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567731

Sigma-Aldrich

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.

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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About This Item

Empirical Formula (Hill Notation):
C15H11ClN2OS · xHCl
CAS Number:
1177741-83-1
Molecular Weight:
302.78 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

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

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

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 PKCα 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.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
GST-hsk
Product competes with ATP.
Reversible: yes
Target IC50: 0.5 µM for GST-hSK

Packaging

Packaged under inert gas

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

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

Other Notes

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

Legal Information

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

Storage Class Code

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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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
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)
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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