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SWAINSONINE

Product Name
SWAINSONINE
CAS No.
72741-87-8
Chemical Name
SWAINSONINE
Synonyms
8AR)-1;SwainMoia;Tridolgosir;SWAINSONINE;D-Swainsonine;(-)-Swainsonine;SWAINSONINE 98+%;(-)-D-Swainsonine;Swainsonine min. 99%;swainsonine synthetic
CBNumber
CB0484750
Molecular Formula
C8H15NO3
Formula Weight
173.21
MOL File
72741-87-8.mol
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SWAINSONINE Property

Melting point:
148-149°C
Boiling point:
353.3±21.0 °C(Predicted)
Density 
1.38±0.1 g/cm3 (20 ºC 760 Torr)
storage temp. 
-20°C
solubility 
H2O: soluble1mg/mL
form 
lyophilized powder
pka
14.01±0.60(Predicted)
color 
white to faint yellow
Water Solubility 
Soluble to 50 mM in water
BRN 
4175740
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO, ethanol or distilled water may be stored at -20°C for up to 3 months.
CAS DataBase Reference
72741-87-8
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
36
WGK Germany 
3
RTECS 
NM2408666
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S9263
Product name
Swainsonine
Purity
synthetic
Packaging
0.1mg
Price
$182
Updated
2024/03/01
Sigma-Aldrich
Product number
S9263
Product name
Swainsonine
Purity
synthetic
Packaging
0.5mg
Price
$248.4
Updated
2024/03/01
Sigma-Aldrich
Product number
S8195
Product name
Swainsonine
Purity
from Metarrhizium anisopliae, ≥98% (TLC)
Packaging
1mg
Price
$505
Updated
2024/03/01
Cayman Chemical
Product number
16860
Product name
Swainsonine
Purity
≥98%
Packaging
500μg
Price
$55
Updated
2024/03/01
Cayman Chemical
Product number
16860
Product name
Swainsonine
Purity
≥98%
Packaging
1mg
Price
$101
Updated
2024/03/01
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SWAINSONINE Chemical Properties,Usage,Production

Description

Swainsonine (72741-87-8) is a naturally occurring alkaloidal toxin found in locoweed. Inhibits the biosynthesis of complex glycoproteins by inhibition of Golgi mannosidase II (IC50 = 0.2 mM).1 Inhibits growth and potentiates the cytotoxic effect of taxol in hepatocellular carcinoma in vivo.2 Induces apoptosis in a variety of cell types including cerebral cortical neurons.3 Impairs adult neurogenesis and spatial learning and memory.4? Abrogation of complex glycosylation by swainsonine results in strain-and cell-specific inhibition of prion replication.5 Induces lysosomal storage disease in farm animals.6

Chemical Properties

White Crystalline Solid

Occurrence

Swainsonia canescens yields this simple alkaloid.

Uses

Swainsonine is an indolizidine alkaloid naturally found in certain plants including locoweed that inhibits N-linked glycoside hydrolases, preventing the processing of asparagine-linked glycoproteins. It reversibly inhibits lysosomal α-mannosidase and Golgi α-mannosidase II (IC50 = 0.2 μM). Swainsonine is used to study the role of N-linked glycosylation in cellular processes and has been shown to have antiproliferative and antimetastatic effects of cancer cells in culture and in mice. The inhibition of α-mannosidase activity in lysosomes produces an accumulation of partially-processed oligosaccharides and glycoproteins, giving rise to lysosomal storage disease. Swainsonine toxicity in herbivores results in a condition known as locoism, characterized by hyperactivity, aggression, stiff and clumsy gait, low head carriage, salivation, seizures, and apparent blindness, culminating in increased miscoordination, weakness and death.

Uses

Swainsonine is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydrolysis of mannosidases.Swainsonine completely inhibits mammalian Golgi a-mannosidase II (a-3/6-mannosidase in the glycoprotein processing pathway) and mammalian lysosomal a-mannosidase (acid mannosidase). At higher concentrations, swainsonine also inhibits mammalian cytosolic a-mannosidase. It has been shown to inhibit growth of transformed fibroblasts in soft agar and to enhance the antiproliferative effects of INF on murine lymphoreticular tumor cells in vitro. It also blocks the expression of b1-6 branched complex-type oligosaccharides and shun

Definition

ChEBI: An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.

General Description

Swainsonine is produced by endophytes, plant and insect pathogens. It is synthesized from the pipecolic acid and mevalonic acid. Swainsonine is a water-soluble indole alkaloid.

Biological Activity

Inhibitor of α -mannosidase II which inhibits glycoprotein processing. Displays anticancer and immune modulatory properties.

