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GSK583

Product NameGSK583
CAS1346547-00-9
MFC20H19FN4O2S
MW398.45
EINECS
MOL File1346547-00-9.mol

Chemical Properties

Boiling point	652.9±55.0 °C(Predicted)
Density	1.402±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
solubility	Soluble in DMSO (up to at least 25 mg/ml).
form	solid
pka	12.59±0.40(Predicted)
color	Pale yellow
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChI	InChI=1S/C20H19FN4O2S/c1-20(2,3)28(26,27)13-5-7-16-14(11-13)17(8-9-22-16)23-19-15-10-12(21)4-6-18(15)24-25-19/h4-11H,1-3H3,(H2,22,23,24,25)
InChIKey	XLOGLWKOHPIJLV-UHFFFAOYSA-N
SMILES	N1C2C(=CC(S(C(C)(C)C)(=O)=O)=CC=2)C(NC2C3=C(NN=2)C=CC(F)=C3)=CC=1

Usage And Synthesis

Description

GSK583 (1346547-00-9) is a highly selective and potent inhibitor of RIP2 kinase, IC50= 5 nM human and IC50= 2 nM rat.1It also potently inhibits isolated RIP3 kinase (IC50= 5 nM) but is inactive against RIP3 in cellular assays due to a very low KM,ATP. GSK583 blocks NOD2 signaling by interfering with XIAP-RIP2 binding resulting in decreased cytokine and chemokine production.1,2

Uses

GSK 583, is a selective inhibitor of RIP-like interacting CLARP kinase RIP2 Kinase is a central component of the innate immune system and enables downstream signaling following activation of the pattern recognition receptors NOD1 and NOD2, leading to the production of inflammatory cytokines.

in vivo

GSK583 (0.1, 1, and 10 mg/kg, p.o.) inhibits serum KC (the rodent orthologue of IL-8) levels in rats in a dose-dependent manner, with an IC₅₀ derived from rat blood concentrations of 50 nM (or 20 ng/mL). Similarly, GSK583 inhibits serum KC levels and recruitment of neutrophils into the peritoneal cavity in mice in a dose-dependent manner, with an IC₅₀ of 37 nM (15 ng/mL) derived from mouse blood concentration^[1].

storage

Store at +4°C

References

[1] PAMELA A. HAILE. The Identification and Pharmacological Characterization of 6-(tert-Butylsulfonyl)-N-(5-fluoro-1H-indazol-3-yl)quinolin-4-amine (GSK583), a Highly Potent and Selective Inhibitor of RIP2 Kinase[J]. Journal of Medicinal Chemistry, 2016, 59 10: 4867-4880. DOI:10.1021/acs.jmedchem.6b00211
[2] TATIANA GONCHAROV. Disruption of XIAP-RIP2 Association Blocks NOD2-Mediated Inflammatory Signaling.[J]. Molecular Cell, 2018, 69 4: 551-565.e7. DOI:10.1016/j.molcel.2018.01.016

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