1 2 dioleoyl sn glycero 3 phosphoethanolamine

Manufactured by Avanti Polar Lipids

Sourced in United States, Canada

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine is a synthetic phospholipid product offered by Avanti Polar Lipids. It is a phosphatidylethanolamine lipid with two oleic acid chains attached to a glycerol backbone and a phosphoethanolamine head group.

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Lab products found in correlation

112 protocols using 1 2 dioleoyl sn glycero 3 phosphoethanolamine

Lipid Composition Analysis for Membrane Studies

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All lipids were purchased from Avanti Polar Lipids: 1,2-dioleoyl-sn-glycero-3-phosphocholine (Cat. 850375, DOPC), 1,2-dioleoyl-sn-glycero-3-phospho-l-serine (Cat. 840035, DOPS), Cholesterol (Cat. 700000), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (Cat. 850725, DOPE), Sphingomyelin (Cat. 860062), l-α-phosphatidylinositol-4,5-bisphosphate (Cat. 840046, PIP2), 1,2-diphytanoyl-sn-glycero-3-phosphocholine (Cat. 850356, DPhPC), and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(7-nitro-2-1,3-benzoxadiazol-4-yl) (Cat. 810145, NBD-PE).

Heo P., Coleman J., Fleury J.B., Rothman J.E, & Pincet F. (2021). Nascent fusion pore opening monitored at single-SNAREpin resolution. Proceedings of the National Academy of Sciences of the United States of America, 118(5), e2024922118.

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Purification and Reconstitution of Membrane Proteins

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Chemicals were from the following sources: Isopropyl-β-D-thiogalactoside (IPTG) (AmericanBio), His60 Ni Superflow Resin (Takara), tris (2-carboxyethyl) phosphine (TCEP) (Thermo), Iodixanol solution (60%, w/v) (Cosmo Bio USA), Octyl β-D-glucopyranoside (OG) (EMD Millipore), n-dodecyl-β-D-maltopyranoside (DDM) (Avanti Polar Lipids). All DNA oligonucleotides were purchased from Integrated DNA Technologies. All lipids were obtained from Avanti Polar Lipids: 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC); 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS); L-α-phosphatidylinositol- 4,5-bisphosphate [PI(4,5)P₂]; 1,2 -dioleoyl-sn-glycero-3-phosphoethanolamine-N-(7-nitro-2–1,3-benzoxadiazol-4-yl) (NBD-PE); 1,2-dioleoyl-sn-glycero-3-phospho-L-serine-N-(7-nitro-2–1,3-benzoxadiazol-4-yl) (NBD-PS); 1,2 -dioleoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (Rhod-PE); 1,2-dioleoyl-sn-glycero-3-[(N-(5-amino-1-carboxypentyl) iminodiacetic acid) succinyl] [DGS-NTA(Ni)]; 1,2 -dioleoyl-sn-glycero-3-phosphoethanolamine-N-[4-(p-maleimidophenyl)butyramide] (MPB-PE).

Bian X., Zhang Z., Xiong Q., Camilli P.D, & Lin C. (2019). A programmable DNA-origami platform for studying lipid transfer between bilayers. Nature chemical biology, 15(8), 830-837.

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Purification and Reconstitution of Membrane Proteins

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Bian X., Zhang Z., Xiong Q., Camilli P.D, & Lin C. (2019). A programmable DNA-origami platform for studying lipid transfer between bilayers. Nature chemical biology, 15(8), 830-837.

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Purification of Coagulation Factors

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Protein S-free C4BP was purified (29) and APC was activated from in house purified protein C as described (30) (31) (32) . Recombinant FV R506Q/R679Q was expressed and quantified as described (33) , bovine FX (34) and human prothrombin were purified from plasma (35) .
Human α-thrombin was prepared from purified prothrombin (36) . Phospholipids were purchased from Avanti Polar Lipids and include the natural phospholipids phosphatidylserine (PS; brain extract), phosphatidylethanolamine (PE; egg extract) and phosphatidylcholine (PC; egg extract) and the synthetic phospholipids 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-Dioleoyl-sn-glycero-3-phosphoserine (DOPS), and 1,2-Dioleoyl-sn-glycero-3phosphoethanolamine (DOPE). Phospholipid vesicles were prepared by extrusion technique (37) .

