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C6013

Cholesteryl hemisuccinate tris salt

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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000550577
0000530825
0000550577
0000530825
0000476792

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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
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
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
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