S9263

Swainsonine

Name: Swainsonine
Brand: SIGMA

solid, ≥99% (HPLC)

Sinónimos:

(1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol

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About This Item

Fórmula empírica (notación de Hill):

C₈H₁₅NO₃

Número CAS:

72741-87-8

Peso molecular:

173.21

NACRES:

NA.32

PubChem Substance ID:

24899832

UNSPSC Code:

12352210

MDL number:

MFCD00017554

Beilstein/REAXYS Number:

4175740

Nombre del producto

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

200

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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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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)

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, an alpha-mannosidase inhibitor, may worsen cervical cancer progression through the increase in myeloid derived suppressor cells population.

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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