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X3004

Sigma-Aldrich

XAV939

≥98% (HPLC), powder, tankyrase inhibitor

Synonym(s):

3,5,7,8-Tetrahydro-2-[4-(trifluoromethyl)phenyl]-4H-thiopyrano[4,3-d]pyrimidin-4-one

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About This Item

Empirical Formula (Hill Notation):
C14H11F3N2OS
CAS Number:
284028-89-3
Molecular Weight:
312.31
MDL number:
MFCD16879017
UNSPSC Code:
12352200
PubChem Substance ID:
329830802
NACRES:
NA.77

Product Name

XAV939, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear

storage temp.

room temp

SMILES string

FC(F)(F)c1ccc(cc1)C2=NC3=C(CSCC3)C(=O)N2

InChI

1S/C14H11F3N2OS/c15-14(16,17)9-3-1-8(2-4-9)12-18-11-5-6-21-7-10(11)13(20)19-12/h1-4H,5-7H2,(H,18,19,20)

InChI key

KLGQSVMIPOVQAX-UHFFFAOYSA-N

Application

XAV939 has been used in the inhibition
  • of tankyrase in neuroblastoma cell lines
  • of diphtheria toxin-like ADP-ribosyltransferases (ARTD) in medulloblastoma cells
  • of wnt signalling in human induced pluripotent stem cells (hiPSCs)

Biochem/physiol Actions

XAV939 is a cell-permeable dihydrothiopyranopyrimidinol, which elicits anti-tumor functionality against colon, lung, breast and liver cancer. It binds to catalytic poly-ADP-ribose polymerase (PARP) domain of the tankyrase enzyme resulting in β-catenin destruction. It also inhibits tankyrase in neuroblastoma promoting apoptosis in tumor cells.
XAV939 is a Tankyrase inhibitor (thereby inhibiting Wnt / β-catenin signaling)

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

XAV939 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the XAV939 probe summary on the Chemical Probes Portal website.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

X3004-25MG:
X3004-VAR:
X3004-5MG:
X3004-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000400542
0000400543
0000321234
0000321233
0000400543

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Robust generation of cardiomyocytes from human iPS cells requires precise modulation of BMP and WNT signaling
Kadari A, et al.
Stem Cell Reviews and Reports, 11(4), 560-569 (2015)
XAV939, a tankyrase 1 inhibitor, promotes cell apoptosis in neuroblastoma cell lines by inhibiting Wntbeta-catenin signaling pathway
Tian XH, et al.
Journal of Experimental & Clinical Cancer Research, 32(1), 100-100 (2013)
XAV939-mediated ARTD activity inhibition in human MB cell lines
Renna C, et al.
Testing, 10(4), e0124149-e0124149 (2015)
Up-regulation of FGF1519 signaling promotes hepatocellular carcinoma in the background of fatty liver
Cui G, et al.
Journal of Experimental & Clinical Cancer Research, 37(1), 136-136 (2018)
Harsha D Devalla et al.
EMBO molecular medicine, 8(12), 1390-1408 (2016-11-20)
Genetic causes of many familial arrhythmia syndromes remain elusive. In this study, whole-exome sequencing (WES) was carried out on patients from three different families that presented with life-threatening arrhythmias and high risk of sudden cardiac death (SCD). Two French Canadian
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