AS1949490 | CAS#1203680-76-5

AS1949490
featured

WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531479

CAS#: 1203680-76-5

Description: AS1949490 is a small molecule inhibitor of SH2 domain-containing inositol 5'-phosphatase 2 (SHIP2, a.k.a. inositol polyphosphate phosphatase-like 1, with gene symbol INPPL1) which can be used as a tool compound to elucidate the normal and pathophysiological roles of SHIP2.

Chemical Structure

AS1949490

CAS# 1203680-76-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531479
Name: AS1949490
CAS#: 1203680-76-5
Chemical Formula: C20H18ClNO2S
Exact Mass: 371.07
Molecular Weight: 371.879
Elemental Analysis: C, 64.60; H, 4.88; Cl, 9.53; N, 3.77; O, 8.60; S, 8.62

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 245
25g	USD 765
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: AS1949490; AS-1949490; AS 1949490

IUPAC/Chemical Name: 3-[(4-chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide

InChi Key: RFZPGNRLOKVZJY-AWEZNQCLSA-N

InChi Code: 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

SMILES Code: O=C(C1=C(OCC2=CC=C(Cl)C=C2)C=CS1)N[C@H](C3=CC=CC=C3)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	AS1949490 is a potent and selective SHIP-2 (SH2 domain-containing inositol 5′ phosphatase 2) inhibitor, with an IC50 of 620 nM.
In vitro activity:	Cells were first treated with vehicle or SHIP2 inhibitor AS1949490 for 24 h then treated with 1 mM H2O2 for 1 h. As indicated in Fig. 1A, western blot analysis showed that SHIP2 inhibition enhances H2O2 induced AKT and ERK1/2 phosphorylation. Furthermore, higher phosphorylation of c-Jun N-terminal kinases (JNKs) also was seen in cells treated with AS1949490 (Fig. 1A). Next, this study analyzed the impact of longer H2O2 treatment on the phosphorylation levels of these proteins. Compared to control cells and similar to the observation above, 6 h H2O2 treatment led to sustained phosphorylation of AKT at Ser473 (Fig. 1B–C). To this study’s surprise, ERK1/2 phosphorylation displayed marked and sustained activation in cells treated with AS1949490 and H2O2. Reference: Arch Biochem Biophys. 2021 Jan 15;697:108667. https://pubmed.ncbi.nlm.nih.gov/33181128/
In vivo activity:	When cultured cortical neurons were exposed to Aβ25–35 (10), survival rate was markedly reduced (Fig. 5A). Pretreatment with AS1949490 (10 μM) significantly increased cell viability in the presence of Aβ25–35, although BDNF (1 ng/ml) had no effect. The protective efficacy of AS1949490 alone was nearly identical to that of AS1949490 plus BDNF. Similarly, when cultured cortical cells (i.e., cells prepared without Ara-C) were exposed to Aβ25–35 (25 μM), marked cell death was detected (Fig. 5B). Pretreatment with 10 μM AS1949490 (Fig. 5B) and higher concentration (10 ng/ml) of BDNF (data not shown) protected the Aβ toxicity, although 1 ng/ml BDNF had no effect. The potency of the effect of AS1949490 alone was not different from that of AS1949490 plus BDNF. These results indicate that AS1949490 directly caused neuroprotection against the Aβ toxicity. Reference: Eur J Pharmacol. 2019 May 15;851:69-79. https://pubmed.ncbi.nlm.nih.gov/30753865/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	43.6	117.24
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.81
	DMF	30.0	80.67
	Ethanol	28.6	76.91

