284028-89-3

Basic information

• Product Name: xav-939
• Synonyms: xav-939;3,5,7,8-Tetrahydro-2-[4-(trifluoromethyl)phenyl]-4H-thiopyrano[4,3-d]pyrimidin-4-one;XAV 939/NVP-XAV939;SteMolecule;1,5,7,8-Tetrahydro-2-[4-(trifluoroMethyl)phenyl]-4H-thiopyrano[4,3-d]pyriMidin-4-one;NVP-XAV 939;2-(4-(trifluoromethyl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-4-ol;XAV 939 3,5,7,8-Tetrahydro-2-[4-(trifluoromethyl)phenyl]-4H-thiopyrano[4,3-d]pyrimidin-4-one
• CAS NO: 284028-89-3
• Molecular Formula: C₁₄H₁₁F₃N₂OS
• Molecular Weight: 312.3101496
• EINECS: -0
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 284028-89-3.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 429.3 °C at 760 mmHg
• Flash Point: 213.4℃
• Appearance: white to beige/
• Density: 1.5
• Storage Temp.: Store at RT
• Solubility: DMSO: soluble5mg/mL, clear
• PKA: 0.23±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: xav-939(CAS DataBase Reference)
• NIST Chemistry Reference: xav-939(284028-89-3)
• EPA Substance Registry System: xav-939(284028-89-3)

Safety Data

• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 26-45-26/45
• RIDADR: UN 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 284028-89-3(Hazardous Substances Data)

Usage

Description

XAV-939 is a tankyrase inhibitor with an IC50 of 11 and 4 nM for TNKS1 and TNKS2, respectively. It functions by antagonizing Wnt signaling through the stimulation of β-catenin degradation and stabilization of actin. XAV-939 is also known for its robust induction of cardiomyogenesis in stem cells and is cell permeable.

Uses

Used in Pharmaceutical Industry:
XAV-939 is used as a tankyrase inhibitor for antagonizing Wnt signaling, which is involved in various cellular processes, including cell proliferation, differentiation, and migration. This makes it a potential therapeutic agent for treating cancer and other diseases associated with Wnt signaling dysregulation.
Used in Cancer Research:
XAV-939 is used as an inhibitor of tankyrase in various cancer cell lines, such as μ-catenin-dependent colon carcinoma cell line DLD-1, neuroblastoma cell lines, diphtheria toxin-like ADP-ribosyltransferases (ARTD) in medulloblastoma cells, and Wnt signaling in human induced pluripotent stem cells (hiPSCs). By inhibiting tankyrase, XAV-939 can help in understanding the role of Wnt signaling in cancer development and progression.
Used in Stem Cell Research:
XAV-939 is used as a promoter of cardiomyogenesis in stem cells. Its ability to induce the differentiation of stem cells into cardiomyocytes makes it a valuable tool in regenerative medicine and the development of novel treatments for heart diseases.
Used in Drug Development:
XAV-939 can be used as a lead compound in the development of new drugs targeting tankyrase and Wnt signaling pathways. Its cell permeability and specificity for tankyrase make it a promising candidate for further research and development in the pharmaceutical industry.

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.

References

1) Huang?et al. (2009),?Tankyrase inhibition stabilizes axin and antagonizes Wnt signaling; Nature,?46?614 2) Wang?et al. (2011),?Cardiac induction of embryonic stem cells by a small molecule inhibitor of Wnt/β-catenin signaling; Chem. Biol.,?6?192