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7α,25-dihydroxy Cholesterol (Synonyms: 7α,25-DHC)

Catalog No.GC14433

A GPR183 agonist

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7α,25-dihydroxy Cholesterol Chemical Structure

Cas No.: 64907-22-8

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Sample solution is provided at 25 µL, 10mM.

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Background

7α,25-dihydroxy Cholesterol (7α,25-DHC, 7α,25-OHC) is a potent and selective GPR183 agonist [1].

Epstein-Barr virus (EBV)-induced gene 2 (EBI2, also known as GPR183) is an orphan G protein-coupled receptor that is highly expressed in spleen and up-regulated upon Epstein–Barr-virus infection. GPR183 is required for humoral immune responses and polymorphisms in the receptor is associated with inflammatory autoimmune diseases [1][2].

7α,25-dihydroxy Cholesterol is a potent and selective GPR183 (EBI2) agonist and most potent EBI2 ligand with EC50 and Kd values of 140 pM and 450 pM, respectively. In a competition binding study, 7α,25-OHC competed for binding with IC50 value of 242 pM. In EBI2-expressing cells, 7α,25-OHC dose-dependently inhibited forskolin-induced cAMP with IC50 value of 2 nM. 7α,25-OHC was probably the endogenous ligand for EBI2. In EBI2-expressing mouse B and T cells, 7α,25-dihydroxy Cholesterol stimulated cell migration with IC50 value of around 500 pM, but had no effect on EBI2-deficient cells [1].

In EBI2-deficient mice, unseparated splenocytes, B cells and T cells were completely unresponsive to 7α,25-OHC stimulation [1]. Mice deficient in Ch25h, a key enzyme for the generation of 7α, 25-OHC, failed to position activated B cells within the spleen to the outer follicle [2].

References:
[1].  Liu C, Yang XV, Wu J, et al. Oxysterols direct B-cell migration through EBI2. Nature. 2011 Jul 27;475(7357):519-23.
[2].  Hannedouche S, Zhang J, Yi T, et al. Oxysterols direct immune cell migration via EBI2. Nature. 2011 Jul 27;475(7357):524-7.

Chemical Properties

Cas No. 64907-22-8 SDF
Synonyms 7α,25-DHC
Chemical Name (3β,7α)-cholest-5-ene-3,7,25-triol
Canonical SMILES O[C@@H]1C=C2C[C@@H](O)CC[C@]2(C)[C@]3([H])[C@]1([H])[C@@](CC[C@]4([H])[C@H](C)CCCC(C)(C)O)([H])[C@]4(C)CC3
Formula C27H46O3 M.Wt 418.7
Solubility ≤2mg/ml in ethanol;0.1mg/ml in DMSO;20mg/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

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1 mg 5 mg 10 mg
1 mM 2.3883 mL 11.9417 mL 23.8834 mL
5 mM 0.4777 mL 2.3883 mL 4.7767 mL
10 mM 0.2388 mL 1.1942 mL 2.3883 mL
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