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C6013

Cholesteryl hemisuccinate tris salt

Name: Cholesteryl hemisuccinate tris salt
Brand: SIGMA

anionic detergent

Synonym(s):

3β-Hydroxy-5-cholestene 3-hemisuccinate, 5-Cholesten-3β-ol 3-hemisuccinate, CHEMS, CHS, Cholesteryl hydrogen succinate

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About This Item

Empirical Formula (Hill Notation):

C₃₁H₅₀O₄ · C₄H₁₁NO₃

CAS Number:

102601-49-0

Molecular Weight:

607.86

UNSPSC Code:

12352211

eCl@ss:

39023139

PubChem Substance ID:

329775108

NACRES:

NA.77

MDL number:

MFCD00058298

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biological source

synthetic (organic)

Quality Level

200

assay

≥98% (TLC)

form

powder

functional group

ester

shipped in

ambient

storage temp.

−20°C

SMILES string

NC(CO)(CO)CO.CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(=O)CCC(O)=O

InChI

1S/C31H50O4.C4H11NO3/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5;5-4(1-6,2-7)3-8/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33);6-8H,1-3,5H2/t21-,23+,24+,25-,26+,27+,30+,31-;/m1./s1

InChI key

SLDYONDUXRBLLR-XTCKSVDZSA-N

Related Categories

Biochemicals

Application

Cholesteryl hemisuccinate tris salt has been used:

to prepare solubilization buffer for glucan synthase assay
to prepare immunoprecipitation buffer for immobilization of opioid receptors on paramagnetic beads.
as a membrane stabilizer for liposomes and protein synaptogyrin-1
as a component of a folate-modified self-microemulsifying drug delivery system.
with N-dodecyl β-D-maltoside (DDM) to solubilize erythrocyte ghosts and chemokine receptor CCR1
for protein solubilization

Biochem/physiol Actions

Cholesteryl hemisuccinate is an ionizable anionic detergent that stabilizes large unilamellar vesicles. These liposome vesicles act as delivery agents for anticancer drugs, oligonucleotides and antibiotics. Cholesteryl succinate also reportedly exhibits antiproliferative activity and may be clinically useful as antitumor agent.

Preparation Note

Cholesteryl hemisuccinate tris salt yields clear, colorless solution in methanol at 10 mg/ml.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Engineering and functional immobilization of opioid receptors.

David Ott et al.

Protein engineering, design & selection : PEDS, 18(3), 153-160 (2005-03-26)

Opioid receptors, like many G protein-coupled receptors (GPCRs), are notoriously unstable in detergents. We have now developed a more stable variant of the mu-opioid receptor (MOR) and also a method for the immobilization of solubilized, functional opioid receptors on a

In vitro activity of 1,3-beta-D-glucan synthase requires the GTP-binding protein Rho1.

P Mazur et al.

The Journal of biological chemistry, 271(24), 14604-14609 (1996-06-14)

In the yeast Saccharomyces cerevisiae, the family of RHO genes are implicated in the control of morphogenetic events although the molecular targets of these GTP-binding proteins remain largely unknown. The activity of 1,3-beta-D-glucan synthase, the product of which is essential

Expression, purification and in vitro functional reconstitution of the chemokine receptor CCR1.

Samantha J Allen et al.

Protein expression and purification, 66(1), 73-81 (2009-03-12)

Chemokine receptors are a specific class of G-protein-coupled receptors (GPCRs) that control cell migration associated with routine immune surveillance, inflammation and development. In addition to their roles in normal physiology, these receptors and their ligands are involved in a large

Cholesteryl hemisuccinate as a membrane stabilizer in dipalmitoylphosphatidylcholine liposomes containing saikosaponin-d.

Ding, W.X., et al.

International Journal of Pharmaceutics, 300, 37-47 (2005)

On the formulation of pH-sensitive liposomes with long circulation times.

Sérgio Simões et al.

Advanced drug delivery reviews, 56(7), 947-965 (2004-04-07)

Strategies used to enhance liposome-mediated drug delivery in vivo include the enhancement of stability and circulation time in the bloodstream, targeting to specific tissues or cells, and facilitation of intracytoplasmic delivery. pH-sensitive liposomes have been developed to mediate the introduction

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Global Trade Item Number

SKU	GTIN
C6013-5G	04061833076064
C6013-25G	04061833076057

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