581810

(-)-Terreic Acid, Synthetic

a cell-permeable quinone epoxide antibiotic

• Synonym(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
• Empirical Formula (Hill Notation): C₇H₆O₄
• CAS Number: 121-40-4
• Molecular Weight: 154.12
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: light beige
• solubility: water: 5 mg/mL
• shipped in: wet ice
• storage temp.: −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
• InChI key: ATFNSNUJZOYXFC-RQJHMYQMSA-N

Description

General description

A cell-permeable quinone epoxide antibiotic that acts as a reversible, substrate competitive, and selective inhibitor of Bruton’s tyrosine kinase catalytic activity (BTK; IC₅₀ = 10 µM and 3 µM for the basal and activation levels). Shown to bind to the BTK pleckstrin homology domain (BTK-PH) and block the interaction between the BTK-PH and PKC (IC₅₀ = ~ 100 µM in human mast cell lysates), thus affecting the catalytic activity of BTK, but not of PKC. Selectively inhibits the autophosphorylating activity of PKC_βI (IC₅₀ = ~ 8 µM) and not of PKC_βII. Reported to effectively inhibit the production of TNF-α (IC₅₀ = ~ 3 µM), and activation of JNK1 (IC₅₀ = ~ 10 µM) in FcεRI-stimulated mast cells. Also inhibits the 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.

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.

Biochem/physiol Actions

Cell permeable: yes

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

Product competes with ATP.

Reversible: yes

Target IC₅₀: 10 µM against BTK

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful (C)

Reconstitution

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

Other Notes

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.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable