569371

SREBP Processing Inhibitor, Betulin

The SREBP Processing Inhibitor, Betulin, also referenced under CAS 473-98-3, controls the biological activity of SCAP (SREBP cleavage activating protein). This small molecule/inhibitor is primarily used for Cell Signaling applications.

• Sinónimos: SREBP Processing Inhibitor, Betulin, Lup-20(29)-ene-3β,28-diol, Sterol Regulatory Element Binding Protein Processing Inhibitor, Betulin
• Fórmula empírica (notación de Hill): C₃₀H₅₀O₂
• Número CAS: 473-98-3
• Peso molecular: 442.72
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00016802
• Assay: ≥95% (NMR)
• Form: powder
• Storage condition: OK to freeze

Propiedades

• Quality Segment: 100
• assay: ≥95% (NMR)
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: off-white
• solubility: DMSO: 3.5 mg/mL
• shipped in: wet ice
• storage temp.: 2-8°C
• SMILES string: O[C@@H]1C([C@H]2[C@@]([C@@H]3[C@]([C@]4([C@@H]([C@@H]5[C@@](CC4)(CC[C@H]5C(=C)C)CO)CC3)C)(CC2)C)(CC1)C)(C)C
• InChI: 1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
• InChI key: FVWJYYTZTCVBKE-ROUWMTJPSA-N

Descripción

General description

A cell-permeable pentacyclic triterpenoid from birch bark extract that interacts with SCAP (SREBP cleavage activating protein) and prevents SREBP (sterol regulatory element-binding protein) Golgi proteolytic activation (1 to 13.55 µM in Rat hepatocytes CRL-1601) via a similar mechanism as oxysterols by inducing the association of SCAP with Insig-1 (insulin-induced gene-1), thereby causing SCAP-SREBPs complex ER retention. Unlike oxysterols, Betulin does not activate LXR to induce concomitant HMGCR (HMG-CoA reductase) degradation and SREBP-1 up-regulation. While both Betulin and HMGCR inhibitor Lovastatin (Cat. No. 438185 ) inhibit cellular cholesterol synthesis (by ~70% in CRL-1601 cultures with respective compound at 13.55 and 1 µM concentration), only Betulin suppresses cellular fatty acid synthesis (by ~55% at 13.55 µM in CRL-1601). Betulin is shown to exhibit comparable in vivo efficacy as Lovastatin (both dosed at 30 mg/kg/day with chow) in ameliorating high fat/cholesterol diet-induced obesity (% fat/lean tissue ratio increase from non-fat diet mice = 167, 44, and 33 in mice consuming fat diet alone, with Lovastatin, with Betulin, respectively). However, only Betulin is demonstrated to lower fasting blood glucose and insulin levels and reduce fat cell size in white adipose tissue in high fat diet mice. Fatostatin (Cat. No. 341329 ) in comparison does not target SCAP via sterol-binding site, nor does it induce SCAP binding to Insig-1.

Other Notes

Tang, J.J., et al. 2011. Cell Metab.13, 44.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Toxic (F)

Información de seguridad

• Clase de almacenamiento: 11 - Combustible Solids
• wgk: WGK 3