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S9263

Sigma-Aldrich

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:
72741-87-8
Molecular Weight:
173.21
Beilstein/REAXYS Number:
4175740
MDL number:
MFCD00017554
UNSPSC Code:
12352210
PubChem Substance ID:
24899832
NACRES:
NA.32

product name

Swainsonine, synthetic

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

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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_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Exposure to swainsonine impairs adult neurogenesis and spatial learning and memory
Wang J, et al.
Toxicology Letters, 232(1), 263-270 (2015)
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
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