Somajo S., Ahnström J., Fernandez-Recio J., Gierula M., Villoutreix B.O, & Dahlbäck B. (2015). Amino acid residues in the laminin G domains of protein S involved in tissue factor pathway inhibitor interaction. Thrombosis and haemostasis, 113(5).

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Lipid Nanoparticle Formulation for Delivery

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The lipids, 1,2-dioleoyl-3-trimethylammonium-propane (chloride salt; DOTAP), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), and cholesterol were obtained from Avanti Polar Lipids, Inc. (Alabaster, Alabama). The nuclear localization peptide (NLS, DKKKRKVDKKKRKVDKKKRKV) was procured from United Biosystems, Inc. (Herndon, Virginia). The TAT-peptide (YGRKKRRQRRR) was synthesized by Biosynthesis, Inc. (Lewisville, Texas).

Wang Y., Rajala A., Cao B., Ranjo-Bishop M., Agbaga M.P., Mao C, & Rajala R.V. (2016). Cell-Specific Promoters Enable Lipid-Based Nanoparticles to Deliver Genes to Specific Cells of the Retina In Vivo. Theranostics, 6(10), 1514-1527.

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Nanorod Binding on Glass, Lipid Bilayers, and Cells

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For glass surface–bound nanorods, nanorods were diluted 1000-fold in PBS containing 1 mM calcium chloride and immediately added to glass coverslips and allowed to nonspecifically adhere. For lipid bilayers, coverslips were initially cleaned with piranha and plasma cleaning, followed by formation of bilayer from l-α-phosphatidylcholine lipids doped with 1 mole percent (mol %) 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(cap biotinyl) and 0.5 mol % Texas Red–1,2-dihexanoyl-sn-glycero-3-phosphoethanolamine (Avanti Polar Lipids) to which nanorods were added. For cell surface binding, nanorods were conjugated to biotin-WGA, as described above, and added to COS-7 cells pretreated with 100 nM Latrunculin B to prevent endocytosis. Imaging was done after 5-min incubation and extensive washing.

Kaplan L., Ierokomos A., Chowdary P., Bryant Z, & Cui B. (2018). Rotation of endosomes demonstrates coordination of molecular motors during axonal transport. Science Advances, 4(3), e1602170.

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Peptide Synthesis and Lipid Characterization

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VLL-28 peptide (VLLVTLTRLHQRGVIYRKWRHFSGRKYR), its fluoresceinated derived form (VLLVTLTRLHQRGVIYRKWRHFSGRKYRGK*) (VLL-28*), bearing the chromophore fluorescein coupled to the last lysine residue, and peptide GKY20 (GKYGFYTHVFRLKKWIQKVI) were synthetized and purified to 95% homogeneity by Inbios (Napoli, Italy) as assessed by LC–MS. GABA peptide was the same used elsewhere [36 (link)].
The phospholipid phosphatidylcholine (PC), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (DOPG), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1-hexadecanoyl-2-(6,7-dibromooctadecanoyl)-sn-glycero-3-phosphocholine (6,7 Br-PC), 1-hexadecanoyl-2-(9,10-dibromooctadecanoyl)-sn-glycero-3-phosphocholine (9,10 Br-PC), 1-hexadecanoyl-2-(11,12-dibromooctadecanoyl)-sn-glycero-3-phosphocholine (11,12 Br-PC) 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine-N-(7-nitro-2-1,3-benzoxadiazol-4-yl) (NBD-PE), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (RHO-PE) were purchased from Avanti Polar Lipids (Birmingham, AL, USA). Triton-X100, 8-Aminonaphthalene-1,3,6-trisulfonic acid disodium salt (ANTS), p-Xylene-bis(N-pyridinium bromide) (DPX) were obtained from Sigma (St. Louis, MO, USA).

Notomista E., Falanga A., Fusco S., Pirone L., Zanfardino A., Galdiero S., Varcamonti M., Pedone E, & Contursi P. (2015). The identification of a novel Sulfolobus islandicus CAMP-like peptide points to archaeal microorganisms as cell factories for the production of antimicrobial molecules. Microbial Cell Factories, 14, 126.

