SML0244
噻托溴铵 G
≥98% (HPLC), O-GlcNAcase inhibitor, powder
别名:
（3AR，5R，6S，7R，7AR）-2-（乙基氨基）-3a，6,7,7a四氢-5-（羟甲基）-5H-吡喃并[3,2-d]噻唑-6,7-二醇
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关于此项目
经验公式（希尔记法）:
C9H16N2O4S
化学文摘社编号:
分子量:
248.30
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
产品名称
噻托溴铵 G, ≥98% (HPLC)
storage condition
desiccated
color
white to beige
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
assay
≥98% (HPLC)
form
powder
optical activity
[α]/D -21 to -26°, c = 0.3 in methanol
solubility
H2O: ≥5 mg/mL at warmed to 60 °C
storage temp.
−20°C
Quality Level
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Application
Thiamet G已用作O-GlcNA酶抑制剂：
- 处理人胚胎肾细胞293，研究其对Wnt/beta-catenin信号通路的作用
- 处理裂解复制中的染病毒细胞
- 孵育小鼠(C57BL/6)主动脉提高整体O-GlcNAc水平
Biochem/physiol Actions
Thiamet G 是 O-GlcNAcase (Ki = 21 nM) 酶的强效抑制剂。该化合物具有口服生物利用度，可通过血脑屏障。Thiamet G 可导致基于细胞和体内检测系统中的 O-GlcNAc 修饰蛋白增加，并可降低大鼠皮质和海马中磷酸化 Tau 蛋白的水平。
Thiamet G 是一种糖苷酶抑制剂
signalword
Warning
hcodes
Hazard Classifications
Skin Sens. 1B
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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)
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
OGA heterozygosity suppresses intestinal tumorigenesis in Apc min/+ mice
Yang YR, et al.
Oncogenesis, 3(7), e109-e109 (2014)
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