| Identification | Back Directory | [Name]
IWR-1-endo | [CAS]
1127442-82-3 | [Synonyms]
IWR-1
CS-624
CS-1858
endo-IWR 1
IWR-1-endo
IWR-1-endo, >=98%
IWR-1(IWR-1-endo)
IWR-1-endo USP/EP/BP
Wnt Antagonist I, IWR-1-endo
IWR-1-endo - IWR-1 | endo-IWR-1
ENDO-IWR 1;IWR-1-ENDO;IWR1;IWR 1
4-(1,3,3a,4,7,7a-Hexahydro-1,3-dioxo-4,7-methano-2H-isoindol-2-yl)-N-8-quinolinyl-Benzamide (IWR-1)
[(3aR*,4S*,7R*,7aS)-1,3,3a,4,7,7a-Hexahydro-1,3-dioxo-4,7-methano-2H-isoindol-2-yl]-N-8-quinolinylbenzamide
rel-4-[(3aR,4S,7R,7aS)-1,3,3a,4,7,7a-Hexahydro-1,3-dioxo-4,7-Methano-2H-isoindol-2-yl]-N-8-quinolinylbenzaMide
rel-4-((3aR,4S,7R,7aS)-1,3-Dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl)-N-(quinolin-8-yl)benzamide
Benzamide, 4-[(3aR,4S,7R,7aS)-1,3,3a,4,7,7a-hexahydro-1,3-dioxo-4,7-methano-2H-isoindol-2-yl]-N-8-quinolinyl-, rel-
rel-4-[(3aR,4S,7R,7aS)-1,3,3a,4,7,7a-Hexahydro-1,3-dioxo-4,7-methano-2H-isoindol-2-yl]-N-8-quinolinylbenzamide IWR-1-endo | [Molecular Formula]
C25H19N3O3 | [MDL Number]
MFCD18086875 | [MOL File]
1127442-82-3.mol | [Molecular Weight]
409.44 |
| Chemical Properties | Back Directory | [alpha ]
-3.0～+3.0°(20℃/D)(c=0.1,CH3CN) | [Boiling point ]
643.9±55.0 °C(Predicted) | [density ]
1.425±0.06 g/cm3(Predicted) | [storage temp. ]
room temp | [solubility ]
DMSO: soluble5mg/mL, clear | [form ]
Liquid | [pka]
11.88±0.43(Predicted) | [color ]
white to beige | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChIKey]
ZGSXEXBYLJIOGF-ALFLXDJESA-N | [SMILES]
N4(C(=O)[C@@H]5[C@@H]([C@H]6C[C@@H]5C=C6)C4=O)c1ccc(cc1)C(=O)Nc2c3ncccc3ccc2 |
| Hazard Information | Back Directory | [Description]
IWR-1 endo (1127442-82-3) is a potent inhibitor of Wnt signaling (IC50=180 nM).1?Inhibits zebrafish tailfin regeneration (0.5 mM).2?Acts via inhibition of tankyrase and attenuates Wnt/β-catenin signaling in cancer stem-like cells.3?Promotes self-renewal and maintains pluripotency of human embryonic stem cells.4?Promotes differentiation of pluripotent stem cells into cardiomyocytes.5 | [Uses]
IWR-1-endo act as inhibitors of Wnt response. It appear that IWR compounds induce stabilization of Axin proteins via a direct interaction, which is a part of the b-catenin destruction complex (consists of Apc, Axin, Ck1 and Gsk3b). Such compounds may be used in the treatment of Wnt protein signaling-related diseases and conditions such as cancer, degenerative diseases, type II diabetes and osteopetrosi s.
| [Definition]
ChEBI: IWR-1-endo is a dicarboximide having an endo bridged phthalimide structure, substituted at nitrogen by a 4-(quinolin-8-ylcarbamoyl)benzoyl group. It has a role as an axin stabilizer and a Wnt signalling inhibitor. It is a dicarboximide, a bridged compound, a member of quinolines and a member of benzamides. | [General Description]
A cell-permeable p-imidobenzamidoquinoline, endo-diastereomer that is shown to inhibit the activity of TNKS1/PARP5a and TNKS2/PARP5b in in vitro auto-PARsylation assays (IC50 = 131 and 56 nM, respectively) and effectively suppress Wnt-stimulated transcription activity in L-Wnt-STF-based reporter assays (IC50 = 180 nM), while exhibiting little activity against PARP1 or PARP2 (IC50 >18.75 μM). Although both IWR-1-endo and XAV939 (Tankyrase1/2 Inhibitor; >Cat. No. 575545) act as reversible Wnt pathway inhibitors and exhibit similar pharmacological effects both in vitro and in vivo, IWR-1-endo exerts its effect via interaction with Axin, while XAV939 binds TNKS directly. | [Biochem/physiol Actions]
Cell permeable: yes | [storage]
Store at RT | [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) Lu?et al.?(2009),?Structure-activity Relationship Studies of Small-Molecule Inhibitors of Wnt Response; Bioorg. Med. Chem. Lett.,?19?3825
3) Martins-Neves?et al.?(2018),?IWR-1, a tankyrase inhibitor, attenuates Wnt/?-catenin signaling in cancer stem-like cells and inhibits in vivo the growth of subcutaneous human osteosarcoma xenograft; Cancer Lett.,?414?1
4) Kim?et al.?(2013),?Modulations of ?-catenin function maintains mouse epiblast stem cell and human embryonic stem cell self-renewal; Nat. Commun., 4?4403
5) Ren?et al.?(2011),?Small Molecule Wnt Inhibitors Enhance the Efficiency of BMP-4-directed Cardiac Differentiation of Human Pluripotent Stem Cells; J. Mol. Cell. Cardiol.,?51?280 |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
LETOPHARM LIMITED
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| Telephone: |
+86-21-5821 5861 |
| Website: |
www.letopharm.com |
| Company Name: |
Sigma-Aldrich
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| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
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