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Curcumin-Loaded Lipid Nanocarriers

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The main lipid used in this study was Dimodan-U/J (DU), supplied by Danisco-DuPont (Denmark). DU (Figure 2) is a distilled glyceride, consisting of 96 % monoglycerides, 4 % diglycerides and free fatty acids. The hydrophobic region of DU primarily contains C18 chains as the two primary monoglyceride elements are linoleate (62%) and oleate (25%). Other lipids, monoelaidin (ME) and phytantriol (PT) were purchased from Tokyo Chemical Industry UK Ltd., whereas 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) and 1,2-dioleoyl-sn-glycero-3phosphocholine (DOPC) were purchased from Avanti Polar Lipids (Figure 2). Chloroform and Pluronic F127 (now on F127) were purchased from Sigma-Aldrich (Dorset, UK) (Figure 2). Curcumin (≥90% pure) was purchased from Cambridge Bioscience Ltd. The DU and F127 were stored below 4 °C, whereas other lipids were stored at approximately -20 °C. All compounds were used without further purification. The water used throughout the study was purified using Barnstead Nanopure system, Thermo Scientific (USA).

Bailey L.F., Vavolil Prabhakaran J., Vishwapathi V.K, & Kulkarni C.V. (2021). Electroformation of Particulate Emulsions Using Lamellar and Nonlamellar Lipid Self-Assemblies. Langmuir : the ACS journal of surfaces and colloids, 37(49).

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Preparation of Lipid Bilayer Membranes

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1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), L-α-phosphatidylinositol from bovine liver (PI), L-α-phosphatidylethanolamine-N-(lissamine-rhodamine B sulfonyl) (rhodamine-PE), 1-palmitoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine (PDPC), and 1-palmitoyl-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamine (PDPE) were purchased from Avanti Polar Lipids (Alabaster, AL). Bovine brain L-α-phosphatidyl-L-serine (PS) was from Sigma (St Louis, MO). All lipids were stored in chloroform at −20°C.

Yoshida Y., Niwa H., Honsho M., Itoyama A, & Fujiki Y. (2015). Pex11mediates peroxisomal proliferation by promoting deformation of the lipid membrane. Biology Open, 4(6), 710-721.

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Proteoliposome Reconstitution and Characterization

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Proteoliposomes were prepared by co-micellisation [31 (link)]. 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1,2-dioleoyl-sn-glycero-3-phosphoserine (DOPS) and cholesterol (Avanti Polar Lipids) were mixed in chloroform/methanol (2:1 (v/v)) at a molar ratio of 5:2:2:1 and dried using a rotary evaporator [21 (link)]. The dried lipid film was hydrated in 20 mM HEPES, pH 7.4, 150 mM KCl, 0.1 mM TCEP, and 5% (w/v) sodium cholate yielding multilamellar vesicles with a total lipid concentration of 15 mM. Syb(1-116) in 1% chaps was added at a lipid to protein ratio of 300:1 (n/n) and incubated for 1 h at 25 °C in a rotary evaporator without evaporation. Detergent removal and spontaneous proteoliposome formation was achieved by size exclusion chromatography using a self-packed Sephadex G25 Superfine column (5/100 mm, bed volume 2 mL) on an Äkta Pure system (GE Healthcare) equilibrated in 20 mM HEPES, pH 7.4, 150 mM KCl, and 0.1 mM TCEP. Proteoliposome-containing fractions were pooled and subjected to a liposome recruitment assay (‘liposome flotation assay’) based on sucrose density gradient centrifugation (sucrose gradient 0 M sucrose (top) – 1.2 M sucrose (bottom)) [32 (link)]. The size distribution of the reconstituted liposomes was determined by dynamic light scattering using a Zetasizer Nano (Malvern Instruments).

Wittig S., Haupt C., Hoffmann W., Kostmann S., Pagel K, & Schmidt C. (2018). Oligomerisation of Synaptobrevin-2 Studied by Native Mass Spectrometry and Chemical Cross-Linking. Journal of the American Society for Mass Spectrometry, 30(1), 149-160.

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