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SML3778

Sigma-Aldrich

T-5224

≥98% (HPLC)

Synonym(s):

3-[5-(4-Cyclopentyloxy-2-hydroxybenzoyl)-2-[(3-oxo-1,2-benzoxazol-6-yl)methoxy]phenyl]propanoic acid, 3-{5-[4-(Cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl} propionic acid, 5-[4-(Cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)methoxy]benzenepropanoic acid, T 5224, T5224

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About This Item

Empirical Formula (Hill Notation):
C29H27NO8
CAS Number:
530141-72-1
Molecular Weight:
517.53
MDL number:
MFCD28053483
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

[nH]1[o]c2c([c]1=O)ccc(c2)COc3c(cc(cc3)C(=O)c4c(cc(cc4)OC5CCCC5)O)CCC(=O)O

InChI

1S/C29H27NO8/c31-24-15-21(37-20-3-1-2-4-20)8-10-22(24)28(34)19-6-11-25(18(14-19)7-12-27(32)33)36-16-17-5-9-23-26(13-17)38-30-29(23)35/h5-6,8-11,13-15,20,31H,1-4,7,12,16H2,(H,30,35)(H,32,33)

InChI key

DALCQQSLNPLQFZ-UHFFFAOYSA-N

Biochem/physiol Actions

T-5224 is an orally active, selective AP-1 transcription complex c-Fos/c-Jun inhibitor that blocks c-Fos and c-Jun DNA-binding activity, but not that of C/EBPα, ATF-2 (bZIP domain), MyoD (bHLH domain), Sp-1 (ZF domain) and NF-κB/p65 (RHD). T-5224 inhibits PMA-induced Fos/AP-1 promoter activity (IC50 ~4 μM by NIH/3T3 reporter assay) without affectingTNFα-stimulated NF-kB activity or the cellular levels of c-Fos family protein members. T-5224 exhibits therapeutic efficacy against collagen-induced arthritis (CIA) in mice in vivo (0.3-30 mg/kg/d p.o.).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000402299
0000402299
0000252730
0000252729
0000244894

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c-Fos is a mechanosensor that regulates inflammatory responses and lung barrier dysfunction during ventilator-induced acute lung injury
BMC Pulmonary Medicine, 22(1), 9-9 (2022)
Yukihiko Aikawa et al.
Nature biotechnology, 26(7), 817-823 (2008-07-01)
To inhibit arthritis upstream of inflammatory cytokine release and matrix metalloproteinase (MMP) action, we designed de novo a small-molecule inhibitor of c-Fos/activator protein-1 (AP-1) using three-dimensional (3D) pharmacophore modeling. This model was based on the 3D structure of the basic
Yohan Choi et al.
Endocrinology, 162(9) (2021-06-26)
FOS, a subunit of the activator protein-1 (AP-1) transcription factor, has been implicated in various cellular changes. In the human ovary, the expression of FOS and its heterodimeric binding partners JUN, JUNB, and JUND increases in periovulatory follicles. However, the
Mari Ishida et al.
Journal of intensive care, 3, 49-49 (2015-11-19)
Sepsis is a potentially fatal syndrome mediated by an early [e.g., tumor necrosis factor-alpha (TNF-α)] and late [high mobility group box-1 (HMGB-1)] proinflammatory cytokine response to infection. Sepsis-induced acute kidney injury (AKI) is associated with a high mortality. C-Fos/activator protein-1
Inhibition of c-Fos expression attenuates IgE-mediated mast cell activation and allergic inflammation by counteracting an inhibitory AP1/Egr1/IL-4 axis
Journal of Translational Medicine, 19(1), 261-261 (2021)
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