Castanospermine

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For Research Use Only.

Category

Alkaloids

Cat.No.

NP0092

CAS

79831-76-8

Product Name

Castanospermine

Structure

Product Details

Description

Castanospermine is an inhibitor of all forms of α- and β-glucosidases, especially glucosidase l. It inhibits lysosomal and neutral α-glucosidases with Ki values of 0.1 and 10 μM, respectively. It also inhibits lysosomal and cytosolic β-glucosidases with Ki values of 7 and 40 μM, respectively. It inhibits HIV syncytium formation and replication. It catalyzes the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. It is effective both in vitro and in vivo. It blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions, including angiogenesis. It also interferes with viral replication and infection. It is a potent and specific inhibitor of mammalian and plant α-and β-D-glucosidases in vitro.

Synonyms

1,6,7,8-Tetrahydroxyoctahydroindolizine

IUPAC Name

(1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol

Molecular Weight

189.21

Molecular Formula

C8H15NO4

Canonical SMILES

C1CN2CC(C(C(C2C1O)O)O)O

InChI

InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1

InChIKey

JDVVGAQPNNXQDW-TVNFTVLESA-N

Boiling Point

421.9±45.0°C

Melting Point

202-208°C (dec.)

Purity

>98%

Density

1.53±0.1 g/cm3

Solubility

Soluble in DMSO, Water

Appearance

White to Yellow Powder

Application

Castanospermine inhibits HIV syncytium formation and replication. It catalyzes the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. It blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions, including angiogenesis. It also interferes with viral replication and infection.

Shelf Life

2 month in rt, long time

Storage

Store at -20°C

Alpha

D25 +79.7° (c = 0.93 in water)

BRN

3588654

Color

Yellow

10-21

Form

Powder

Hazard Codes

Xn,Xi

Merck

13,1906

pKa

6.09(at 25°C)

Risk Statements

20/21/22-36/37/38

Safety Statements

26-36

Stability

Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.

Uses

Castanospermine, is used as a glycosidase inhibitor and antiinflammatory agent. Castanospermine is used to inhibit syncytium formation between HIV-infected and CD4-expressing cells and may also interfere with infectivity. It has also been demonstrated that this agent inhibits inflammation at the level of leukocyte extravasation in rat models of experimental adjuvant-induced arthritis and autoimmune encephalomyelitis.

Water Solubility

Soluble in water

WGK Germany

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