1 palmitoyl 2 oleoyl sn glycero 3 phosphoserine

Manufactured by Avanti Polar Lipids

Sourced in United States

1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine is a synthetic phospholipid compound. It is a structural component of cell membranes.

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14 protocols using 1 palmitoyl 2 oleoyl sn glycero 3 phosphoserine

Reconstitution of SNARE Proteoliposomes

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All lipids were obtained from Avanti Polar Lipids Inc. For t-SNARE reconstitution, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE), 1-palmitoyl-2-oleoyl-sn-glyc-ero-3-phosphoserine (POPS) and cholesterol were mixed in a molar ratio of 60:20:10:10. For v-SNARE reconstitution, POPC, POPE, POPS, cholesterol, (N-(7-nitro-2,1,3-benzoxadiazole-4-yl)-1,2-dipalmi-toylphosphatidylethanolamine (NBD-DPPE) and N-(Lissamine rhod-amine B sulfonyl)-1,2-dipalmitoylphosphatidylethanolamine (rhod-amine-DPPE) were mixed at a molar ratio of 60:17:10:10:1.5:1.5. SNARE proteoliposomes were prepared by detergent dilution and isolated on a Nycodenz density gradient flotation.^{13 (link)} Complete detergent removal was achieved by overnight dialysis of the samples in Novagen dialysis tubes against the reconstitution buffer (25 mM HEPES [pH 7.4], 100 mM KCl, 10% glycerol, and 1 mM DTT). To prepare sulforhodamine-loaded liposomes, t- or v-SNARE liposomes were reconstituted in the presence of 50 mM sulforhodamine B (Sigma). Free sulforhodamine B was removed by overnight dialysis followed by liposome flotation on a Nycodenz gradient. The protein: lipid ratio was at 1:200 for v-SNAREs and at 1:500 for t-SNARE liposomes.

Yu H., Rathore S.S., Shen C., Liu Y., Ouyang Y., Stowell M.H, & Shen J. (2015). Reconstituting Intracellular Vesicle Fusion Reactions: The Essential Role of Macromolecular Crowding. Journal of the American Chemical Society, 137(40), 12873-12883.

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Planar Lipid Bilayer Formation and CFTR Channel Reconstitution

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To prepare planar lipid bilayers, we drill a 0.2 mm hole in a Teflon cup and paint the hole with a phospholipid solution containing a 3 : 1 mixture of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine (Avanti Polar Lipids) in n-decane. The lipid bilayer separates 1 ml of solution in the Teflon cup (cis side) from 5 ml of solution in the outer glass chamber (trans side). Both chambers are magnetically stirred and thermally insulated. We utilize a temperature control system (TC2BIP, Cell Micro Controls).
We transfer CFTR ion channels into the pre-formed lipid bilayer by spontaneous fusion of membrane vesicles containing the CFTR variants. To maintain uniform orientation and functional activity of the CFTR channels transferred into the bilayer, we add 2 mM ATP, 50 nM PKA, and membrane vesicles into the cis compartment only. We perform all measurements in symmetrical salt solution (300 mM Tris–HCl, pH 7.2, 3 mM MgCl₂ and 1 mM EGTA) under voltage-clamp conditions using an Axopatch 200B amplifier. We maintain a membrane voltage potential of –75 mV, the difference between cis and trans (ground) compartments. We analyze the resulting data as previously described.^{50 (link)}

Proctor E.A., Kota P., Aleksandrov A.A., He L., Riordan J.R, & Dokholyan N.V. (2014). Rational coupled dynamics network manipulation rescues disease-relevant mutant cystic fibrosis transmembrane conductance regulator †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc01320d Click here for additional data file.. Chemical Science, 6(2), 1237-1246.

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Lipid Membrane Characterization via Spin and Fluorescent Labels

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All materials were reagent grade unless otherwise specified. Synthetic lipids 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (phosphatidylcholine, POPC, PC) and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine (phosphatidylserine, POPS, PS) were obtained from Avanti Polar Lipids (Alabaster, AL) in chloroform. The spin label 1-oxyl-2,2,5,5-tetramethyl-Δ³-pyrroline-3-methylmethanethiosulfonate (MTSSL, R1) was from Toronto Research Chemicals. Fluorescein-5-maleimide was from AnaSpec (Fremont, CA). Doxyl lipids 1-palmitoyl-2-stearoyl-(12-doxyl)-sn-glycero-3-phophocholine (12-doxyl PC), 1-palmitoyl-2-stearoyl-(10-doxyl)-sn-glycero-3-phophocholine (10-doxyl PC), 1-palmitoyl-2-stearoyl-(7-doxyl)-sn-glycero-3-phophocholine (7-doxyl PC), and 1-palmitoyl-2-stearoyl-(5-doxyl)-sn-glycero-3-phophocholine (5-doxyl PC) were from Avanti Polar Lipids. N-[5-(dimethylamino)naphthalene-1-sulfonyl]-1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine (dansyl-PE, dPE) was from Life Technologies.

