810605P

16:0-14 Doxyl PC

Avanti Research^™ - A Croda Brand 810605P, powder

• Synonym(s): 1-palmitoyl-2-stearoyl-(14-doxyl)-sn-glycero-3-phosphocholine
• Empirical Formula (Hill Notation): C₄₆H₉₀N₂O₁₀P
• CAS Number: 321595-12-4
• Molecular Weight: 862.19
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• assay: >99% (TLC)
• form: powder
• packaging: pkg of 1 × 1 mg (810605P-1mg)
• manufacturer/tradename: Avanti Research^™ - A Croda Brand 810605P
• shipped in: dry ice
• storage temp.: −20°C

Description

General description

16:0-14 Doxyl Phosphatidylcholine (PC) is a doxyl probe with a nitroxyl ring attached at carbon 14 on the chain of 1-palmitoyl-2-stearoyl-(14-doxyl)-sn-glycero-3-phosphocholine (PSPC).[1][2]

Avanti′s nitroxide spin product listing is a group of compounds designed to act as membrane probes. A variety of positions down the hydrophobic chain are labeled with the nitroxide functional groups to allow probing the membrane at various depths. These compounds have been synthesized from 1-palmitoyl-2-hydroxy-sn-glycerol-3-phosphocholine with the product being purified by column chromatography. Various n-doxyl phosphocholines have been recently used as biophysical tools to elucidate membrane trafficking with phosphatidylinositol transfer proteins and as fluorescent quenchers in lipid bilayer structural studies.[3][4]

application

16:0-14 Doxyl PC (1-palmitoyl-2-stearoyl-(14-doxyl)-sn-glycero-3-phosphocholine) has been used:

• in the labeling of small unilamellar vesicles for electron spin resonance (ESR) spectra[5]
• as spin label for labeling at different depths of 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine (PSPC) multilamellar vesicles (MLVs) for nuclear magnetic resonance (NMR) studies[1]
• as paramagnetic spin labels for ¹H-¹⁵N heteronuclear single quantum coherence (HSQC) spectra[2]

Biochem/physiol Actions

16:0-14 Doxyl Phosphatidylcholine (PC) is used as a label to probe various membrane depths from the hydrocarbon-water interface.[5] It quenches the fluorescence of 7-nitrobenz-2-oxa-1,3-diazole (NBD), a fluorescent label in the lipid bilayer.[6] There is a progressive increase in the depth and degree of mobility of the probe as the doxyl group substitution proceeds towards the end of the lipid chain,[6][7] and flexibility also increases.[7]

Packaging

5 mL Clear Glass Sealed Ampule (810605P-1mg)

Preparation Note

Product use: To prevent aggregation, prepare water-based solutions of 2 mM stock solutions of n-DOXYL PCs and store in plastic. Dilute stock solutions to 0.03- 0.1 mM solutions for EPR studies.[8] For liposome preparations in fluorescent quenching measurements, dissolve the doxyl lipid in 150 μl absolute ethanol for a concentration of 40.3 mM [3], Additional supplemental information.

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Storage Class: 11 - Combustible Solids