581810

(-)-Terreic Acid, Synthetic

a cell-permeable quinone epoxide antibiotic

• Sinónimos: (-)-Terreic Acid, Synthetic, (1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione, BTK Inhibitor II, Bruton′s Tyrosine Kinase Inhibitor II
• Fórmula empírica (notación de Hill): C₇H₆O₄
• Número de CAS: 121-40-4
• Peso molecular: 154.12
• Código UNSPSC: 12352200

Propiedades

• Nivel de calidad: 100
• Ensayo: ≥98% (HPLC)
• Formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: light beige
• solubilidad: water: 5 mg/mL
• Condiciones de envío: wet ice
• temp. de almacenamiento: −20°C
• InChI: 1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
• Clave InChI: ATFNSNUJZOYXFC-RQJHMYQMSA-N

Descripción

Descripción general

A cell-permeable quinone epoxide antibiotic that acts as a reversible, substrate competitive, and selective inhibitor of Bruton′s tyrosine kinase (BTK; IC₅₀ = 10 µM and 3 µM for the basal and activation levels), both in vitro and in vivo. Shown to bind to the BTK pleckstrin homology domain (BTK-PH) and block the interaction between BTK-PH and protein kinase C (PKC) (IC₅₀ ~100 µM in human mast cell lysates), thus affecting the catalytic activity of BTK, but not the activity of PKC. Selectively inhibits the autophosphorylation of PKC_βI (IC₅₀ ~8 µM) but not that of PKC_βII. Reported to effectively inhibit the production of TNF-α (IC₅₀ ~3 µM) and block the activation of JNK1 (IC₅₀ ~10 µM) in FcεRI-stimulated mast cells. Also reported to inhibit DNA synthesis in activated spleen cells (IC₅₀ ~1.5 µM). Does not significantly affect the activities of Lyn, Syk, PKA, CK-1, ERK1, ERK2 and p38 kinases.

Acciones bioquímicas o fisiológicas

Cell permeable: yes

Primary Target
Bruton′s tyrosine kinase catalytic activity (BTK)

Product competes with ATP.

Reversible: yes

Target IC₅₀: 10 µM against BTK

Envase

Packaged under inert gas

Advertencia

Toxicity: Harmful (C)

Reconstitución

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Otras notas

Kawakami, Y., et al. 2000. Proc. Natl. Acad. Sci. USA97, 7423.
Kawakami, Y., et al. 1999. Proc. Natl. Acad. Sci. USA96, 2227.
Yamamoto, H., et al. 1980. Jpn. J. Antibiot.33, 320.

Información legal

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

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable