Sphingosine Kinase Inhibitor

Name: Sphingosine Kinase Inhibitor
Brand: MM
Price: 149 USD

The Sphingosine Kinase Inhibitor, also referenced under CAS 1177741-83-1, controls the biological activity of Sphingosine Kinase. This small molecule/inhibitor is primarily used for Cell Signaling applications.

Synonym(s):

Sphingosine Kinase Inhibitor, 2-( p-Hydroxyanilino)-4-( p-chlorophenyl) thiazole, HCl, SK Inhibitor I, 2-(p-Hydroxyanilino)-4-(p-chlorophenyl) thiazole, HCl, SK Inhibitor I

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10 MG

$149.00

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₁ClN₂OS · xHCl

CAS Number:

1177741-83-1

Molecular Weight:

302.78 (free base basis)

MDL number:

MFCD28137718

UNSPSC Code:

12352200

NACRES:

NA.77

Key Documents

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Product Name

Sphingosine Kinase Inhibitor, The Sphingosine Kinase Inhibitor, also referenced under CAS 1177741-83-1, controls the biological activity of Sphingosine Kinase. This small molecule/inhibitor is primarily used for Cell Signaling applications.

SMILES string

[s]1c(nc(c1)c3ccc(cc3)Cl)Nc2ccc(cc2)O.Cl

InChI

1S/C15H11ClN2OS.ClH/c16-11-3-1-10(2-4-11)14-9-20-15(18-14)17-12-5-7-13(19)8-6-12;/h1-9,19H,(H,17,18);1H

InChI key

ZDRVLAOYDGQLFI-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

white

solubility

DMSO: 5 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Related Categories

Bioactive Small Molecule Inhibitors

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This Item	567732	310500	569397
Sigma-Aldrich 567731 Sphingosine Kinase Inhibitor	Sigma-Aldrich 567732 Sphingosine Kinase 1 Inhibitor, SKI-178	Sigma-Aldrich 310500 D-erythro-Sphingosine, N,N-Dimethyl-	Sigma-Aldrich 569397 Staurosporine, Streptomyces sp.
assay ≥98% (HPLC)	assay ≥92% (HPLC)	assay ≥98% (TLC)	assay ≥99% (HPLC)
form solid	form powder	form oil (Clear), waxy solid	form solid
manufacturer/tradename Calbiochem^®	manufacturer/tradename Calbiochem^®	manufacturer/tradename Calbiochem^®	manufacturer/tradename Calbiochem^®
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. −20°C	storage temp. 2-8°C
storage condition OK to freeze, protect from light, desiccated (hygroscopic)	storage condition OK to freeze, protect from light	storage condition OK to freeze	storage condition OK to freeze, protect from light

Biochem/physiol Actions

Cell permeable: yes

Primary Target
GST-hsk

Product competes with ATP.

Reversible: yes

Target IC₅₀: 0.5 µM for GST-hSK

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

General description

A cell-permeable disubstituted thiazole compound that displays anti-tumor properties. Acts as a potent, substrate competitive, reversible, and highly specific inhibitor of sphingosine kinase (IC₅₀ = 0.5 µM for GST-hSK). Does not affect the kinase activity of hERK2, hPI3K, or PKCα even at concentrations as high as 60 µM. Induces apoptosis in human cancer cells that express the drug transport proteins Pgp or MRP1 (IC₅₀ = ~ 1-5 µM) through inhibiting sphingosine-1-phosphate production.

A cell-permeable, potent non-ATP-competitive, reversible, and specific inhibitor of sphingosine kinase (IC₅₀ = 500 nM for GST-hSK) that also exhibits anti-tumor properties. Does not affect the kinase activity of hERK2, hPI3 K, or PKC_α at cocentrations as high as 60 µM. Shown to induce apoptosis in human cancer cells that express the drug transport proteins Pgp or MRP1 (IC₅₀ ~1-5 µM) by inhibiting sphingosine-1-phosphate production.

Other Notes

French, K.J., et al. 2003. Cancer Res.63, 5962.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 1

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Macrophage's proinflammatory response to a mycobacterial infection is dependent on sphingosine kinase-mediated activation of phosphatidylinositol phospholipase C, protein kinase C, ERK1/2, and phosphatidylinositol 3-kinase.

Mahesh Yadav et al.

Journal of immunology (Baltimore, Md. : 1950), 176(9), 5494-5503 (2006-04-20)

Previous studies have shown that the ability of Mycobacterium tuberculosis to block a Ca(2+) flux is an important step in its capacity to halt phagosome maturation. This affect on Ca(2+) release results from M. tuberculosis inhibition of sphingosine kinase (SPK)

Constitutive activation of S1P receptors at the trans-Golgi network is required for surface transport carrier formation.

Taro Okada et al.

iScience, 24(11), 103351-103351 (2021-11-23)

The importance of the G-protein βγ subunits in the regulation of cargo transport from the trans-Golgi network (TGN) to the plasma membrane (PM) is well accepted; however, the molecular mechanism underlying the G-protein activation at the TGN remains unclear. We

A novel chimeric aequorin fused with caveolin-1 reveals a sphingosine kinase 1-regulated Ca²⁺ microdomain in the caveolar compartment.

Ilari Pulli et al.

Biochimica et biophysica acta, 1853(9), 2173-2182 (2015-04-22)

Caveolae are plasma membrane invaginations enriched in sterols and sphingolipids. Sphingosine kinase 1 (SK1) is an oncogenic protein that converts sphingosine to sphingosine 1-phosphate (S1P), which is a messenger molecule involved in calcium signaling. Caveolae contain calcium responsive proteins, but

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