S9263
Swainsonine
solid, ≥99% (HPLC)
Synonym(s):
(1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol
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About This Item
Empirical Formula (Hill Notation):
C8H15NO3
CAS Number:
Molecular Weight:
173.21
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352210
MDL number:
Beilstein/REAXYS Number:
4175740
Product Name
Swainsonine, synthetic
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
SMILES string
O[C@@H]1CCCN2C[C@@H](O)[C@@H](O)C12
InChI key
FXUAIOOAOAVCGD-DCDLSZRSSA-N
biological source
synthetic
assay
≥95% (HPLC)
form
solid
solubility
methanol: 5 mg/mL, clear, colorless to light yellow
storage temp.
−20°C
Quality Level
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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
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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 biosynthesis genes in diverse symbiotic and pathogenic fungi
Cook D, et al.
G3 (Bethesda, Md.), 7(6), 1791-1797 (2017)
Caio Raony Farina Silveira et al.
PloS one, 14(3), e0213184-e0213184 (2019-03-07)
Cervical cancer, caused by high oncogenic risk Human Papillomavirus (HPV) infection, continues to be a public health problem, mainly in developing countries. Using peptide phage display as a tool to identify potential molecular targets in HPV associated tumors, we identified
Exposure to swainsonine impairs adult neurogenesis and spatial learning and memory
Wang J, et al.
Toxicology Letters, 232(1), 263-270 (2015)
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