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810601 | 16:0-5 Doxyl PC

1-palmitoyl-2-stearoyl-(5-doxyl)-sn-glycero-3-phosphocholine

16:0-5 Doxyl PC

Chloroform

Size SKU Packaging Price
1mg 810601C-1mg 810601C-1mg 1 x 1mg 1mg/mL 1mL $733.01
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Powder

Size SKU Packaging Price
1mg 810601P-1mg 810601P-1mg 1 x 1mg $733.01 733.01
Request Bulk Pricing
Info

16:0-5 Doxyl PC

1-palmitoyl-2-stearoyl-(5-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
188004-24-2
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

Sastre DE, Basso LGM, Trastoy B, Cifuente JO, Contreras X, Gueiros-Filho F, de Mendoza D, Navarro MVAS, Guerin ME. Membrane fluidity adjusts the insertion of the transacylase PlsX to regulate phospholipid biosynthesis in Gram-positive bacteria. J Biol Chem. 2019 Dec 3;jbc.RA119.011122. doi: 10.1074/jbc.RA119.011122. [Epub ahead of print]. PMID: 31796629.

 PubMed ID: 31796629

Bakarić D, Carić D, Vazdar K, Vazdar M. Vibrational spectroscopy combined with molecular dynamics simulations as a tool for studying behavior of reactive aldehydes inserted in phospholipid bilayers. Chem Phys Lipids. 2019 Jul 29;225:104793. doi: 10.1016/j.chemphyslip.2019.104793. [Epub ahead of print]

 PubMed ID: 31369738

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

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

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]

 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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