| Identification | Back Directory | [Name]
7α,25-dihydroxy Cholesterol | [CAS]
64907-22-8 | [Synonyms]
7α,25-OHC
25-dihydroxycholesterol
5-Cholesten-3β,7α,25-triol
7α,25-dihydroxy Cholesterol
7-alpha,25-Dihydroxycholesterol
3β,7α,25-Trihydroxycholest-5-ene
(3β,7α)-Cholest-5-ene-3,7,25-triol
7Α,25-DIHYDROXYCHOLESTEROL;7Α;25-DIHYDROXYCHOLESTEROL | [Molecular Formula]
C27H46O3 | [MDL Number]
MFCD20488904 | [MOL File]
64907-22-8.mol | [Molecular Weight]
418.65 |
| Chemical Properties | Back Directory | [Boiling point ]
548.5±35.0 °C(Predicted) | [density ]
1.08±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble5mg/mL (clear solution) | [form ]
powder | [pka]
14.11±0.70(Predicted) | [color ]
white to beige |
| Hazard Information | Back Directory | [Uses]
3β,7α,25-Trihydroxycholest-5-ene is a potent agonist of GPR183 that induces specific activation of the receptor. | [Uses]
GPR183 (also known as Epstein-Barr virus-induced gene 2) is an orphan G protein-coupled receptor (GPCR) that is highly expressed in spleen and is required for humoral immune responses, including B cell migration and T cell-dependent antibody production. 7α,25-dihydroxy Cholesterol (7α,25-DHC) is a potent agonist of GPR183 that induces specific activation of the receptor with an EC50 value of 50 nM (Kd = 450 pM). At concentrations below 3 μM, it does not show any appreciable binding activity when tested against eight different nuclear hormone receptors including LXR and thirty-one different G protein-coupled receptors in a panel of reporter gene assays. 7α,25-DHC can act as a potent chemokine, affecting migration of immune cells expressing GPR183 both in vitro (EC50 = 500 pM) and in vivo.[Cayman Chemical] | [Definition]
ChEBI:7alpha,25-dihydroxycholesterol is a 7alpha-hydroxy steroid, a 25-hydroxy steroid, an oxysterol and a 3beta-hydroxy-Delta(5)-steroid. It has a role as a human metabolite. It is functionally related to a cholesterol. | [General Description]
7α,25-dihydroxycholesterol (7α,25-OHC) is synthesized by the hydroxylation of cholesterol by the action of enzyme cholesterol 25-hydroxylase (CH25H) and cytochrome P450, family 7, subfamily b, polypeptide 1 (CYP7B1). The catabolic breakdown of 7α,25-OHC to bile acid precursors is catalyzed by the enzymes hydroxy-Δ-5-steroid dehydrogenase, 3β- and steroid Δ-isomerase 7 (HSD3B7). | [Biological Activity]
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]. | [Biochem/physiol Actions]
7α,25-dihydroxycholesterol (7α,25-OHC) serves as an endogenous ligand for G-protein-coupled receptor 183 (GPR183) or Epstein-Barr virus-induced gene 2 (EBI2). It plays a key role in the migration of type 3 innate lymphoid cells (ILC3) in the small intestine and colon. 7α,25-OHC mediates immune cell migration functionality by their chemoattractant property. Inhibition of 7α,25-OHC synthesis leads to impairment in the migration of B cells. | [storage]
Store at -20°C | [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. |
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