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S9263

Sigma-Aldrich

Swainsonine

synthetic

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Synonym(s):
(1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol
Empirical Formula (Hill Notation):
C8H15NO3
CAS Number:
Molecular Weight:
173.21
Beilstein/REAXYS Number:
4175740
MDL number:
PubChem Substance ID:
NACRES:
NA.32

biological source

synthetic

Quality Level

assay

≥99% (HPLC)

form

solid

solubility

methanol: 5 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

SMILES string

O[C@@H]1CCCN2C[C@@H](O)[C@@H](O)C12

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-DCDLSZRSSA-N

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General description

Swainsonine is produced by endophytes, plant and insect pathogens. It is synthesized from the pipecolic acid and mevalonic acid. Swainsonine is a water-soluble indole alkaloid.

Application

Swainsonine has been used:
  • to test its effect on neural stem cell proliferation
  • to inhibit α-mannosidase in TC-1 tumor cells
  • to inhibit β1,6-branching synthesis in hepatocellular carcinoma (HCC) cells

Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II. It inhibits glycoprotein processing and also acts as immune modulator.

Biochem/physiol Actions

Swainsonine is an inhibitor of α-mannosidase in endoplasmic reticulum and Golgi apparatus. It also activates the natural killer cells. Swainsonine elicits neurologic toxicity and its exposure impairs learning and memory resulting in cognitive deficit. It inhibits hepatocellular carcinoma and sensitizes them to respond to anti-cancer drug paclitaxel.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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