Osterberg J.R., Chon N.L., Boo A., Maynard F.A., Lin H, & Knight J.D. (2015). Membrane Docking of the Synaptotagmin 7 C2A Domain: Electron Paramagnetic Resonance Measurements Show Contributions from Two Membrane Binding Loops. Biochemistry, 54(37), 5684-5695.

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Phosphoinositide Signaling Pathway Analysis

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1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine (POPS) were purchased from Avanti Polar Lipids.1,2-dipalmitoyl derivatives of phosphatidylinositol-4,5-bisphosphate (PI(4,5)P₂), phosphatidylinositol-3,4,5-bisphosphate (PIP₃), and other phosphoinositides were from Cayman Chemical Co. N-dimethylaminoazo-benzenesulfonyl-phosphatidylethanolamine (dabsyl-PE) was synthesized as described ^{34 (link)}. The custom designed peptide was purchase from AlanScientific. shRNA’s for human Syk were purchased from Integrated DNA Technologies and the transfection reagent JetPRIME was from Polyplus transfection. Antibodies against phospho-Syk (pS465/pS467), STAT3, phospho-STAT3 (pY705), STAT5, phospho-STAT5 (pY694), ERK1/2, and phospho-ERK1/2 (pT202/Y204) were purchased from Cell Signaling Technologies. Syk and BLNK antibodies were from Santa Cruz Biotechnology. The GAPDH antibody was from Sigma-Aldrich. Entospletinib and GDC-0941 were purchased from MedChemPress and Selleckchem, respectively. Jurkat, MV4-11, and HL60 cells were purchased from ATCC.

Singaram I., Sharma A., Pant S., Lihan M., Park M.J., Pergande M., Buwaneka P., Hu Y., Mahmud N., Kim Y.M., Cologna S., Gevorgyan V., Khan I., Tajkhorshid E, & Cho W. (2022). Targeting lipid-protein interaction to treat Syk-mediated acute myeloid leukemia. Nature chemical biology, 19(2), 239-250.

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Lipid Extraction and Characterization Protocol

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The phospholipids 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1-hexadecanoyl-2-(9-Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine (POPE), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (POPG), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine (POPS), and Liss-Rhod-DOPE were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Cholesterol was obtained from Sigma Aldrich (Shanghai, China). Sodium chloride, chloroform, 4-hydroxyethyl piperazine sulfonic acid (HEPES), hydrochloric acid, sodium hydroxide and propranolol hydrochloride were of analytical grade and were purchased from Titan (Shanghai, China). Microscope coverslips (22 × 40 mm, no. 1.5) was supplied by Fisher Scientific (Pittsburgh, Pennsylvania, USA). PDMS (Dow Corning Sylgard Silicone Elastomer-184) was provided from Krayden, Inc. (El Paso, TX). Purified water (18.25 mΩ cm) was produced from a Direct-pure UP Water System (RephiLe Bioscience, Ltd, China).

He N, & Zhao T. (2023). Propranolol induces large-scale remodeling of lipid bilayers: tubules, patches, and holes. RSC Advances, 13(11), 7719-7730.

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Lipid Reagents for Membrane Studies

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1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine (PS), liver phosphatidylinositol (PI), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (PE), 1,2-diacyl-sn-glycero-3- phosphocholine (PC), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(5-dimethylamino-1- naphthalenesulfonyl) (dPE), cholesterol, and brain sphingomyelin (SM) were from Avanti Polar Lipids (Alabaster, AL). Nitrilotriacetic acid (NTA) was from Alfa Aesar (Ward Hill, MA). All reagents were American Chemical Society grade or higher.

Beaven A.H., Bikkumalla V., Chon N.L., Matthews A.E., Lin H., Knight J.D, & Sodt A.J. (2024). Synaptotagmin 7 C2 domains induce membrane curvature stress via electrostatic interactions and the wedge mechanism. bioRxiv.

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Reconstitution of SNARE Proteoliposomes

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All lipids were obtained from Avanti Polar Lipids Inc. To prepare t-SNARE liposomes, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine (POPS) and cholesterol were mixed in a molar ratio of 60:20:10:10. To prepare v-SNARE liposomes, POPC, POPE, POPS, cholesterol, (N-(7-nitro-2,1,3-benzoxadiazole-4-yl)-1,2-dipalmitoyl phosphatidylethanolamine (NBD-DPPE) and N-(Lissamine rhodamine B sulfonyl)-1,2-dipalmitoyl phosphatidylethanolamine (rhodamine-DPPE) were mixed at a molar ratio of 60:17:10:10:1.5:1.5. SNARE proteoliposomes were formed by detergent dilution and isolated on a Nycodenz density gradient flotation (78 (link)). Complete detergent removal was achieved by overnight dialysis of the samples in Novagen dialysis tubes against the reconstitution buffer (25 mM HEPES [pH 7.4], 100 mM KCl, 10% glycerol, and 1 mM DTT). The protein: lipid ratio was 1:200 for v-SNARE liposomes, and 1:500 for t-SNARE liposomes.

