Swainsonine
SIGMA/S9263 - synthetic
Synonym: (1S,2R,8R,8aR)
CAS Number: 72741-87-8
Empirical Formula (Hill Notation): C8H15NO3
Molecular Weight: 173.21
MDL Number: MFCD00017554
Linear Formula: C8H15NO3
Product Type: Chemical
| assay | ≥95% (HPLC) |
| biological source | synthetic |
| form | solid |
| InChI | 1S/C8H15NO3/c10-5-2-1-3-9 |
| InChI key | FXUAIOOAOAVCGD-DCDLSZRSSA |
| Quality Level | 200  |
| SMILES string | O[C@@H]1CCCN2C[C@@H](O)[C |
| solubility | methanol: 5 mg/mL, clear, colorless to light yellow |
| storage temp. | −20°C |
| 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 |
| Application: | 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. |
| 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. |
| Hazard Codes | Xn |
| Risk Statements | 20/21/22 |
| Safety Statements | 36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Purity | ≥95% (HPLC) |
| Storage Temp. | −20°C |
| UNSPSC | 12352210 |