Pyrazolanthrone (SP600125)

Modify Date: 2024-01-02 14:19:35

Pyrazolanthrone (SP600125) Structure
Pyrazolanthrone (SP600125) structure
 Common Name Pyrazolanthrone (SP600125)
CAS Number 129-56-6 Molecular Weight 220.226
Density 1.5±0.1 g/cm3 Boiling Point 489.3±14.0 °C at 760 mmHg
Molecular Formula C14H8N2O Melting Point 281~282℃
MSDS USA Flash Point 246.8±26.5 °C

 Use of Pyrazolanthrone (SP600125)


SP600125 is a reversible and ATP-competitive JNK inhibitor with IC50s of 40, 40 and 90 nM for JNK1, JNK2 and JNK3, respectively.

 Names

Name Dibenzo[cd,g]indazol-6(2H)-one
Synonym More Synonyms

 Pyrazolanthrone (SP600125) Biological Activity

Description SP600125 is a reversible and ATP-competitive JNK inhibitor with IC50s of 40, 40 and 90 nM for JNK1, JNK2 and JNK3, respectively.
Related Catalog
Target

JNK1:40 nM (IC50)

JNK2:40 nM (IC50)

JNK3:90 nM (IC50)

Autophagy

In Vitro SP600125 is an ATP-competitive inhibitor of JNK2 with a Ki value of 0.19±0.06 μM. SP600125 inhibits the phosphorylation of c-Jun with IC50 of 5 μM to 10 μM in Jurkat T cells. In CD4+ cells, such as Th0 cells isolated from either human cord or peripheral blood, SP600125 blocks cell activation and differentiation and inhibits the expression of inflammatory genes COX-2, IL-2, IL-10, IFN-γ, and TNF-α, with IC50 of 5 μM to 12 μM[1]. In a mouse beta cells MIN6, SP600125 (20 μM) induces the phosphorylation of p38 MAPK and its downstream CREB-dependent promoter activation[2]. In HCT116 cells, SP600125 (20 μM) blocks the G2 phase to mitosis transition and induces endoreplication. This ability of SP600125 is independent of JNK inhibition, but due to its inhibition of CDK1-cyclin B activation upstream of Aurora A and Polo-like kinase 1[3].
In Vivo Administration of SP600125 at 15 or 30 mg/kg i.v. significantly inhibits TNF-α serum levels, whereas oral administration dose-dependently blocks TNF-α expression with significant inhibition observed at 30 mg/kg per os[1]. SP600125 attenuates LPS-induced ALI in rats in vivo. The expression levels of TNF-α and IL-6 in the BALF in rats in the SP600125 group are significantly decreased[4].
Cell Assay Determination of mRNA half-life is performed essentially, except that CD14+ cells are stimulated with (bacterial) lipopolysaccharide (LPS; 50 ng/mL) for 2 h before addition of actinomycin D (5 μg/mL). SP600125 (25 μM) or vehicle (0.5% DMSO vol/vol) is added immediately following the actinomycin D. Analysis is performed by using real-time reverse transcription (RT)-PCR. Total RNA is extracted with an RNeasy Mini kit. TNF mRNA is measured by real time RT-PCR, using a TNF Taqman probe. All data are normalized by using glyceraldehyde-3-phosphate dehydrogenase (GAPDH) expression. The TNF-α forward primer is 5′-CTGGCCCAGGCAGTCAGAT-3′ and the reverse primer is 5′-TATCTCTCAGCTCCACGCCATT-3′. The Taqman probe sequence is 5′-FAM-CCTGTAGCCCATGTTGTAGCAAACCCTCA-TAMRA-3′[1].
Animal Admin Mice[1] Female CD-1 mice (8-10 weeks of age) are dosed i.v. or per oswith SP600125 in PPCES vehicle (30% PEG-400/20% polypropylene glycol/15% Cremophor EL/5% ethanol/30% saline), final volume of 5 mL/kg, 15 min before i.v. injection with LPS in saline (0.5 mg/kg). At 90 min, a terminal bleed is obtained from the abdominal vena cava, and the serum is recovered. Samples are analyzed for mouse TNF-α by using an ELISA. Rats[4] A total of 40 male Wistar rats are randomly divided into four groups (n=10): the control group, LPS group, normal saline group (NS) and the SP600125 group. Acute lung injury (ALI) is induced via intratracheal injection of LPS. Briefly, the rats are anesthetized with pentobarbital sodium followed by intratracheal injection of 5 mg/kg LPS. The rats are then placed in a vertical position and rotated for 1 min to distribute the LPS in the lungs. Normal saline or SP600125 is administered via intraperitoneal injection (15 mg/kg) 10 min after the LPS injection.
References

[1]. Bennett BL, et al. SP600125, an anthrapyrazolone inhibitor of Jun N-terminal kinase. Proc Natl Acad Sci U S A, 2001, 98(24), 13681-13686.

[2]. Vaishnav D, et al. SP600125, an inhibitor of c-jun N-terminal kinase, activates CREB by a p38 MAPK-mediated pathway. Biochem Biophys Res Commun, 2003, 307(4), 855-860.

[3]. Kim JA, et al. SP600125 suppresses Cdk1 and induces endoreplication directly from G2 phase, independent of JNK inhibition. Oncogene, 2010, 29(11), 1702-1716.

[4]. Zheng Y, et al. JNK inhibitor SP600125 protects against lipopolysaccharide-induced acute lung injury via upregulation ofclaudin-4. Exp Ther Med. 2014 Jul;8(1):153-158.

[5]. Zhang H, et al. SP600125 Suppresses Keap1 Expression and Results in NRF2-mediated Prevention of Diabetic Nephropathy. J Mol Endocrinol. J Mol Endocrinol. 2018 Feb;60(2):145-157.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 489.3±14.0 °C at 760 mmHg
Melting Point 281~282℃
Molecular Formula C14H8N2O
Molecular Weight 220.226
Flash Point 246.8±26.5 °C
Exact Mass 220.063660
PSA 45.75000
LogP 3.18
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.799
Water Solubility H2O: insoluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CB4585000
CHEMICAL NAME :
Anthra(1,9-cd)pyrazol-6(2H)-one
CAS REGISTRY NUMBER :
129-56-6
LAST UPDATED :
199701
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C14-H8-N2-O
MOLECULAR WEIGHT :
220.24
WISWESSER LINE NOTATION :
T C6665 1A P IV OMNJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
178 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#00640

 Safety Information

Hazard Codes Xi: Irritant;
Risk Phrases R36/37/38
Safety Phrases S26-S36
WGK Germany 3
RTECS CB4585000
HS Code 2933990090

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Synonyms

anthra[1,9-cd]pyrazol-6(2H)-one
1,9-PYRAZOLOANTHRONE
Dibenz[cd,g]indazol-6(2H)-one
1,6-dihydrodibenzo[cd,g]indazol-6-one
Dibenzo[cd,g]indazol-6(2H)-one
2H-Dibenzo[CD,G]Indazol-6-One
MFCD00022289
EINECS 204-955-6
SP600125
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