Preparing Stock Solutions

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	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Azzi A. Scaffold dependent role of the inositol 5'-phosphatase SHIP2, in regulation of oxidative stress induced apoptosis. Arch Biochem Biophys. 2021 Jan 15;697:108667. doi: 10.1016/j.abb.2020.108667. Epub 2020 Nov 9. PMID: 33181128. 2. Saurus P, Tolvanen TA, Lindfors S, Kuusela S, Holthöfer H, Lehtonen E, Lehtonen S. Inhibition of SHIP2 in CD2AP-deficient podocytes ameliorates reactive oxygen species generation but aggravates apoptosis. Sci Rep. 2017 Sep 6;7(1):10731. doi: 10.1038/s41598-017-10512-w. PMID: 28878342; PMCID: PMC5587593. 3. Tsuneki H, Yoshida H, Okamoto K, Yamaguchi M, Endo K, Nakano A, Tsuda M, Toyooka N, Wada T, Sasaoka T. 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. 2019 May 15;851:69-79. doi: 10.1016/j.ejphar.2019.02.003. Epub 2019 Feb 10. PMID: 30753865. 4. Suwa A, Yamamoto T, Sawada A, Minoura K, Hosogai N, Tahara A, Kurama T, Shimokawa T, Aramori I. Discovery and functional characterization of a novel small molecule inhibitor of the intracellular phosphatase, SHIP2. Br J Pharmacol. 2009 Oct;158(3):879-87. doi: 10.1111/j.1476-5381.2009.00358.x. Epub 2009 Aug 19. PMID: 19694723; PMCID: PMC2765606.
In vitro protocol:	1. Azzi A. Scaffold dependent role of the inositol 5'-phosphatase SHIP2, in regulation of oxidative stress induced apoptosis. Arch Biochem Biophys. 2021 Jan 15;697:108667. doi: 10.1016/j.abb.2020.108667. Epub 2020 Nov 9. PMID: 33181128. 2. Saurus P, Tolvanen TA, Lindfors S, Kuusela S, Holthöfer H, Lehtonen E, Lehtonen S. Inhibition of SHIP2 in CD2AP-deficient podocytes ameliorates reactive oxygen species generation but aggravates apoptosis. Sci Rep. 2017 Sep 6;7(1):10731. doi: 10.1038/s41598-017-10512-w. PMID: 28878342; PMCID: PMC5587593.
In vivo protocol:	1. Tsuneki H, Yoshida H, Okamoto K, Yamaguchi M, Endo K, Nakano A, Tsuda M, Toyooka N, Wada T, Sasaoka T. 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. 2019 May 15;851:69-79. doi: 10.1016/j.ejphar.2019.02.003. Epub 2019 Feb 10. PMID: 30753865. 2. Suwa A, Yamamoto T, Sawada A, Minoura K, Hosogai N, Tahara A, Kurama T, Shimokawa T, Aramori I. Discovery and functional characterization of a novel small molecule inhibitor of the intracellular phosphatase, SHIP2. Br J Pharmacol. 2009 Oct;158(3):879-87. doi: 10.1111/j.1476-5381.2009.00358.x. Epub 2009 Aug 19. PMID: 19694723; PMCID: PMC2765606.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

1: Ichihara Y, Fujimura R, Tsuneki H, Wada T, Okamoto K, Gouda H, Hirono S, Sugimoto K, Matsuya Y, Sasaoka T, Toyooka N. Rational design and synthesis of 4-substituted 2-pyridin-2-ylamides with inhibitory effects on SH2 domain-containing inositol 5'-phosphatase 2 (SHIP2). Eur J Med Chem. 2013 Apr;62:649-60. doi: 10.1016/j.ejmech.2013.01.014. PubMed PMID: 23434638.

2: Suwa A, Yamamoto T, Sawada A, Minoura K, Hosogai N, Tahara A, Kurama T, Shimokawa T, Aramori I. Discovery and functional characterization of a novel small molecule inhibitor of the intracellular phosphatase, SHIP2. Br J Pharmacol. 2009 Oct;158(3):879-87. doi: 10.1111/j.1476-5381.2009.00358.x. PubMed PMID: 19694723; PubMed Central PMCID: PMC2765606.

Your view history

AS1949490 featured