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22(R)-hydroxy Cholesterol (Synonyms: Narthesterol)

Catalog No.GC14972

22(R)-hydroxy Cholesterol is an endogenous agonist of the liver X receptor (LXR), with an EC50 value of 325nM.

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22(R)-hydroxy Cholesterol Chemical Structure

Cas No.: 17954-98-2

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1mg
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10mg
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Sample solution is provided at 25 µL, 10mM.

Description of 22(R)-hydroxy Cholesterol

22(R)-hydroxy Cholesterol is an endogenous agonist of the liver X receptor (LXR), with an EC50 value of 325nM [1]. The LXRs (LXRα and LXRβ) can regulate the expression of cholesterol 7α-hydroxylase induced by oxidosteroids, and cholesterol 7α-hydroxylase is the rate-limiting enzyme in the classical bile acid synthesis process [2]. 22(R)-hydroxy Cholesterol can be used to induce cell differentiation and protect neuronal cells [3-4].

In vitro, 22(R)-hydroxy Cholesterol (30nM-3μM; 96h) treatment significantly inhibited the proliferation of LNCaP prostate cancer cells in a dose-dependent manner [5]. 22(R)-hydroxy Cholesterol (2μM; 14 days) treatment induced hMSCs cells to exhibit neuronal cell-like characteristics, increasing the average cell area, the length of neurites and axons, and increasing the expression of dopamine neuron cell-specific proteins and the percentage of MAP2-positive cells [6].

References:
[1] Spencer, T.A., Dansu, L., Russel, J.S., et al. Pharmacophore analysis of the nuclear oxysterol receptor LXRα. J. Med. Chem. 44(6), 886-897 (2001).
[2] Repa, J.J., Turley, S.D., Lobaccaro, J.-M.A., et al. Regulation of absorption and ABC1-mediated efflux of cholesterol by RXR heterodimers. Science 289(5484), 1524-1529 (2000).
[3] Yao Z X, Han Z, Xu J, et al. 22R-Hydroxycholesterol induces differentiation of human NT2 precursor (Ntera2/D1 teratocarcinoma) cells[J]. Neuroscience, 2007, 148(2): 441-453.
[4] Yao Z X, Brown R C, Teper G, et al. 22R‐Hydroxycholesterol protects neuronal cells from β‐amyloid‐induced cytotoxicity by binding to β‐amyloid peptide[J]. Journal of neurochemistry, 2002, 83(5): 1110-1119.
[5] Chuu C P, Lin H P. Antiproliferative effect of LXR agonists T0901317 and 22 (R)-hydroxycholesterol on multiple human cancer cell lines[J]. Anticancer research, 2010, 30(9): 3643-3648.
[6] Singh M, Jain M, Bose S, et al. 22 (R)-hydroxycholesterol for dopaminergic neuronal specification of MSCs and amelioration of Parkinsonian symptoms in rats[J]. Cell death discovery, 2021, 7(1): 13.

Protocol of 22(R)-hydroxy Cholesterol

Cell experiment [1]:

Cell lines

Human mesenchymal stem cells (hMSCs)

Preparation Method

For neuronal differentiation, induction medium containing neurobasal media, B27 supplement, EGF, FGF2 (10ng/mL each) and 22(R)-hydroxy Cholesterol (2µM), l-glutamine, PenStrep was used. The induction protocol was carried out for 14 days with media change on every 3rd day. After the 14-day induction period ended, these cells were then used for subsequent immunocytochemical analysis.

Reaction Conditions

2μM; 14 days

Applications

22(R)-hydroxy Cholesterol induction significantly increased the expression of dopamine neuron-specific proteins in hMSCs cells and the percentage of MAP2-positive cells.

References:
[1] Singh M, Jain M, Bose S, et al. 22 (R)-hydroxycholesterol for dopaminergic neuronal specification of MSCs and amelioration of Parkinsonian symptoms in rats[J]. Cell death discovery, 2021, 7(1): 13.

Chemical Properties of 22(R)-hydroxy Cholesterol

Cas No. 17954-98-2 SDF
Synonyms Narthesterol
Chemical Name cholest-5-ene-3β,22R-diol
Canonical SMILES CC(C)CC[C@@H](O)[C@@H](C)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C
Formula C27H46O2 M.Wt 402.7
Solubility ≤20mg/ml in ethanol;0.1mg/ml in DMSO;2mg/ml in dimethyl formamide Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 22(R)-hydroxy Cholesterol

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1 mg 5 mg 10 mg
1 mM 2.4832 mL 12.4162 mL 24.8324 mL
5 mM 496.6 μL 2.4832 mL 4.9665 mL
10 mM 248.3 μL 1.2416 mL 2.4832 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 14 reference(s) in Google Scholar.)

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