GSK583
GSK583 Basic information
- Product Name:
- GSK583
- Synonyms:
-
- GSK583
- SK583
- 6-[(1,1-Dimethylethyl)sulfonyl]-N-(5-fluoro-1H-indazol-3-yl)-4-quinolinamine
- RIP2 kinase inhibitor 583
- CS-2216
- GSK583, >98%
- GSK-583;GSK 583
- 4-Quinolinamine, 6-[(1,1-dimethylethyl)sulfonyl]-N-(5-fluoro-1H-indazol-3-yl)-
- CAS:
- 1346547-00-9
- MF:
- C20H19FN4O2S
- MW:
- 398.45
- Mol File:
- 1346547-00-9.mol
GSK583 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).
- pka
- 12.59±0.40(Predicted)
- form
- solid
- 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
GSK583 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.1?It 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
GSK583Supplier
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- 13621943973
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- sales@boylechem.com
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- 0411-62910999 13889544652
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