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Merck

C6013

Cholesteryl hemisuccinate tris salt

anionic detergent

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C31H50O4 · C4H11NO3
Número CAS:
102601-49-0
Peso molecular:
607.86
UNSPSC Code:
12352211
eCl@ss:
39023139
PubChem Substance ID:
329775108
NACRES:
NA.77
MDL number:
MFCD00058298

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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 key

SLDYONDUXRBLLR-XTCKSVDZSA-N

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

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

functional group

ester

shipped in

ambient

storage temp.

−20°C

Quality Level

200

Categorías relacionadas

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000476792
0000475843
0000475843
0000476792
0000455989

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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
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)
Megan L Grove et al.
PloS one, 8(7), e68095-e68095 (2013-07-23)
Genotyping arrays are a cost effective approach when typing previously-identified genetic polymorphisms in large numbers of samples. One limitation of genotyping arrays with rare variants (e.g., minor allele frequency [MAF] <0.01) is the difficulty that automated clustering algorithms have to
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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