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810602 | 16:0-7 Doxyl PC

1-palmitoyl-2-stearoyl-(7-doxyl)-sn-glycero-3-phosphocholine

16:0-7 Doxyl PC

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1mg 810602P-1mg 810602P-1mg 1 x 1mg $733.01
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16:0-7 Doxyl PC

1-palmitoyl-2-stearoyl-(7-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].
Data
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
213331-17-0
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
862.188
Exact Mass
861.633
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References

Doktorova M, Kučerka N, Kinnun JJ, Pan J, Marquardt D, Scott HL, Venable RM, Pastor RW, Wassall SR, Katsaras J, Heberle FA. Molecular Structure of Sphingomyelin in Fluid Phase Bilayers Determined by the Joint Analysis of Small-Angle Neutron and X-ray Scattering Data. J Phys Chem B. 2020 Jun 25;124(25):5186-5200. doi: 10.1021/acs.jpcb.0c03389. Epub 2020 Jun 16. PMID: 32468822.

 PubMed ID: 32468822

Ober K, Volz-Rakebrand P, Stellmacher J, Brodwolf R, Licha K, Haag R, Alexiev U. Expanding the Scope of Reporting Nanoparticles: Sensing of Lipid Phase Transitions and Nanoviscosities in Lipid Membranes. Langmuir. 2019 Sep 3;35(35):11422-11434. doi: 10.1021/acs.langmuir.9b01372. Epub 2019 Aug 19.

 PubMed ID: 31378067

Bai J, Tucker WC, Chapman ER. PIP2 increases the speed of response of synaptotagmin and steers its membrane-penetration activity toward the plasma membrane. Nat Struct Mol Biol. 2004 Jan;11(1):36-44. Epub 2003 Dec 29.

 PubMed ID: 14718921

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 ID: 22496416

Lonnfors, M., O. Langvik, A. Bjorkbom, and J.P. Slotte. (2013). Cholesteryl Phosphocholine - A Study on Its Interactions with Ceramides and Other Membrane Lipids. Langmuir. 2013 Feb 19;29(7):2319-29. doi: 10.1021/la3051324. Epub 2013 Feb 4.

 PubMed ID: 23356741

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 Commun 93:235-42.

PubMed ID: 7378080

Chan HC, Magin RL, Swartz HM. (1988) Delivery of nitroxide spin label to cultured cells by liposomes. Magn Reson Med 8:160-70.

PubMed ID: 3210953

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 ID: 2159806

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 ID: 8908298

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 ID: 16859937

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 ID: 17029406

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 ID: 17325006

Kondo M, Mehiri M, Regen SL. (2008) Viewing membrane-bound molecular umbrellas by parallax analyses. J Am Chem Soc. 130:13771-7.

PubMed ID: 18783220
Certificates of Analysis

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