X3004

Sigma-Aldrich

XAV939

≥98% (HPLC)

Synonym(s):
3,5,7,8-Tetrahydro-2-[4-(trifluoromethyl)phenyl]-4H-thiopyrano[4,3-d]pyrimidin-4-one
Empirical Formula (Hill Notation):
C14H11F3N2OS
CAS Number:
Molecular Weight:
312.31
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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)

Packaging

5, 25 mg in glass bottle

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)

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.

RIDADR

UN 2811 6.1 / PGIII

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

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)
Tankyrase inhibitors attenuate WNTbeta-catenin signaling and inhibit growth of hepatocellular carcinoma cells
Ma L, et al.
Testing, 6(28), 25390-25390 (2015)
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)
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