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810604 | 16:0-16 Doxyl PC

1-palmitoyl-2-stearoyl-(16-doxyl)-sn-glycero-3-phosphocholine

16:0-16 Doxyl PC

Chloroform

Size SKU Packaging Price
1mg 810604C-1mg 810604C-1mg 1 x 1mg 1mg/mL 1mL $755.00
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Powder

Size SKU Packaging Price
1mg 810604P-1mg 810604P-1mg 1 x 1mg $755.00 755
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Info

16:0-16 Doxyl PC

1-palmitoyl-2-stearoyl-(16-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
216491-65-5
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

Gupta A, Korte T, Herrmann A, Wohland T. Plasma membrane asymmetry of lipid organization: fluorescence lifetime microscopy and correlation spectroscopy analysis. J Lipid Res. 2019 Dec 19;jlr.D119000364. doi: 10.1194/jlr.D119000364. [Epub ahead of print]. PMID: 31857388.

 PubMed ID: 31857388

Geudens N, Kovács B, Sinnaeve D, Oni FE, Höfte M, Martins JC. Conformation and Dynamics of the Cyclic Lipopeptide Viscosinamide at the Water-Lipid Interface. Molecules. 2019 Jun 17;24(12). pii: E2257. doi: 10.3390/molecules24122257.

 PubMed ID: 31213011

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]

 PubMed ID: 22496416

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

 PubMed ID: 18783220

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]

 PubMed ID: 17325006

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]

 PubMed ID: 17029406

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]

 PubMed ID: 16859937

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]

 PubMed ID: 8908298

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]

 PubMed ID: 2159806

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

 PubMed ID: 3210953

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]

 PubMed ID: 7378080

Ausili A, Torrecillas A, deGodos AM, Corbalan-Garcia S, Gomez-Fernandez JC. The phenolic group of α-tocopherol anchors in the lipid-water interface of fully saturated membranes. Langmuir. 2018 Feb 15. doi: 10.1021/acs.langmuir.7b04142. [Epub ahead of print]

PubMed ID: 29447442
Certificates of Analysis

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