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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:
Molecular Weight:
320.34
MDL number:
UNSPSC Code:
12352203
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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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)
Jan Kroon et al.
Oncotarget, 5(19), 8986-8994 (2014-10-27)
Cancer cells with stem or progenitor properties play a pivotal role in the initiation, recurrence and metastatic potential of solid tumors, including those of the human prostate. Cancer stem cells are generally more resistant to conventional therapies thus requiring the
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
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
Aftab Taiyab et al.
Investigative ophthalmology & visual science, 57(13), 5736-5747 (2016-10-28)
Transforming growth factor-β-induced epithelial-mesenchymal transition (EMT) is one of the main causes of posterior capsular opacification (PCO) or secondary cataract; however, the signaling events involved in TGF-β-induced PCO have not been fully characterized. Here, we focus on examining the role

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