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C6512 Sigma

Cholesteryl hemisuccinate

Synonym: 3β-Hydroxy-5-cholestene 3-hemisuccinate, 5-Cholesten-3β-ol 3-hemisuccinate, Cholesteryl hydrogen succinate

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Description

Packaging

5, 25 g in poly bottle

General description

Cholesteryl hemisuccinate (CHEMS) is an acidic cholesterol ester. It self assembles into bilayers in alkaline and neutral aqueous media. CHEMS exhibits pH sensitive polymorphism. It consists of succinic acid esterified to the beta-hydroxyl group of cholesterol. This chemical modification results in the ability of CHEMS to adopt a lamellar assembly in suitable aqueous media, whereas cholesterol forms monohydrate crystals in an aqueous environment.1

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Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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1. Cholesteryl hemisuccinate exhibits pH sensitive polymorphic phase behavior. Hafez IM and Cullis PR Biochimica et Biophysica Acta (BBA) - General Subjects 1463(1), 107-114, (2000)

The selective antiproliferative effects of α-tocopheryl hemisuccinate and cholesteryl hemisuccinate on murine leukemia cells result from the action of the intact compounds Fariss MW et al Cancer Res. 54, 3346-51, (1994)

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Relationship between Thylakoid Membrane Fluidity and the Functioning of Pea Chloroplasts EFFECT OF CHOLESTERYL HEMISUCCINATE Plant Physiol. 67(6), 1069-1072, (1981)

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RNAi-based therapeutics targeting survivin and PLK1 for treatment of bladder cancer. Seth S, Matsui Y, Fosnaugh K, et al. Mol. Ther. 19, 928-935, (2011)

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Long-circulating, pH-sensitive liposomes sterically stabilized by copolymers bearing short blocks of lipid-mimetic units. Momekova D, Rangelov S, Yanev S, et al. Eur. J. Pharm. Sci. 32(4-5), 308-17, (2007)

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Glycosaminoglycan-resistant and pH-sensitive lipid-coated DNA complexes produced by detergent removal method. Lehtinen J, Hyvönen Z, Subrizi A, et al. J. Control. Release 131(2), 145-9, (2008)

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Cholesterol increases kinetic, energetic, and mechanical stability of the human β2-adrenergic receptor. Zocher M, Zhang C, Rasmussen SG, et al. Proc. Natl. Acad. Sci. U. S. A. 109(50), E3463-72, (2012)

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Esterase-catalyzed dePEGylation of pH-sensitive vesicles modified with cleavable PEG-lipid derivatives. Xu H, Deng Y, Chen D, et al. J. Control. Release 130(3), 238-45, (2008)

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Synthesis and evaluation of a novel ligand for folate-mediated targeting liposomes. Xiang G, Wu J, Lu Y, et al. Int. J. Pharm. 356(1-2), 29-36, (2008)

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pH and temperature dual-sensitive liposome gel based on novel cleavable mPEG-Hz-CHEMS polymeric vaginal delivery system. Chen D, Sun K, Mu H, et al. Int. J. Nanomedicine 7, 2621-30, (2012)

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Folate receptor-targeted fluorescent paramagnetic bimodal liposomes for tumor imaging. Ding N Int. J. Nanomedicine 6, 2513-20, (2011)

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The morphology and composition of cholesterol-rich micellar nanostructures determine transmembrane protein (GPCR) activity. O'Malley MA, Helgeson ME, Wagner NJ, et al. Biophys. J. 100(2), L11-3, (2011)

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A purified C-terminally truncated human adenosine A(2A) receptor construct is functionally stable and degradation resistant. Singh S, Hedley D, Kara E, et al. Protein Expr. Purif. 74(1), 80-7, (2010)

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Recombinant cannabinoid type 2 receptor in liposome model activates g protein in response to anionic lipid constituents. Kimura T, Yeliseev AA, Vukoti K, et al. J. Biol. Chem. 287(6), 4076-87, (2012)

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Toward rational design of protein detergent complexes: determinants of mixed micelles that are critical for the in vitro stabilization of a G-protein coupled receptor. O'Malley MA, Helgeson ME, et al. Biophys. J. 101, 1938-1948, (2011)

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Anionic pH-sensitive pegylated lipoplexes to deliver DNA to tumors. Mignet N, Richard C, Seguin J, et al. Int. J. Pharm. 361(1-2), 194-201, (2008)

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The role of cholesterol on the activity and stability of neurotensin receptor 1. Oates J, Faust B, Attrill H, et al. Biochim. Biophys. Acta 1818(9), 2228-33, (2012)

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Preparation, therapeutic efficacy and intratumoral localization of targeted daunorubicin liposomes conjugating folate-PEG-CHEMS. Xiong S, Yu B, Wu J, et al. Biomed. Pharmacother. 65(1), 2-8, (2011)

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Morphological effect of lipid carriers on permeation of lidocaine hydrochloride through lipid membranes. Shim J, Kim MJ, Kim HK, Kim DH, et al. Int. J. Pharm. 388, 251-256, (2010)

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Enhanced depigmenting effects of N-glycosylation inhibitors delivered by pH-sensitive liposomes into HM3KO melanoma cells. Park JY, Choi H, Hwang JS, et al. J. Cosmet. Sci. 59(2), 139-50, (2008)

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Activation of Toll-like receptor 9 and production of epitope specific antibody by liposome-encapsulated CpG-DNA. Kim D, Kwon HJ, and Lee Y BMB Rep. 44(9), 607-12, (2011)

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Preparation and characterization of 5-fluorouracil pH-sensitive niosome and its tumor-targeted evaluation: in vitro and in vivo. Wang M, Yuan Y, Gao Y, et al. Drug Dev. Ind. Pharm. 38(9), 1134-41, (2012)

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Fusion-relevant changes in lipid shape of hydrated cholesterol hemisuccinate induced by pH and counterion species. Klasczyk B, Panzner S, Lipowsky R, et al. J. Phys. Chem. B 114(46), 14941-6, (2010)

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Preparation and characterization of pH-sensitive vesicles made of cholesteryl hemisuccinate. Xu H, Deng Y, Chen D, et al. Drug Dev. Ind. Pharm. 34(2), 134-41, (2008)

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Alpha-tocopheryl succinate induces rapid and reversible phosphatidylserine externalization in histiocytic lymphoma through the caspase-independent pathway. Fujita H, Shiva D, Utsumi T, et al. Mol. Cell Biochem. 333(1-2), 137-49, (2010)

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LHRHa aided liposomes targeting to human ovarian tumor cells: preparation and cellular uptake. Yuan WM, Song QG, Zhang ZR, et al. Pharmazie 63(6), 434-8, (2008)

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Long-circulating, pH-sensitive liposomes. Momekova D, Rangelov S, and Lambov N Methods Mol. Biol. 605, 527-44, (2010)

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GPCR stabilization using the bicelle-like architecture of mixed sterol-detergent micelles Thompson AA, Liu JJ, Chun E, et al. Methods 55(4), 310-7, (2011)

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