1 2 dimyristoyl sn glycero 3 phosphoethanolamine

Manufactured by Avanti Polar Lipids

Sourced in United States

1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine is a synthetic phospholipid compound. It is a dialkyl phosphatidylethanolamine lipid with two myristic acid (14:0) chains esterified to the glycerol backbone and a phosphoethanolamine head group.

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18 protocols using 1 2 dimyristoyl sn glycero 3 phosphoethanolamine

Lipid Bilayer Phase Behavior

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L-a-phosphatidylcholine (egg-PC), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), dipalmitoyl-sn-glycerol-3-phosphocholine (DMPC), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (DMPE) were purchased from Avanti Polar Lipids (Alabaster, AJ, USA) and used without further purification. All lipids had a purity of 499%, except egg-PC 495%. All lipids were studied exclusively in their fluid phase, therefore all measurements were carried out above their melting temperature T m . The experimental temperatures ranged from a few degrees above T m (note, melting points are given in Section 3.1) up to 80 1C.

Vancuylenberg G., Sadeghpour A., Tyler A.I.I, & Rappolt M. (2023). Planar confined water organisation in lipid bilayer stacks of phosphatidylcholine and phosphatidylethanolamine. Soft matter, 19(27).

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Analytical Techniques for Phospholipid Identification

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Chloroform (HPLC grade) was from Baker (Deventer, The Netherlands). Methanol and water (analytical grade) were from Fluka Analytical/Sigma-Aldrich (Munich, Germany). Internal phospholipid standards, 1,2-diarachidoyl-sn-glycero-3-phosphocholine (diarachidoyl-phosphatidylcholine, PC20:0/20:0) and 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (dimyristoyl-phosphatidylethanolamine, PE14:0/14:0) were purchased from Avanti Polar Lipids (Alabaster, Alabama, USA). Purity of chemicals was checked by liquid chromatography heated electrospray ionization tandem mass spectrometry (LC–H-ESI-MS/MS) (see below). All further chemicals were of analytical grade and from various commercial sources.

Böckmann K.A., von Stumpff A., Bernhard W., Shunova A., Minarski M., Frische B., Warmann S., Schleicher E., Poets C.F, & Franz A.R. (2020). Fatty acid composition of adipose tissue at term indicates deficiency of arachidonic and docosahexaenoic acid and excessive linoleic acid supply in preterm infants. European Journal of Nutrition, 60(2), 861-872.

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Phospholipid Monolayer Preparation

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HPLC grade chloroform solutions of 1,2-dilauroyl-sn-glycero-3-phosphoethanolamine (DLPE) and 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (DMPE) were purchased from Avanti Polar Lipids, Alabaster, AL, and used as received. Texas Red® 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine, triethylammonium salt, (TXR-DHPE) was purchased in the dried form from Life Technologies (Invitrogen) and dissolved in HPLC grade chloroform. All organic solvents were purchased from Fisher Scientific. The subphase water (resistivity 18.2 MΩ/cm) was prepared using a Millipore Gradient System (Billerica, MA). The lipids were stored at −20 °C when not in use.

Ghazvini S., Ricke B., Zasadzinski J.A, & Dhar P. (2015). Monitoring Phases and Phase Transitions in Phosphatidylethanolamine Monolayers Using Active Interfacial Microrheology. Soft matter, 11(17), 3313-3321.

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Lipid Standards and Reagents for Lipidomics

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TOCP (purity >99%) was purchased from BDH Chemicals Co. Ltd. (Poole, England). Phenylmethylsulfonyl fluoride (PMSF) was purchased from Fluka Chemika (Buchs, Switzerland). Mipafox and phenyl valerate were synthesized in our laboratory as described previously25 (link). 4-aminoantipyrine was obtained from Beijing Xizhong Chemical Factory (Beijing, China). Glycerophosphocholine (GPC), paraoxon, ammonium formate and formic acid were obtained from Sigma-Aldrich (St. Louis, MO, USA). The following synthetic lipid standards were purchased from Avanti Polar Lipids (Alabaster, AL, USA): 1,2-dimyristoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt) [PG(14:0/14:0)]; 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine [PE(14:0/14:0)]; 1,2-dimyristelaidoyl-sn-glycero-3-phosphocholine [PC(14:1/14:1)]; 1-(10Z-heptadecenoyl)-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt) [LPG(17:1)]; and 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine [LPE(17:1)]. N-hexane, isopropanol, methanol and chloroform of HPLC grade were obtained from CNW Technology (Shanghai, China). ELISA kits for chicken DAG and PA were obtained from Shanghai Guyan Industrial Co. Ltd. (Shanghai, China).

