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BAMB-4

Inositol-1,4,5-trisphosphate-3-kinase A (ITPKA) inhibitor CAS# 891025-25-5

BAMB-4

Catalog No. BCC5428----Order now to get a substantial discount!

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Chemical structure

BAMB-4

3D structure

Chemical Properties of BAMB-4

Cas No. 891025-25-5 SDF Download SDF
PubChem ID 8087347 Appearance Powder
Formula C15H12N2O2 M.Wt 252.27
Type of Compound N/A Storage Desiccate at -20°C
Synonyms ITPKA-IN-C14
Solubility DMSO : ≥ 40 mg/mL (158.56 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name N-(1,2-benzoxazol-3-yl)-4-methylbenzamide
SMILES CC1=CC=C(C=C1)C(=O)NC2=NOC3=CC=CC=C32
Standard InChIKey IEPCQLHHUYRTEY-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H12N2O2/c1-10-6-8-11(9-7-10)15(18)16-14-12-4-2-3-5-13(12)19-17-14/h2-9H,1H3,(H,16,17,18)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of BAMB-4

DescriptionBAMB-4(ITPKA-IN-C14) is a new membrane-permeable inhibitor against inositol-1,4,5-trisphosphate-3-kinase A((ITPKA) with IC50 of 37 uM in ADP-Glo Assay. IC50 value: 37 uM Target: ITPKA inhibitor BAMB-4 exhibit the lowest inhibition frequency among the InsP3- Kinase inhibitors. only in one from 42 targets tested, BAMB-4 showed an inhibitory effect. Noteworthy, in kinase screens no targets of BAMB-4 were detected, indicating that the compound does not belong to the typical kinase inhibitors. Thus, the relative high speci?city and the high cellular uptake of BAMB-4 now for the ?rst provide the possibility to effectively inhibit InsP3kinase in vivo. e InsP3Kinase activity is essentially involved in ITPKA promoted metastasis of lung cancer cells, BAMB-4 is a promising therapeutic approach in lung cancer therapy.

References:
[1]. Schroder D, et al. Identification of a new membrane-permeable inhibitor against inositol-1,4,5-trisphosphate-3-kinase A. Biochem Biophys Res Commun. 2013 Sep 20;439(2):228-34.

BAMB-4 Dilution Calculator

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Preparing Stock Solutions of BAMB-4

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.964 mL 19.82 mL 39.6401 mL 79.2801 mL 99.1002 mL
5 mM 0.7928 mL 3.964 mL 7.928 mL 15.856 mL 19.82 mL
10 mM 0.3964 mL 1.982 mL 3.964 mL 7.928 mL 9.91 mL
50 mM 0.0793 mL 0.3964 mL 0.7928 mL 1.5856 mL 1.982 mL
100 mM 0.0396 mL 0.1982 mL 0.3964 mL 0.7928 mL 0.991 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on BAMB-4

BAMB-4 is an inhibitor of inositol-1,4,5-trisphosphate-3-kinase A (ITPKA) with an IC50 value of 20 µM [1].

ITPKA is an InsP3 kinase. It binds to actin filaments and bundles them. This protein regulates actin dynamics as well as inositol phosphate signaling [1].

BAMB-4 was almost completely taken up by H1299 cells. BAMB-4 did not belong to typical kinase inhibitors. Its relatively high specificity and high cellular uptake provide the possibility to effectively inhibit InsP3 kinase in vivo. Among InsP3Kinase inhibitors, BAMB-4 exhibit the lowest inhibition frequency. BAMB-4 showed an inhibitory effect only in 1 from 42 tested targets. There was no detected BAMB-4 target in kinase screens. These results indicated that BAMB-4 is not a typical kinase inhibitor. In vitro, data showed that BAMB-4 increased Km and reduced Vmax with respect to InsP3. BAMB-4 at the lowest concentration (10 µM) increased the Km-value for InsP3 by 160%. BAMB-4 at elevated concentrations did not further rise the Km-value for InsP3. BAMB-4 dose-dependently decreased Vmax from 75% to 50%. Decreased Vmax and increased Km in presence of inhibitor indicated that BAMB-4 might belong to mixed type inhibitors. Data showed that BAMB-4 also reduced Vmax and increased Km with respect to ATP [2].

There is still no any available result of the application of BAMB-4 in animals.

References:
[1].  Schrder D, Tdter K, Gonzalez B, et al. The new InsP 3 Kinase inhibitor BIP-4 is competitive to InsP 3 and blocks proliferation and adhesion of lung cancer cells. Biochemical pharmacology, 2015, 96(2): 143-150.
[2].  Schrder D, Rehbach C, Seyffarth C, et al. Identification of a new membrane-permeable inhibitor against inositol-1, 4, 5-trisphosphate-3-kinase A. Biochemical and biophysical research communications, 2013, 439(2): 228-234.

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References on BAMB-4

The new InsP3Kinase inhibitor BIP-4 is competitive to InsP3 and blocks proliferation and adhesion of lung cancer cells.[Pubmed:25986882]

Biochem Pharmacol. 2015 Jul 15;96(2):143-50.

As ectopic expression of the neuronal inositol-1,4,5-trisphosphate-3-kinase A (InsP3Kinase) in tumor cells increases the metastatic potential, InsP3Kinase is an interesting target for tumor therapy. Recently, we have identified a membrane-permeable InsP3Kinase inhibitor (BAMB-4) exhibiting an IC50-value of 20 muM. Here we characterized a new InsP3Kinase inhibitor which shows a 130-fold lower IC50 value (157 +/- 57 nM) as compared to BAMB-4. We demonstrate that this nitrophenolic compound, BIP-4, is non-competitive to ATP but competitive to InsP3, thus exhibits a high selectivity for inhibition of InsP3Kinase activity. Docking analysis suggested a putative binding mode of this molecule into the InsP3Kinase active site. Determination of cellular uptake in lung cancer cells (H1299) revealed that 6% of extracellular BIP-4 is internalized by non-endosomal uptake, showing that BIP-4 is not trapped inside endo/lysosomes but is available to inhibit cellular InsP3Kinase activity. Interestingly, we found that BIP-4 mediated inhibition of InsP3Kinase activity in the two lung cancer cell lines H1299 and LN4323 inhibited proliferation and adhesion at IC50 values of 3 muM or 2 muM, respectively. InsP3Kinase inhibition did not alter ATP-induced calcium signals but significantly reduced the level of Ins(1,3,4,5,6)P5. From these data we conclude that the inhibitory effect of BIP-4 on proliferation and adhesion of lung cancer cells does not result from alterations of calcium but from alterations of inositol phosphate signals. In summary, we reveal that inhibition of cellular InsP3Kinase by BIP-4 impairs proliferation and adhesion and therefore BIP-4 might be a promising compound to reduce the metastatic potential of lung carcinoma cells.

Identification of a new membrane-permeable inhibitor against inositol-1,4,5-trisphosphate-3-kinase A.[Pubmed:23981806]

Biochem Biophys Res Commun. 2013 Sep 20;439(2):228-34.

Ectopic expression of the neuron-specific inositol-1,4,5-trisphosphate-3-kinase A (ITPKA) in lung cancer cells increases their metastatic potential because the protein exhibits two actin regulating activities; it bundles actin filaments and regulates inositol-1,4,5-trisphosphate (InsP3)-mediated calcium signals by phosphorylating InsP3. Thus, in order to inhibit the metastasis-promoting activity of ITPKA, both its actin bundling and its InsP3kinase activity has to be blocked. In this study, we performed a high throughput screen in order to identify specific and membrane-permeable substances against the InsP3kinase activity. Among 341,44 small molecules, 237 compounds (0.7%) were identified as potential InsP3kinase inhibitors. After determination of IC50-values, the three compounds with highest specificity and highest hydrophobicity (EPPC-3, BAMB-4, MEPTT-3) were further characterized. Only BAMB-4 was nearly completely taken up by H1299 cells and remained stable after cellular uptake, thus exhibiting a robust stability and a high membrane permeability. Determination of the inhibitor type revealed that BAMB-4 belongs to the group of mixed type inhibitors. Taken together, for the first time we identified a highly membrane-permeable inhibitor against the InsP3kinase activity of ITPKA providing the possibility to partly inhibit the metastasis-promoting effect of ITPKA in lung tumor cells.

Description

BAMB-4(ITPKA-IN-C14) is a new membrane-permeable inhibitor against inositol-1,4,5-trisphosphate-3-kinase A((ITPKA) with IC50 of 37 μM in ADP-Glo Assay.

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