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S8195

Sigma-Aldrich

Swainsonin

from Metarrhizium anisopliae, ≥98% (TLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C8H15NO3
CAS-Nummer:
72741-87-8
Molekulargewicht:
173.21
Beilstein:
4175740
MDL-Nummer:
MFCD00017554
UNSPSC-Code:
51102829
PubChem Substanz-ID:
24899779
NACRES:
NA.85

Biologische Quelle

Metarrhizium anisopliae

Qualitätsniveau

200

Assay

≥98% (TLC)

Form

lyophilized powder

Lagerbedingungen

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

Farbe

white to faint yellow

Löslichkeit

H2O: soluble 1 mg/mL

Wirkungsspektrum von Antibiotika

neoplastics

Wirkungsweise

enzyme | inhibits

Lagertemp.

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

InChIKey

FXUAIOOAOAVCGD-DCDLSZRSSA-N

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Anwendung

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 .
Hemmer zahlreicher pflanzlichen und tierischen α-Mannosidasen

Biochem./physiol. Wirkung

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

Verpackung

1MG

Angaben zur Herstellung

Soluble in water, methanol, DMSO

Sonstige Hinweise

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (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
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.
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
Daniel Cook et al.
Journal of chemical ecology, 38(2), 195-203 (2012-01-28)
Locoweeds are defined as Astragalus and Oxytropis species that cause intoxication due to the alkaloid swainsonine. Swainsonine concentrations in Oxytropis sericea were influenced by location, plant part, and the developmental stage of the plant. Concentrations followed similar trends at each
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