1 2 dipalmitoyl sn glycero 3 phosphate

Manufactured by Avanti Polar Lipids

Sourced in United States

1,2-dipalmitoyl-sn-glycero-3-phosphate is a phospholipid compound used in various laboratory applications. It serves as a structural component in the study of biological membranes and lipid bilayers.

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11 protocols using 1 2 dipalmitoyl sn glycero 3 phosphate

Lipid-based Nanoparticle Delivery for Breast Cancer

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1,2-Dipalmitoyl-sn-glycero-3-phosphate (DPPA), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE), 1,2-dipalmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) (DPPG) and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N [amino (polyethylene glycol)-2000] (DSPE-PEG (2000) NH₂) were obtained from Avanti Polar Lipids Inc. (Alabaster, AL, USA, supplied by Labco LLC. Dubai, UAE). Epithelial breast cancer (HCC1954) cell line was purchased from American Type Culture Collection (ATCC, Manassas, VA, USA), Trastuzumab (Herceptin) was obtained from Hoffmann-La Roche Limited (Basel, Switzerland, supplied by Aster pharmacy, Sharjah, UAE). All the other chemicals used here were obtained from Sigma Aldrich Chemie GmbH (Munich, Germany, supplied by Labco LLC. Dubai, UAE).

Awad N.S., Paul V., AlSawaftah N.M, & Husseini G.A. (2023). Effect of phospholipid head group on ultrasound-triggered drug release and cellular uptake of immunoliposomes. Scientific Reports, 13, 16644.

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Novel Lipid-Based Nanoparticle Formulation

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1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (MPPC), 1,2-dipalmitoyl-sn-glycero-3-phosphate (DPPA), 1,2 distearoyl-sn-glycero-3-phosphoethanolamine-N-Methoxypolyethyleneglycol-2000 (DSPE-PEG2k), and 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine-N-Methoxypolyethyleneglycol-5000 (DPPE-PEG5k) were obtained from Avanti Polar Lipids Inc. (Alabaster, AL). Doxorubicin hydrochloride (USP grade), fatty acid- and globulin-free bovine serum albumin, copper (II) gluconate, ammonium sulfate, and triethanolamine (TEA) were purchased from Sigma (St. Louis, MO). Prohance was purchased from Merry X-Ray (Sacramento, CA). IRDye 800CW NHS ester was obtained from LI-COR Biosciences (Lincoln, NE). The neu deletion (NDL) metastatic mammary carcinoma cell line was obtained from the Alexander Borowsky Laboratory (UC Davis) [39 (link), 40 (link)]. TCC-SUP tumorigenic human bladder cancer cells were obtained from the American Type Culture Collection (HTB-5, Manassas, VA).

Fite B.Z., Kheirolomoom A., Foiret J.L., Seo J.W., Mahakian L.M., Ingham E.S., Tam S.M., Borowsky A.D., Curry F.R, & Ferrara K.W. (2017). Dynamic Contrast Enhanced MRI Detects Changes in Vascular Transport Rate Constants Following Treatment with Thermally-Sensitive Liposomal Doxorubicin. Journal of controlled release : official journal of the Controlled Release Society, 256, 203-213.

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Lipid-Based Nanobubble Fabrication

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Nanobubbles were made from a combination of 1,2-dibehenoyl-sn-glycero-3-phosphocholine (DBPC), 1,2-dipalmitoyl-sn-glycero-3-phosphate (DPPA) and 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE), all purchased from Avanti Polar Lipids, Pelham, AL, USA, along with 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-(methoxy(polyethylene glycol)-2000) (ammonium salt) (DSPE-mPEG 2000) from Laysan Lipids, Arab, AL, USA. The lipids were dissolved in propylene glycol (PG, Sigma Aldrich, Milwaukee, WI, USA), glycerol (Acros Organics) and Gibco phosphate buffered saline (PBS, pH 7.4, 1×) from Thermo Fisher, Waltham, MA, USA.

Johansen M.L., Perera R., Abenojar E., Wang X., Vincent J., Exner A.A, & Brady-Kalnay S.M. (2021). Ultrasound-Based Molecular Imaging of Tumors with PTPmu Biomarker-Targeted Nanobubble Contrast Agents. International Journal of Molecular Sciences, 22(4), 1983.

