687561-60-0

Basic information

• Product Name: IWP-3
• Synonyms: IWP-3;2-[[3-(4-Fluorophenyl)-3,4,6,7-tetrahydro-4-oxothieno[3,2-d]pyrimidin-2-yl]thio]-N-(6-methyl-2-benzothiazolyl)-acetamide;Wnt Inhibitor IWP-3;2-((3-(4-fluorophenyl)-4-oxo-3,4,6,7-tetrahydrothieno[3,2-d]pyrimidin-2-yl)thio)-N-(6-methylbenzo[d]thiazol-2-yl)acetamide
• CAS NO: 687561-60-0
• Molecular Formula: C22H17FN4O2S3
• Molecular Weight: 484.5893832
• EINECS: 200-258-5
• Mol File: 687561-60-0.mol
• Article Data: 0

Chemical Properties

• Appearance: white to beige/
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble2mg/mL (clear solution, warmed)
• CAS DataBase Reference: IWP-3(CAS DataBase Reference)
• NIST Chemistry Reference: IWP-3(687561-60-0)
• EPA Substance Registry System: IWP-3(687561-60-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 687561-60-0(Hazardous Substances Data)

Usage

Uses

IWP-3 is a potent inhibitor for porcupine which is known to catalyze the palmitoylation of Wnt proteins which are crucial in tumorigenesis.

Biological Activity

iwp-3 is an inhibitor of wnt production.wnt signaling proteins, a group of small secreted proteins, are active in tissue homeostasis, embryonic development, as well as tumorigenesis. wnt proteins can bind to the cell surface receptors, initiating a signaling cascade that results in the β-catenin activation of gene transcription.

Biochem/physiol Actions

IWP-3 is a Wnt inhibitor that prevents palmitylation of Wnt proteins by Porcupine (Porcn). IWP-3 is an inactivator of Porcn function that acts as inhibitors of Wnt production. Studies revealed that IWP-3 induces differentiation of human mesoderm cells to form cardiomyocytes.

in vitro

in previous study, iwp-3 was identified as an inhibitor of wnt production that could regulate in vitro wnt pathway activity with an ic50 value of 40 nm. in addition, iwp-3 was found to be able to inactivate porcupine, a o-acyltransferase for palmitoylating wnt proteins that was critical for the signaling ability and secretion. moreover, iwp-3 at 5 μm was found to block wnt-dependent phosphorylation of the low-density lipoprotein receptor-related protein 6 and the scaffold protein dishevelled, resulting in preventing the accumulation of β-catenin [1]. in another study, iwp-3 was applied to promote cardiomyocyte generation from human embryonic stem cells by inhibiting wnt signaling [2].

IC 50

40 nm

references

[1] b. chen, m. e. dodge, w. tang, et al. small molecule-mediated disruption of wnt-dependent signaling in tissue regeneration and cancer. nature chemical biology 5(2), 100-107 (2009).[2] e. willems, s. spiering, h. davidovics, et al. small molecule inhibitors of the wnt pathway potently promote cardiomyocytes from human embryonic stem cell derived mesoderm. circulation research 109(4), 360-364 (2011).