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SML0244

Sigma-Aldrich

Thiamet G

≥98% (HPLC)

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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:
Molecular Weight:
248.30
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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Thiamet G ≥98% (HPLC)

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NButGT ≥98% (HPLC)

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SML3123

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Brinzolamide ≥98% (HPLC)

Sigma-Aldrich

SML0216

Brinzolamide

form

powder

form

powder

form

powder

form

powder

storage condition

desiccated

storage condition

desiccated

storage condition

-

storage condition

desiccated

color

white to beige

color

white to beige

color

white to beige

color

white to beige

solubility

H2O: ≥5 mg/mL at warmed to 60 °C

solubility

H2O: ≥5 mg/mL (warmed)

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: ≥10 mg/mL

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-10 to -25°C

storage temp.

−20°C

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 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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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25G
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1000309185

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OGA heterozygosity suppresses intestinal tumorigenesis in Apc min/+ mice
Yang YR, et al.
Oncogenesis, 3(7), e109-e109 (2014)
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
O-Glycosylation with O-linked beta-N-acetylglucosamine increases vascular contraction: Possible modulatory role on Interleukin-10 signaling pathway
Miguez JSG, et al.
Life Sciences, 23(10), 1114-1130 (2018)
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)

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