Inhibitor of α- and β-glucosidases
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Castanospermine

Item No. 11313

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(8aR)-octahydro-1S,6S,7R,8R-indolizinetetrol
CAS Number
79831-76-8
Synonyms
  • 6,7-Diepicastanospermine
  • 6-Epicastanospermine
  • NSC 625381
  • 1,6,7,8-Tetrahydroxyoctahydroindolizine
Molecular Formula
C8H15NO4
Formula Weight
189.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.1 mg/mlDMSO: 10 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O[C@H]1CCN2C[C@H](O)[C@@H](O)[C@H](O)[C@]21[H]
InChi Code
InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1
InChi Key
JDVVGAQPNNXQDW-TVNFTVLESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Glucosidases catalyze the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. Castanospermine is an inhibitor of both α- and β-glucosidases, inhibiting lysosomal and neutral α-glucosidases with Ki values of 0.1 and 10 μM, respectively, and lysosomal and cytosolic β-glucosidases with Ki values of 7 and 40 μM, respectively.1 It is effective both in vitro and in vivo.2,3 Through its effects on glucosidases, castanospermine blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions that are dependent on glycosylation, including angiogenesis.3,4 Castanospermine also interferes with viral replication and infection that is dependent on glucosidase activity.5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Winchester, B.G., di Bello, I.C., Richardson, A.C., et al. The structural basis of the inhibition of human glycosidases by castanospermine analogues. Biochem. J. 269(1), 227-231 (1990).

    2. Saul, R., Ghidoni, J.J., Molyneux, R.J., et al. Castanospermine inhibits α-glucosidase activities and alters glycogen distribution in animals. Proc. Natl. Acad. Sci. USA 82(1), 93-97 (1985).

    3. Pili, R., Chang, J., Partis, R.A., et al. The α-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, prevents angiogenesis, and inhibits tumor growth. Cancer Res. 55(13), 2920-2926 (1995).

    4. Simsolo, R.B., Ong, J.M., and Kern, P.A. Characterization of lipoprotein lipase activity, secretion, and degredation at different sites of post-translational processing in primary cultures of rat adipocytes. J. Lipid Res. 33(12), 1777-1784 (1992).

    5. Montefiori, D.C., Robinson, W.E., Jr., and Mitchell, W.M. Role of protein N-glycosylation in pathogenesis of human immunodeficiency virus type 1. Proc. Natl. Acad. Sci. USA 85(23), 9248-9252 (1988).

    6. Walker, B.D., Kowalski, M., Goh, W.C., et al. Inhibition of human immunodeficiency virus syncytium formation and virus replication by castanospermine. Proc. Natl. Acad. Sci. USA 84(22), 8120-8124 (1987).

    7. Whitby, K., Pierson, T.C., Geiss, B., et al. Castanospermine, a potent inhibitor of dengue virus infection in vitro and in vivo. J. Virol. 79(14), 8698-8706 (2005).