Inhibitor of N-linked glycoside hydrolases
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Swainsonine

Item No. 16860

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,2R,8aR)-octahydro-indolizinetriol
CAS Number
72741-87-8
Synonyms
  • Tridolgosir
Molecular Formula
C8H15NO3
Formula Weight
173.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 0.25 mg/ml
SMILES
O[C@@H]1CN2CCC[C@@H](O)[C@]2([H])[C@@H]1O
InChi Code
InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1
InChi Key
FXUAIOOAOAVCGD-WCTZXXKLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $61

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    1 mg

    $112

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    5 mg

    $462

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    10 mg

    $807

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    Cayman Chemical
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    Product Description

    Swainsonine is an indolizidine alkaloid naturally found in certain plants including locoweed that inhibits N-linked glycoside hydrolases, preventing the processing of asparagine-linked glycoproteins. It reversibly inhibits lysosomal α-mannosidase and Golgi α-mannosidase II (IC50 = 0.2 μM).1 Swainsonine is used to study the role of N-linked glycosylation in cellular processes and has been shown to have antiproliferative and antimetastatic effects on cancer cells in culture and in mice.2,3,4 The inhibition of α-mannosidase activity in lysosomes produces an accumulation of partially-processed oligosaccharides and glycoproteins, giving rise to lysosomal storage disease. Swainsonine toxicity in herbivores results in a condition known as locoism, characterized by hyperactivity, aggression, stiff and clumsy gait, low head carriage, salivation, seizures, and apparent blindness, culminating in increased miscoordination, weakness and death.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tulsiana, D.R.P., Broquist, H.P., and Touster, O. Marked differences in the swainsonine inhibition of rat liver lysosomal α-D-Mannosidase, Rat Liver Golgi Mannosidase II, and Jack Bean α-D-Mannosidase. Arch. Biochem. Biophys. 236, 427-434 (1985).

    2. Dennis, J.W., Koch, K., Yousefi, S., et al. Growth inhibition of human melanoma tumor xenografts in athymic nude mice by swainsonine. Cancer Res. 50, 1867-1872 (1990).

    3. Reddy, B.V.V.G., and Kalraiya, R.D. Sialilated β1,6 branched N-oligosaccharides modulate adhesion, chemotaxis, and motility of melanoma cells: Effect on invasion and spontaneous metastasis properties. Biochim. Biophys. Acta 1760, 1393-1402 (2006).

    4. Sun, J.Y., Zhu, M.Z., Wang, S.W., et al. Inhibition of the growth of human gastric carcinoma in vivo and in vitro by swainsonine. Phytomedicine 14, 353-359 (2007).

    Product Citations

    Traini, M., Kumaran, R., Thaysen-Andersen, M., et al. N-glycosylation of human sphingomyelin phosphodiesterase acid-like 3A (SMPDL3A) is essential for stability, secretion and activity. Biochem. J. 474(7), 1071-1092 (2017).