SML0244

Thiamet G

≥98% (HPLC)

• Synonym(s): (3aR,5R,6S,7R,7aR)-2-(ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-Pyrano[3,2-d]thiazole-6,7-diol
• Empirical Formula (Hill Notation): C₉H₁₆N₂O₄S
• CAS Number: 1009816-48-1
• Molecular Weight: 248.30
• MDL number: MFCD15144964
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825254
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D -21 to -26°, c = 0.3 in methanol
• storage condition: desiccated
• color: white to beige
• solubility: H₂O: ≥5 mg/mL at warmed to 60 °C
• storage temp.: −20°C
• SMILES string: CCNC1=N[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]2S1
• InChI: 1S/C9H16N2O4S/c1-2-10-9-11-5-7(14)6(13)4(3-12)15-8(5)16-9/h4-8,12-14H,2-3H2,1H3,(H,10,11)/t4-,5-,6-,7-,8-/m1/s1
• InChI key: PPAIMZHKIXDJRN-FMDGEEDCSA-N

Description

Application

Thiamet G has been used as an O-GlcNAcase inhibitor:

• to treat human embryonic kidney 293 cells in order to study its effect on Wnt/beta-catenin signalling
• to treat lytically-replicating producer
• to incubate mice (C57BL/6) aortic segments to increase global O-GlcNAc levels

Biochem/physiol Actions

Thiamet G is a glycosidase inhibitor

Thiamet G is a potent inhibitor of the enzyme O-GlcNAcase (Ki = 21 nM). The compound is orally bioavailable and crosses the blood brain barrier. Thiamet G leads to an increase in O-GlcNAc-modified proteins in cell-based and in vivo assay systems, and reduces levels of phosphorylated Tau protein in rat cortex and hippocampus.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H317
• Precautionary Statements: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Hazard Classifications: Skin Sens. 1B
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable