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SML2176

Sigma-Aldrich

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:
135273-74-4
Molecular Weight:
220.72
MDL number:
MFCD00898949
UNSPSC Code:
12352200

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

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

InChI key

NFZZAUJDSJWLTQ-UHFFFAOYSA-M

Biochem/physiol Actions

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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