A cholesterol ester with anticancer activity
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Alternative(s)
25698Cholesteryl Hemisuccinate
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Cholesteryl Hemisuccinate (tris salt)

Item No. 45505

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β)-cholest-5-en-3-ol 3-(hydrogen butanedioate), 2 amino-2-(hydroxymethyl)-1,3-propanediol
CAS Number
102601-49-0
Synonyms
  • Cholesterol Hemisuccinate
  • Cholesterol Hydrogen Succinate
  • Cholesterol Monosuccinate
  • Succinate Cholesterol Monoester
Molecular Formula
C31H50O4 • C4H11NO3
Formula Weight
607.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
SMILES
OCC(CO)(N)CO.C[C@@]12[C@]3([H])[C@](CC=C1C[C@H](CC2)OC(CCC(O)=O)=O)([H])[C@@]4([H])[C@](CC3)([C@]([C@@H](CCCC(C)C)C)([H])CC4)C
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    Product Description

    Cholesteryl hemisuccinate is a cholesterol ester with anticancer activity.1 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.2 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.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fariss, M.W., Fortuna, M.B., Everett, C.K., et al. The selective antiproliferative effects of alpha-tocopheryl hemisuccinate and cholesteryl hemisuccinate on murine leukemia cells result from the action of the intact compounds. Cancer Res. 54(13), 3346-3351 (1994).

    2. Ding, W.X., Qi, X.R., Li, P., et al. Cholesteryl hemisuccinate as a membrane stabilizer in dipalmitoylphosphatidylcholine liposomes containing saikosaponin-d. Int. J. Pharm. 300(1-2), 38-47 (2005).

    3. Simões, S., Moreira, J.N., Fonseca, C., et al. On the formulation of pH-sensitive liposomes with long circulation times. Adv. Drug Deliv. Rev. 56(7), 947-965 (2004).

    4. Allen, S.J., Ribeiro, S., Horuk, R., et al. Expression, purification and in vitro functional reconstitution of the chemokine receptor CCR1. Protein Expr. Purif. 66(1), 73-81 (2009).

    5. Grodecka, M., Bertrand, O., Karolak, E., et al. One-step immunopurification and lectinochemical characterization of the Duffy atypical chemokine receptor from human erythrocytes. Glycoconj. J. 29(2-3), 93-105 (2012).