An inhibitor of eIF2α dephosphorylation
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Salubrinal

Item No. 14735

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-3-phenyl-N-[2,2,2-trichloro-1-[[(8-quinolinylamino)thioxomethyl]amino]ethyl]-2-propenamide
CAS Number
405060-95-9
Molecular Formula
C21H17Cl3N4OS
Formula Weight
479.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.3 mg/ml
λmax
216, 246, 275 nm
SMILES
O=C(NC(NC(NC1=C(N=CC=C2)C2=CC=C1)=S)C(Cl)(Cl)Cl)/C=C/C3=CC=CC=C3
InChi Code
InChI=1S/C21H17Cl3N4OS/c22-21(23,24)19(27-17(29)12-11-14-6-2-1-3-7-14)28-20(30)26-16-10-4-8-15-9-5-13-25-18(15)16/h1-13,19H,(H,27,29)(H2,26,28,30)/b12-11+
InChi Key
LCOIAYJMPKXARU-VAWYXSNFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Salubrinal is a selective phosphatase inhibitor that prevents dephosphorylation of eukaryotic translation initiation factor 2 subunit α (eIF2α), protecting PC12 cells from endoplasmic reticulum stress-mediated apoptosis (EC50 = 15 μM).1,2 It appears to block the action of protein phosphatase 1 (PP1) on eIF2α although it does not mimic calyculin A, another PP1-selective inhibitor, in toxicity or phosphorylation pattern.1 Salubrinal also prevents replication of herpes virus (IC50 = 3 μM), by inhibiting dephosphorylation of eIF2α.1 As eIF2α has a role in bone formation, salubrinal is being studied for its effects in osteoporosis.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Boyce, M., Bryant, K.F., Jousse, C., et al. A selective inhibitor of eIF2α dephosphorylation protects cells from ER stress. Science 307(5711), 935-939 (2005).

    2. Long, K., Boyce, M., Lin, H., et al. Structure-activity relationship studies of salubrinal lead to its active biotinylated derivative. Bioorg. Med. Chem. Lett. 15(17), 3849-3852 (2005).

    3. Yokota, H., Hamamura, K., Chen, A., et al. Effects of salubrinal on development of osteoclasts and osteoblasts from bone marrow-derived cells. BMC Musculoskelet. Disord. 14, 197 (2013).