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S8195

Sigma-Aldrich

Swainsonine

from Metarrhizium anisopliae, ≥98% (TLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C8H15NO3
Numéro CAS:
72741-87-8
Poids moléculaire :
173.21
Numéro Beilstein :
4175740
Numéro MDL:
MFCD00017554
Code UNSPSC :
51102829
ID de substance PubChem :
24899779
Nomenclature NACRES :
NA.85

Source biologique

Metarrhizium anisopliae

Niveau de qualité

200

Pureté

≥98% (TLC)

Forme

lyophilized powder

Conditions de stockage

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

Couleur

white to faint yellow

Solubilité

H2O: soluble 1 mg/mL

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

enzyme | inhibits

Température de stockage

2-8°C

Chaîne 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

Clé InChI

FXUAIOOAOAVCGD-DCDLSZRSSA-N

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Catégories apparentées

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.

Actions biochimiques/physiologiques

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

Conditionnement

1MG

Notes préparatoires

Soluble in water, methanol, DMSO

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (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
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.
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
Guo-Dong Yang et al.
Toxicon : official journal of the International Society on Toxinology, 60(1), 44-49 (2012-04-10)
Endophytic Undifilum oxytropis found within toxic locoweeds (Astragalus and Oxytropis spp.) produces the indolizidine alkaloid swainsonine, which is responsible for locoism in grazing animals. The aim of the current study is to establish an easy and accurate method for the
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
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