| Identification | Back Directory | [Name]
IWP-3 | [CAS]
687561-60-0 | [Synonyms]
IWP-3
IWP 3;IWP3
IWP-3 >=98% (HPLC)
Wnt Inhibitor 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
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
Acetamide, 2-[[3-(4-fluorophenyl)-3,4,6,7-tetrahydro-4-oxothieno[3,2-d]pyrimidin-2-yl]thio]-N-(6-methyl-2-benzothiazolyl)- | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C22H17FN4O2S3 | [MDL Number]
MFCD04457889 | [MOL File]
687561-60-0.mol | [Molecular Weight]
484.59 |
| Chemical Properties | Back Directory | [Melting point ]
>248°C (dec.) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble2mg/mL (clear solution, warmed) | [form ]
powder | [color ]
white to beige | [InChI]
1S/C22H17FN4O2S3/c1-12-2-7-15-17(10-12)32-21(24-15)26-18(28)11-31-22-25-16-8-9-30-19(16)20(29)27(22)14-5-3-13(23)4-6-14/h2-7,10H,8-9,11H2,1H3,(H,24,26,28) | [InChIKey]
XVMHQSDMKWQNBK-UHFFFAOYSA-N | [SMILES]
Cc1ccc2nc(NC(=O)CSC3=NC4=C(SCC4)C(=O)N3c5ccc(F)cc5)sc2c1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [WGK Germany ]
3 | [Storage Class]
13 - Non Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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). |
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| Company Name: |
Sigma-Aldrich
|
| Tel: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
Cckinase, Inc.
|
| Tel: |
+1 (732)236-3202 |
| Website: |
www.cckinase.com |
|