128136

7α, 25-dihydroxycholesterol

• Synonym(e): 7α, 25-dihydroxycholesterol, EBI2 agonist, EBI2 Activator, GPR183 Activator, 7alpha,25-OHC
• Empirische Formel (Hill-System): C₂₇H₄₆O₃
• CAS-Nummer: 64907-22-8
• Molekulargewicht: 418.65
• MDL number: MFCD20488904
• UNSPSC Code: 12352211
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: powder
• Quality level: 100
• Storage condition: OK to freeze, protect from light

Eigenschaften

• assay: ≥98% (HPLC)
• Quality Level: 100
• 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

Beschreibung

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)

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable