N lignoceroyl d erythro sphingosine

Manufactured by Avanti Polar Lipids

Sourced in United States

N-lignoceroyl-D-erythro-sphingosine is a lipid compound produced by Avanti Polar Lipids. It is a synthetic analogue of a naturally occurring sphingolipid. This compound can be used in research applications as a biochemical tool.

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D-erythro-sphingosine

7 protocols using n lignoceroyl d erythro sphingosine

Synthesis and Characterization of Ceramides

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N-lauroyl-D-erythro-sphingosine (C12 : 0 CER), N-palmitoyl-D-erythro-sphingosine (C16 : 0 CER), and N-lignoceroyl-D-erythro-sphingosine (C24 : 0 CER) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). CER from bovine brain was obtained from Sigma-Aldrich (St. Louis, MO, USA). All other reagents were of reagent, HPLC, or LC-MS grade.

Morito K., Shimizu R., Ali H., Shimada A., Miyazaki T., Takahashi N., Rahman M.M., Tsuji K., Shimozawa N., Nakao M., Sano S., Azuma M., Nanjundan M., Kogure K, & Tanaka T. (2023). Molecular species profiles of plasma ceramides in different clinical types of X-linked adrenoleukodystrophy. The journal of medical investigation : JMI, 70(3.4).

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Ceramide Extraction and Quantification

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All chemicals were purchased from Sigma-Aldrich (Steinheim, Germany) and had purities greater than 95%. Ceramide internal standards [N-stearoyl 4-hydroxysphinganine, N-(2′-(R)-hydroxystearoyl)-d-erythro-sphingosine, N-lignoceroyl-d-erythro-sphingosine and N-lignoceroyl-d-erythro-sphinganine] were purchased from Avanti Polar Lipids (Alabaster, AL, USA). All solvents used were of LC-MS grade.

Łuczaj W., Wroński A., Domingues P., Domingues M.R, & Skrzydlewska E. (2020). Lipidomic Analysis Reveals Specific Differences between Fibroblast and Keratinocyte Ceramide Profile of Patients with Psoriasis Vulgaris. Molecules, 25(3), 630.

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Sphingolipid Standards Acquisition

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N-palmitoyl-D-erythro-sphingosine (Cer16:0), N-stearoyl-D-erythro-sphingosine (Cer18:0), N-lignoceroyl-D-erythro-sphingosine (Cer24:0) and N-nervonoyl-D-erythro-sphingosine (Cer24:1) were obtained from Avanti Polar Lipids, Inc., Alabaster, AL, while their respective isotope-labeled standards used as an internal standard (IS) were purchased as a mixture (LIPIDOMIX^® Mass Spec Standard solution) from Avanti Polar Lipids, Inc., Alabaster, AL, USA.

Lantzanaki M., Veneti S., Mintziori G., Begou O., Pappas P.D., Gika H., Goulis D.G., Bili H., Taousani E, & Vavilis D. (2022). Plasma Ceramide Concentrations in Full-Term Pregnancies Complicated with Gestational Diabetes Mellitus: A Case-Control Study. Metabolites, 12(11), 1123.

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UPLC-ESI-QTOF-MS Characterization of Ceramide Profiles

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An Agilent UPLC-ESI-QTOF-MS system (Agilent 1290; Agilent 6540; Agilent Technologies, Santa Clara, CA, USA) was used to characterize the CER profiles. The mobile phase was composed of solvent A (water with 20 mM ammonium formate pH 5) and solvent B (methanol). Initially, 70% of B was held isocratically for 1 min, followed by a linear increase to 100% of B within 75 min, and return to initial conditions in 5 min. The CERs were separated on an RP C18 column (Acquity BEH Shield 2.1 × 100 mm; 1.7 μm; Waters, Milford, MA, USA) with a flow rate of 0.5 mL/min. The QTOF mass spectrometer was operated in positive ion mode (electrospray voltage 3.5 kV) with a capillary temperature of 300 °C and a sheath gas flow rate of 8 L/min. The data was collected in DDA mode. Identification of CER species was based on the presence of the [M + H]⁺ molecular ion, retention time and characteristic fragmentation patterns observed in MS/MS spectra, which was previously described in detail^{19 (link)}. Cermide internal standards, N-lignoceroyl-d-erythro-sphingosine and N-lignoceroyl-d-erythro-sphinganine (Avanti Polar Lipids, Alabaster, AL, USA) were used for quantification of CERs.

Groth M., Łuczaj W., Dunaj-Małyszko J., Skrzydlewska E, & Moniuszko-Malinowska A. (2022). Differences in the plasma phospholipid profile of patients infected with tick-borne encephalitis virus and co-infected with bacteria. Scientific Reports, 12, 9538.

