Control for IWR-1-endo
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Isomer(s)
13659IWR-1-endo
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IWR-1-exo

Item No. 13598

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
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-benzamide
CAS Number
1127442-87-8
Molecular Formula
C25H19N3O3
Formula Weight
409.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 1 mg/mlDMF: 5 mg/mlDMF:PBS (pH 7.2) (1:3): 0.25 mg/mlDMSO: 0.3 mg/ml
λmax
202, 241, 320 nm
SMILES
[H][C@]12[C@](C(N(C3=CC=C(C(NC4=CC=CC5=C4N=CC=C5)=O)C=C3)C2=O)=O)([H])[C@@H]6C=C[C@H]1C6
InChi Code
InChI=1S/C25H19N3O3/c29-23(27-19-5-1-3-14-4-2-12-26-22(14)19)15-8-10-18(11-9-15)28-24(30)20-16-6-7-17(13-16)21(20)25(28)31/h1-12,16-17,20-21H,13H2,(H,27,29)/t16-,17+,20+,21-
InChi Key
ZGSXEXBYLJIOGF-BTYSMDAFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Wnt signaling proteins are small secreted proteins that are active in embryonic development, tissue homeostasis,1 and tumorigenesis.2,3 Wnt proteins bind to receptors on the cell surface, initiating a signaling cascade that leads to β-catenin activation of gene transcription. IWR-1-exo is a diastereomer of IWR-1-endo, the potent inhibitor of the Wnt response.4 Whereas IWR-1-endo strongly blocks cell-based Wnt/β-catenin pathway reporter response (IC50 = 180 nM)4 and suppresses Wnt-dependent zebrafish tail fin regeneration (0.5 μM),5 IWR-1-exo has little effect in either assay at 10 μM.4 Thus, this compound is an ideal control for tests involving the active form, IWR-1-endo.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Clevers, H. Wnt/β-catenin signaling in development and disease. Cell 127(3), 469-480 (2006).

    2. Polakis, P. Wnt signaling and cancer. Genes Dev. 14(15), 1837-1851 (2000).

    3. Reya, T., and Clevers, H. Wnt signalling in stem cells and cancer. Nature 434(7035), 834-850 (2005).

    4. Chen, B., Dodge, M.E., Tang, W., et al. Small molecule-mediated disruption of Wnt-dependent signaling in tissue regeneration and cancer. Nat. Chem. Biol. 5(2), 100-107 (2009).

    5. Lu, J., Ma, Z., Hsieh, J.C., et al. Structure-activity relationship studies of small-molecule inhibitors of Wnt response. Bioorg. Med. Chem. Lett. 19(14), 3825-3827 (2009).