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S8195

Sigma-Aldrich

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:
72741-87-8
Molecular Weight:
173.21
Beilstein:
4175740
MDL number:
MFCD00017554
UNSPSC Code:
51102829
PubChem Substance ID:
24899779
NACRES:
NA.85

biological source

Metarrhizium anisopliae

Quality Level

200

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

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Application

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 .
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 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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

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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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
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International journal of biological sciences, 8(3), 394-405 (2012-03-07)
Swainsonine (1, 2, 8-trihyroxyindolizidine, SW), a natural alkaloid, has been reported to exhibit anti-cancer activity on several mouse models of human cancer and human cancers in vivo. However, the mechanisms of SW-mediated tumor regression are not clear. In this study
S Mohla et al.
Journal of the National Medical Association, 81(10), 1049-1056 (1989-10-01)
Swainsonine, an indolizidine alkaloid with immunomodulatory activity, has been found to be effective in inhibiting metastatic dissemination and growth of primary tumors of both murine and human origins. The unique ability of swainsonine to exhibit antimetastatic, anti-proliferative, and immunomodulatory activity
Glenn Archibald et al.
The Journal of organic chemistry, 77(18), 7968-7980 (2012-08-16)
Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine
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Organic letters, 15(8), 1914-1917 (2013-04-05)
A short synthesis of hydroxyalkyl dihydropyrroles has been developed that involves the coupling of propargylamines with α-chloroaldehydes, followed by Lindlar reduction and a one-pot epoxide formation/opening sequence. The application of this process to the synthesis of unnatural iminosugars and a
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