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810600P

Avanti

16:0-12 Doxyl PC

Avanti Polar Lipids 810600P, powder

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Synonym(s):
1-palmitoyl-2-stearoyl-(12-doxyl)-sn-glycero-3-phosphocholine
Empirical Formula (Hill Notation):
C46H90N2O10P
CAS Number:
217499-54-2
Molecular Weight:
862.19
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (810600P-1mg)

manufacturer/tradename

Avanti Polar Lipids 810600P

lipid type

ESR probes
phospholipids

shipped in

dry ice

storage temp.

−20°C

General description

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.
Phosphatidylcholine (PC) is a strong bilayer-forming lipid. It the most common phospholipid in mammalian membranes. It is also an important component of the mucosal layer of the colon. 1-palmitoyl-2-stearoyl-(12-doxyl)-sn-glycero-3-phosphocholine (12-NO-PC) is a nitroxide-labeled phospholipid.

Application

16:0-12 Doxyl PC is suitable for use:
  • as a lipophilic collisional quencher to prepare liposomes used in lipophilic quenching experiments
  • to prepare liposomes used in nitroxide quenching experiments to examine the location of each NBD (7-nitrobenz-2-oxa-1,3-diazole) probe in mutants
  • as a component in POPC or 1:1 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC)/1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-rac-1-glycerol (POPG) mixtures to prepare unlabelled large unilamellar liposomes

Biochem/physiol Actions

Phosphatidylcholine (PC) functions as a surfactant within the mucus to form a hydrophobic surface to inhibit bacterial penetrance. It is used to treat fat embolism. Phosphatidylcholine lowers the levels of cholesterol and triglycerides.

Packaging

5 mL Clear Glass Sealed Ampule (810600P-1mg)

Preparation Note

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. For liposome preparations in fluorescent quenching measurements, dissolve the doxyl lipid in 150 μl absolute ethanol for a concentration of 40.3 mM. href="https://pubs.acs.org/doi/suppl/10.1021/ja804929m/suppl_file/ja804929m_si_001.pdf"target="_blank">Supplemental information

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Description
Pricing

Storage Class Code

11 - Combustible Solids

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Structural insights into the membrane-anchoring mechanism of a cholesterol-dependent cytolysin
Ramachandran R, et al.
Nature Structural and Molecular Biology, 9(11), 823-823 (2002)
Lipid-specific binding of the calcium-dependent antibiotic daptomycin leads to changes in lipid polymorphism of model membranes
Jung D, et al.
Chemistry and Physics of Lipids, 154(2), 120-128 (2008)
The Membranes of Cells, 154(2), 120-128 (2016)
Integrative Medicine - E-Book, 154(2), 120-128 (2017)
The mechanism of membrane insertion for a cholesterol-dependent cytolysin: a novel paradigm for pore-forming toxins
Shatursky O, et al.
Cell, 99(3), 293-299 (1999)
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