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Lipidomic Internal Standards Protocol

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1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (C16:0 LPC), 1-stearoyl-2-hydroxy-sn-glycero-3-phosphocholine (C18:0 LPC), N-palmitoyl-D-erythro-sphingosylphosphorylcholine (d18:1/16:0 SM), N-stearoyl-D-erythro-sphingosylphosphorylcholine (d18:1/18:0 SM), N-palmitoyl-D-erythro-sphingosine (d18:1/16:0 ceramide), N-lignoceroyl-D-erythro-sphingosine (d18:1/24:0 ceramide) and ceramide/sphingolipid internal standard mixture I (contains C17 base sphingosine, C17 base sphinganine, C17 base sphingosine-1-P, C17 base sphinganine-1-P, lactosyl(ß) C12 ceramide, 12:0 sphingomyelin, glucosyl(ß) C12 ceramide, 12:0 ceramide, 12:0 ceramide-1-P, 25:0 ceramide) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Standard stock solutions were dissolved in chloroform/methanol 1:1 (v/v) at a concentration of 1 mM and stored at −20 °C. Lipid standard mixtures were prepared freshly every day in lipid buffer (2:1:1; Isopropanol, LC/MS Grade Merck Millipore, MA, USA; Acetonitrile; H₂O, LC/MS reagent, 9831-2, J.T.Baker, Phillipsburg, NY, USA) at a concentration of 25 μM and used immediately.

Law S.H., Chan H.C., Ke G.M., Kamatam S., Marathe G.K., Ponnusamy V.K, & Ke L.Y. (2023). Untargeted Lipidomic Profiling Reveals Lysophosphatidylcholine and Ceramide as Atherosclerotic Risk Factors in apolipoprotein E Knockout Mice. International Journal of Molecular Sciences, 24(8), 6956.

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Characterization of Sphingoid Lipids

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High-resolution mass spectra were recorded on an Agilent Technologies G6520A Q-TOF mass spectrometer using electrospray ionization. NMR spectra were recorded on Bruker Avance I and III spectrometers (400 or 500 MHz), and chemical shifts are expressed in parts per million (δ) relative to chloroform (7.26 ppm for ¹H and 77.2 ppm for ¹³C) or DMSO (2.50 ppm for ¹H and 39.5 ppm for ¹³C) as an internal reference. TLC was performed on 0.25-μm silica gel 60 F₂₅₄ aluminum-backed plates. Silica gel 60 (230–400 mesh) was used for flash column chromatography. The compounds were visualized by UV light and by spraying with 10% phosphomolybdic acid in ethanol. THF and toluene were distilled from sodium and benzophenone. D-erythro-Sphingosine, N-stearoyl-D-erythro-sphingosine, and N-lignoceroyl-D-erythro-sphingosine were purchased from Avanti Polar Lipids. Flash column chromatography for 10–15 was performed using a Biotage Isolera One automated system with Flash KP-Sil™ silica cartridges. Microwave-assisted experiments were carried out in a microwave instrument (Smithcreator™) in Pyrex vials using standard procedures.

Kim Y.A., Day J., Lirette C.A., Costain W.J., Johnston L.J, & Bittman R. (2015). Synthesis and photochemical properties of PEGylated coumarin-caged ceramides for cell studies. Chemistry and physics of lipids, 194, 117-124.

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Lipid Composition Analysis Protocol

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1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC), N-lignoceroyl-D-erythro-sphingosylphosphorylcholine (24:0 SM, lSM), N-nervonoyl-D-erythro-sphingosyl-phosphorylcholine (24:1 SM, nSM), N-lignoceroyl-D-erythro-sphingosine (24:0 Cer, lCer), N-nervonoyl-D-erythro-sphingosine (24:1 Cer, nCer), cholesterol (Chol), and the lipophilic fluorescent probe 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (Rho-PE) were purchased from Avanti Polar Lipids (Alabaster, AL). DiI (1,1′-Dioctadecyl-3,3,3′,3′-Tetramethylindocarbocyanine Perchlorate ('DiI'; DiIC18(3))) was supplied by Thermo Fisher (Waltham, MA, USA). Methanol and chloroform were from Fisher (Suwanee, GA). Buffer solution, unless otherwise stated, was 20 mM PIPES, 1 mM EDTA, 150 mM NaCl, pH 7.4. All salts and organic solvents were of analytical grade.

González-Ramírez E.J., García-Arribas A.B., Sot J., Goñi F.M, & Alonso A. (2020). C24:0 and C24:1 sphingolipids in cholesterol-containing, five- and six-component lipid membranes. Scientific Reports, 10, 14085.

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