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SML2239
INF39
≥98% (HPLC)
Synonym(e):
2-Chloro-α-methylene-benzenepropanoic acid ethyl ester, Ethyl 2-(2-chlorobenzyl)acrylate
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Über diesen Artikel
Empirische Formel (Hill-System):
C12H13ClO2
CAS-Nummer:
Molekulargewicht:
224.68
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
oil
assay
≥98% (HPLC)
form
oil
color
colorless to light brown
storage temp.
−20°C
SMILES string
ClC1=C(CC(C(OCC)=O)=C)C=CC=C1
InChI
1S/C12H13ClO2/c1-3-15-12(14)9(2)8-10-6-4-5-7-11(10)13/h4-7H,2-3,8H2,1H3
InChI key
VTAOWWAFBSFWSG-UHFFFAOYSA-N
Biochem/physiol Actions
INF39 is an orally active acrylate derivative and a non-cytotoxic INF4E analog (no toxicity at 100 μM in THP-1 cultures vs. TC50 = 65 μM with INF4E) that acts as an irreversible inhibitor against NLRP3 (NACHT, LRR and PYD domains-containing protein 3) ATPase activity (52% inhibition in 15 min by 100 μM INF39; 105 ng human NLP3 & 250 μM ATP) essential for the NLRP3 inflammasome assembly and activation. INF39 effectively decreases 5 mM (30 min) ATP-induced interleukin-1β (IL-1β) release and pyroptosis of murine bone marrow-derived macrophages in cultures (by 55-58% and 43-65%, respectively, with 1-hr 10 μM INF39 pretreatment of LPS-primed BMDM) and alleviates gut-associated inflammation in a rat model of 2,4-dinitrobenzenesulfonic acid (DNBS)-induced colitis in vivo (12.5-50 mg/kg/day in 0.2 mL olive oil p.o.).
Orally active irreversible NLRP3 inhibitor that suppresses ATP-dependent macrophage activation and alleviates DNBS-induced colitis in rats.
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Dieser Artikel | |||
|---|---|---|---|
| assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) |
| form oil | form paste | form solid | form powder |
| storage temp. −20°C | storage temp. 2-8°C | storage temp. 2-8°C | storage temp. 2-8°C |
| color colorless to light brown | color white to beige | color - | color white to beige |
Lagerklasse
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Mattia Cocco et al.
Journal of medicinal chemistry, 60(9), 3656-3671 (2017-04-15)
Pharmacological inhibition of NLRP3 inflammasome activation may offer a new option in the treatment of inflammatory bowel disease. In this work, we report the design, synthesis, and biological screening of a series of acrylate derivatives as NLRP3 inhibitors. The in
Design, Synthesis, and Evaluation of Acrylamide Derivatives as Direct NLRP3 Inflammasome Inhibitors.
Mattia Cocco et al.
ChemMedChem, 11(16), 1790-1803 (2016-03-19)
NLRP3 inflammasome plays a key role in the intracellular activation of caspase-1, processing of pro-inflammatory interleukin-1β (IL-1β), and pyroptotic cell death cascade. The overactivation of NLRP3 is implicated in the pathogenesis of autoinflammatory diseases, known as cryopyrin-associated periodic syndromes (CAPS)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML2239-25MG | 04061835503629 |
| SML2239-5MG | 04061835503636 |