1 2 dioleoyl sn glycero 3 phosphoethanolamine n

Manufactured by Avanti Polar Lipids

Sourced in United States

1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N is a phospholipid compound. It is a synthetic analog of a naturally occurring phosphatidylethanolamine lipid.

Automatically generated - may contain errors

Lab products found in correlation

1 2 dioleoyl sn glycero 3 phosphocholine, by Avanti Polar Lipids (3 mentions) 1 2 dioleoyl sn glycero 3 phosphoethanolamine, by Avanti Polar Lipids (2 mentions) 1 2 dioleoyl sn glycero 3 phospho 1 rac glycerol, by Avanti Polar Lipids (1 mentions) Peg sh4, by JenKem Technology (1 mentions) 1 octanol, by Merck Group (1 mentions) 2 dioleoyl sn glycero 3 phosphocholine, by Avanti Polar Lipids (1 mentions) Protocatechuate 3 4 dioxygenase, by Merck Group (1 mentions) Anapoe x 100, by Anatrace (1 mentions) Adenosine triphosphate (atp), by Roche (1 mentions) Tris 2 carboxyethyl phosphine, by Thermo Fisher Scientific (1 mentions) Glutathione sepharose 4 fast flow, by Cytiva (1 mentions) Mgoac, by Merck Group (1 mentions) Mpeg sva 5000, by Laysan Bio (1 mentions) Biotin peg sva 5000, by Laysan Bio (1 mentions) Gtpγs, by Roche (1 mentions) Ni sepharose 6 fast flow, by Cytiva (1 mentions) 1 palmitoyl 2 oleoyl glycero 3 phosphocholine, by Avanti Polar Lipids (1 mentions) 1 palmitoyl 2 oleoyl sn glycero 3 phospho l serine, by Avanti Polar Lipids (1 mentions) Benzoic acid, by Merck Group (1 mentions) N dodecyl β d maltoside, by Avanti Polar Lipids (1 mentions)

9 protocols using 1 2 dioleoyl sn glycero 3 phosphoethanolamine n

Functionalized PEG-based Hydrogel Synthesis

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Thiol end-functionalized four-arm PEG (5 kDa, PEG-SH₄) and vinylsulfone end-functionalized four-arm PEG (5 kDa, PEG-VS₄) were purchased from JenKem Technology USA Inc. (Allen, TX). Fluorescent FITC-dextran (4 kDa) was purchased from Sigma-Aldrich (St. Louis, MO). All lipids were purchased from Avanti Polar Lipids (Alabaster, AL), including: 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (DOPG), 1,2-dioleoylsn-glycero-3-phosphoethanolamine-N-[4-(p-maleimidophenyl)butyramide] (MPB-PE), and 1,2-dioleoyl-sn-glycero-3-phosphocholine-N-(Cyanine 5) (Cy5-PC).

Palmese L.L., LeValley P.J., Pradhan L., Parsons A.L., Oakey J.S., Abraham M., D’Addio S.M., Kloxin A.M., Liang Y, & Kiick K.L. (2024). Injectable liposome-containing click hydrogel microparticles for release of macromolecular cargos. Soft Matter, 20(8), 1736-1745.

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Liposome Preparation and Characterization

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1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt) (DOPG), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (ammonium salt) (18:1 Liss Rhod PE), and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(7-nitro-2-1,3-benzoxadiazol-4-yl) (ammonium salt) (18:1 NBD PE) were purchased from Avanti Polar Lipids (Alabaster, AL) as powder and dissolved in chloroform to a final concentration of 100 mg/mL (DOPC and DOPG) and 1 mg/mL (Liss Rhod PE and NBD PE). 8-Hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (HPTS) was purchased from Merck (Kenilworth, NJ) and used as received. 1-Octanol was purchased from Sigma (St. Louis, MO) and used as received. Polydimethylsiloxane (PDMS) Sylgard 184 was purchased from Dow Corning (Midland, MI) and used as received.

Tivony R., Fletcher M, & Keyser U.F. (2022). Quantifying proton-induced membrane polarization in single biomimetic giant vesicles. Biophysical Journal, 121(12), 2223-2232.

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Purification and Labeling of Proteins

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Reagents were obtained from the following sources: Ni Sepharose 6 Fast Flow (Cytiva, 17531802), Glutathione Sepharose 4 Fast Flow (Cytiva, 17513201), tris(2-carboxyethyl)phosphine (Thermo, 75259), EDTA-free protease inhibitor cocktail (Roche, 11873580001), PreScission Protease (Absin, abs01243), Anapoe-X-100 (Anatrace, 9002-93-1), ATP (Roche, 11140965001), MgOAc (Sigma-Aldrich, M0631), L-glutamic acid potassium (Sigma-Aldrich, G1501), biotinylated anti-His antibody (Bioss Antibodies, bs-0287R-bio), streptavidin (Sangon Biotech, A610492), LD555-MAL (Lumidyne, 04), LD655-MAL (Lumidyne, 10), GDP (Sigma-Aldrich, G7127), GTPγS (Roche, 10220647001), GMppNHp (Sigma-Aldrich, G0635), mPEG-SVA-5000 (Laysan Bio, 170-106), Biotin-PEG-SVA-5000 (Laysan Bio, 170-124), benzoic acid (Sigma-Aldrich, 242381), protocatechuate 3,4-dioxygenase (Sigma-Aldrich, P8279), and n-dodecyl-β-D-maltoside (Avanti Polar Lipids, 850520). All lipids were obtained from Avanti Polar Lipids: 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC, 850457); 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS, 840034); 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(7-nitro-2-1,3-benzoxadiazol-4-yl) (NBD-PE, 810144); and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (Rhodamine-PE, 810150).

Shi L., Yang C., Zhang M., Li K., Wang K., Jiao L., Liu R., Wang Y., Li M., Wang Y., Ma L., Hu S, & Bian X. (2024). Dissecting the mechanism of atlastin-mediated homotypic membrane fusion at the single-molecule level. Nature Communications, 15, 2488.

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Synthesis and Characterization of Fluorescent Lipid-Polymer Nanoparticles

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DMPC (

M_{W}

677.94,

C_{36} H_{72} {N O}_{8}

P), DOPE (

M_{W}

, 744.034,

C_{41} H_{78} {N O}_{8}

P), DOPC (

M_{W}

786.113,

C_{44} H_{8} 4 {N O}_{8}

P); 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (ammonium salt; Liss Rhod-PE,

M_{W}

1,301.75,

C_{68} H_{109} N_{4} O_{14} {P S}_{2}

), and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(7-nitro-2-1,3-benzoxadiazol-4-yl; ammonium salt) (

C_{47} H_{8} 2 N_{5} O_{1} 1

P; NBD-PE; ∼98

%

purity) were purchased from Avanti Polar Lipids. Chloroform (analytical grade,

\geq 99.8 %

) was purchased from Sigma-Aldrich. Methanol (analytical grade,

\geq 99.9 %

) was purchased from Merck.

N

-isopropylacrylamide,

N

N'

-methylenebisacrylamide, 2,2′-azobis(2-methylpropionamidine) dihydrochloride, and FMA were all purchased from Sigma and used as received. Milli-Q water was used in all the experiments. The PNIPAM microgel particles were synthesized by using 5 mol

%

cross-linker and FMA as labeled by precipitation polymerization as described in former studies (34 (link), 36 (link)) and in SI Appendix.

Wang M., Mihut A.M., Rieloff E., Dabkowska A.P., Månsson L.K., Immink J.N., Sparr E, & Crassous J.J. (2019). Assembling responsive microgels at responsive lipid membranes. Proceedings of the National Academy of Sciences of the United States of America, 116(12), 5442-5450.

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Lipid Characterization of Membrane Composition

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16:0–18:1 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine
(POPC), 16:0–18:1 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-[1′-rac-glycerol]
(POPG), 18:1 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-[lissamine rhodamine B sulfonyl] (Rh-PE), and 18:1 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-[7-nitro-2–1,3-benzoxadiazol-4-yl]
(NBD-PE) were all purchased from Avanti Polar Lipids (Alabaster, AL,
USA).

Pennington H.N., Birtles D., Shi Z.W, & Lee J. (2024). A Salt Bridge and Disulfide Bond within the Lassa Virus Fusion Domain Are Required for the Initiation of Membrane Fusion. ACS Omega, 9(4), 4920-4930.

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Lipid Composition and Characterization

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ergosta-5,7,9(11),22-tetraen-3ß-ol, cholesterol, and calcium chloride (CaCl₂) were purchased from Sigma. POPC, POPE, POPS, L-α-PI (Liver PI), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(5-dimethylamino-1-naphthalenesulfonyl) (dansyl-PE), 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1′-myo-inositol-4′,5′-bisphosphate) (PI(4,5)P₂), 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1′-myo-inositol-3′,5′-bisphosphate) (PI(3,5)P₂), 1,2-dioleoyl-sn-glycero-3-phospho-(1′-myo-inositol-3′-phosphate) (PI(3)P), 1,2-dioleoyl-sn-glycero-3-phospho-(1′-myo-inositol-4′-phosphate) (PI(4)P), 1,2-dioleoyl-sn-glycero-3-phospho-(1′-myo-inositol-5′-phosphate) (PI(5)P), NBD-DOPE, and Rho-DOPE were purchased from Avanti Polar Lipids (Alabaster). The concentrations of unlabeled lipids were determined by dry weight and that of fluorescent lipids by absorbance using εNBD-DOPE = 21, 000 M⁻¹ cm⁻¹ at 460 nm in methanol and εRho-DOPE = 95,000 M⁻¹ cm⁻¹ at 560 nm in methanol.

