128136
7α, 25-dihydroxycholesterol
Synonym(s):
7α, 25-dihydroxycholesterol, EBI2 agonist, EBI2 Activator, GPR183 Activator, 7alpha,25-OHC
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About This Item
Empirical Formula (Hill Notation):
C27H46O3
CAS Number:
Molecular Weight:
418.65
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
Storage condition:
OK to freeze, protect from light
assay
≥98% (HPLC)
Quality Level
form
powder
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, protect from light
color
white
solubility
DMSO: 25 mg/mL
shipped in
wet ice
storage temp.
−20°C
SMILES string
O[C@H]1[C@H]2[C@H]3[C@@]([C@H](CC3)[C@@H](CCCC(O)(C)C)C)(CC[C@@H]2[C@]4(CC[C@@H](CC4=C1)O)C)C
InChI key
BQMSKLCEWBSPPY-IKVTXIKFSA-N
General description
A highly potent and specific oxysterol EBI2 (GPR183) agonist with a kd of 450 pM in a saturation binding analysis, and activates EBI2 (EC50=140 pM compared with 2.1nM for its enantiomer 7b,25-OHC) in a GTP-γ assay. Dose-dependenty suppresses forskolin-induced cAMP accumulation in EBI2-expressing SK-N-MC/CRE-β galactosidase cell line with an IC50 of 2 nM, but not in control cells. Stimulates migration of LPS-activated spleen B cells and T cells in a dose-dependent manner. In addition, pharmacological inhibition of its biosynthesis in vivo by Clotrimazole, a CYP7B1inhibitor promotes the migration of adoptively transferred pre-activated B cells to the T/B boundary, mimicking the phenotype of pre-activated B cells from EBI2-deficient mice.
Packaging
Packaged under inert gas
Preparation Note
Following reconstitution, aliquot and freeze (-20°C. Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Liu, C., et al. 2011. Nature475, 519.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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