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P0052

Sigma-Aldrich

PNU-74654

≥98% (HPLC), solid

Synonym(s):

Benzoic acid, 2-phenoxy-, 2-[(5-methyl-2-furanyl)methylene]hydrazide

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About This Item

Empirical Formula (Hill Notation):
C19H16N2O3
CAS Number:
113906-27-7
Molecular Weight:
320.34
MDL number:
MFCD12912438
UNSPSC Code:
12352203
PubChem Substance ID:
329820000
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

Cc1ccc(\C=N\NC(=O)c2ccccc2Oc3ccccc3)o1

InChI

1S/C19H16N2O3/c1-14-11-12-16(23-14)13-20-21-19(22)17-9-5-6-10-18(17)24-15-7-3-2-4-8-15/h2-13H,1H3,(H,21,22)/b20-13+

InChI key

JJEDWBQZCRESJL-DEDYPNTBSA-N

Application

PNU-74654 has been used:
  • as a β-catenin signaling inhibitor to study its effects on the funnel cartilage differentiation in Sepia sp. embryos
  • as a Wnt signaling inhibitor to study its effects on glycogen synthase kinase 3β (GSK-3β) inhibition in prostate cancer cell lines
  • as a Wnt signaling inhibitor to study its effects on leptin-induced cell proliferation in breast cancer cells

Biochem/physiol Actions

PNU-74654 inhibits the Wnt-β catenin pathway by blocking the interaction between β-catenin and TCF (T cell factor). PNU-74654 is also an anti-tumor agent. Aberrant activation of the Wnt/β-catenin pathway (canonical pathway) is implicated in driving development/progression of different tumors, such as colon cancer, through interaction between β-catenin and T cell factor (TCF), which regulates the expression of target genes in cell proliferation and differentiation. Inhibition of this pathway activity in cancer cell lines efficiently blocks their growth. PNU-74654 inhibits this pathway by blocking the interaction between β-catenin and TCF.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rudolf Käfer et al.
International immunopharmacology, 32, 118-124 (2016-01-30)
Many tumors are characterized by mutation-induced constitutive activation of β-catenin which promotes tumor growth and survival. Consequently, the development of specific β-catenin inhibitors for tumor therapy has come into the focus of drug development. β-Catenin was also shown to contribute
Letícia F Leal et al.
Oncotarget, 6(40), 43016-43032 (2015-10-31)
To date, there is no effective therapy for patients with advanced/metastatic adrenocortical cancer (ACC). The activation of the Wnt/beta-catenin signaling is frequent in ACC and this pathway is a promising therapeutic target. To investigate the effects of the inhibition of
Oscar A Tarazona et al.
Nature, 533(7601), 86-89 (2016-04-26)
The evolution of novel cell types led to the emergence of new tissues and organs during the diversification of animals. The origin of the chondrocyte, the cell type that synthesizes cartilage matrix, was central to the evolution of the vertebrate
Jieun Lee et al.
Biochemical and biophysical research communications, 525(3), 563-569 (2020-03-03)
Supercentenarians (≥110-year-old, SC) are a uniquely informative population not only because they surpass centenarians in age, but because they appear to age more slowly with fewer incidences of chronic age-related disease than centenarians. We reprogramed donor B-lymphoblastoid cell lines (LCL)
Hong Quan Duong et al.
Cancer research, 78(16), 4533-4548 (2018-06-20)
MAPK signaling pathways are constitutively active in colon cancer and also promote acquired resistance to MEK1 inhibition. Here, we demonstrate that BRAFV600E -mutated colorectal cancers acquire resistance to MEK1 inhibition by inducing expression of the scaffold protein CEMIP through a
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