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S8195

Sigma-Aldrich

Swainsonine

from Metarrhizium anisopliae, ≥98% (TLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C8H15NO3
Numero CAS:
72741-87-8
Peso molecolare:
173.21
Beilstein:
4175740
Numero MDL:
MFCD00017554
Codice UNSPSC:
51102829
ID PubChem:
24899779
NACRES:
NA.85

Origine biologica

Metarrhizium anisopliae

Livello qualitativo

200

Saggio

≥98% (TLC)

Forma fisica

lyophilized powder

Condizioni di stoccaggio

(Keep container tightly closed in a dry and well-ventilated place.)

Colore

white to faint yellow

Solubilità

H2O: soluble 1 mg/mL

Spettro attività antibiotica

neoplastics

Modalità d’azione

enzyme | inhibits

Temperatura di conservazione

2-8°C

Stringa SMILE

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
FXUAIOOAOAVCGD-DCDLSZRSSA-N

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Categorie correlate

Applicazioni

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.

Azioni biochim/fisiol

Swainsonine is a potent α-mannosidase inhibitor. It also has antimetastatic, antiproliferative, and immunomodulatory activity . It also inhibits glycoprotein processing.

Confezionamento

1MG

Nota sulla preparazione

Soluble in water, methanol, DMSO

Altre note

Keep container tightly closed in a dry and well-ventilated place.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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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
Zhaocai Li et al.
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
Vijay Dhand et al.
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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