Zhu L., Wang P., Sun Y.J., Xu M.Y, & Wu Y.J. (2016). Disturbed phospholipid homeostasis in endoplasmic reticulum initiates tri-o-cresyl phosphate-induced delayed neurotoxicity. Scientific Reports, 6, 37574.

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Phospholipid Standards for Lipidomics Analysis

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HPLC grade dichloromethane (CH₂Cl₂) and methanol (CH₃OH) were purchased from Fisher Scientific Ltd. (Loughborough, UK). All other reagents were purchased from major commercial sources. Milli-Q water was obtained from a water purification system (Synergy, Millipore Corporation, Billerica, MA, USA). Phospholipid internal standards 1,2-dimyristoyl-sn-glycero-3-phosphocholine (dMPC), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (dMPE), 1,2-dimyristoyl-sn-glycero-3-phospho-(10-rac-glycerol) (dMPG), 1,2-dimyristoyl-sn-glycero-3-phospho-L-serine (dMPS), 1,2-dipalmitoyl-sn-glycero-3-phosphatidylinositol (dPPI), N-palmitoyl-D-erythro-sphingosylphosphorylcholine (NPSM), 1-nonadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine (LPC (19:0)), 1,2-dimyristoyl-sn-glycero-3-propionic acid (dMPA), 1′,3′-bis[1–dimyristoyl-sn-glycero-3-phospho]-glycerol (tMCL) and N-heptadecanoyl-D-erythro-sphingosine (Cer (d18:1/17:0)) were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL, USA).

Aveiro S.S., Melo T., Figueiredo A., Domingues P., Pereira H., Maia I.B., Silva J., Domingues M.R., Nunes C, & Moreira A.S. (2020). The Polar Lipidome of Cultured Emiliania huxleyi: A Source of Bioactive Lipids with Relevance for Biotechnological Applications. Biomolecules, 10(10), 1434.

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HPLC-Based Lipid Analysis Protocol

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HPLC grade chloroform, methanol and acetonitrile were obtained from Fisher Scientific Ltd. (Loughborough, UK). Lipid internal standards 1,2-dimyristoyl-sn-glycero-3-phosphate (dMPA), 1,2-dimyristoyl-sn-glycero-3-phosphocholine (dMPC), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (dMPE), 1,2-dimyristoyl-sn-glycero-3-phospho-(10-rac-glycerol) (dMPG), 1,2-dipalmitoyl-sn-glycero-3-phosphatidylinositol (dPPI) and 1-nonadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine (LPC) were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL). Milli-Q water (Synergy, Millipore Corporation, Billerica, MA, USA) was produced when ultrapure water was necessary. All other reagents were purchased from major commercial sources.

Custódio M., Maciel E., Domingues M.R., Lillebø A.I, & Calado R. (2020). Nutrient availability affects the polar lipidome of Halimione portulacoides leaves cultured in hydroponics. Scientific Reports, 10, 6583.

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HILIC-MS Lipidomic Analysis Protocol

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LC–MS grade water, methanol, and acetonitrile, used for HILIC mobile phase preparation, HPLC-grade methanol, and chloroform, employed for lipid extraction, perdeuterated methanol (CD₃OD), and reagent-grade ammonium acetate, used as mobile phase additive, were all purchased from Sigma-Aldrich (Milan, Italy). Standards of 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (PE 14:0/14:0) and 1,2-dipalmitoyl-sn-glycero-3-phospho-l-serine (PS 16:0/16:0) were purchased from Avanti Polar Lipids (Alabaster, AL, USA).

Castellaneta A., Porcelli V., Losito I., Barile S., Maresca A., Del Dotto V., Guadalupi L.S., Calvano C.D., Carelli V., Palmieri L, & Cataldi T.R. (2023). Methyl carbamates of phosphatidylethanolamines and phosphatidylserines reveal bacterial contamination in mitochondrial lipid extracts of mouse embryonic fibroblasts. Scientific Reports, 13, 13972.

