Key Documents

View All Documentation

5.33062

S1P3 Receptor Antagonist, TY-52156

Name: S1P3 Receptor Antagonist, TY-52156
Brand: MM

Synonym(s):

S1P3 Receptor Antagonist, TY-52156, S1P3 Antagonist, TY-52156, Sphingosine 1-phosphate Receptor Antagonist, TY-52156, TY52156, TY 52156, [1-Chloro-1-(4-chlorophenylhydrazono)]-3,3-dimethyl-2-butanone

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₁₈H₁₉Cl₂N₃O

CAS Number:

934369-14-9

Molecular Weight:

364.27

MDL number:

MFCD28396419

UNSPSC Code:

41116158

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze, protect from light

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

assay

≥98% (HPLC)

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

orange

solubility

DMSO: 50 mg/mL

storage temp.

−20°C

SMILES string

Clc1ccc(cc1)N\N=C(\Nc2ccc(cc2)Cl)/C(=O)C(C)(C)C

InChI

1S/C18H19Cl2N3O/c1-18(2,3)16(24)17(21-14-8-4-12(19)5-9-14)23-22-15-10-6-13(20)7-11-15/h4-11,22H,1-3H3,(H,21,23)

InChI key

XONRRGIRSGNWFP-UHFFFAOYSA-N

Description

General description

A cell-permeable hydrazonamide derivative that acts as a selective and competitive antagonist of S1P3 receptor (K_i = 110 nM) and suppresses S1P-induced expansion of A549, LNCaP, U251MG, and OVCAR-5 cancer cells (~ 10 µM). Displays about 30-fold lower effect on S1P1, S1P2, S1P4, or S1P5 receptors and does not affect 24 different G-protein coupled receptors (~10 µM). Shown to block S1P-induced expression of Hes1 and reduce ALDH-positive cell population. Inhibits the tumorigenicity of SphK1-overexpressing ALDH-positive cells following chronic administration over a period of 6 weeks. Preferentially inhibits S1P-induced increase in [Ca2+]i and Rho activation in vascular smooth muscle cells. Shown to reduce S1P3 receptor-induced bradycardia in vivo in rats and diminishes coronary flow in perfused rat heart. Also shown to relax cerebral arteries precontracted with S1P.

Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.

A hydrazonamide derivative that suppresses the S1P-induced cancer stem cell expansion effects in multiple human cancer cell lines including, breast cancer MCF-7 cells, lung cancer A549 cells, glioma U251MG cells and ovarian cancer OVCAR-5 cells at 10 µM. Significantly inhibits the tumorigenicity of SphK1-overexpressing ALDH-positive cells after chronic continuous injection for 6 weeks (167mg/ml) in a mouse xenograft model. In addition, shown to suppress the S1P-induced effects such as Ca2+ increase and Rho activation in vascular smooth muscle cells and decrease of coronary flow in isolated perfused rat hearts.

Biochem/physiol Actions

Primary Target
S1P3

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-70°C). Stock solutions are stable for up to 4 weeks at -70°C.

Other Notes

Hirata, N., et al. 2014, Nat. Comm.5, in press.
Murakami, A., et al. 2010. Mol. Pharm.77, 704.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c