Castanospermine

Modify Date: 2024-01-02 01:03:15

Castanospermine Structure
Castanospermine structure
 Common Name Castanospermine
CAS Number 79831-76-8 Molecular Weight 189.209
Density 1.5±0.1 g/cm3 Boiling Point 421.9±45.0 °C at 760 mmHg
Molecular Formula C8H15NO4 Melting Point 213-217 °C(lit.)
MSDS Chinese USA Flash Point 267.6±27.4 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Castanospermine


Castanospermine inhibits all forms of α- and β-glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids).target：α- and β-glucosidases.IC 50: 1.2 uM [2] in vitro :Castanospermine, [(1 S,6S,7R,8R,8aR)-1 ,6,7,8-tetrahydroxyoctahydroindolizine]is a potent and specific inhibitor of mammalian and plant α-and β-D-glucosidases in vitro [1] in vivo: Experiments in vivo with castanospermine, an inhibitor of the glucosidases that convert protein N-linked high mannose carbohydrates to complex oligosaccharides, resulted in significant inhibition of tumor growth in nude mice.[3]

 Names

Name castanospermine
Synonym More Synonyms

 Castanospermine Biological Activity

Description Castanospermine inhibits all forms of α- and β-glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids).target：α- and β-glucosidases.IC 50: 1.2 uM [2] in vitro :Castanospermine, [(1 S,6S,7R,8R,8aR)-1 ,6,7,8-tetrahydroxyoctahydroindolizine]is a potent and specific inhibitor of mammalian and plant α-and β-D-glucosidases in vitro [1] in vivo: Experiments in vivo with castanospermine, an inhibitor of the glucosidases that convert protein N-linked high mannose carbohydrates to complex oligosaccharides, resulted in significant inhibition of tumor growth in nude mice.[3]
Related Catalog
References

[1]. Bryan G, Anthony C et al. The structural basis of the inhibition of human glycosidases by castanospermine analogues. Biochem. J. (1990) 269, 227-231.

[2]. Eisaku Tsujii et al. Nectrisine Is a Potent Inhibitor of a-Glucosidases, Demonstrating Activities Similarly at Enzyme and Cellular Levels. Biochemical and Biophysical Research Communications 220, 459-466 (1996)

[3]. Pili R et al. The alpha-glucosidase I inhibitor castanospermine alters endothelial cell glycosylation, preventsangiogenesis, and inhibits tumor growth. Cancer Res. 1995 Jul 1;55(13):2920-6.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 421.9±45.0 °C at 760 mmHg
Melting Point 213-217 °C(lit.)
Molecular Formula C8H15NO4
Molecular Weight 189.209
Flash Point 267.6±27.4 °C
Exact Mass 189.100113
PSA 84.16000
LogP -1.61
Vapour Pressure 0.0±2.3 mmHg at 25°C
Index of Refraction 1.647
Storage condition 2-8°C
Water Solubility 1 M HCl: 20 mg/mL, clear, very faintly yellow

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H312-H332
Precautionary Statements P280
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn: Harmful;Xi: Irritant;
Risk Phrases 20/21/22
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3

 Synthetic Route

 Articles36

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 Synonyms

1,6,7,8-Indolizinetetrol, octahydro-, (1S,6S,7R,8R,8aR)-
Castanospermine
(1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol
Castanospermine,[1S-(1α,6β,7α,8β,8aβ)]-Octahydro-1,6,7,8-indolizinetetrol
(1S,6S,7R,8R,8aR)-Octahydroindolizine-1,6,7,8-tetrol
MFCD00017555
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Related Compounds: More...
Castanospermine
171335-80-1
Castanospermine ester
121104-76-5
6-epi-castanospermine
107244-34-8
1-deoxycastanospermine
115649-93-9
7-O-deriv,Castanospermine
121104-88-9
Castanospermine,6-O-furoyl
121104-92-5
castanospermine tetraacetate
79831-77-9
6,7-anhydro-epi-castanospermine
156205-61-7
6-ACETAMIDO-6-DEOXY-CASTANOSPERMINE
134100-29-1
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