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25(R)-27-hydroxy Cholesterol (Synonyms: (25R)-26-hydroxy cholesterol)

Catalog No.GC13887

25(R)-27-hydroxy Cholesterol is a selective estrogen receptor modulator and an agonist of the liver X receptor.

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25(R)-27-hydroxy Cholesterol Chemical Structure

Cas No.: 20380-11-4

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1 mg
$54.00
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5 mg
$189.00
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Sample solution is provided at 25 µL, 10mM.

Description of 25(R)-27-hydroxy Cholesterol

25(R)-27-hydroxy Cholesterol ((25R)-26-hydroxy cholesterol) is the naturally occurring isomer of the endogenous the endogenous 27-hydroxycholesterol. And approximately 80% is the naturally occurring (25R) isomer [1][2]. 27-hydroxycholesterol is an endogenous ligand of liver X receptor with EC50 values of 85 and 71 nM for LXRα and LXRβ, respectively [2][3].

The liver x receptors (LXRα and LXRβ) are nuclear hormone receptors that are important regulators of cholesterol and fatty acid metabolism [2].

27-hydroxycholesterol is synthesized by a mitochondrial P-450 enzyme that appears to be widely distributed in tissues [1]. 27-hydroxycholestero1 can inhibit both cholesterol synthesis and low density lipoprotein (LDL) receptor activity [1]. In cholesterol-loaded human macrophage cells, 27-hydroxycholestero1 is an endogenous ligand for LXRs with Kd values of 85 and 71 nM for LXRα and LXRβ, respectively [3]. In human fibroblasts, low density lipoprotein cholesterol is converted to 27-hydroxycholesterol, which was sufficient to reduce the activity of HMG-CoA reductase [4].

References:
[1].  Javitt NB. 26-Hydroxycholesterol: synthesis, metabolism, and biologic activities. J Lipid Res. 1990 Sep;31(9):1527-33.
[2].  Fu X, Menke JG, Chen Y, et al. 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87.
[3].  Zhang Y, Mangelsdorf DJ. LuXuRies of lipid homeostasis: the unity of nuclear hormone receptors, transcription regulation, and cholesterol sensing. Mol Interv. 2002 Apr;2(2):78-87.
[4].  Axelson M, Larsson O. Low density lipoprotein (LDL) cholesterol is converted to 27-hydroxycholesterol in human fibroblasts. Evidence that 27-hydroxycholesterol can be an important intracellular mediator between LDL and the suppression of cholesterol production. J Biol Chem. 1995 Jun 23;270(25):15102-10.

Protocol of 25(R)-27-hydroxy Cholesterol

Cell experiment:

Stock solutions of 27-Hydroxycholesterol are prepared in 100% ethanol and stored at −80°C. 27-Hydroxycholesterol stock solution is dissolved in appropriate volumes of media to prepare the working solutions of 1 μM.

Animal experiment:

Proliferation assays are conducted on black 96 well plates using a commercial kit which quantifies cell number using DNA content and membrane integrity. LNCaP and PC3 cells are treated with 1 µM 27-Hydroxycholesterol for 48 hours[2].

References:

[1]. DuSell CD, et al. 27-hydroxycholesterol is an endogenous selective estrogen receptor modulator. Mol Endocrinol. 2008 Jan;22(1):65-77.
[2]. Raza S, et al. The cholesterol metabolite 27-hydroxycholesterol stimulates cell proliferation via ERβ in prostate cancer cells. Cancer Cell Int. 2017 May 11;17:52.
[3]. Kimbung S, et al. Impact of 27-hydroxylase (CYP27A1) and 27-hydroxycholesterol in breast cancer. Endocr Relat Cancer. 2017 Jul;24(7):339-349.
[4]. Fu X, et al. 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87.

Chemical Properties of 25(R)-27-hydroxy Cholesterol

Cas No. 20380-11-4 SDF
Synonyms (25R)-26-hydroxy cholesterol
Chemical Name (25R)-cholest-5-ene-3β,26-diol
Canonical SMILES O[C@@H]1CC2=CC[C@]3([H])[C@@](CC[C@]4([C@@]3([H])CC[C@]4([H])[C@@H](CCC[C@@H](C)CO)C)C)([H])[C@](C)2CC1
Formula C27H46O2 M.Wt 402.7
Solubility ≤20mg/ml in ethanol;0.1mg/ml in DMSO;2mg/ml in dimethyl formamide Storage Store at 2-8°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 25(R)-27-hydroxy Cholesterol

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.4832 mL 12.4162 mL 24.8324 mL
5 mM 0.4966 mL 2.4832 mL 4.9665 mL
10 mM 0.2483 mL 1.2416 mL 2.4832 mL
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In vivo Formulation Calculator (Clear solution) of 25(R)-27-hydroxy Cholesterol

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.

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