1 2 distearoyl sn glycero 3 phosphocholine

Manufactured by Avanti Polar Lipids

Sourced in United States

1,2-distearoyl-sn-glycero-3-phosphocholine is a lipid molecule that is commonly used as a component in various research and laboratory applications. It is a synthetic phospholipid that belongs to the class of phosphatidylcholines. The core function of this compound is to serve as a model system for studying membrane properties and behaviors in a controlled environment.

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Distearoyl-sn-glycero-3-phosphocholine (5 citations)

81 protocols using 1 2 distearoyl sn glycero 3 phosphocholine

Lipid Bilayer Formation and Characterization

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The lipids used in the study were 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC), and 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), purchased from Avanti Polar Lipids; porcine globotriaosylceramide (Gb 3 ) was purchased from Matreya LLC. The Shiga toxin B unit (STxB) was supplied by Prof. Ludger Johannes, Institut Curie, UMR144 Curie/ CNRS, Paris, France. 8 All lipids were dissolved in methanol before sample preparation. All used chemicals were of HPLC grade quality and Milli-Q water was used for the buffer preparation. HEPES buffer (5 mM, 150 mM NaCl), pH7.0 was prepared by mixing HEPES acid, HEPES base and NaCl components. Muscovite mica from Plano GmbH (Germany) was cut into approx. 10 Â 10 mm 2 pieces, freshly cleaved, and used as a substrate.

Solovyeva V., Johannes L, & Simonsen A.C. (2015). Shiga toxin induces membrane reorganization and formation of long range lipid order. Soft matter, 11(1).

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Preparation and Characterization of RN18 Microbubbles

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RN18 microbubbles were prepared according to the previously described protocol [18 (link)]. The MB shells were comprised of lipids at a 82:10:8 M ratio of 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), 1,2-distearoyl-sn-glycero-3-phosphate (DSPA), and N-(Carbonylmethoxypolyethyleneglycol 5000)-1,2-distearoyl-sn-glycero-e-phosphoethanolamine (MPEG-5000-DSPE) purchased from Avanti^® Polar Lipids, Inc. (Alabaster, AL). Before use, MBs were produced by vigorous agitation of the lipid emulsion for 45 s using a Vialmix™ (Lantheus Medical Imaging, N. Billerica, MA), yielding an average concentration of 2–5 × 10⁹ MBs/mL.

Tran D.M., Harrang J., Song S., Chen J., Smith B.M, & Miao C.H. (2018). Prolonging pulse duration in ultrasound-mediated gene delivery lowers acoustic pressure threshold for efficient gene transfer to cells and small animals. Journal of controlled release : official journal of the Controlled Release Society, 279, 345-354.

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Lipid-DNA Nanoparticle Formulation and Characterization

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1,2-Dipalmitoyl-sn-glycero-3-phosphocholine
(DPPC); 1,2- distearoyl-sn-glycero-3-phosphocholine
(DSPC); 1,2-dibehenoyl-sn-glycero-3-phosphocholine
(DBPC); and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene
glycol)] (ammonium salt) (DSPE-PEG) (PEG molecular weights of 1000,
2000, and 5000) were obtained from Avanti Polar Lipids (Alabaster,
AL). 4-Cyano-4′-pentylbiphenyl (5CB) and 9,10-bis(phenylethynyl)anthracene
(BPEA) dye were obtained from TCI America (Portland, OR). Cholesterol-modified
DNA sequences (Chol-DNA) and thrombin aptamer (TA) were obtained from
Integrated DNA Technologies (Coralville, IA). 1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine
perchlorate (DiI) and 3,3′-dioctadecyloxacarbocyanine perchlorate
(DiO) dyes were obtained from Sigma-Aldrich (St. Louis, MO). Chloroform,
Tris base, and sodium chloride (NaCl) were obtained from Fisher Scientific
(Pittsburgh, PA).

Mohan P., Noonan P.S., Nakatsuka M.A, & Goodwin A.P. (2014). On-Demand Droplet Fusion: A Strategy for Stimulus-Responsive Biosensing in Solution. Langmuir, 30(41), 12321-12327.