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Phospholipid Library Characterization

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L-α-PC from egg yolk, 1,2-dipalmitoyl-sn-glycero-3-phosphoserine (16:0/16:0-PS), 1,2-dipalmitoyl-sn-glycero-3-phosphate (16:0/16:0-PA), 1,2-distearoyl-sn-glycero-3-phosphate (18:0/18:0-PA), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphate (16:0/18:1-PA), 1-stealoyl-2-oleoyl-sn-glycero-3-phosphate (18:0/18:1-PA), 1,2-dioleoyl-sn-glycero-3-phosphate (18:1/18:1-PA), 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphate (18:0/20:4-PA), and 1-stearoyl-2-docosahexaenoyl-sn-glycero-3-phosphate (18:0/22:6-PA) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Cholesterol (Chol) was purchased from Wako Pure Chemical Industries (Tokyo, Japan). Membrane Lipid Strips were purchased from Echelon Biosciences (Salt Lake City, UT, USA).

Yachida N., Hoshino F., Murakami C., Ebina M., Miura Y, & Sakane F. (2023). Saturated fatty acid– and/or monounsaturated fatty acid–containing phosphatidic acids selectively interact with heat shock protein 27. The Journal of Biological Chemistry, 299(3), 103019.

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Reconstitution of Lipid Biosynthesis Pathways

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1-palmitoyl-2-oleoyl-glycero-3-phosphatidylcholine (POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (POPG), 1-myristoyl-2-hydroxy-sn-glycero-3-phosphate (14:0 Lyso PA), 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphate (16:0 Lyso PA), 1-stearoyl-2-hydroxy-sn-glycero-3-phosphate (18:0 Lyso PA), 1-oleoyl-2-hydroxy-sn-glycero-3-phosphate (18:1 Lyso PA), 1,2-dipalmitoyl-sn-glycero-3-phosphate (DPPA), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphate (POPA), and 1,2-dioleoyl-sn-glycero-3-phosphate (DOPA) were purchased from Avanti Polar lipids. Fatty acid LC/MS mixture (#17942) was purchased from Funakoshi (Japan). ¹³C-Acetyl-CoA, ¹³C-Malonyl-CoA, Acetyl-CoA, Malonyl-CoA, NADH, NADPH, and sn-glycerol-3-phosphate were purchased from Sigma Aldrich. PUREfrex 2.0 and its Sol.I buffer, which was customized for the volume down, and DnaKJE mix were given or purchased from GeneFrontier (Japan).

Eto S., Matsumura R., Shimane Y., Fujimi M., Berhanu S., Kasama T, & Kuruma Y. (2022). Phospholipid synthesis inside phospholipid membrane vesicles. Communications Biology, 5, 1016.

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Lipid-based Microbubble Fabrication

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All solutions were prepared using filtered, sterile, deionized water (Direct-Q 3 Millipore, Billerica, MA, USA. 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), 1,2-dipalmitoyl-sn-glycero-3-phosphate (DPPA) and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Perfluorobutane gas (n-C4F10, PFB) was purchased from FluroMed (Round Rock, TX, USA). Polyoxyethylene-40 stearate (PEG40S), 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-5000] (DPPE-PEG5K) and chloroform were purchased from Sigma-Aldrich (St. Louis, MO, USA). Phosphate-buffered saline was procured from Fisher Scientific (Pittsburg, PA, USA). All reagents were ≥99% pure and used as received without further purification.

Martinez P.J., Song J.J., Castillo J., DeSisto J., Song K.H., Green A.L, & Borden M. (2024). Effect of Microbubble Size, Composition and Multiple Sonication Points on Sterile Inflammatory Response in Focused Ultrasound-Mediated Blood-Brain Barrier Opening. bioRxiv.

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Lipids and Detergents for Structural Studies

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Lipids: 1,2-dipalmitoyl-sn-glycero-3-phosphate (16:0/16:0-PA), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoinositol (16:0/18:1-PI), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (16:0/18:1-PS), 1,2-dioleoyl-sn-glycero-3-phosphate (18:1/18:1-PA), 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoinositol (18:0/20:4-PI), 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-myo-inositol-4',5'-bisphosphate) (18:0/20:4-PI(4,5)P₂), 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphate (18:0/20:4-PA), and 1-stearoyl-2-docosahexaenoyl-sn-glycero-3-phosphate (18:0/22:6-PA) were obtained from Avanti Polar Lipids. 1,2-dimyristoyl-sn-glycerol (14:0/14:0-DG), 1-palmitoyl-2-oleoyl-sn-3-phosphoglycerol (16:0/18:1-PG), and N-stearoyl-D-erythro-sphingosine (d18:1/18:0-Cer) were obtained from Cayman Chemical Company. 16:0/18:1-sn-glycero-3-phosphocholine (16:0/18:1-PC) was purchased from Sigma-Aldrich.
Detergents: n-dodecyl-β-D-maltoside (DDM) was obtained from Cayman Chemical Company. Cholesteryl hemisuccinate (CHS) was purchased from Sigma-Aldrich.

