Skip to Content
Merck

S9263

Swainsonine

solid, ≥99% (HPLC)

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C8H15NO3
CAS Number:
72741-87-8
Molecular Weight:
173.21
NACRES:
NA.32
PubChem Substance ID:
24899832
UNSPSC Code:
12352210
MDL number:
MFCD00017554
Beilstein/REAXYS Number:
4175740

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

200

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

S9263-PH: + S9263-.1MG-PW: + S9263-.1MG: + S9263-BULK-N: + S9263-.5MG-PW: + S9263-PPG: + S9263-.5MG: + S9263-BULK: + S9263-VAR: + S9263PROC: + S9263-2MG:

jan

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SLCL5831
SLCD6196
SLCB1078
SLBW0305
SLBV4808

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service