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1-palmitoyl-2-cholesterylhemisuccinoyl-sn-glycero-3-phosphocholine

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1-palmitoyl-2-cholesterylhemisuccinoyl-sn-glycero-3-phosphocholine

Sterol-modified phospholipids stabilize bilayers but do not exchange between membranes as freely as cholesterol. This new class of phospholipids provides a new tool for biophysical studies on membranes and may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung or blood.

Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C55H98NO10P
Percent Composition
C 68.50%, H 10.24%, N 1.45%, O 16.59%, P 3.21%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
155401-40-4
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
964.341
Exact Mass
963.693
Synonyms
PCholPC
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References

Flasiński M, Konderla B, Broniatowski M, Wydro P. Sterol-Phospholipid Hybrids at the Air/Water Interface: Studies on Properties and Interactions with Parent Lipid Molecules. Langmuir. 2016 Apr 26;32(16):4095-102. doi: 10.1021/acs.langmuir.5b04311. Epub 2016 Apr 13. PMID: 27046325.

 PubMed ID: 27046325

Foglia F, Barlow DJ, Szoka FC, Huang Z, Rogers SE, Lawrence MJ. Structural studies of the monolayers and bilayers formed by a novel cholesterol-phospholipid chimera. Langmuir. 2011 Jul 5;27(13):8275-81. doi: 10.1021/la200739y. Epub 2011 Jun 2. PMID: 21634402.

 PubMed ID: 21634402

Iman M, Huang Z, Szoka FC Jr, Jaafari MR. Characterization of the colloidal properties, in vitro antifungal activity, antileishmanial activity and toxicity in mice of a di-stigma-steryl-hemi-succinoyl-glycero-phosphocholine liposome-intercalated amphotericin B. Int J Pharm. 2011 Apr 15;408(1-2):163-72. doi: 10.1016/j.ijpharm.2011.01.044. Epub 2011 Jan 26. PMID: 21277963; PMCID: PMC3071037.

 PubMed ID: 21277963

Huang Z, Jaafari MR, Szoka FC Jr. Disterolphospholipids: nonexchangeable lipids and their application to liposomal drug delivery. Angew Chem Int Ed Engl. 2009;48(23):4146-9. doi: 10.1002/anie.200900111. PMID: 19425026; PMCID: PMC2773798.

 PubMed ID: 19425026

Huang Z, Szoka FC Jr. Sterol-modified phospholipids: cholesterol and phospholipid chimeras with improved biomembrane properties. J Am Chem Soc. 2008 Nov 19;130(46):15702-12. doi: 10.1021/ja8065557. Epub 2008 Oct 25. PMID: 18950160; PMCID: PMC2701441.

 PubMed ID: 18950160
Physical/Chemical Properties

A summary of the physical/chemical properties of Sterol-Modified Phospholipids is presented in a PowerPoint presentation. This information was kindly provided by Dr. Francis C. Szoka, Jr., Department of Biopharmaceutical Sciences, University of California, San Francisco, California.

Certificates of Analysis

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