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Synthesis and Characterization of 3'-CE sLeX-DSPE-PEG Conjugate

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1,2-Distearoyl-sn-glycero-3-phosphocholine (DSPC) was purchased from Avanti Polar Lipids (Alabaster, AL, USA). Cholesterol, ethanol, and dimethyl sulfoxide (DMSO) were purchased from Nacalai Tesque (Kyoto, Japan). N-(methylpolyoxyethylene oxycarbonyl)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine (DSPE-PEG2000) was purchased from NOF Corporation (Tokyo, Japan). 3′-CE sLeX-DSPE-PEG (Fig. 1) were synthesized by the method reported previously.^{24 (link)} EVE was purchased from Chem Scene (South Brunswick Township, NJ, USA). Phosphate-buffered saline (PBS) was purchased from Nissui Pharmaceutical (Tokyo, Japan). TNF-α was purchased from Life Technologies (Carlsbad, CA, USA) and IL-1β was from Sigma-Aldrich (St. Louis, MO, USA).

Chantarasrivong C., Higuchi Y., Tsuda M., Yamane Y., Hashida M., Konishi M., Komura N., Ando H, & Yamashita F. (2019). Sialyl LewisX mimic-decorated liposomes for anti-angiogenic everolimus delivery to E-selectin expressing endothelial cells. RSC Advances, 9(36), 20518-20527.

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Lipid-based Nanoparticle Formulation

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Cholesterol, 1,2-dioleyl-3-trimethylam monium-propane (DODAP), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), and N-palmitoyl-sphingosine-1-[succinyl(polyethylene glycol)]2000 (DSPE-PEG) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). All other chemicals were of reagent grade and were used without further purification.

Li J, & Sun C.K. (2018). In vitro analysis of microRNA-26a in chronic lymphocytic leukemia cells. International Journal of Molecular Medicine, 42(6), 3364-3370.

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Synthesis of SMAnh Polymer Composites

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The commercially available SMAnh
(∼2:1) with the product name XiranSZ30010 was a kind gift from
Polyscope Polymers (Geleen, Netherlands). Phospholipids were obtained
from Avanti Polar Lipids (Alabaster, United States), namely, 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC). 4-Iodostyrene was purchased
from Apollo Scientific (Stockport, United Kingdom). All other chemicals
were sourced from Sigma-Aldrich (Darmstadt, Germany). Demineralized
water that has run through a Milli-Q water purification system is
simply referred to as water. Styrene and acrylic acid were freshly
distilled before use.

Kopf A.H., Lijding O., Elenbaas B.O., Koorengevel M.C., Dobruchowska J.M., van Walree C.A, & Killian J.A. (2022). Synthesis and Evaluation of a Library of Alternating Amphipathic Copolymers to Solubilize and Study Membrane Proteins. Biomacromolecules, 23(3), 743-759.

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Lipid-Polymer Nanoparticle Synthesis for Cytokine Delivery

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1,2-dioleoyl-sn-glycero-3-[(N-(5-amino-1-carboxypentyl)iminodiacetic acid)succinyl] (nickel salt) (DGS-NTA (Ni)), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), Cholesterol, and 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1’-rac-glycerol) (sodium salt) (POPG) 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) were purchased from Avanti Polar Lipids and used without modification. PLR and PLE were purchased from Alamanda Polymers and used without modification. Single chain IL-12 was produced in house from HEK-293 cells.

Barberio A.E., Smith S.G., Correa S., Nguyen C., Nhan B., Melo M., Tokatlian T., Suh H., Irvine D.J, & Hammond P.T. (2020). Cancer Cell Coating Nanoparticles for Optimal Tumor-Specific Cytokine Delivery. ACS nano, 14(9), 11238-11253.

