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S8195

Sigma-Aldrich

Swainsonine

from Metarrhizium anisopliae, ≥98% (TLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C8H15NO3
Número de CAS:
72741-87-8
Peso molecular:
173.21
Beilstein:
4175740
Número MDL:
MFCD00017554
Código UNSPSC:
51102829
ID de la sustancia en PubChem:
24899779
NACRES:
NA.85

origen biológico

Metarrhizium anisopliae

Nivel de calidad

200

Análisis

≥98% (TLC)

formulario

lyophilized powder

condiciones de almacenamiento

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

color

white to faint yellow

solubilidad

H2O: soluble 1 mg/mL

espectro de actividad antibiótica

neoplastics

Modo de acción

enzyme | inhibits

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

FXUAIOOAOAVCGD-DCDLSZRSSA-N

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Aplicación

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.

Acciones bioquímicas o fisiológicas

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

Envase

1MG

Nota de preparación

Soluble in water, methanol, DMSO

Otras notas

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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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