1 2 dioleoyl sn glycero 3 phosphocholine dopc

Manufactured by Avanti Polar Lipids

Sourced in United States

1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) is a synthetic phospholipid commonly used in research applications. It is a neutral phospholipid composed of a glycerol backbone, two oleic acid chains, and a choline headgroup. DOPC serves as a building block for model lipid membranes and is widely employed in studies involving membrane structure and function.

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Lab products found in correlation

148 protocols using 1 2 dioleoyl sn glycero 3 phosphocholine dopc

Electroformation of DOPC-based GUVs

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1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC) was purchased from Avanti
Polar
Lipids (Alabaster, Alabama, USA). GUVs were prepared by electroformation.^{16 (link)} One microliter of DOPC/X (X = C22:1, C22:1 Gb3_EG₁, C22:1 Gb3_EG₃, or C22:1 Gb3_EG₇) at
95:5 ratio at 1 mg/mL in chloroform was spread on two indium tin oxide-coated
glass plate electrodes that were spaced 4 mm apart. The electrodes
with the lipid films were immersed in a chamber containing 320 mM
sucrose solution and were connected to a power generator. Electroformation
was performed at 2 V and 10 Hz for 1 h at 65 °C. The GUVs were
released from the electrodes by changing the frequency to 2 Hz for
30 min, and transferred into a chamber with equiosmolar PBS.

Pezeshkian W., Gao H., Arumugam S., Becken U., Bassereau P., Florent J.C., Ipsen J.H., Johannes L, & Shillcock J.C. (2016). Mechanism of Shiga Toxin Clustering on Membranes. ACS Nano, 11(1), 314-324.

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Simvastatin Nanoparticle Formulation Protocol

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Simvastatin was purchased from Cayman Chemical (Ann Arbor, MI). Simvastatin was activated prior to its use as previously described (Borahay et al., 2015 ). Activation converts the prodrug (lactone structure) to its active form (β-hydroxyacid structure). Briefly, Simvastatin (25 mg) was dissolved in 625μL of ethanol. This solution was then added to 935μL of 0.1 NaOH and heated in a water bath (50°C) for 2 hours before diluting with water. The pH was adjusted to reach 7 using HCl. This solution was diluted 8-fold with water to reach a 2mg/mL concentration and was sterile filtered before being stored at 4°C until use.
Simvastatin-loaded liposome nanoparticles (Simvastatin-NP) was prepared using 1,2-Dioleoyl-sn-Glycero-3-Phosphocholine (DOPC) which were purchased from Avanti Polar Lipids (Alabaster, AL) and 1,2-Distearoyl-sn-glycero-3-phosphorylethanolamine (DSPE). DOPC/DSPE-Peg2000 were prepared in 10:1 mixture and Simvastatin-DOPC/DSPE-Peg2000 was prepared in 1:10 mixture. Simvastatin-DOPC/DSPE-Peg2000 was kept lyophilized at −20°C and dissolved in normal saline immediately prior to use.

El Sabeh M., Vincent K.L., Afrin S., Motamedi M., Saada J., Yang J., Ozpolat B., Kilic G.S, & Borahay M.A. (2022). Simvastatin-loaded Liposome Nanoparticles Treatment for Uterine Leiomyoma in a Patient-Derived Xenograft Mouse Model: A Pilot Study. Journal of obstetrics and gynaecology : the journal of the Institute of Obstetrics and Gynaecology, 42(6), 2139-2143.

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Supported Bilayer Formation from GUVs

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1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), cholesterol and 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (ammonium salt) (Rh-DPPE) were obtained from Avanti Polar Lipids. All lipid bilayers used in fluorescence imaging were doped with 0.1 mol% Rh-DPPE. Giant unilamellar vesicles were formed via electro-formation in 300 mM sucrose solution, using standard protocols. [25] [26] [27] Around 0.5-2 µL of GUV solution was pipetted onto the PDMS substrate, previously wetted with 500 µL trizma buffer (10 mM trizma base, 150 mM NaCl, 2 mM CaCl 2 ). Within two minutes, the vesicles fused to the PDMS substrates (both partially and fully oxidized) and formed membrane patches. The remaining unfused vesicles were gently washed away with 500 µL trizma buffer.

Miller E.J., Voïtchovsky K, & Staykova M. (2018). Substrate-led cholesterol extraction from supported lipid membranes. Nanoscale, 10(34).

