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S8195

Swainsonin

Name: Swainsonin
Brand: SIGMA

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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Terminal N-linked galactose is the primary receptor for adeno-associated virus 9.

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

Swainsonine activates mitochondria-mediated apoptotic pathway in human lung cancer A549 cells and retards the growth of lung cancer xenografts.

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

Swainsonine: a new antineoplastic immunomodulator.

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

A divergent approach to 3-piperidinols: a concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton.

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

A short, organocatalytic formal synthesis of (-)-swainsonine and related alkaloids.

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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