S9263

Swainsonine

synthetic

• Synonym(s): (1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol
• Empirical Formula (Hill Notation): C₈H₁₅NO₃
• CAS Number: 72741-87-8
• Molecular Weight: 173.21
• Beilstein: 4175740
• MDL number: MFCD00017554
• UNSPSC Code: 12352200
• PubChem Substance ID: 24899832
• NACRES: NA.32

Properties

• biological source: synthetic
• Quality Level: 200
• 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 Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves