ChemicalBook Product Catalog Biochemical Engineering Biochemical Reagents Agonist Inhibitors Benzenepropanoic acid, 5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)Methoxy]-

Benzenepropanoic acid, 5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)Methoxy]-

Product NameBenzenepropanoic acid, 5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)Methoxy]-
CAS530141-72-1
MFC29H27NO8
MW517.53
EINECS
MOL File530141-72-1.mol

Chemical Properties

Density	1.376±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMSO:30.5(Max Conc. mg/mL);58.93(Max Conc. mM) DMSO:PBS (pH 7.2) (1:2):0.33(Max Conc. mg/mL);0.64(Max Conc. mM) DMF:30.0(Max Conc. mg/mL);57.97(Max Conc. mM)
form	A crystalline solid
pka	4.61±0.10(Predicted)
color	White to yellow
InChIKey	DALCQQSLNPLQFZ-UHFFFAOYSA-N
SMILES	C1(CCC(O)=O)=CC(C(=O)C2=CC=C(OC3CCCC3)C=C2O)=CC=C1OCC1=CC2=C(C=C1)C(=O)NO2

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

T-5224 is an inhibitor of c-fos/activator protein 1 (AP-1). It inhibits the DNA binding activity of c-fos/AP-1 without affecting the activity of C/EBPα, ATF2, MyoD, Sp1, and NF-κB/p65 in vitro. It shows inhibitory activity in a c-fos/AP-1 promoter luciferase assay without changing c-fos family protein expression levels in TNF-α-stimulated NIH/3T3 cells. Administration of T-5224 (30 mg/kg) inhibits the development of collagen-induced arthritis in mice through reduction of IL-1β production, neutrophil infiltration, and synovial cell proliferation. It reduces the inflammatory cytokine response in LPS-challenged mice, lowering levels of TNF-α and HMGB1 in the serum and MIP-1α and MCP-1 in the liver. T-5224 reduces in vivo necrosis of liver tissue and improves survival rates in LPS-challenged mice. T-5224 also exhibits anticancer activity, reducing proliferation and migration of HSC-3-M3 head and neck squamous carcinoma cells in vitro and the number of metastases in an HSC-3-M3 orthotopic xenograft model in vivo.

Uses

T-5224 is a selective activator protein-1 inhibitor that prevents lymph node metastasis in an oral cancer model.

in vivo

Administration of T-5224 (300 mg/kg, p.o.) after intraperitoneal injection of LPS impartes appreciable protection against acute elevations in serum levels of TNFα, HMGB1, ALT/AST as well as in liver tissue levels of MIP-1α and MCP-1, and reduces the lethality (27%)^[4].
G2 is observed in rat and monkey liver microsomes as a major metabolite of T-5224, suggesting that G2 is not a human-specific metabolite^[5].
T-5224 (300 mg/kg, p.o.) inhibits the production of TNF-alpha and other downstream effectors in C57BL/6 mice^[6].

IC 50

c-Fos

storage

Store at -20°C

References

[1] YUKIHIKO AIKAWA. Treatment of arthritis with a selective inhibitor of c-Fos/activator protein-1[J]. Nature biotechnology, 2008, 26 7: 817-823. DOI: 10.1038/nbt1412
[2] SHINICHIRO IZUTA. T-5224, a selective inhibitor of c-Fos/activator protein-1, attenuates lipopolysaccharide-induced liver injury in mice.[J]. Biotechnology Letters, 2012, 34 12: 2175-2182. DOI: 10.1007/s10529-012-1022-4
[3] DAISUKE KAMIDE. Selective activator protein-1 inhibitor T-5224 prevents lymph node metastasis in an oral cancer model[J]. Cancer Science, 2016, 107 5: 666-673. DOI: 10.1111/cas.12914

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