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Lipid Nanoparticle Synthesis and Characterization

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Amines, epoxides, acyl chlorides, TEA were purchased from Sigma Aldrich (Burlington, Massachusetts, USA), Tokyo Chemical Industry (TCI, Tokyo, Japan) and Ambeed (Arlington Heights, Illinois, USA). Alanine transaminase (ALT) colorimetric activity assay kit (#700260) and aspartate aminotransferase (AST) colorimetric activity assay kit (#701640) were purchased from Cayman Chemical (Ann Arbor, Michigan, USA). 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), 1,2-dimyristoyl-rac-glycero-3-methoxypolyethylene glycol-2000 (DMG-PEG 2000) and cholesterol were obtained from Avanti Polar Lipids (Alabaster, Alabama, USA). DLin-MC3-DMA and SM-102 were purchased from MedChem Express (Monmouth Junction, New Jersey, USA). Cas9 mRNA (5moU) was purchased from TriLink (San Diego, California, USA). Highly modified sgRNA target mouse TTR (guide No. G211) was chemically synthesized by AxoLabs (Kulmbach, Bayern, Germany) based on the previous publication^{43 (link)}. Anhydrous DCM, porcine liver esterase, amiloride hydrochloride, chlorpromazine, genistein, methyl-beta-cyclodextrin and TTR siRNAs (#NM_013697, siRNA IDs: SASI_Mm01_00076059, SASI_Mm01_00076060 and SASI_Mm01_00076061) were purchased from Sigma Aldrich (Burlington, Massachusetts, USA).

Han X., Xu J., Xu Y., Alameh M.G., Xue L., Gong N., El-Mayta R., Palanki R., Warzecha C.C., Zhao G., Vaughan A.E., Wilson J.M., Weissman D, & Mitchell M.J. (2024). In situ combinatorial synthesis of degradable branched lipidoids for systemic delivery of mRNA therapeutics and gene editors. Nature Communications, 15, 1762.

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Lipid and Sterol Composition Modulation of Membrane Permeability

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Synthetic 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (POPG), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), cholesterol (CHOL), stigmasterol (STIGM), 7-dehydrocholesterol (7DCHOL), desmosterol (DESM), and camposterol (CAMPO) were purchased from Avanti Polar Lipids (Avanti Polar Lipids, Inc., Alabaster, AL, USA). Amphotericin B (AmB), nystatin (NyS), ergosterol (ERG), phloretin, biochanin A, genistein, quercetin, NaCl, KCl, NaOH, KOH, HEPES, EDTA, dimethylsulfoxide (DMSO), triton X-100, calcein, sephadex G-50, ethanol, methanol, chloroform, and hexadecane were obtained from Sigma-Aldrich Company Ltd. (Gillingham, UK). Figure 1 presents the chemical structures of the phospholipids, sterols, antibiotics, and polyphenols used in this study.

Efimova S.S, & Ostroumova O.S. (2024). Antibiotic Loaded Phytosomes as a Way to Develop Innovative Lipid Formulations of Polyene Macrolides. Pharmaceutics, 16(5), 665.

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Lipid Nanoparticle-mediated mRNA Delivery

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N-methyl-1-phenylmethanamine, Et₃N, Pd/C, epoxides and other chemicals were purchased from Sigma-Aldrich. 1,2-distearoyl- sn-glycero-3-phosphocholine (DSPC), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), and 1-palmitoyl-2-oleoyl- sn-glycero-3-phosphoethanolamine (POPE) were purchased from Avanti Polar Lipids, Inc. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) was purchased from Amresco (Solon, OH). Buffered formaldehyde (10%, pH 7.4) was purchased from Ricca Chemical (Arlington, TX). Firefly luciferase mRNA (FLuc mRNA) was purchased from TriLink Biotechnologies, Inc. (San Diego, CA). Alexa fluor 488 conjugate of wheat germ agglutinin, NucBlue Fixed cell ready probes DAPI, ProLong diamond antifade mountant reagent, Ribogreen reagent and fetal bovine serum (FBS) were purchased from Life Technologies (Grand Island, NY). Alexa-Fluor 647-labeled RNA was purchased from Integrated DNA Technologies. Bright-Glo luciferase assay substrate was from Promega (Madison, WI, USA).

Li B., Luo X., Deng B., Giancola J.B., McComb D.W., Schmittgen T.D, & Dong Y. (2016). Effects of local structural transformation of lipid-like compounds on delivery of messenger RNA. Scientific Reports, 6, 22137.

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