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7α,25-dihydroxy Cholesterol

In stock
Catalog No.
C4241
GPR183 agonist
Grouped product items
SizePriceStock Qty
1mg
$54.00
In stock
5mg
$257.00
In stock
10mg
$486.00
In stock

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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

Physical AppearanceA crystalline solid
StorageStore at -20°C
M.Wt418.7
Cas No.64907-22-8
FormulaC27H46O3
Synonyms7α,25-DHC
Solubility≤2mg/ml in ethanol;0.1mg/ml in DMSO;20mg/ml in dimethyl formamide
Chemical Name(3β,7α)-cholest-5-ene-3,7,25-triol
SDFDownload SDF
Canonical SMILESO[[email protected]@H]1C=C2C[[email protected]@H](O)CC[[email protected]]2(C)[[email protected]]3([H])[[email protected]]1([H])[[email protected]@](CC[[email protected]]4([H])[[email protected]](C)CCCC(C)(C)O)([H])[[email protected]]4(C)CC3
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Quality Control

Quality Control & MSDS

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Chemical structure

7α,25-dihydroxy Cholesterol