1510-21-0

Cholesteryl hemisuccinate is a cholesterol ester with anticancer activity. It inhibits the growth of murine C1498 myeloid and L1210 lymphocytic leukemia cells when used at concentrations of 50 and 150 μM, respectively. Cholesteryl hemisuccinate acts as an ionizable anionic detergent and is commonly used to stabilize unilamellar vesicles and liposomes. It has also been used as an emulsifying agent in various vesicular drug delivery systems for anticancer drugs, antibiotics, and oligonucleotides and to solubilize various proteins including chemokine receptor 1 as well as erythrocyte ghosts.

Cholesteryl Hemisuccinate is an oxidation product of polyunsaturated fatty acid of cholesterol that alters lysosome structure and functions and induces proinflammatory cytokine production in macrophages.

ChEBI:Cholesteryl hemisuccinate is a dicarboxylic acid monoester resulting from the formal condensation of the hydroxy group of cholesterol with one of the carboxy groups of succinic acid. A detergent that is often used to replace cholesterol in protein crystallography, biochemical studies of proteins, and pharmacology. It has a role as a detergent. It is a cholestane ester, a dicarboxylic acid monoester and a hemisuccinate. It is functionally related to a cholesterol.

CHEMS can help to maintain the stability of dioleoylphosphatidylethanolamine (DOPE). This amphipathic lipid is used in mixtures with dioleoylphosphatidylethanolamine (DOPE) to form ′pH sensitive′ fusogenic vesicles. It can control cell growth.

GENERAL METHOD: Succinic anhydride (14.7 mmol, 1.57 eq.) and 4-dimethylaminopyridine (DMAP, 1.584 mmol, 0.17 eq.) were sequentially added to a solution of (3β)-cholest-5-en-3-ol (9.37 mmol) in pyridine (28 mL). The reaction mixture was stirred at room temperature for 7 days. Upon completion of the reaction, the mixture was poured into ice water and the pH was adjusted to 7 with dilute hydrochloric acid and subsequently extracted with chloroform. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography to afford the target compounds in 79% or 96% yield and >99.9% analytical purity (see Scheme 1-2). Analytical data for compounds 2 and 12 are detailed in the Supplementary Material.

Store at -20°C

[1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 8, p. 1189 - 1191
[2] Steroids, 2013, vol. 78, # 14, p. 1347 - 1352
[3] Patent: US2005/201972, 2005, A1. Location in patent: Page/Page column 15
[4] Polymer, 2016, vol. 86, p. 98 - 104
[5] Arzneimittel-Forschung/Drug Research, 1994, vol. 44, # 11, p. 1259 - 1264