IWP-2
- CAS No.
- 686770-61-6
- Chemical Name:
- IWP-2
- Synonyms
- IWP 2;CS-803;IWP IWP;IWP-2;IWP 2;IWP-2-salt2;IWP 2, >=98%;IWP-2 USP/EP/BP;WNT INHIBITOR IWP-2;ABC 294640;ABC-294640;Wnt Antagonist II, IWP-2
- CBNumber:
- CB12518935
- Molecular Formula:
- C22H18N4O2S3
- Molecular Weight:
- 466.6
- MDL Number:
- MFCD04457599
- MOL File:
- 686770-61-6.mol
| 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 price More Price(38)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | I0536 | IWP-2 ≥98% (HPLC) | 686770-61-6 | 5mg | $158 | 2024-03-01 | Buy |
| Sigma-Aldrich | I0536 | IWP-2 ≥98% (HPLC) | 686770-61-6 | 25mg | $616 | 2024-03-01 | Buy |
| Sigma-Aldrich | 5.06072 | InSolution Wnt Antagonist II, IWP-2 - CAS 686770-61-6 - Calbiochem | 686770-61-6 | 5mg | $142 | 2024-03-01 | Buy |
| Cayman Chemical | 13951 | IWP-2 ≥95% | 686770-61-6 | 1mg | $26 | 2024-03-01 | Buy |
| Cayman Chemical | 13951 | IWP-2 ≥95% | 686770-61-6 | 5mg | $93 | 2024-03-01 | Buy |
IWP-2 Chemical Properties,Uses,Production
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-2 Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hangzhou FandaChem Co.,Ltd. | 008657128800458; +8615858145714 | fandachem@gmail.com | China | 9352 | 55 |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 22968 | 58 |
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| Zhengzhou Alfa Chemical Co.,Ltd | +8618530059196 | sale04@alfachem.cn | China | 12431 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| Dideu Industries Group Limited | +86-29-89586680 +86-15129568250 | 1026@dideu.com | China | 29474 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6393 | 58 |
| LEAP CHEM CO., LTD. | +86-852-30606658 | market18@leapchem.com | China | 24738 | 58 |
| ShenZhen Trendseen Biological Technology Co.,Ltd. | 13417589054 | trendseenbio@gmail.com | China | 11681 | 58 |