SML0244
Thiamet G
≥98% (HPLC), O-GlcNAcase inhibitor, powder
Sinónimos:
(3aR,5R,6S,7R,7aR)-2-(ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-Pyrano[3,2-d]thiazole-6,7-diol
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Fórmula empírica (notación de Hill):
C9H16N2O4S
Número CAS:
Peso molecular:
248.30
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Servicio técnico
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Permítanos ayudarleNombre del producto
Thiamet G, ≥98% (HPLC)
Quality Level
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
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.
signalword
Warning
hcodes
Hazard Classifications
Skin Sens. 1B
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Scott A Yuzwa et al.
Nature chemical biology, 4(8), 483-490 (2008-07-01)
Pathological hyperphosphorylation of the microtubule-associated protein tau is characteristic of Alzheimer's disease (AD) and the associated tauopathies. The reciprocal relationship between phosphorylation and O-GlcNAc modification of tau and reductions in O-GlcNAc levels on tau in AD brain offers motivation for
O-GlcNAc transferase inhibits KSHV propagation and modifies replication relevant viral proteins as detected by systematic O-GlcNAcylation analysis
Jochmann R, et al.
Glycobiology, 23(10), 1114-1130 (2013)
Scott A Yuzwa et al.
Nature chemical biology, 8(4), 393-399 (2012-03-01)
Oligomerization of tau is a key process contributing to the progressive death of neurons in Alzheimer's disease. Tau is modified by O-linked N-acetylglucosamine (O-GlcNAc), and O-GlcNAc can influence tau phosphorylation in certain cases. We therefore speculated that increasing tau O-GlcNAc