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Preparation of Fluorescent Lipid Bilayer Vesicles

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A lipid film composed of 1,2‐dioleoyl‐sn‐glycero‐3‐phosphocholine (DOPC) (Avanti Polar Lipids), 1,2‐dioleoyl‐sn‐glycero‐3‐phosphoethanolamine (DOPE) (Avanti Polar Lipids) and cholesterol (Sigma Aldrich) with a mass ratio of 50:25:25 (total mass 1.25 mg) and 2 mol% additional 1,1′‐Dioctadecyl‐3,3,3′,3′‐Tetramethylindodicarbocyanine Perchlorate (DiD’) (Invitrogen, Thermo Fisher Scientific) was prepared via evaporation from a chloroform solution in a glass vial. After being thoroughly dried by lyophilisation (Labconco), it was rehydrated (1.25 mg/ml) in TE buffer (pH 8.0) containing 10 mM Tris‐HCl (Sigma‐Aldrich), 1 mM EDTA (Sigma‐Aldrich) and 150 mM NaCl (Sigma‐Aldrich) at 37 ˚C for 1 h. After being fully resuspended by vortex, the emulsion was extruded 31 times through a 100 nm polycarbonate membrane (Whatman) at 37 ˚C using an Avanti MiniExtruder (Avanti Polar Lipids). The liposome suspension was stored in a low adsorption glass vial (Supelco, Sigma‐Aldrich) at 4 ˚C protected from light, until use.

Görgens A., Corso G., Hagey D.W., Jawad Wiklander R., Gustafsson M.O., Felldin U., Lee Y., Bostancioglu R.B., Sork H., Liang X., Zheng W., Mohammad D.K., van de Wakker S.I., Vader P., Zickler A.M., Mamand D.R., Ma L., Holme M.N., Stevens M.M., Wiklander O.P, & EL Andaloussi S. (2022). Identification of storage conditions stabilizing extracellular vesicles preparations. Journal of Extracellular Vesicles, 11(6), e12238.

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Synthesis and Purification of PGN Precursors

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Large scale synthesis and purification of the PGN precursors lipid I and lipid II were performed as previously described (Ling et al., 2015 (link)). UDP-N-acetyl-muramic acid pentapeptide (UDP-MurNAc-pp) was purified according to the protocol elaborated by Kohlrausch and Höltje (Kohlrausch and Höltje, 1991 (link)). Undecaprenyl phosphate (C₅₅P) and undecaprenyl diphosphate (C₅₅PP) were purchased from Larodan Fine Chemicals AB (Malmö, Sweden). The phospholipids 1,2-dioleoyl-sn-glycero-3- phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phosphoglycerol (DOPG) and 1′,3′-bis[1,2-distearoyl-sn-glycero-3-phospho]-glycerol (DOCL, cardiolipin) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). The concentration of purified PGN and wall teichoic acid precursors was quantified on the basis of their phosphate content as described (Rouser et al., 1970 (link)).

Shukla R., Peoples A.J., Ludwig K.C., Maity S., Derks M.G., de Benedetti S., Krueger A.M., Vermeulen B.J., Lavore F., Honorato R.V., Grein F., Bonvin A., Kubitscheck U., Breukink E., Achorn C., Nitti A., Schwalen C.J., Spoering A.L., Ling L.L., Hughes D., Lelli M., Roos W.H., Lewis K., Schneider T, & Weingarth M. (2023). A new antibiotic from an uncultured bacterium binds to an immutable target. bioRxiv.

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Preparation of Unilamellar DOPC Liposomes

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Unilamellar liposomes (DOPC, 0.8% DGS-NTA, Avanti Polar Lipids) were prepared as previously described [5] . Briefly, 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) (Avanti Polar Lipids) was combined with 0.

Sugiman-Marangos S., Gill S.K., Mansfield M.J., Orrell K.E., Doxey A.C., & Melnyk R.A. (2021). Structure-function analysis of distant diphtheria toxin homologs reveals insights into host adaptation.

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DOPC and TLR9 Ligand Preparation

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1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC) was purchased from Avanti Polar Lipids as a solution in chloroform. TLR9 ligands CpG ODN 1585 (Class A), 1826 (Class B), and their corresponding GpC control sequences were synthesized on an ABI 3900 DNA oligonucleotide synthesizer with all reagents purchased from Glen Research (see Supporting Information).

