| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| Other Sizes |
| Targets |
Bruton's tyrosine kinase (BTK). Reversible, substrate-competitive inhibitor of BTK catalytic activity. Blocks the interaction between PKC and the PH domain of BTK. Inhibits BTK-mediated signaling pathways involved in B-cell development and function.
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|---|---|
| ln Vitro |
In mouse mast cells, téréic acid can block Btk binding to PKCβII at lower doses (IC50 = 30 μM). Btk's catalytic activity is inhibited by earth acid, although PKC is not [1]. With an IC50 of 10 μM and 3 μM, respectively, terra acid, pretreated for 30 minutes prior to antigen stimulation for 3 minutes, can suppress Btk autophosphorylation activity at both the baseline and activation levels [1]. In a dose-dependent way, tau acid blocks the autophosphorylation activity of partly purified Btk from recombinant baculovirus-infected Sf9 insect cells [1].
Terreic acid is a potent and selective BTK inhibitor. It acts as a reversible, substrate-competitive inhibitor of BTK catalytic activity. The compound also blocks the interaction between protein kinase C (PKC) and the PH domain of BTK. By inhibiting BTK, terreic acid modulates B-cell receptor signaling, which is important for B-cell development, activation, and survival. It has antibiotic activity as well. |
| ln Vivo |
Earth acid has the ability to prevent the body's delayed responses to allergic skin reactions [1].
In vivo, terreic acid has been studied for its potential in treating B-cell malignancies and inflammatory diseases. Its BTK inhibitory activity makes it a valuable tool for studying BTK-mediated signaling and for developing targeted therapies for conditions such as chronic lymphocytic leukemia, mantle cell lymphoma, and autoimmune diseases. |
| Enzyme Assay |
BTK kinase activity assays are performed using purified BTK and a peptide substrate. Phosphorylation of the substrate is measured using radioactive ATP (e.g., 33P-ATP) or by time-resolved fluorescence resonance energy transfer (TR-FRET). Inhibition is assessed by incubating BTK with terreic acid at various concentrations and measuring remaining activity. IC50 values are calculated.
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| Cell Assay |
Western Blot Analysis[1]
Cell Types: Mouse bone marrow-derived mast cells Tested Concentrations: 0, 5, 10, 20 μM Incubation Duration: Pretreatment 30 minutes Experimental Results: Inhibition of basal levels and activation of Btk autophosphorylation activity at a certain dose Horizontal dependence mode. Cell-based assays use B-cell lines or cells expressing BTK (e.g., Ramos, Raji, or primary B cells). BTK phosphorylation and downstream signaling (e.g., PLCγ2, ERK) are measured by Western blotting. Cell viability and proliferation are assessed by MTT or CellTiter-Glo assays. Apoptosis is measured by Annexin V staining or caspase activity. B-cell receptor-induced calcium flux may be measured using fluorescent indicators. |
| Animal Protocol |
Animal/Disease Models: balb/c (Bagg ALBino) mouse [1]
Doses: 0, 0.15, 1.5 and 15 mg/kg Route of Administration: intraperitoneal (ip) injection 1 hour before antigen challenge. Ear thickness measurements at 1 hour and 24 hrs (hrs (hours)) Experimental Results: Early responses examined 1 hour after antigen challenge were not affected by TA. In contrast, TA inhibited late (24 h) responses in a dose-dependent manner. Animal models of B-cell lymphoma or autoimmune diseases are used to evaluate in vivo efficacy. Tumor-bearing mice or mice with autoimmune conditions are treated with terreic acid via intraperitoneal or oral routes. Tumor volume is measured in xenograft models. Disease severity is assessed in autoimmune models. BTK inhibition in tissues is confirmed by measuring BTK phosphorylation. Pharmacokinetic studies evaluate compound bioavailability and distribution. |
| References | |
| Additional Infomation |
Terreic acid is a 2-hydroxy-1,4-benzoquinone with a 5,6-epoxy structure. It is a natural product of Aspergillus terreus. Terreic acid has antibacterial activity, the mechanism of which lies in the inhibition of bacterial enzymes MurA and GlmU. It is also an inhibitor of Bruton's tyrosine kinase and has antitumor activity against HeLa and EAC cells. Terreic acid has multiple functions, including as a mycotoxin, antibacterial agent, EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor, EC 2.3.1. (non-aminoacyltransferase) inhibitor, EC 2.7.10.2 (non-specific protein tyrosine kinase) inhibitor, Aspergillus metabolite, and antitumor agent. It is an aromatic epoxide, tertiary α-hydroxy ketone, monohydroxy-1,4-benzoquinone compound, and diketone. Its function is related to 2-hydroxy-1,4-benzoquinone. According to reports, Terreic acid is present in both Aspergillus terreus and Aspergillus flavipes, and there is relevant data available.
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| Molecular Formula |
C7H6O4
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|---|---|
| Molecular Weight |
154.121
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| Exact Mass |
154.027
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| CAS # |
121-40-4
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| PubChem CID |
91437
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| Appearance |
White to off-white solid powder
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| Density |
1.613 g/cm3
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| Boiling Point |
333.6ºC at 760 mmHg
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| Vapour Pressure |
9.63E-06mmHg at 25°C
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| Index of Refraction |
1.618
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| Source |
Originated from microorganisms
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| LogP |
-0.2
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
289
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC1=C(C(=O)[C@H]2[C@@H](C1=O)O2)O
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| InChi Key |
ATFNSNUJZOYXFC-RQJHMYQMSA-N
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| InChi Code |
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
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| Chemical Name |
(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
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| Synonyms |
(-)-Terreic AcidTerreic Acid TA
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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