810605 | 16:0-14 Doxyl PC

1-palmitoyl-2-stearoyl-(14-doxyl)-sn-glycero-3-phosphocholine


Chloroform

Size SKU Packaging Price
1mg 810605C-1mg 810605C-1mg 1 x 1mg 1mg/mL 1mL $546.00

Powder

Size SKU Packaging Price
1mg 810605P-1mg 810605P-1mg 1 x 1mg $546.00
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}

16:0-14 Doxyl PC

16:0-14 Doxyl PC

1-palmitoyl-2-stearoyl-(14-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
321595-12-4
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
862.188
Exact Mass
861.633

Vasquez-Montes V, Vargas-Uribe M, Pandey NK, Rodnin MV, Langen R, Ladokhin AS. Lipid-modulation of membrane insertion and refolding of the apoptotic inhibitor Bcl-xL. Biochim Biophys Acta Proteins Proteom. 2019 Jul - Aug;1867(7-8):691-700. doi: 10.1016/j.bbapap.2019.04.006. Epub 2019 Apr 18.

PubMed ID: 31004798

Aloi E, Oranges M, Guzzi R, Bartucci R. Low-Temperature Dynamics of Chain-Labeled Lipids in Ester- and Ether-Linked Phosphatidylcholine Membranes. J Phys Chem B. 2017 Oct 5;121(39):9239-9246. doi: 10.1021/acs.jpcb.7b07386. Epub 2017 Sep 20.

PubMed ID: 28892381

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.

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.

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. Epub 2007 Feb 26.

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.

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. Epub 2006 Jul 21.

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.

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.

PubMed ID: 2159806

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

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.

PubMed ID: 7378080