A dual CDK and GSK3 inhibitor
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Alsterpaullone

Item No. 14428

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7,12-dihydro-9-nitro-indolo[3,2-d][1]benzazepin-6(5H)-one
CAS Number
237430-03-4
Synonyms
  • 9-Nitropaullone
  • NSC 705701
Molecular Formula
C16H11N3O3
Formula Weight
293.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
223, 245, 297 nm
SMILES
O=C1CC2=C(NC3=C2C=C([N+]([O-])=O)C=C3)C4=CC=CC=C4N1
InChi Code
InChI=1S/C16H11N3O3/c20-15-8-12-11-7-9(19(21)22)5-6-14(11)18-16(12)10-3-1-2-4-13(10)17-15/h1-7,18H,8H2,(H,17,20)
InChi Key
OLUKILHGKRVDCT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Alsterpaullone is a derivative of kenpaullone (Item No. 10010239), an ATP-competitive inhibitor of several cyclin-dependent kinases (CDKs) as well as glycogen synthase kinase 3β (GSK3β). With slightly improved potency over kenpaullone, alsterpaullone selectively inhibits Cdk1/cyclin B, Cdk2/cyclin A, Cdk2/cyclin E, Cdk5/p25, and GSK3α/β with IC50 values of 35, 15, 200, 40, and 4 nM, respectively.1,2 Alsterpaullone has been used to inhibit the cytosolic degradation of β-catenin to alter the canonical Wnt signaling pathway in primary axis patterning, to reduce tau phosphorylation in an effort to modify neuropathological events associated with Alzheimer’s disease, and to alter cell proliferation or protein expression in various diseases.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Leost, M., Schultz, C., Link, A., et al. Paullones are potent inhibitors of glycogen synthase kinase-3β and cyclin-dependent kinase 5/p25. Eur. J. Biochem. 267(19), 5983-5994 (2000).

    2. Bain, J., McLauchlan, H., Elliot, M., et al. The specificities of protein kinase inhibitors: An update. Biochem. J. 371(Pt. 1), 199-204 (2003).

    3. Trevino, M., Stefanik, D.J., Rodriguez, R., et al. Induction of canonical Wnt signaling by alsterpaullone is sufficient for oral tissue fate during regeneration and embryogenesis in Nematostella vectensis. Dev. Dyn. 240(12), 2673-2679 (2011).

    4. Selenica, M.L., Jensen, H.S., Larsen, A.K., et al. Efficacy of small-molecule glycogen synthase kinase-3 inhibitors in the postnatal rat model of tau hyperphosphorylation. Br J Pharmacol. Br. J. Pharmacol. 152(6), 959-979 (2007).

    5. Makhortova, N.R., Hayhurst, M., Cerqueira, A., et al. A screen for regulators of survival of motor neuron protein levels. Nat. Chem. Biol. 7(8), 544-552 (2011).