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Phospholipid Internal Standards Protocol

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Phospholipid internal standards 1,2-dimyristoyl-sn-glycero-3-phosphocholine (dMPC), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (dMPE), 1,2-dimyristoyl-sn-glycero-3-phospho-(10-rac-)glycerol (dMPG), 1,2-dimyristoyl-sn-glycero-3-phospho-L-serine (dMPS), tetramyristoylcardiolipin (TMCL), 1,2-dipalmitoyl-sn-glycero-3-phosphatidylinositol (dPPI), N-palmitoyl-D-erythro-sphingosylphosphorylcholine (NPSM), 1-nonadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine (LPC) were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL). Chloroform, methanol and acetonitrile were purchased from Fisher scientific (Leicestershire, UK); all the solvents were of high performance liquid chromatography (HPLC) grade and were used without further purification. All the other reagents and chemicals used were of the highest grade of purity commercially available. The water was of Milli-Q purity (Synergy1, Millipore Corporation, Billerica, MA).

Colombo S., Melo T., Martínez-López M., Carrasco M.J., Domingues M.R., Pérez-Sala D, & Domingues P. (2018). Phospholipidome of endothelial cells shows a different adaptation response upon oxidative, glycative and lipoxidative stress. Scientific Reports, 8, 12365.

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Mass Spectrometry Lipid Standards

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Lipid standards for mass spectrometry studies including 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (14:0/14:0-PE), 1,2-dimyristoyl-sn-glycero-3-phosphocholine (14:0/14:0-PC), and 1,2-dipalmitoyl-sn-glycero-3-phosphoinositol (16:0/16:0-PI) were purchased from Avanti Polar Lipids (Alabaster, AL). For the EPCT activity assay, phosphoryl ethanolamine [1,2-¹⁴C] (50–60 mCi/mmol) or [¹⁴-C] EtN-P was purchased from American Radiolabeled Chemicals (St Louis, MO). All other reagents were purchased from ThermoFisher Scientific or Sigma Aldrich Inc unless otherwise specified.

Basu S., Pawlowic M.C., Hsu F.F., Thomas G, & Zhang K. (2023). Ethanolaminephosphate cytidylyltransferase is essential for survival, lipid homeostasis and stress tolerance in Leishmania major. PLOS Pathogens, 19(7), e1011112.

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Phospholipid Standards Characterization

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Phospholipid standards 1,2-dimyristoyl-sn-glycero-3-phosphocholine (dMPC), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (dMPE), 1,2-dimyristoyl-sn-glycero-3-phospho-(1′-rac-)glycerol (dMPG), 1,2-dimyristoyl-sn-glycero-3-phospho-L-serine (dMPS), 1′,3′-bis[1–dimyristoyl-sn-glycero-3-phospho]-glycerol (tMCL), 1,2-dipalmitoyl-sn-glycero-3-phosphatidylinositol (dPPI), N-palmitoyl-D-erythro-sphingosylphosphorylcholine (NPSM), and 1-nonadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine (LPC) were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL). Chloroform (CHCl₃), methanol (MeOH), ethanol absolute, and acetonitrile were purchased from Fisher scientific (Leicestershire, UK); all the solvents were of high-performance liquid chromatography (HPLC) grade and were used without further purification. DPPH^● was purchased from Aldrich (Milwaukee, WI). 2,20-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS^●+) was obtained from Fluka (Buchs, Switzerland). Ammonium acetate and 6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (Trolox) were purchased from Sigma-Aldrich (St Louis, MO, USA). All the other reagents and chemicals used were of the highest grade of purity commercially available. Milli-Q water was also used (Synergysup^®, Millipore Corporation, Billerica, MA, USA).

Lopes D., Melo T., Meneses J., Abreu M.H., Pereira R., Domingues P., Lillebø A.I., Calado R, & Domingues M.R. (2019). A New Look for the Red Macroalga Palmaria palmata: A Seafood with Polar Lipids Rich in EPA and with Antioxidant Properties. Marine Drugs, 17(9), 533.

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