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
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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
Fábio S Mendonça et al.
Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc, 24(1), 90-95 (2012-03-01)
A disease of the nervous system is reported in goats in the semiarid region of northeastern Brazil. Histological examination showed diffuse vacuolation of neurons and epithelial cells of the pancreas, thyroid, renal tubules, and liver. The swainsonine-containing plant Ipomoea verbascoidea
Julien Louvel et al.
Organic letters, 13(24), 6452-6455 (2011-11-16)
The asymmetric synthesis of (-)-swainsonine and (-)-8-epi-swainsonine is reported through the addition of either the allenylzinc or the allenyl lithio cyanocuprate reagents derived from [3-(methoxymethoxy)prop-1-ynyl]trimethylsilane to enantiopure α,β-dialkoxy N-tert-butanesulfinylimines derived from d-erythronolactone.