Zhang X., Xie H., Iaea D., Khelashvili G., Weinstein H, & Maxfield F.R. (2022). Phosphatidylinositol phosphates modulate interactions between the StarD4 sterol trafficking protein and lipid membranes. The Journal of Biological Chemistry, 298(7), 102058.

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Fabrication of Lipid Bilayers on Chromium Barriers

Cited 1 time

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Chrome barriers were deposited on quartz microscope slides via e-beam lithography and thermal evaporation, as described (63 (link), 84 (link)). Lipid bilayers were prepared with 91.5% 1,2-dioleoyl-sn-glycero-3-phosphocholine, 0.5% 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(cap biotinyl), and 8% 1,2-dioleoyl-sn-glycero-3-phosphoethanoloamine-N-[methoxy(polyethyleneglycol)-2,000] (Avanti Polar Lipids, Inc., catalog nos. 850375P, 870273P, and 880130P, respectively). Lipid bilayers were deposited in preformed flow chambers through sequential deposition of a lipid master mix in lipid buffer (20 mM Tris-Cl [pH 7.5], 100 mM NaCl).

Meir A., Crickard J.B., Kwon Y., Sung P, & Greene E.C. (2022). Rad54 and Rdh54 prevent Srs2-mediated disruption of Rad51 presynaptic filaments. Proceedings of the National Academy of Sciences of the United States of America, 119(4), e2113871119.

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Lipid Vesicle Formation with Peptides

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In this study, the following chemicals were used: 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC; Avanti Polar Lipids, Birmingham, AL, USA), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (ammonium salt) (Rhodamine PE; Avanti Polar Lipids, Birmingham, AL, USA), liquid paraffin (FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan), calcein (Sigma-Aldrich Co, LCC., St. Louis, MO, USA), glucose (FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan), sucrose (FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan), n-decane (FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan), 3-morpholinopropane-1-sulfonic acid (MOPS, Nacalai Tesque, Kyoto, Japan), potassium chloride (KCl, Nacalai Tesque, Kyoto, Japan). As peptides, we used C105Y (GenScuript, Piscataway, NJ, USA), melittin (synthesized and purified as powder), ovispirin (KareBay Biochem, Inc., Monmouth Junction, NJ, USA), and TAT (BACHEM, Bubendorf, Switzerland). Peptides were stored at −20 °C. For use, samples were diluted to their designated concentration using a buffered electrolyte solution and stored at 4 °C.

Izumi K., Saito C, & Kawano R. (2023). Liposome Deformation Induced by Membrane-Binding Peptides. Micromachines, 14(2), 373.

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Fluorescence Imaging of Lipid Vesicles

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All of the chemical reagents were of analytical grade, obtained from commercial suppliers, and used without further purification, unless otherwise noted. Alexa Fluor 647 phalloidin was purchased from ThermoFisher. 1,2-diphytanoyl-sn-glycero-3-phophoscholine (DPhPC), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamineN-[methoxy(polyethylene glycol)-2000], ammonium salt (DOPE-PEG), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-[4-(p-maleimidophenyl)butyramide], sodium salt (DOPE-MPB) were obtained from Avanti Polar Lipids, Inc. 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine labeled with Atto 390 (DOPE-Atto 390) and Lucifer yellow were purchased from Atto-tec and Sigma Aldrich, respectively.
Fluorescence imaging was carried out on a Ti Eclipse microscope (Nikon) equipped with a CSU-X spinning disk confocal module (Yokogawa) and a Zyla sCMOS camera (Andor). Fluorescence micrographs of giant vesicles or cells were acquired with either a 20× objective (Nikon, NA 0.45) or a 60× objective (Nikon, NA 1.49 TIRF). TIRF imaging was performed on the Ti Eclipse microscope (Nikon) using a 60× objective (Nikon, NA 1.49 TIRF) and an iXon Ultra EM-CCD camera (Andor).

Belardi B., Hamkins-Indik T., Harris A.R., Kim J., Xu K, & Fletcher D.A. (2020). A weak link with actin organizes tight junctions to control epithelial permeability. Developmental cell, 54(6), 792-804.e7.

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