Swainsonine

Base Information

• Chemical Name: Swainsonine
• CAS No.: 72741-87-8
• Molecular Formula: C8H15NO3
• Molecular Weight: 173.212
• Hs Code.: 29339900
• European Community (EC) Number: 615-797-6
• NSC Number: 614553
• UNII: RSY4RK37KQ
• DSSTox Substance ID: DTXSID5046356
• Nikkaji Number: J12.698E
• Wikipedia: Swainsonine
• Wikidata: Q415324
• NCI Thesaurus Code: C152742
• Pharos Ligand ID: 8KU45WX6YPXL
• Metabolomics Workbench ID: 53458
• ChEMBL ID: CHEMBL371197
• Mol file: 72741-87-8.mol

Synonyms:Swainsonine;Swainsonine, (1R-(2 beta,8a alpha))-Isomer;Swainsonine, (2 beta,8a alpha)-Isomer;Swainsonine, (8 alpha)-Isomer;Swainsonine, (8 alpha,8a alpha)-Isomer;Swainsonine, (8a alpha)-Isomer

Chemical Property of Swainsonine

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Vapor Pressure: 2.1E-06mmHg at 25°C
• Melting Point: 148-149oC
• Refractive Index: 1.608
• Boiling Point: 353.302 °C at 760 mmHg
• PKA: 14.01±0.60(Predicted)
• Flash Point: 209.735 °C
• PSA: 63.93000
• Density: 1.382 g/cm³
• LogP: -1.51500
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble1mg/mL
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 173.10519334
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

98%,99%, ^*data from raw suppliers

Swainsonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(C2C(C(CN2C1)O)O)O
• Isomeric SMILES: C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)O)O
• 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
• 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 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 shunts the pathway towards hybrid-type oligosaccharides. Swainsonine does not appear to inhibit secretion or expression of glycoproteins at the cell surface. Swainsonine is stable for at least 24 h at 37oC in culture media at physiological pH. Working concentration range is 17-1700 ng/ml (0.1-10mM). Swainsonine (at 1 mg/ml) is not cytotoxic and does not inhibit the growth of a variety of mammalian cell lines. Concentrations required to inhibit Golgi a-mannosidase II in vivo may be somewhat higher, as swainsonine tends to concentrate in the acid environment of cell lysosomes, where it exists as a charged cation and does not permeate through membranes readily. Swainsonine blocks the processing of high-mannose oligosaccharides to complex oligosaccharides. Glycoproteins synthesized in the presence of swainsonine tend to carry mostly high-mannose and hybrid oligosaccharide chains. With short treatments (<24 h) with the inhibitor, cells may retain some complex glycoproteins due to asynchronous cell growth and glycoprotein synthesis. 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.

Technology Process of Swainsonine

There total 470 articles about Swainsonine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester (72741-89-0) → swainsonine (72741-87-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

Reference yield: 96.0%

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol (85624-09-5) → swainsonine (72741-87-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1021/jo961101b

Reference yield: 95.0%

(1S,2R,8R,8aR)-1,2-(cyclohexylidenedioxy)-8-hydroxyindolizidine (129421-04-1) → swainsonine (72741-87-8)

Guidance literature:

With hydrogenchloride; at 65 - 70 ℃; for 0.5h;

upstream raw materials:

Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester

(1S,2R,8R,8aR)-1,2-(cyclohexylidenedioxy)-8-hydroxyindolizidine

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol

(R)-4-((3aS,4R,6aR)-5-Benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-4-benzyloxy-butan-1-ol

Downstream raw materials:

swainsonine N-oxide

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol

Refernces

• 1、 Schneider,Ungemach,Broquist,Harris. "(1S,2R,8R,8aR)-1,2,8-Trihydroxyoctahydroindolizine (Swainsonine), an α-mannosidase inhibitor from Rhizoctonia leguminicola". . p. 29 - 32. Retrieved 1983.
• 2、 Harris,Campbell,Molyneux,Harris. "Biosynthesis of swainsonine in the diablo locoweed (Astragalus oxyphysus)". . p. 4815 - 4818. Retrieved 1988.
• 3、 -. "A process for preparing the swainsonine [( -) - Swainsonine] method". . . Retrieved 2017/08/25.
• 4、 Singh, Priyanka,Manna, Sudipta Kumar,Panda, Gautam. "Synthesis of polyhydroxylated indolizidines and piperidines from Garner's aldehyde: Total synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, (+)-8,8a-di-epi-castanospermine, pentahydroxy indolizidines, (-)-1-deoxynojirimycin, (-)-1-deoxy-altro-nojirimycin, and related diversity". . p. 1363 - 1374. Retrieved 2014/02/14.