SKI II

SIGMA/S5696 - ≥98% (HPLC), solid

Synonym: 4-[[4-(4-Chlorophenyl)-2-thiazolyl]amino]phenol

CAS Number: 312636-16-1
Empirical Formula (Hill Notation): C₁₅H₁₁ClN₂OS
Molecular Weight: 302.78
MDL Number: MFCD00733553
Linear Formula: C₁₅H₁₁ClN₂OS
Product Type: Chemical

Catalog Number	PKG Qty.	Price	Quantity


45-S5696-10MG	10 mg	$230.00 1/EA		Add To Favorites
45-S5696-50MG	50 mg	$704.00 1/EA		Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

assay	≥98% (HPLC)
color	off-white
form	solid
InChI	1S/C15H11ClN2OS/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)
InChI key	ZFGXZJKLOFCECI-UHFFFAOYSA-N
Quality Level	100
SMILES string	Oc1ccc(Nc2nc(cs2)-c3ccc(Cl)cc3)cc1
solubility	DMSO: ≥20 mg/mL
storage condition	protect from light
storage temp.	2-8°C

Application:	Human cisplatin-resistant gastric cancer cell line was treated with SKI-II to study the mechanism of reversion of multidrug resistance.¹
Application:	SKI II has been used to study the regulatory mechanism and signaling pathway induced by SKI II in inhibiting tumor growth.
Biochem/physiol Actions:	SKI II is a selective non-lipid sphingosine kinase (SK) inhibitor. IC₅₀ = 0.5 μM; does not act at ATP-binding site. Displays no inhibition of ERK2, PI 3-kinase, or PKCα at concentrations up to 60 μM. Induces apoptosis and inhibits proliferation in several other tumor cell lines in vitro (IC₅₀ = 0.9-4.6 μM).
Biochem/physiol Actions:	Sphingosine kinase (SK) plays a pivotal role in regulating tumor growth and SK can act as an oncogene. Expression of SK RNA is significantly elevated in a variety of solid tumors, compared with normal tissue from the same patient. A number of novel inhibitors of human SK were identified, and several representative compounds were characterized in detail. These compounds demonstrated activity at sub- to micromolar concentrations, making them more potent than any other reported SK inhibitor, and were selective toward SK compared with a panel of human lipid and protein kinases. Kinetic studies revealed that the compounds were not competitive inhibitors of the ATP-binding site of SK. 4-[4-(4-chloro-phenyl)-thiazol-2-ylamino]-phenol (SKI-II) inhibitor is orally bioavailable, detected in the blood for at least 8 h, and showed a significant inhibition of tumor growth in mice with IC₅₀ = 0.5 μM; SKI II does not act at ATP-binding site. Displays no inhibition of ERK2, PI 3-kinase, or PKCa at concentrations up to 60 μM.SKI II induces apoptosis and inhibits proliferation in several other tumor cell lines in vitro (IC₅₀ = 0.9-4.6 μM).
Features and Benefits:	This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm .
Other Notes:	Product is air and light sensitive
Packaging:	10, 50 mg in glass bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥98% (HPLC)
Storage Temp.	2-8°C
UNSPSC	12352200

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