810603 | 16:0-10 Doxyl PC

1-palmitoyl-2-stearoyl-(10-doxyl)-sn-glycero-3-phosphocholine


Chloroform

Size SKU Packaging Price
1mg 810603C-1mg 810603C-1mg 1 x 1mg 1mg/mL 1mL $520.00

Powder

Size SKU Packaging Price
1mg 810603P-1mg 810603P-1mg 1 x 1mg $520.00
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16:0-10 Doxyl PC

16:0-10 Doxyl PC

1-palmitoyl-2-stearoyl-(10-doxyl)-sn-glycero-3-phosphocholine

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 [Smirnova et al, 2007] and as fluorescent quenchers in lipid bilayer structural studies [Kondo et al, 2008].
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 [Wu and Gaffney, 2006]. For liposome preparations in fluorescent quenching measurements, dissolve the doxyl lipid in 150 µl absolute ethanol for a concentration of 40.3 mM [Kondo et al, 2008, supplemental info found at http://pubs.acs.org/doi/suppl/10.1021/ja804929m/suppl_file/ja804929m_si_001.pdf].
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C46H90N2O10P•
Percent Composition
C 64.08%, H 10.52%, N 3.25%, O 18.56%, P 3.59%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
188004-25-3
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
862.188
Exact Mass
861.633
Kay, J.G., M. Koivusalo, X. Ma, T. Wohland, and S. Grinstein. (2012). Phosphatidylserine dynamics in cellular membranes. Mol Biol Cell 23:2198-212. [PubMed] Kondo M, Mehiri M, Regen SL. (2008) Viewing membrane-bound molecular umbrellas by parallax analyses. J Am Chem Soc. 130:13771-7. [PubMed] Smirnova TI, Chadwick TG, Voinov MA, Poluektov O, van Tol J, Ozarowski A,Schaaf G, Ryan MM, Bankaitis VA. (2007) Local polarity and hydrogen bonding inside the Sec14p phospholipid-binding cavity: high-field multi-frequency electron paramagnetic resonance studies. Biophys J. 92:3686-95. [PubMed] Wu F, Gaffney BJ. (2006) Dynamic behavior of fatty acid spin labels within a binding site of soybean lipoxygenase-1. Biochemistry 45:12510-8. [PubMed] Alaouie AM, Smirnov AI. (2006) Ultra-stable temperature control in EPR experiments: thermodynamics of gel-to-liquid phase transition in spin-labeled phospholipid bilayers and bilayer perturbations by spin labels. J Magn Reson. 182:229-38. [PubMed] McConnell HM, Martinez-Yamout M. (1996)Insight into antibody combining sites using nuclear magnetic resonance and spin label haptens. Adv Protein Chem 49:135-48. Review. [PubMed] de Jongh HH, Hemminga MA, Marsh D. (1990) ESR of spin-labeled bacteriophage M13 coat protein in mixed phospholipid bilayers. Biochim Biophys Acta 1024:82-8. [PubMed] Chan HC, Magin RL, Swartz HM. (1988) Delivery of nitroxide spin label to cultured cells by liposomes. Magn Reson Med 8:160-70. [PubMed] Parce JW, McConnell HM, Bartholomew RM, Esser AF. (1980) Kinetics of antibody-dependent activation of the first component of complement on lipid bilayer membranes. Biochem Biophys Res Commun93:235-42. [PubMed]