581810

(-)-Terreic Acid, Synthetic

a cell-permeable quinone epoxide antibiotic

• Synonyme(s) : (-)-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
• Formule empirique (notation de Hill): C₇H₆O₄
• Numéro CAS: 121-40-4
• Poids moléculaire : 154.12
• Code UNSPSC : 12352200

Propriétés

• Niveau de qualité: 100
• Essai: ≥98% (HPLC)
• Forme: solid
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze; protect from light
• Couleur: light beige
• Solubilité: water: 5 mg/mL
• Conditions d'expédition: wet ice
• Température de stockage: −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
• Clé InChI: ATFNSNUJZOYXFC-RQJHMYQMSA-N

Description

Description générale

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.

Actions biochimiques/physiologiques

Cell permeable: yes

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

Product competes with ATP.

Reversible: yes

Target IC₅₀: 10 µM against BTK

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Harmful (C)

Reconstitution

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

Autres remarques

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.

Informations légales

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

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable