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SML1979 Sigma-Aldrich

FM-381

≥98% (HPLC)

Synonym: (E)-2-Cyano-3-(5-(1-cyclohexyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2-yl)furan-2-yl)-N,N-dimethylacrylamide, 2-Cyano-3-(5-(1-cyclohexyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2-yl)furan-2-yl)-N,N-dimethylacrylamide

  • Empirical Formula (Hill Notation) C24H24N6O2

  • Molecular Weight 428.49

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, F
assay   ≥98% (HPLC)
form   powder
color   white to beige
solubility   DMSO: 2 mg/mL, clear (warmed)
storage temp.   2-8°C
SMILES string   CN(C(/C(C#N)=C/C(O1)=CC=C1C2=NC3=CN=C(NC=C4)C4=C3N2C5CCCCC5)=O)C

Description

Biochem/physiol Actions

FM-381 is a highly potent and JAK3-selective janus kinase (JAK) inhibitor (IC50 = 127 pM/JAK3, 52 nM/JAK1, 346 nM/JAK2, 459 nM/TYK2 by radiometric assay; [ATP] = 10 μM) that targets JAK3 gatekeeper (GK) Cys909 for a reversible covalent interaction, exhibiting much reduced or little potency against a panel of 409 other kinases. FM-381 is >3-fold more potent than the JAK1/3 inhibitor Tofacitinib (IC50 = 292 pM/JAK3, 496 pM/JAK1, 2.2 nM/JAK2, 8.9 nM/TYK2 by radiometric assay; [ATP] = 10 μM) in blocking JAK1/JAK3-mediated STAT5 phosphorylation in human CD4+ T-cells upon IL-2 stimulation (ECmax ∼100 nM with FM-381), while being ineffective (up to 1 μM) against JAK3-independent STAT1/3 phosphorylation following IL-6 or TNFα stimulation. For characterization details of FM-381, please visit the FM-381 probe summary on the Structural Genomics Consortium (SGC) website.

FM-479 is the negative control for the active probe, FM-381. FM-479 is available from Sigma. To learn more about and purchase FM-479, click here.

To learn about other SGC chemical probes, visit sigma.com/sgc

Features and Benefits

FM-381 is a chemical probe available through a partnership with the Structural Genomics Consortium (SGC). To learn more and view other SGC chemical probes, visit sigma.com/SGC.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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