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S5696

SKI II

≥98% (HPLC), selective non-lipid sphingosine kinase (SK) inhibitor, solid

Synonym(s):

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

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10 mg

Available to ship TODAYfromMILWAUKEE

$230.00
$195.50
50 mg

Available to ship TODAYfromMILWAUKEE

$704.00
$598.40

About This Item

Empirical Formula (Hill Notation):
C15H11ClN2OS
CAS Number:
312636-16-1
Molecular Weight:
302.78
UNSPSC Code:
12352200
PubChem Substance ID:
24724614
NACRES:
NA.77
MDL number:
MFCD00733553
Assay:
≥98% (HPLC)
Form:
solid
Storage condition:
protect from light

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Product Name

SKI II, ≥98% (HPLC), solid

Quality Segment

100

assay

≥98% (HPLC)

form

solid

storage condition

protect from light

color

off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

Oc1ccc(Nc2nc(cs2)-c3ccc(Cl)cc3)cc1

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

Application

SKI II has been used to study the regulatory mechanism and signaling pathway induced by SKI II in inhibiting tumor growth.
Human cisplatin-resistant gastric cancer cell line was treated with SKI-II to study the mechanism of reversion of multidrug resistance.1

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).
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

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SKI II ≥98% (HPLC), solid

Sigma-Aldrich

S5696

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PIK93 ≥98% (HPLC)

Sigma-Aldrich

SML0546

PIK93

SGI-1027 ≥98% (HPLC)

Sigma-Aldrich

SML1358

SGI-1027

LY 2087101 ≥98% (HPLC)

Sigma-Aldrich

SML0870

LY 2087101

description

≥98% (HPLC), solid

description

≥98% (HPLC)

description

≥98% (HPLC)

description

≥98% (HPLC)

form

solid

form

powder

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage condition

protect from light

storage condition

protect from light

storage condition

-

storage condition

(dry room)

solubility

DMSO: ≥20 mg/mL

solubility

DMSO: 15 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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