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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (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
C A Harrison et al.
The British journal of dermatology, 156(2), 247-257 (2007-01-17)
The transglutaminase (TG) family consists of eight distinct isoforms. TG types 1, 3 and 5 play a major role in normal skin development, with TG2 also being elevated during dermal wounding. TG1, 3 and 5 are responsible for the cross-linking
Zita Balklava et al.
The Journal of biological chemistry, 277(19), 16567-16575 (2002-02-28)
Increasing evidence suggests that tissue transglutaminase (tTGase; type II) is externalized from cells, where it may play a key role in cell attachment and spreading and in the stabilization of the extracellular matrix (ECM) through protein cross-linking. However, the relationship
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
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
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