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850311 | DOCP

2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl hydrogen phosphate

DOCP

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Chloroform

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25mg 850311C-25mg 850311C-25mg 1 x 25mg 10mg/mL 2.5mL $190.00 190
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Info

DOCP

2-((2,3-bis(oleoyloxy)propyl)dimethylammonio)ethyl hydrogen phosphate

Inverse-phosphocholine lipids, a remix of a common phospholipid, contain headgroups with an inverted charge orientation relative to phosphocholine (PC) lipids. The iPC lipid headgroup has a quaternary amine adjacent to the bilayer interface and a phosphate that extends into the aqueous phase.
Therefore iPC lipids afford a unique opportunity to investigate the biophysical and bioactivity-related ramifications of a charge inversion at the bilayer surface.

Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C43H82NO8P
Percent Composition
C 66.89%, H 10.70%, N 1.81%, O 16.58%, P 4.01%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
1360461-57-9
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
772.087
Exact Mass
771.578
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References

Nazemidashtarjandi S, Vahedi A, Farnoud AM. Lipid Chemical Structure Modulates the Disruptive Effects of Nanomaterials on Membrane Models. Langmuir. 2020 Apr 20. doi: 10.1021/acs.langmuir.0c00295. Epub ahead of print. PMID: 32312045.

 PubMed ID: 32312045

Cardenas AE, Anderson CM, Elber R, Webb LJ. Partition of Positively and Negatively Charged Tryptophan Ions in Membranes with Inverted Phospholipid Heads: Simulations and Experiments. J Phys Chem B. 2019 Apr 9. doi: 10.1021/acs.jpcb.9b00754. [Epub ahead of print]

 PubMed ID: 30912653

Wang X, Li X, Wang H, Zhang X, Zhang L, Wang F, Liu J. Charge and Coordination Directed Liposome Fusion onto SiO2 and TiO2 Nanoparticles. Langmuir. 2019 Feb 5;35(5):1672-1681. doi: 10.1021/acs.langmuir.8b02979. Epub 2018 Dec 26.

 PubMed ID: 30558422

Zhang X, Barraza KM, Upton KT, Beauchamp JL. Subtle Changes in Lipid Environment Have Profound Effects on Membrane Oxidation Chemistry. J Am Chem Soc. 2018 Nov 21. doi: 10.1021/jacs.8b08610. [Epub ahead of print]

 PubMed ID: 30461271

Wang X, Li X, Wang H, Zhang X, Zhang L, Wang F, Liu J. Charge and Coordination Directed Liposome Fusion onto SiO2 and TiO2 Nanoparticles. Langmuir. 2018 Dec 18. doi: 10.1021/acs.langmuir.8b02979. [Epub ahead of print]

 PubMed ID: 30558422

Liu Y, Wang F, Liu J. Headgroup-Inversed Liposomes: Biointerfaces, Supported Bilayers and Applications. Langmuir. 2018 Aug 14;34(32):9337-9348. doi: 10.1021/acs.langmuir.7b04369. Epub 2018 Mar 16.

 PubMed ID: 29526108

Liu Y, Liu J. Cu2+-Directed Liposome Membrane Fusion, Positive-Stain Electron Microscopy, and Oxidation. Langmuir. 2018 Jun 12. doi: 10.1021/acs.langmuir.8b00864. [Epub ahead of print]

 PubMed ID: 29804456

Wang, F. and J. Liu. (2015). A Stable Lipid/TiO Interface with Headgroup-Inversed Phosphocholine and a Comparison with SiO. J Am Chem Soc

PubMed ID: 26302371

Perttu, E.K., A.G. Kohli, and F.C. Szoka Jr. (2012). Inverse-phosphocholine lipids: a remix of a common phospholipid. J Am Chem Soc 134:4485-8.

PubMed ID: 22364493
Certificates of Analysis

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