AS 1949490

Selective SHIP2 inhibitor CAS# 1203680-76-5

AS 1949490

Catalog No. BCC7762----Order now to get a substantial discount!

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AS 1949490: 5mg $92 In Stock
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Chemical structure

AS 1949490

3D structure

Chemical Properties of AS 1949490

Cas No. 1203680-76-5 SDF Download SDF
PubChem ID 44473434 Appearance Powder
Formula C20H18ClNO2S M.Wt 371.88
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO and to 100 mM in ethanol
Chemical Name 3-[(4-chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide
SMILES CC(C1=CC=CC=C1)NC(=O)C2=C(C=CS2)OCC3=CC=C(C=C3)Cl
Standard InChIKey RFZPGNRLOKVZJY-AWEZNQCLSA-N
Standard InChI InChI=1S/C20H18ClNO2S/c1-14(16-5-3-2-4-6-16)22-20(23)19-18(11-12-25-19)24-13-15-7-9-17(21)10-8-15/h2-12,14H,13H2,1H3,(H,22,23)/t14-/m0/s1
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 AS 1949490

DescriptionSelective SHIP2 (SH2 domain-containing inositol 5'-phosphatase 2) inhibitor (IC50 values are 0.34 μM and 0.62 μM for mouse and human respectively); displays approximately 30-fold affinity for SHIP2 over SHIP1. Increases insulin-induced phosphorylation of Akt in L6 myotubules. Stimulates activation of glucose metabolism; regulates gluconeogenesis in vitro and in vivo and exhibits antidiabetic effects.

AS 1949490 Dilution Calculator

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AS 1949490 Molarity Calculator

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Preparing Stock Solutions of AS 1949490

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.689 mL 13.4452 mL 26.8904 mL 53.7808 mL 67.226 mL
5 mM 0.5378 mL 2.689 mL 5.3781 mL 10.7562 mL 13.4452 mL
10 mM 0.2689 mL 1.3445 mL 2.689 mL 5.3781 mL 6.7226 mL
50 mM 0.0538 mL 0.2689 mL 0.5378 mL 1.0756 mL 1.3445 mL
100 mM 0.0269 mL 0.1345 mL 0.2689 mL 0.5378 mL 0.6723 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 AS 1949490

AS 1949490 is a selective inhibitor of Src homology 2 domain-containing inositol-5-phosphatase 2 (SHIP2), [1] with IC50 values of 0.34 µM and 0.62 µM to mouse and human SHIP2s, respectively [2].

SHIP2 is an intracellular phosphatase and appears to be important in insulin signaling as a negative regulator. SHIP2 has potential to act as a treatment for type 2 diabetes because of its inhibition [2].

Akt is a key enzyme to regulated insulin signaling. AS 1949490 treatment dose-dependently increased insulin-induced phosphorylation of Akt in L6 myotubes, but did not result in any associated changes in the overall level of Akt protein and the fetal bovine serum-induced phosphorylation of Akt. Treatments with AS 1949490 at several concentrations of and 1 nM insulin for 48 h, showed more consumption of glucose in the medium in a concentration-dependent manner [2].

In diabetic db/db mice, administered with AS 1949490 twice daily p.o. for 7 or 10 days significantly decreased plasma glucose (23% reduction, relative to vehicle), without affecting insulin levels, food intake or body weight. In the 10th day, treatment with AS 1949490 resulted in significant reduction in both the area under the blood glucose concentration time curve (AUC) and fasting blood glucose (37% reduction, compared with vehicle; time = -30 min) [2].

References:
[1].  Laura Beth J. McIntire, Kyu-In Lee, Belle Chang-IIeto, et al. Screening assay for small molecule inhibitors of synaptojanin 1, a synaptic phosphoinositide phosphatase. J Biomol Screen, 2014, 19(4):585-594.
[2].  A Suwa, T Yamamoto, A Sawada, et al. Discovery and functional characterization of a novel small molecule inhibitor of the intracellular phosphatase, SHIP2. British Journal of Pharmacology, 2009, 158:879-887.

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References on AS 1949490

Glucose metabolism activation by SHIP2 inhibitors via up-regulation of GLUT1 gene in L6 myotubes.[Pubmed:20558154]

Eur J Pharmacol. 2010 Sep 10;642(1-3):177-82.

Lipid phosphatase SH2 domain-containing inositol 5'-phosphatase 2 (SHIP2) plays an important role in the regulation of insulin signaling. In this report, we identified AS1938909, a novel small-molecule SHIP2 inhibitor. AS1938909 showed potent inhibition of SHIP2 (Ki=0.44 microuM) and significant selectivity over other related phosphatases. Further, AS1938909 increased Akt phosphorylation, glucose consumption, and glucose uptake in L6 myotubes. Treatment of L6 myotubes with SHIP2 inhibitors for 48 h significantly induced expression of GLUT1 mRNA, but not that of GLUT4. These results suggest that pharmacological inhibition of SHIP2 activates glucose metabolism due, at least in part, to up-regulation of GLUT1 gene expression.

Description

AS1949490 is a potent and selective SHIP-2 (SH2 domain-containing inositol 5′ phosphatase 2) inhibitor, with an IC50 of 620 nM. AS1949490 activated glucose metabolism via up-regulation of GLUT1 gene in L6 myotubes.

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