IWP-2
IWP-2 Basic information
- Product Name:
- IWP-2
- Synonyms:
-
- IWP 2
- N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]-acetamide
- Acetamide, N-(6-methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]-
- IWP 2 N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2d]pyrimidin-2-yl)thio]acetamide
- IWP 2, >=98%
- IWP-2;IWP 2
- Wnt Antagonist II, IWP-2
- N-(6-methylbenzo[d]thiazol-2-yl)-2-((4-oxo-3-phenyl-3,4,6,7-tetrahydrothieno[3,2-d]pyrimidin-2-yl)thio)acetamide
- CAS:
- 686770-61-6
- MF:
- C22H18N4O2S3
- MW:
- 466.6
- Product Categories:
-
- Inhibitors
- Aromatics
- Heterocycles
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Sulfur & Selenium Compounds
- Mol File:
- 686770-61-6.mol
IWP-2 Chemical Properties
- Melting point:
- 257 °C(dec.)
- Density
- 1.52±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- solubility
- DMSO: >5mg/mL
- pka
- 9.01±0.70(Predicted)
- form
- powder
- color
- Beige
- Stability:
- Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
- InChIKey
- WRKPZSMRWPJJDH-UHFFFAOYSA-N
- CAS DataBase Reference
- 686770-61-6
IWP-2 Usage And Synthesis
Description
IWP-2 is an inhibitor of Wnt processing and secretion with IC50 of 27 nM in a cell-free assay, selective blockage of Porcn-mediated Wnt palmitoylation, does not affect Wnt/β-catenin in general and displays no effect against Wnt-stimulated cellular responses.
Features
Selective inhibitor of Porcn-mediated Wnt secretion.
In vitro
IWP-2 is useful in both regenerative medicine and anticancer efforts. IWP-2 inactivates Porcn, a membrane-bound O-acyltransferase (MBOAT), and selectively inhibits palmitoylation of Wnt. IWP-2 blocks Wnt-dependent phosphorylation of Lrp6 receptor and Dvl2, and β-catenin accumulation.
Description
IWP-2 (686770-61-6) is an inhibitor of Wnt secretion and processing. It blocks Wnt-dependent signaling (IC50= 27 nM) by inhibition of the O-acyltransferase Porcn.1 Induces cardiomyocyte differentiation from human pluripotent stem cells.2 IWP-2 is an important tool to probe the involvement of the Wnt pathway in physiological processes.3,4?Cell permeable.
Uses
IWP-2 is an inactivator of Porcn function; inhibitor of Wnt production. IWP-2 is useful in the treatment diseases and conditions such as cancer, degenerative diseases, type II diabetes and osteopetrosis.
Uses
IWP-2 has been used to treat the cell lines L-Wnt-3a and L-Wnt-5a, to demonstrate the inhibitory effect of IWP-2. It has also been used as a Wnt signaling inhibitor to treat WT and?Gja1Jrt/+ stromal cells to confirm that, theWnt/β-catenin signaling pathway pathway was not involved in the increased marker expression by?Gja1Jrt/+ osteoblasts.
Definition
ChEBI: N-(6-methyl-1,3-benzothiazol-2-yl)-2-[(4-oxo-3-phenyl-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)thio]acetamide is an organonitrogen heterocyclic compound, an organic heterobicyclic compound and an organosulfur heterocyclic compound.
General Description
A cell-permeable benzothiazolyl-acetamide compound that inhibits the cellular Wnt processing and secretion via selective blockage of MBOAT (membrane-bound O-acyltranferase) family member Porcn- (Porcupine) mediated Wnt palmitoylation. IWP-2 does not affect Wnt/β-catenin signaling pathway in general and, unlike IWR-1-endo (Cat. No. 681669), displays no effect against Wnt-stimulated cellular responses. Also available as a 10 mM solution in DMSO (Cat. No. 506072).
Biochem/physiol Actions
IWP-2 is an inactivator of Porcn function; inhibitor of Wnt production. Wnt/b-catenin (‘canonical′) pathway maintains transcriptional programs that enable stem cells to remain multipotent. Hyperactivation of the Wnt/b-catenin pathway leads to disease stage. IWP-2 inhibits Wnt production. It appears that IWP inactivates Porcn function either by directly inhibiting the Porcn active site or by modulating the function of a Porcn regulator. Porcn is a member of the membrane-bound O-acyltransferase (MBOAT) family, which adds a palmitoyl group to Wnt proteins that is essential to their signaling ability and is required for Wnt secretion. IWP-2 is useful in both regenerative medicine and anticancer efforts.
in vitro
expression of porcn but not evi alleviated the effects of iwp-2 on pathway activity and wnt secretion, which suggests that in general iwp-2 may act on porcn [1].
in vivo
in order to test the in vivo activity of iwp-2, the authors turned to a simple and rapid assay of wnt/b-catenin pathway activity: regeneration of the zebrafish caudal fin following resection. the addition of iwp-2 to the aquarium water of zebrafish failed to suppress fin regeneration after mechanical resection, which suggests either that iwp-2 have poor bioavailability or that the determinants in the gene product that they target are not conserved in zebrafish [1].
IC 50
27 nm for wnt pathway activity
storage
+4°C
References
1) Chen et al. (2009), Small molecule-mediated disruption of Wnt-dependent signaling in tissue regeneration and cancer; Nature Chem. Biol., 5 100 2) Lian et al. (2012), Robust Cardiomyocyte differentiation from human pluripotent stem cells via temporal modulation of canonical Wnt signaling; Proc. Natl. Acad. Sci. USA, 109 1848 3) ten Berge et al. (2011), Embryonic stem cells require Wnt proteins to prevent differentiation to epiblast stem cells; Nature Cell. Biol., 13 1070 4) Uyama et al. (2013), Wasf2: a novel target of intermittent parathyroid hormone administration; Int. J. Mol. Med., 31 1243
IWP-2Supplier
- Tel
- +86-21-20908456
- sales@BioChemBest.com
- Products Intro
- Product Name:IWP-2; N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]-acetamide
CAS:686770-61-6
Purity:98%
- Tel
- 13774214275
- zhouzz@univ-bio.com
- Products Intro
- Product Name:IWP 2
CAS:686770-61-6
Package:10mg Remarks: 见优宁维官网
- Tel
- sales@boylechem.com
- Products Intro
- Product Name:IWP-2
CAS:686770-61-6
Purity:98%
- Tel
- 010-82848833 400-666-7788
- jkinfo@jkchemical.com
- Products Intro
- Product Name:IWP-2
CAS:686770-61-6
Package:250Mg,25Mg
- Tel
- 821-50328103-801 18930552037
- 3bsc@sina.com
- Products Intro
- Product Name:IWP 2;N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyriMidin-2-yl)thio]-acetaMide
CAS:686770-61-6
Purity:99% HPLC Package:1Mg ; 5Mg;10Mg ;100Mg;250Mg ;500Mg ;1g;2.5g ;5g ;10g