All Photos(1)
Synonym(s):
(1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol
Empirical Formula (Hill Notation):
C8H15NO3
CAS Number:
Molecular Weight:
173.21
Beilstein:
4175740
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32
Recommended Products
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.
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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N-glycosylation by N-acetylglucosaminyltransferase V enhances the interaction of CD147/basigin with integrin beta1 and promotes HCC metastasis
Cui J, et al.
The Journal of Pathology, 245(1), 41-52 (2018)
Swainsonine, an alpha-mannosidase inhibitor, may worsen cervical cancer progression through the increase in myeloid derived suppressor cells population
SilveiraCRF, et al.
PLoS ONE, 14(3), e0213184-e0213184 (2019)
Swainsonine biosynthesis genes in diverse symbiotic and pathogenic fungi
Cook D, et al.
G3 (Bethesda, Md.), 7(6), 1791-1797 (2017)
Exposure to swainsonine impairs adult neurogenesis and spatial learning and memory
Wang J, et al.
Toxicology Letters, 232(1), 263-270 (2015)
Julien Louvel et al.
Organic letters, 13(24), 6452-6455 (2011-11-16)
The asymmetric synthesis of (-)-swainsonine and (-)-8-epi-swainsonine is reported through the addition of either the allenylzinc or the allenyl lithio cyanocuprate reagents derived from [3-(methoxymethoxy)prop-1-ynyl]trimethylsilane to enantiopure α,β-dialkoxy N-tert-butanesulfinylimines derived from d-erythronolactone.
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