A GSK3β inhibitor
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AZD 2858

Item No. 16728

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-amino-6-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-N-3-pyridinyl-2-pyrazinecarboxamide
CAS Number
486424-20-8
Molecular Formula
C21H23N7O3S
Formula Weight
453.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:5): 0.1 mg/mlDMSO: 5 mg/ml
λmax
224, 304, 383 nm
SMILES
NC1=NC=C(C2=CC=C(S(N3CCN(C)CC3)(=O)=O)C=C2)N=C1C(NC4=CC=CN=C4)=O
InChi Code
InChI=1S/C21H23N7O3S/c1-27-9-11-28(12-10-27)32(30,31)17-6-4-15(5-7-17)18-14-24-20(22)19(26-18)21(29)25-16-3-2-8-23-13-16/h2-8,13-14H,9-12H2,1H3,(H2,22,24)(H,25,29)
InChi Key
FHCSBLWRGCOVPT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $37

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    5 mg

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    10 mg

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    Product Description

    Glycogen synthase kinase 3β (GSK3β) was originally identified for its ability to constitutively phosphorylate and inactivate glycogen synthase, preventing glycogen synthesis.1 It can also phosphorylate proteins that are relevant to osteogenesis and Alzheimer’s disease, the latter for which it has earned the moniker, tau phosphorylating kinase.2,3,4 AZD 2858 is a pyrazine analog that inhibits GSK3β with a Ki value of 4.9 nM.5 It crosses the blood brain barrier and inhibits tau phosphorylation in vitro with an IC50 value of 76 nM.5 AZD 2858 has also been shown to increase bone mass (via Wnt activation) in rats after a two-week treatment with a maximum effective oral dose of 20 mg/kg once daily.6 Furthermore, by inhibiting GSK3β, AZD 2858 can stabilize β-catenin in rat mesenchymal stem cells (EC50 = 234 nM), spurring osteoblast differentiation.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ring, D.B., Johnson, K.W., Henriksen, E.J., et al. Selective glycogen synthase kinase 3 inhibitors potentiate insulin activation of glucose transport and utilization in vitro and in vivo. Diabetes 52(3), 588-595 (2003).

    2. Asuni, A.A., Hooper, C., Reynolds, C.H., et al. GSK3α exhibits β-catenin and tau directed kinase activities that are modulated by Wnt. Eur. J. Neurosci. 24(12), 3387-3392 (2006).

    3. Phiel, C.J., Wilson, C.A., Lee, V.M., et al. GSK-3α regulates production of Alzheimer’s disease amyloid-β peptides. Nature 423(6938), 435-439 (2003).

    4. Guerrero, F., Herencia, C., Almadén, Y., et al. TGF-β prevents phosphate-induced osteogenesis through inhibition of BMP and Wnt/β-catenin pathways. PLoS One 9(2), e89179 (2014).

    5. Berg, S., Bergh, M., Hellberg, S., et al. Discovery of novel potent and highly selective glycogen synthase kinase-3ß (GSK3ß) inhibitors for Alzheimer’s disease: Design, synthesis, and characterization of pyrazines. J. Med. Chem. 55(21), 9107-9119 (2012).

    6. Marsell, R., Sisask, G., Nilsson, Y., et al. GSK-3 inhibition by an orally active small molecule increases bone mass in rats. Bone 50(3), 619-627 (2012).

    7. Gilmour, P.S., O'Shea, P.J., Fagura, M., et al. Human stem cell osteoblastogenesis mediated by novel glycogen synthase kinase 3 inhibitors induces bone formation and a unique bone turnover biomarker profile in rats. Toxicol. Appl. Pharmacol. 272(2), 399-407 (2013).