S8195
Swainsonine
from Metarrhizium anisopliae, ≥98% (TLC)
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
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4175740
biological source
Metarrhizium anisopliae
Quality Level
assay
≥98% (TLC)
form
lyophilized powder
storage condition
(Keep container tightly closed in a dry and well-ventilated place.)
color
white to faint yellow
solubility
H2O: soluble 1 mg/mL
antibiotic activity spectrum
neoplastics
mode of action
enzyme | inhibits
storage temp.
2-8°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
Application
Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II. It inhibits glycoprotein processing and also acts as immune modulator.
Swainsonine is an indolizidine alkaloid from the plant Metarrhizium anisopliae that is used as a potent α-mannosidase inhibitor. Product S8195 has been used in chemical inhibition assays of CHO Lec2 cells to inhibit glycosylation .
Biochem/physiol Actions
Swainsonine is a potent α-mannosidase inhibitor. It also has antimetastatic, antiproliferative, and immunomodulatory activity . It also inhibits glycoprotein processing.
Packaging
1MG
Preparation Note
Soluble in water, methanol, DMSO
Other Notes
Keep container tightly closed in a dry and well-ventilated place.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
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Shen Shen et al.
The Journal of biological chemistry, 286(15), 13532-13540 (2011-02-19)
Sialylated glycans serve as cell surface attachment factors for a broad range of pathogens. We report an atypical example, where desialylation increases cell surface binding and infectivity of adeno-associated virus (AAV) serotype 9, a human parvovirus isolate. Enzymatic removal of
K Olden et al.
Pharmacology & therapeutics, 50(3), 285-290 (1991-01-01)
Swainsonine, an indolizidine alkaloid, was initially used in biomedical research as a tool to investigate the biosynthesis and function of asparagine-linked 'complex' type oligosaccharide moieties of glycoproteins. Recently, swainsonine has generated interest in its potential use as an anticancer agent
Daniel S Grum et al.
Journal of natural products, 76(10), 1984-1988 (2013-09-24)
Legumes belonging to the Astragalus, Oxytropis, and Swainsona genera have been noted by ranchers in the Americas, Asia, and Australia to cause a neurologic disease often referred to as locoism or peastruck. The toxin in these legumes is swainsonine, an