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(-)-Terreic acid (Synonyms: TA, (-)-Terreic Acid)

Katalog-Nr.GC12164

(-)-Terreinsäure, ein Chinonepoxid-Antibiotikum, wirkt als wirksamer Btk-Hemmer.

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(-)-Terreic acid Chemische Struktur

Cas No.: 121-40-4

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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

IC50: about 100 μM for binding of GST-BtkPH to PKC, about 30 μM for association of Btk with PKCbII, about 10 μM for JNK1 activity, and about 7 μM for TNF-a and about 3 μM for IL-2.

Terreic acid (TA), which was known as Aspergillus sp. No. Y-8980, was isolated from a soil sample abtained at Yoron Island of Kagoshima Prefecture.

Terreic acid is a quinone epoxide with antibiotic activity. At a mechanism view for its antibiotic action, it inhibits protein synthesis by blocking the formation of leucyl-tRNA in sensitive bacteria [1]. TA was also an inhibitor of Bruton’s tyrosine kinase (Btk) that blocks the PKC-Btk PH domain interaction. Btk plays core roles in mast cell activation and in B cell development [2].

In vitro: Terreic acid showed MIC (minimal inhibitory concentration) of 25 approximately 100 mcg/ml, 50 mcg/ml and 12.5 mcg/ml against Gram-positive and Gram-negative bacteria, Xanthomonas citri and Xanthomonas oryzae and, respectively. TA also showed anti-tumor effect in the concentrations of > 6.25 mcg/ml on human carcinoma cells (HeLa cells) [1]. In lysates of HMC-1 human mast cells, TA can inhibit the binding of GST-BtkPH to PKC with an IC50 of ~100 uM. In mouse mast cells, TA can inhibit the association of Btk with PKCbII at IC50 of ~ 30 uM. JNK1 activity can be inhibited by TA with an IC50 of ~10 uM. Cytokine secretion was severely impaired by TA with an IC50 of ~7 uM for TNF-a and ~ 3 uM for IL-2) [2].

In vivo: In mice, the LD50 (median lethal dose) of TA was 75 mg/kg through i.p. and i.v. TA showed the enough survival effect in dd mice which have been implanted with Ehrlich ascites carcinoma cells, and the effect also was confirmed by anatomies of mice [1].

Clinical trial: So far, no clinical study has been conducted.

References:
[1] Yamamoto H, Moriyama K, Jinnouchi H, Yagishita K.  Studies on terreic acid. Jpn J Antibiot. 1980 Mar;33(3):320-8.
[2] Kawakami Y, Hartman SE, Kinoshita E, Suzuki H, Kitaura J, Yao L, Inagaki N, Franco A, Hata D, Maeda-Yamamoto M, Fukamachi H, Nagai H, Kawakami T.  Terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase. Proc Natl Acad Sci U S A. 1999 Mar 2;96(5):2227-32.

Chemical Properties

Cas No. 121-40-4 SDF
Überlieferungen TA, (-)-Terreic Acid
Chemical Name (1S,6R)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Canonical SMILES O=C(C(C)=C1O)[C@@H]2O[C@@H]2C1=O
Formula C7H6O4 M.Wt 154.12
Löslichkeit DMF: soluble,DMSO: 10 mg/ml,Ethanol: soluble,Methanol: soluble,Water: 5 mg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 6.4885 mL 32.4423 mL 64.8845 mL
5 mM 1.2977 mL 6.4885 mL 12.9769 mL
10 mM 0.6488 mL 3.2442 mL 6.4885 mL
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