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Submit ReviewAS 1949490
Description: SH2 domain-containing inositol 5'-phosphatase 2 (SHIP2) inhibitor
Chemical Name: 3-[(4-Chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide
Purity: ≥99% (HPLC)
Biological Activity for AS 1949490
AS 1949490 is a selective 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. Also promotes increased BDNF mRNA levels in cultured cortical neurons and has memory enhancing and antidepressant effects in vivo.
Compound Libraries for AS 1949490
AS 1949490 is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for AS 1949490
| M. Wt | 371.88 |
| Formula | C20H18ClNO2S |
| Storage | Store at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 1203680-76-5 |
| PubChem ID | 44473434 |
| InChI Key | RFZPGNRLOKVZJY-AWEZNQCLSA-N |
| Smiles | ClC(C=C2)=CC=C2COC1=C(C(N[C@@H](C)C3=CC=CC=C3)=O)SC=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for AS 1949490
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 37.19 | 100 | |
| ethanol | 37.19 | 100 |
Preparing Stock Solutions for AS 1949490
The following data is based on the product molecular weight 371.88. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.69 mL | 13.45 mL | 26.89 mL |
| 5 mM | 0.54 mL | 2.69 mL | 5.38 mL |
| 10 mM | 0.27 mL | 1.34 mL | 2.69 mL |
| 50 mM | 0.05 mL | 0.27 mL | 0.54 mL |
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Product Datasheets for AS 1949490
References for AS 1949490
References are publications that support the biological activity of the product.
Suwa et al (2010) Glucose metabolism activation by SHIP2 inhibitors via up-regulation of GLUT1 gene in L6 myotubes. Eur.J.Pharmacol. 642 177 PMID: 20558154
Suwa et al (2009) Discovery and functional characterization of a novel small molecule inhibitor of the intracellular phosphatase, SHIP2. Br.J.Pharmcol. 158 879 PMID: 19694723
Tsuneki et al (2019) AS1949490, an inhibitor of 5'-lipid phosphatase SHIP2, promotes protein kinase C-dependent stabilization of brain-derived neurotrophic factor mRNA in cultured cortical neurons. Eur.J.Pharmacol. 851 69 PMID: 30753865
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Keywords: AS 1949490, AS 1949490 supplier, AS1949490, SHIP2, inhibitor, inhibits, SH2, domain, containing, inositol, 5'phosphate, 2, diabetes, antidiabetic, inhibitors, Inositol, Phosphatases, 3718, Tocris Bioscience
9 Citations for AS 1949490
Citations are publications that use Tocris products. Selected citations for AS 1949490 include:
Sérgio B et al (2017) Fibroblasts derived from patients with opsismodysplasia display SHIP2-specific cell migration and adhesion defects. Hum Mutat 38 1731-1739 PMID: 28869677
Justyna et al (2022) Cell Culture Media, Unlike the Presence of Insulin, Affect α-Synuclein Aggregation in Dopaminergic Neurons. Biomolecules 12 PMID: 35454152
Hak et al (2018) FBP17 and CIP4 recruit SHIP2 and lamellipodin to prime the plasma membrane for fast endophilin-mediated endocytosis. Nat Cell Biol 20 1023 PMID: 30061681
Ghosh et al (2018) Inhibition of SHIP2 activity inhibits cell migration and could prevent metastasis in breast cancer cells. J Cell Sci 131 PMID: 30012834
Hughes et al (2015) PTP1B-dependent regulation of receptor tyrosine kinase signaling by the actin-binding protein Mena. Front Neurosci 26 3867 PMID: 26337385
Polianskyte-Prause et al (2019) MetF. increases glucose uptake and acts renoprotectively by reducing SHIP2 activity. FASEB J 33 2858 PMID: 30321069
Chang et al (2014) Seizure-induced reduction in PIP3 levels contributes to seizure-activity and is rescued by valproic acid. Mol Biol Cell 62 296 PMID: 24148856
Stéphane et al (2023) Obesity control by SHIP inhibition requires pan-paralog inhibition and an intact eosinophil compartment. iScience 26 106071 PMID: 36818285
Cheng-Han et al (2021) PI(3,4)P2-mediated membrane tubulation promotes integrin trafficking and invasive cell migration. Proc Natl Acad Sci U S A 118 PMID: 33947811
Do you know of a great paper that uses AS 1949490 from Tocris? Please let us know.
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