SML2176
R283
≥98% (HPLC)
Synonym(s):
1,3-Dimethyl-2-(2-oxopropylthio)-1H-imidazol-3-ium chloride, 1,3-Dimethyl-2-[(2-oxopropyl)thio]imidazolium chloride, NTU283, Rob283
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About This Item
Empirical Formula (Hill Notation):
C8H13N2OS · Cl
CAS Number:
Molecular Weight:
220.72
UNSPSC Code:
12352200
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
InChI key
NFZZAUJDSJWLTQ-UHFFFAOYSA-M
InChI
1S/C8H13N2OS.ClH/c1-7(11)6-12-8-9(2)4-5-10(8)3;/h4-5H,6H2,1-3H3;1H/q+1;/p-1
SMILES string
C[N+]1=C(SCC(C)=O)N(C)C=C1.[Cl-]
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
H2O: 2 mg/mL, clear
storage temp.
−20°C
Related Categories
Biochem/physiol Actions
Cell-permeable factor XIIIa and transglutaminase 2 irreversible inhibitor that targets active site Cys for acetonylation with little GSH inhibitory potency.
R283 (NTU283; Rob283) is a cell-permeable 2-[(2-oxopropyl)thio] imidazolium derivative that acts as an irreversible inhibitor against factor XIIIa (FXIIIa) and transglutaminase 2 (TG2, TGase II) by targeting FXIIIa and TG2 active site cysteine (Cys) for acetonylation in a selective manner with little glutathione (GSH) inhibitory potency (app 2nd order rate const = 23000/M/s, 19000/M/s, 0.12/M/s, respectively). A useful tool for investigating TG2-mediated cellular functions (typical conc. range: 25-500 μM).
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Yirong Ding et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 89, 1310-1319 (2017-03-23)
In view of the facts that tTG protein expression level and its enzyme activity increase in AD brains of both individuals and transgenic animals and compelling evidence of the involvement of inflammation in AD pathogenesis, tTG could be involved in
Alanood S Algarni et al.
Biochemical pharmacology, 128, 55-73 (2017-01-10)
The PAC
Monica Currò et al.
Amino acids, 49(3), 659-669 (2016-11-20)
Deposition of amyloid-beta (Aβ) peptides has been shown to induce the release of inflammatory factors by activated microglia and brain infiltrating monocytes/macrophages. Interestingly, the enzyme transglutaminase 2 (TG2) has been shown to play a key role in neuroinflammation and regulation
Ronak Shrestha et al.
Scientific reports, 7(1), 4746-4746 (2017-07-08)
We previously reported the importance of induced nuclear transglutaminase (TG) 2 activity, which results in hepatic cell death, in ethanol-induced liver injury. Here, we show that co-incubation of either human hepatic cells or mouse primary hepatocytes derived from wild-type but
K F Freund et al.
Biochemistry, 33(33), 10109-10119 (1994-08-23)
The physiologic role of several transglutaminases could be more precisely defined with the development of specific inhibitors for these enzymes. In addition, specific plasma transglutaminase (fXIIIa) inhibitors may have therapeutic utility in the treatment of thrombosis. For these purposes, the
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