Cholesteryl hemisuccinate tris salt

• CAT Number: M008643
• CAS Number: 102601-49-0
• Molecular Formula: C35H61NO7
• Molecular Weight: 607.873
• Purity: ≥95%
• Synonyms: Cholesteryl hemisuccinate tris salt, anionic detergent
• Target: Apoptosis
• Storage: Store at RT
• IUPAC Name: 2-amino-2-(hydroxymethyl)propane-1,3-diol;4-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid
• InChI: 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
• InChIKey: SLDYONDUXRBLLR-XTCKSVDZSA-N
• SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)CCC(=O)O)C)C.C(C(CO)(CO)N)O

Cholesteryl hemisuccinate(CAS: 102601-49-0) is a water-soluble cholesterol derivative that mimics native cholesterol function in cell membrane systems. Cholesterol hemisuccinate and Lauryl Maltose Neopentyl Glycol (cat. no. 60110) have been shown to easily exchange membrane proteins into Lipid-Cubic Phase (LPC). Commonly used in combination with N-Dodecyl-β-D-Maltopyranoside (DDM, cat. no. 60099) for extracting membrane proteins. Solubility: 1.2 % in a 6 % water solution of CHAPS.

Reference

[1]. Toxicol Lett. 1997 Feb 7;90(2-3):133-44. doi: 10.1016/s0378-4274(96)03837-4.
Cholesteryl hemisuccinate treatment protects rodents from the toxic effects of acetaminophen, adriamycin, carbon tetrachloride, chloroform and galactosamine.
Fariss MW(1), Lippman HR, Mumaw VR, Ray SD.
Author information: (1)Department of Pharmaceutical Sciences, College of Pharmacy, Washington State University, Pullman 99164-6510, USA.
In addition to its use as a stabilizer/rigidifier of membranes, cholesteryl hemisuccinate, tris salt (CS) administration has also been shown to protect rats from the hepatotoxic effects of carbon tetrachloride (CCl4). To further our understanding of the mechanism of CS cytoprotection, we examined in rats and mice the protective abilities of CS and the non-hydrolyzable ether form of CS, gamma-cholesteryloxybutyric acid, tris salt (CSE) against acetaminophen-, adriamycin-, carbon tetrachloride-, chloroform- and galactosamine-induced toxicity. The results of these studies demonstrated that CS-mediated protection is not selective for a particular species, organ system or toxic chemical. A 24-h pretreatment of both rats and mice with a single dose of CS (100mg/kg, i.p.), resulted in significant protection against the hepatotoxic effects of CCl4, CHCl3, acetaminophen and galactosamine and against the lethal (and presumably cardiotoxic) effect of adriamycin administration. Maximal CS-mediated protection was observed in experimental animals pretreated 24 h prior to the toxic insult. These data suggest that CS intervenes in a critical cellular event that is an important common pathway to toxic cell death. The mechanism of CS protection does not appear to be dependent on the inhibition of chemical bioactivation to a toxic reactive intermediate (in light of the protection observed against galactosamine hepatotoxicity). However, based on the data presented, we can not exclude the possibility that CS administration inhibits chemical bioactivation. Our findings do suggest that CS-mediated protection is dependent on the action of the intact anionic CS molecule (non-hydrolyzable CSE was as protective as CS), whose mechanism has yet to be defined.
DOI: 10.1016/s0378-4274(96)03837-4 PMID: 9067481

[2]. Biochim Biophys Acta. 2013 Oct;1834(10):2045-56. doi: 10.1016/j.bbapap.2013.06.003. Epub 2013 Jun 15.
Expression, surface immobilization, and characterization of functional recombinant cannabinoid receptor CB2.
Locatelli-Hoops SC(1), Gorshkova I, Gawrisch K, Yeliseev AA.
Author information: (1)National Institute on Alcohol Abuse and Alcoholism, National Institutes of Health, 5625 Fishers Lane, Bethesda, MD 20892, USA.
Human peripheral cannabinoid receptor CB2, a G protein-coupled receptor (GPCR) involved in regulation of immune response has become an important target for pharmaceutical drug development. Structural and functional studies on CB2 may benefit from immobilization of the purified and functional receptor onto a suitable surface at a controlled density and, preferably in a uniform orientation. The goal of this project was to develop a generic strategy for preparation of functional recombinant CB2 and immobilization at solid interfaces. Expression of CB2 as a fusion with Rho-tag (peptide composed of the last nine amino acids of rhodopsin) in E. coli was evaluated in terms of protein levels, accessibility of the tag, and activity of the receptor. The structural integrity of CB2 was tested by ligand binding to the receptor solubilized in detergent micelles, captured on tag-specific monoclonal 1D4 antibody-coated resin. Highly pure and functional CB2 was obtained by sequential chromatography on a 1D4- and Ni-NTA-resin and its affinity to the 1D4 antibody characterized by surface plasmon resonance (SPR). Either the purified receptor or fusion CB2 from the crude cell extract was captured onto a 1D4-coated CM4 chip (Biacore) in a quantitative fashion at uniform orientation as demonstrated by the SPR signal. Furthermore, the accessibility of the extracellular surface of immobilized CB2 and the affinity of interaction with a novel monoclonal antibody NAA-1 was studied by SPR. In summary, we present an integral strategy for purification, surface immobilization, ligand- and antibody binding studies of functional cannabinoid receptor CB2.
Published by Elsevier B.V.
DOI: 10.1016/j.bbapap.2013.06.003 PMCID: PMC3779079 PMID: 23777860

[3]. Biomaterials. 2010 Jun;31(17):4757-63. doi: 10.1016/j.biomaterials.2010.02.049. Epub 2010 Mar 19.
Effects of cleavable PEG-cholesterol derivatives on the accelerated blood clearance of PEGylated liposomes.
Xu H(1), Wang KQ, Deng YH, Chen DW.
Author information: (1)College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, PR China.
The "accelerated blood clearance" (ABC) phenomenon describes a syndrome whereby the circulation time of a second dose of injected liposomes is substantially reduced, while the hepatic and splenic accumulations increase. To avoid this unexpected immune response, we have modified liposomes with cleavable PEG-lipid derivatives (PEG-CHEMS and PEG-CHMC). The ABC phenomenon was induced by repeated injection of conventional PEG-DSPE-liposomes in rat body and was accompanied by a greatly increased uptake in the liver. In contrast, only a slight ABC phenomenon was induced by repeated injection of PEG-CHMC-liposomes and was accompanied by increased uptake in the liver. Repeated injection of PEG-CHEMS-liposomes did not induce either an ABC phenomenon or an increase in liver accumulation. Repeated injection of the cleavable PEG-lipid modified vesicles (tris (hydroxymethyl) aminomethane salt of cholesteryl hemisuccinate(CHST)) showed similar results to those found with the cleavable PEG-lipid modified liposomes. These cleavable PEG-lipid derivatives could lessen or eliminate the ABC phenomenon produced by repeated injection of PEGylated liposomes or vesicles. Consequently, these two cleavable PEG-lipid derivatives may not only prolong the circulation time of nanoparticles, but may also represent a solution to the ABC phenomenon.
DOI: 10.1016/j.biomaterials.2010.02.049 PMID: 20303164