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810603 | 16:0-10 Doxyl PC

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

16:0-10 Doxyl PC

Chloroform

Size SKU Packaging Price
1mg 810603C-1mg 810603C-1mg 1 x 1mg 1mg/mL 1mL $733.01
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Powder

Size SKU Packaging Price
1mg 810603P-1mg 810603P-1mg 1 x 1mg $733.01 733.01
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Info

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].
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
188004-25-3
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

Kay JG, Koivusalo M, Ma X, Wohland T, Grinstein S. Phosphatidylserine dynamics in cellular membranes. Mol Biol Cell. 2012 Jun;23(11):2198-212. doi: 10.1091/mbc.E11-11-0936. Epub 2012 Apr 11. PMID: 22496416; PMCID: PMC3364182.

 PubMed ID: 22496416

Kondo M, Mehiri M, Regen SL. Viewing membrane-bound molecular umbrellas by parallax analyses. J Am Chem Soc. 2008 Oct 15;130(41):13771-7. doi: 10.1021/ja804929m. Epub 2008 Sep 11. PMID: 18783220; PMCID: PMC2822653.

 PubMed ID: 18783220

Smirnova TI, Chadwick TG, Voinov MA, Poluektov O, van Tol J, Ozarowski A, Schaaf G, Ryan MM, Bankaitis VA. Local polarity and hydrogen bonding inside the Sec14p phospholipid-binding cavity: high-field multi-frequency electron paramagnetic resonance studies. Biophys J. 2007 May 15;92(10):3686-95. doi: 10.1529/biophysj.106.097899. Epub 2007 Feb 26. PMID: 17325006; PMCID: PMC1853156.

 PubMed ID: 17325006

Wu F, Gaffney BJ. Dynamic behavior of fatty acid spin labels within a binding site of soybean lipoxygenase-1. Biochemistry. 2006 Oct 17;45(41):12510-8. doi: 10.1021/bi061415l. PMID: 17029406; PMCID: PMC2515559.

 PubMed ID: 17029406

Alaouie AM, Smirnov AI. 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. 2006 Oct;182(2):229-38. doi: 10.1016/j.jmr.2006.07.002. Epub 2006 Jul 21. PMID: 16859937.

 PubMed ID: 16859937

McConnell HM, Martinez-Yamout M. Insight into antibody combining sites using nuclear magnetic resonance and spin label haptens. Adv Protein Chem. 1996;49:135-48. doi: 10.1016/s0065-3233(08)60489-1. PMID: 8908298.

 PubMed ID: 8908298

de Jongh HH, Hemminga MA, Marsh D. ESR of spin-labeled bacteriophage M13 coat protein in mixed phospholipid bilayers. Biochim Biophys Acta. 1990 May 9;1024(1):82-8. doi: 10.1016/0005-2736(90)90210-f. PMID: 2159806.

 PubMed ID: 2159806

Chan HC, Magin RL, Swartz HM. Delivery of nitroxide spin label to cultured cells by liposomes. Magn Reson Med. 1988 Oct;8(2):160-70. doi: 10.1002/mrm.1910080206. PMID: 3210953.

 PubMed ID: 3210953

Parce JW, McConnell HM, Bartholomew RM, Esser AF. Kinetics of antibody-dependent activation of the first component of complement on lipid bilayer membranes. Biochem Biophys Res Commun. 1980 Mar 13;93(1):235-42. doi: 10.1016/s0006-291x(80)80271-3. PMID: 7378080.

 PubMed ID: 7378080
Certificates of Analysis

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