S5696

SKI II

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

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

Properties

• 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

Description

Application

SKI II has been used to study the regulatory mechanism and signaling pathway induced by SKI II in inhibiting tumor growth.[1]

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)