810604 | 16:0-16 Doxyl PC

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


Chloroform

Size SKU Packaging Price
1mg 810604C-1mg 810604C-1mg 1 x 1mg 1mg/mL 1mL $559.65

Powder

Size SKU Packaging Price
1mg 810604P-1mg 810604P-1mg 1 x 1mg $559.65
Base Price: ${originalprice|money}
Custom Packaging: (${concentration} @$4.00/ea. + $100) ${custompackagingtotal|money}
Packaging: ${concentration}
Item Total: ${totalprice|money}
Please select an option above.
${sku} - ${concentration}

16:0-16 Doxyl PC

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].
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

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