Biochem/physiol Actions

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

storage

Store at -20°C

References

1) Tulsiani et al. (1985), Marked differences in the swainsonine inhibition of rat liver lysomal alpha-D-mannosidase, rat liver Golgi mannosidase II, and jack bean alpha-D-mannosidase; Arch. Biochem. Biophys., 236 427 2) You et al. (2012), Swainsonine inhibits growth and potentiates the cytotoxic effect of paclitaxel in hepatocellular carcinoma in vitro and in vivo; Oncol. Rep., 28 2091 3) Lu et al. (2015), Swainsonine-induced apoptosis pathway in cerebral cortical neurons; Res. Vet. Sci., 102 34 4) Wang et al. (2015), Exposure to swainsonine impairs adult neurogenesis and spatial learning and memory; Toxicol. Lett., 232 263 5) Browning et al. (2011), Abrogation of complex glycosylation by swainsonine results in strain- and cell-specific inhibition of prion replication; J. Biol. Chem., 286 40962 6) Dantas et al. (2007), Swainsonine-induced lysosomal storage disease in goats caused by the ingestion of Turbina cordata in Northeastern Brazil; Toxicon, 49 111

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Raw materials

Preparation Products

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View Lastest Price from SWAINSONINE manufacturers

Career Henan Chemical Co
Product
SWAINSONINE 72741-87-8
Price
US $1.00/ASSAYS
Min. Order
1ASSAYS
Purity
85.0-99.8%
Supply Ability
20tons
Release date
2020-01-08

72741-87-8, SWAINSONINERelated Search:

CONDURITOL B EPOXIDE (-)-Gossypol Mitomycin C C2 CERAMIDE 1-Hexanol Betaine 1-Octacosanol SWAINSONINE(P) 1,2-di-epi-swainsonine swainsonine N-oxide L-(+)-SWAINSONINE 1,2-ISOPROPYLIDENE SWAINSONINE SWAINSONINE-6,7-3H 6,7-DIHYDROXYSWAINSONINE SWAINSONINE (1S,2R,8R,8AR)-1,2,8-TRIACETOXY-OCTAHYDRO-5-OXYINDOLIZINE

  • Swainsonine, Swainsona canescens - CAS 72741-87-8 - Calbiochem
  • 8-indolizinetriol,octahydro-,(1s,2r,8r,8ar)-2
  • (1S,2S,8R,8AR)-TRIHYDROXYINDOLIZIDINE
  • (1S,2R,8R,8AR)-1,2,8-OCTAHYDROINDOLIZIDINETRIOL
  • 8ALPHA,BETA-INDOLIZIDINE-1,2ALPHA,8BETA-TRIOL
  • 8ALPHA,BETA-INDOLIZIDINE-1ALPHA,2ALPHA,8BETA-TRIOL
  • 8A-BETA-INDOLIZIDINE-1ALPHA,2ALPHA,8BETA-TRIOL
  • 8A,B-INDOLIZIDINE-1,2A,8B-TRIOL
  • 8A,B-OCTAHYDROINDOLIZIDINE-1A,2A,8B-TRIOL
  • swainsonine from locoweed
  • swainsonine from rhizoctonia*leguminicola
  • swainsonine synthetic
  • SWAINSONINE FROM METARRHIZIUM ANISOPLIAE
  • SWAINSONINE FROM RHIZOCTONIA &
  • SWAINSONINE FROM LOCOWEED, 500 UG*
  • SWAINSONINE 98+%
  • Tridolgosir
  • (-)-D-Swainsonine
  • (1S,2α,8β,8aβ)-Octahydro-1,2,8-indolizinetriol
  • (1S,8aβ)-Octahydroindolizine-1α,2α,8β-triol
  • D-Swainsonine
  • (1S,2R,8R,8aR)-Octahydro-1,2,8-indolizinetriol
  • SwainMoia
  • 8a,-Octahydroindolizidine-1a,2a,8-triol
  • SWAINSONINE
  • SWAINSONINE, SWAINSONA CANESCENS
  • 8-indolizinetriol(1s-(1-alpha,2-alpha,8-beta,8a-beta))-octahydro-2
  • 8-indolizinetriol,octahydro-,(1s-(1-alpha,2-alpha,8-beta,8a-beta))-2
  • (-)-SWAINSONINE (1S,2R,8R,8AR)-1,2,8-OCTAHYDROINDOLIZIDINETRIOL (1S,2S,8R,8AR)-TRIHYDROXYINDOLIZIDINE
  • 8α,β-Octahydroindolizidine-1α,2α,8β-triol
  • (1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-Octahydroindolizine-1,2,8-triol
  • Swainsonine min. 99%
  • 8AR)-1
  • 1,2,8-Indolizinetriol,octahydro-, (1S,2R,8R,8aR)-
  • (-)-Swainsonine
  • 72741-87-8
  • Enzymes, Inhibitors, and Substrates
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