFP (eGFP) siRNA was obtained from ThermoFisher Scientific. For initial optimization studies, the plasmid pEGFP-N1 (BD Biosciences Clontech, Palo Alto, USA) was amplified in Escherichia coli and purified using PureLink™ HiPure Plasmid pDNA Purification Kit (Invitrogen, Carlsband, USA).

Eş I., Malfatti-Gasperini A.A, & de la Torre L.G. (2022). The diffusion-driven microfluidic process to manufacture lipid-based nanotherapeutics with stealth properties for siRNA delivery. Colloids and surfaces. B, Biointerfaces, 215.

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Lipid-based Nanoparticle Fabrication

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The materials Poly (D,L-lactide) (PLA) (Mw = 18-24 kDa), Plur-onic® F68 (suitable for cell culture), Nile Blue (NB, Basic Blue 12) (Mw = 732.8 g/mol; predicted LogP = 0.7 according to Molinspiration Cheminformatics free web services, https://www.molinspiration.com, Slovensky Grob, Slovakia) and cholesterol were purchased from Sigma-Aldrich (Sigma Chemical Co., St. Louis, MO, U.S.A.). Nile Red (NR, Nile Blue oxazone) (Mw = 318.4 g/mol; predicted LogP = 4.58 according to Molinspiration Cheminformatics free web services, https://www. molinspiration.com, Slovensky Grob, Slovakia) was purchased from TCI (Tokyo Chemical Industry Co., Ltd., Tokyo, Japan) . 2-Propanol was purchased from Fisher Scientific (Hampton, NH, U.S.A). 1,2-dioleoyl-snglycero-3-phosphoethanolamine (DOPE), and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[amino(polyethylene glycol)-2000] (DSPE-mPEG) were purchased from Lipoid GmbH (Ludwigshafen am Rhein, Germany). Acetone and ethanol were of the highest grade commercially available and purchased from several suppliers.

Costa C., Fernandes B., Guimarães D., Nogueira E., Martins M., Matamá T, & Cavaco-Paulo A. (2021). Comparing the delivery to the hair bulb of two fluorescent molecules of distinct hydrophilicities by different nanoparticles and a serum formulation. International journal of pharmaceutics, 602.

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