Huang Z.N., Cole L.E., Callmann C.E., Wang S, & Mirkin C.A. (2020). Sequence Multiplicity within Spherical Nucleic Acids. ACS nano, 14(1), 1084-1092.

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Synthesis and Characterization of Glucuronide Prodrugs

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DSPC, 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (DSPE-PEG-2000), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (DOPE-PEG), and cholesterol were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL). BQC was a generous gift from Daiichi (Tokyo, Japan). 9AC^{51 (link)}, 9-aminocamptothecin-β-D-glucuronide (9AC-G^W), and 5,6-dihydro-4H-benzo[de]quinoline-camptothecin-β-D-glucuronide (BQC-G^W) were chemically synthesized. Briefly, the glycosidic switch was coupled to 9AC via a self-immolative carbamate linker^{24 (link)} and to BQC via a self-immolative benzyl-ether spacer^{25 (link)}. 4-methylumbelliferyl-β-D-glucuronide (4MU-G^W), beta-glucuronidase inhibitor (saccharolactone) and lysotracker-red DND99 were from Sigma Aldrich (St. Louis, MO). Fluorescein-di-glucuronide (fluorescein-G^W, F2915) was from ThermoFisher Scientific. PEGylated liposomal doxorubicin (Doxisome) was a generous gift from the Taiwan Liposome Company (TLC, Taipei, Taiwan).

Burnouf P.A., Leu Y.L., Su Y.C., Wu K., Lin W.C, & Roffler S.R. (2018). Reversible glycosidic switch for secure delivery of molecular nanocargos. Nature Communications, 9, 1843.

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Supported Lipid Bilayer Formation

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N-Stearoyl-d-erythro-sphingosine (C18:0-Cer), N-stearoyl-d-erythro-sphingosylphosphoryl-choline (C18:0-SM), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and cholesterol were purchased from Avanti Polar Lipids (Alabaster, AL, USA). We prepared supported lipid bilayers (SLBs) by deposition and fusion of small unilamellar vesicles (SUVs) as described elsewhere (Chiantia et al., 2006 (link)). SUVs composed of DOPC:cholesterol:SM:caCer, containing additional 0.1 mol% ATTO655-DOPE (ATTO Technology GmbH, Siegen, Germany), were obtained by bath sonication of multilamellar vesicles. SUV suspensions (1 mM total lipid concentration in buffer containing 10 mM HEPES, 150 mM NaCl, pH 7.4) were deposited in the presence of 2 mM CaCl₂ on freshly-cleaved mica glued to glass coverslips. The samples were incubated at 65 ˚C for 30 min, rinsed with buffer and then allowed to cool slowly to room temperature for at least 1 hr.

Kol M., Williams B., Toombs-Ruane H., Franquelim H.G., Korneev S., Schroeer C., Schwille P., Trauner D., Holthuis J.C, & Frank J.A. (2019). Optical manipulation of sphingolipid biosynthesis using photoswitchable ceramides. eLife, 8, e43230.

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DNA Origami Membrane Binding Protocol

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Single-stranded M13mp18 scaffold plasmid (p7249) and high purity salt free (HPSF) purified staple oligonucleotides required for DNA origami preparation were purchased from Bayou Biolabs (Metairie, LA, USA) and Eurofins Genomics (Ebersberg, Germany), respectively. 5 0 -Alexa488-functionalized oligonucleotides (HPLC-purified) needed for fluorescence detection were acquired from Eurofins Genomics. 5 0 -TEG-chol-functionalized oligonucleotides (also HPLC-purified) required for membrane binding were obtained from Sigma-Aldrich (Taufkirchen, Germany). Detailed list of functionalized oligonucleotides can be found in Table S1 (ESI †). 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC) utilized for producing supported and freestanding lipid bilayers was purchased from Avanti Polar Lipids (Alabaster, AL, USA). The fluorescent lipid Atto655-DOPE was obtained from AttoTEC GmbH (Siegen, Germany) and DiIC18(5) (DiD) from Thermo Fischer Scientifics (Waltham, MA, USA).

Franquelim H.G., Dietz H, & Schwille P. (2021). Reversible membrane deformations by straight DNA origami filaments. Soft matter, 17(2).

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