Murakami C, & Sakane F. (2021). Sphingomyelin synthase-related protein generates diacylglycerol via the hydrolysis of glycerophospholipids in the absence of ceramide. The Journal of Biological Chemistry, 296, 100454.

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Lipid-based Perfluorocarbon Nanoemulsion

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The lipids 1,2-dibehenoyl-sn-glycero-3-phosphocholine (DBPC), 1,2 dipalmitoyl-sn-glycero-3-phosphate (DPPA), and 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE) were obtained from Avanti Polar Lipids (Pelham, AL, USA), and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (ammonium salt) (mPEG–DSPE) was obtained from Laysan Lipids (Arab, AL, USA). Propylene glycol was purchased from Sigma Aldrich (Milwaukee, WI, USA). Glycerol (99+%, Acros Organics, Morris Plains, NJ, USA) and phosphate-buffered saline solution (PBS, Gibco, Life Technologies, Waltham, MA, USA) were purchased from Fisher Scientific (Pittsburgh, PA, USA). Perfluoropropane (C₃F₈) was obtained from AirGas (Cleveland, OH, USA).

Abenojar E.C., Bederman I., de Leon A.C., Zhu J., Hadley J., Kolios M.C, & Exner A.A. (2020). Theoretical and Experimental Gas Volume Quantification of Micro- and Nanobubble Ultrasound Contrast Agents. Pharmaceutics, 12(3), 208.

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Synthesis and Purification of Deuterated Phospholipids

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1,2-dipalmitoyl-sn-glycero-3-phosphate (sodium salt) and 1,2-dioleoyl-sn-glycero-3-phosphate (sodium salt) were purchased from Avanti Polar Lipids. [N(CD3)3]Choline tetraphenylborate was synthesised using the published method of Lin et al [37] .
]choline were synthesised from the sodium salt of the corresponding phosphatidic acid and [N(CD3)3]choline tetraphenylborate via the published method of Lin et al [37] . The product was purified using automated medium pressure chromatography (Grace Reveleris), eluting first with CHCl3:MeOH (80:20), followed by CHCl3:MeOH:H2O (80:20:2) to elute the product.
Head deuterated DPPC: Data were consistent with that previously reported [37] . 1 -9).

Bryant G., Taylor M.B., Darwish T.A., Krause-Heuer A.M., Kent B, & Garvey C.J. (2019). Effect of deuteration on the phase behaviour and structure of lamellar phases of phosphatidylcholines - Deuterated lipids as proxies for the physical properties of native bilayers. Colloids and surfaces. B, Biointerfaces, 177.

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Lipid Synthesis Reagents Specifications

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Palmitoyl coenzyme A (p-CoA), oleoyl coenzyme A (o-CoA), palmitoyl lysophosphatidic acid (16:0 LPA), oleoyl lysophosphatidic acid (18:1 LPA), 1,2-dipalmitoyl-sn-glycero-3-phosphate (DPPA), 1,2-dioleoyl-sn-glycero-3-phosphate (DOPA), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phosphatidylethanolamine (DOPE), 1,2-dioleoyl-sn-glycero-3-phospho-(1'-rac-glycerol) (DOPG), 1',3'-bis[1,2-dioleoyl-sn-glycero-3-phospho]-sn-glycerol (cardiolipin), and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[biotinyl(polyethylene glycol)-2000] (DSPE-PEG-biotin) were purchased from Avanti Polar Lipids. N-(6-tetramethylrhodaminethiocarbamoyl)-1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine (TRITC-DHPE) was from Invitrogen. Texas Red 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine, triethylammonium salt (Texas Red DHPE), 212 μm-300 μm acid washed glass beads, chloroform, methanol, acetylacetone, glycerol-3-phosphate (G3P), β-mercaptoethanol, and L-serine were from Sigma-Aldrich. Formic acid, ammonium formate and ULC grade organic solvents for mobile phases were from Biosolve. Cytidine triphosphate (CTP) was from Promega.

Scott A., Noga M.J., de Graaf P., Westerlaken I., Yildirim E, & Danelon C. (2016). Cell-Free Phospholipid Biosynthesis by Gene-Encoded Enzymes Reconstituted in Liposomes. PLoS ONE, 11(10), e0163058.

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