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S9263 Sigma-Aldrich

Swainsonine

synthetic

Synonym: (1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol

  • CAS Number 72741-87-8

  • Empirical Formula (Hill Notation) C8H15NO3

  • Molecular Weight 173.21

  •  Beilstein/REAXYS Number 4175740

  •  MDL number MFCD00017554

  •  PubChem Substance ID 24899832

  •  NACRES NA.32

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Properties

Related Categories Biochemicals and Reagents, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, Glycobiology,
Quality Level   200
biological source   synthetic
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

Description

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
NM2408666
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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92210 Timestrip Plus 0 °C
06693 Timestrip Plus -20 °C

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