Wang S., Liu Y., Crisman L., Wan C., Miller J., Yu H, & Shen J. (2020). Genetic evidence for an inhibitory role of tomosyn in insulin-stimulated GLUT4 exocytosis. Traffic (Copenhagen, Denmark), 21(10), 636-646.

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Supported Lipid Bilayer Formation

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1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine
(POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine
(POPS), and cholesterol were purchased from Avanti Polar Lipids and
used without further purification. Small unilamellar vesicles (SUV)
were prepared by dissolving POPC, POPS, and cholesterol in chloroform,
mixing according to desired membrane composition, (i.e., 3:1:1 molar
ratio, respectively, as previously described in the Fusion Peptide
literature^{19 (link),20 (link)}) (Table S2), dried under gentle Argon flow and placed in a vacuum overnight
to ensure evaporation of all solvent. The resulting lipid films were
rehydrated at room temperature in buffer at up to 1 mg·mL^–1 lipid concentration, and vortexed to fully suspend
vesicles. Immediately before use for supported lipid bilayer (SLB)
formation, the suspension was tip sonicated for 5 min at pulses of
1 s on/off to produce a visually clear solution of SUVs. SLB formed
from vesicle fusion on the surface.

Santamaria A., Batchu K.C., Matsarskaia O., Prévost S.F., Russo D., Natali F., Seydel T., Hoffmann I., Laux V., Haertlein M., Darwish T.A., Russell R.A., Corucci G., Fragneto G., Maestro A, & Zaccai N.R. (2022). Strikingly Different Roles of SARS-CoV-2 Fusion Peptides Uncovered by Neutron Scattering. Journal of the American Chemical Society, 144(7), 2968-2979.

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Biochemical Analysis of Wnt3a Signaling

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Cholesterol, POPC, and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine (POPS) were purchased from Avanti Polar Lipids. Human Wnt3a protein was purchased from R&D Systems (Cat no. 5036-WN-010; lot no. RSK9221052). siRNA for human TSC2 was purchased from Integrated DNA Technologies (Ref. no. 311363879) and the transfection reagent JetPRIME was from Polyplus-transfection. Antibodies against β-catenin (Cat no. 9587S), active (nonphospho) β-catenin (Cat no. 8814S), Tuberin/TSC2 (Cat no. 4308S), p70 S6 kinase (S6K) (Cat no. 2708S), phospho-p70 S6K (pS6K) (Cat no. 9205S), and glyceraldehyde 3-phosphate dehydrogenase (Cat no. 5174S) were purchase from Cell Signaling Technologies. Anti-Rabbit IgG, HRP-linked antibody (Cat no. 7074S) and anti-Mouse IgG as well as HRP-linked antibody (Cat no. 7076S) were also from Cell Signaling Technologies. HEK293T and HeLa cells were purchased from ATCC. Chemicals for Cholesterol oxidase assay activity, including 4-aminoantipyrine (Cat no. A4382-10G), phenol (Cat no. P1037-25G), and peroxidase from horseradish (Cat no. P8375-1KU) were purchased from Millipore Sigma.

Pham H., Singaram I., Sun J., Ralko A., Puckett M., Sharma A., Vrielink A, & Cho W. (2022). Development of a novel spatiotemporal depletion system for cellular cholesterol. Journal of Lipid Research, 63(3), 100178.

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Lipid Bilayer Formation and CFTR Channel Reconstitution

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To prepare planar lipid bilayers, we drill a 0.2 mm hole in a Teflon cup and paint the hole with a phospholipid solution containing a 3:1 mixture of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoserine (Avanti Polar Lipids) in n-decane. The lipid bilayer separates 1 mL of solution in the Teflon cup (cis side) from 5 mL of solution in the outer glass chamber (trans side). Both chambers are magnetically stirred and thermally insulated. We utilize a temperature control system (TC2BIP, Cell Micro Controls).
We transfer CFTR ion channels into the pre-formed lipid bilayer by spontaneous fusion of membrane vesicles containing the CFTR variants. To maintain uniform orientation and functional activity of the CFTR channels transferred into the bilayer, we add 2 mM ATP, 50 nM PKA, and membrane vesicles into the cis compartment only. We perform all measurements in symmetrical salt solution (300 mM Tris-HCl, pH 7.2, 3 mM MgCl₂ and 1 mM EGTA) under voltage-clamp conditions using an Axopatch 200B amplifier. We maintain a membrane voltage potential of −75 mV, the difference between cis and trans (ground) compartments. We analyze the resulting data as previously described^{50 (link)}.

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