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SML2176

Sigma-Aldrich

R283

≥98% (HPLC)

Sinônimo(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

Fórmula empírica (Notação de Hill):
C8H13N2OS · Cl
Número CAS:
135273-74-4
Peso molecular:
220.72
Número MDL:
MFCD00898949
Código UNSPSC:
12352200

Ensaio

≥98% (HPLC)

forma

powder

cor

white to beige

solubilidade

H2O: 2 mg/mL, clear

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

C[N+]1=C(SCC(C)=O)N(C)C=C1.[Cl-]

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

chave InChI

NFZZAUJDSJWLTQ-UHFFFAOYSA-M

Ações bioquímicas/fisiológicas

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).

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

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Luigi Maiuri et al.
Gastroenterology, 129(5), 1400-1413 (2005-11-16)
In celiac disease (CD), transglutaminase type II (TG2) has 2 fundamental roles: (1) as the autoantigen recognized by highly specific autoantibodies and (2) the modifier of pathogenic gliadin T-cell epitopes. It follows that inhibition of TG2 might represent an attractive
Alanood S Algarni et al.
Biochemical pharmacology, 128, 55-73 (2017-01-10)
The PAC
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
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
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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