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HomeProduct name list1,9-Pyrazoloanthrone

1,9-Pyrazoloanthrone

Synonym(s):1,9-Pyrazoloanthrone;Anthrapyrazolone;JNK Inhibitor II - CAS 129-56-6 - Calbiochem;SAPK Inhibitor II, Anthra[1,9- cd]pyrazol-6(2 H)-one, 1,9-pyrazoloanthrone, SP600125

  • CAS NO.:129-56-6
  • Empirical Formula: C14H8N2O
  • Molecular Weight: 220.23
  • MDL number: MFCD00022289
  • EINECS: 204-955-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:08:57
1,9-Pyrazoloanthrone Structural

What is 1,9-Pyrazoloanthrone?

Description

SP-600125 (129-56-6) is a selective inhibitor of c-Jun N-terminal kinase (JNK). Reversibly inhibits JNK1,2 and 3 (IC50‘s range from 40-90 nM). >300-fold selectivity for JNK as compared to related MAP kinases. Anti-inflammatory activity. SP-600125 inhibits expression of presenilin-1 and Notch signaling in mouse brain. Cell permeable and active in vivo.

The Uses of 1,9-Pyrazoloanthrone

A broad-spectrum serine/threonine kinase inhibitor of JNK with an IC50 range from 40 to 90 nM.

The Uses of 1,9-Pyrazoloanthrone

SP 600125 is a Jun N-terminal kinase (JNK) inhibitor.

The Uses of 1,9-Pyrazoloanthrone

C2C12 myoblasts were treated with SP600125 to test the stimulation of myogenesis.11 It was used to treat HepG2 cells to test the effects on oxysterol-induced necrosis.12

What are the applications of Application

SP600125 is a potent, selective and reversible inhibitor of JNK1, JNK2 and JNK3.

Definition

ChEBI: A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.

General Description

A potent, cell-permeable, selective, and reversible inhibitor of c-Jun N-terminal kinase (JNK) (IC50 = 40 nM for JNK-1 and JNK-2 and 90 nM for JNK-3). The inhibition is competitive with respect to ATP. Exhibits over 300-fold greater selectivity for JNK as compared to ERK1 and p38-2 MAP kinases. Inhibits the phosphorylation of c-Jun and blocks the expression of IL-2, IFN-γ, TNF-α, and COX-2 in cells. Blocks IL-1-induced accumulation of phospho-Jun and induction of c-Jun transcription.

Biological Activity

Selective inhibitor of c-Jun N-terminal kinase (JNK). Competitively and reversibly inhibits JNK1, 2 and 3 (IC 50 = 40-90 nM) with negligible activity at ERK2, p38 β and a range of enzymes (IC 50 > 10 μ M). Active in vivo . Shown to have reduced selectivity over other protein kinases under certain conditions. Protects renal tubular epithelial cells against ischemia/reperfusion-induced apoptosis. Also available as part of the MAPK Inhibitor Tocriset™ .

Biochem/physiol Actions

SP600125 is an anthrapyrazolone inhibitor of JNK that competes with ATP to inhibit the phosphorylation of c-Jun. It prevents the activation of inflammatory genes such as COX-2, IL-2 IFN-γ and TNF-α.8,9 It prevents the activation of JNK after brain ischemia and may be effective in treatment of ischemic stroke.10

Safety Profile

Poison by intravenous route.When heated to decomposition it emits toxic fumes ofNOx.

Synthesis

1,9-Pyrazolanthrone is prepared by diazotization of 1-aminoanthraquinone, reaction of the diazonium salt with sodium hydrogen sulfite, and cyclization of the resulting hydrazinosulfonic acid .

storage

-20°C (desiccate)

References

1)Bennett et al. (2001), SP600125, an anthrapyrazolone inhibitor of Jun N-terminal kinase; Proc. Natl. Acad. Sci. USA., 98 13681 2) Rahman et al. (2012), Intraperitoneal injection of JNK-specific inhibitor SP600125 inhibits the expression of presenilin-1 and Notch signaling in mouse brain without induction of apoptosis; Brain Res., 1448 117

Properties of 1,9-Pyrazoloanthrone

Melting point: 281~282℃
Boiling point: 361.16°C (rough estimate)
Density  1.1702 (rough estimate)
refractive index  1.5910 (estimate)
storage temp.  2-8°C
solubility  H2O: insoluble
form  Yellowish orange solid
pka 11.75±0.20(Predicted)
color  yellow
Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months
CAS DataBase Reference 129-56-6(CAS DataBase Reference)
EPA Substance Registry System Anthra[1,9-cd]pyrazol-6(2H)-one (129-56-6)

Safety information for 1,9-Pyrazoloanthrone

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for 1,9-Pyrazoloanthrone

InChIKey ACPOUJIDANTYHO-UHFFFAOYSA-N

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