5.09164

Windorphen

• Sinonimo/i: Windorphen, Wnt inhibitor dorsalizing, Histone Acetyltransferase Inhibitor XII, ( E) & ( Z)-3-Chloro-2,3- bis(4-methoxyphenyl)acrylaldehyde, WD, HAT Inhibitor XII, Wnt Pathway Inhibitor XXII, Wnt inhibitor dorsalizing, Histone Acetyltransferase Inhibitor XII, (E) & (Z)-3-Chloro-2,3-bis(4-methoxyphenyl)acrylaldehyde, WD, HAT Inhibitor XII, Wnt Pathway Inhibitor XXII
• Formula empirica (notazione di Hill): C₁₇H₁₅ClO₃
• Numero CAS: 19881-70-0
• Peso molecolare: 302.75
• Numero MDL: MFCD00547134
• Codice UNSPSC: 12352200
• NACRES: NA.77

Proprietà

• Saggio: ≥98% (HPLC)
• Livello qualitativo: 100
• Forma fisica: powder
• Produttore/marchio commerciale: Calbiochem^®
• Condizioni di stoccaggio: OK to freeze; protect from light
• Colore: off-white
• Solubilità: DMSO: 50 mg/mL
• Temperatura di conservazione: 2-8°C
• Stringa SMILE: Cl\C(=C(/c2ccc(cc2)OC)\C=O)\c1ccc(cc1)OC
• InChI: 1S/C17H15ClO3/c1-20-14-7-3-12(4-8-14)16(11-19)17(18)13-5-9-15(21-2)10-6-13/h3-11H,1-2H3/b17-16-; VNRALGZMXHFBPG-MSUUIHNZSA-N

Descrizione

Descrizione generale

A cell-permeable bis(4-methoxyphenyl)chloroacrylaldehyde whose (Z)-isomer (isomeric content 12-15%) acts as a p300-selective histone acetytransferase (HAT) inhibitor (IC₅₀ = 4.2 µM) and selectively disrupts β-catenin association with p300, but not CBP or LEF1/TCF4, exhibiting much reduced potency against KAT5, CBP, MYST4, MYST2 (IC₅₀ = 38.2, 51.3, 59.5, 62.2 µM, respectively) and little or no inhibitory efficacy toward GCN5 and PCAF HAT activity (IC₅₀ >100 µM). Shown to preferentially suppress human and mouse β-catenin-, zebrafish β-catenin-1-, but not zebrafish β-catenin-2-, mediated transcription activity in various reporter assays (20 µM) without affecting β-catenin activation or nuclear translocation. Induces apoptosis in Wnt signaling-dependent cancer cultures (IC₅₀ in µM = 15.0/SW480, 19.2/RKO, 21.8/DU135, and 19.0/PC3; 72 h) in vitro without affecting the viability of Wnt-independent human lung cander cell line H460 (up to 200 µM & 72 h) and selectively abrogates Wnt signaling in ventral & lateral regions, but not within dorsal organizer, in 5.3 hpf epiboly stage zebrafish embryos in vivo, indicating that the Zebrafish β-catenin-1 & -2 regulate separate Wnt signaling events during zebrafish embryo development by associating with distinct binding partners. A great complement to the selective β-catenin-CBP interaction blocker ICG-001 (Cat. no. 504712). Pure (E)-isomer is available separately (Cat. no. xxxxxx) as a negative control.

The racemic mixture of a cell-permeable (4-methoxyphenyl)chloroacrylaldehyde compound whose (Z)-isomer (isomer content 12-15%) acts as a p300-selective histone acetytransferase (HAT) inhibitor (IC₅₀ = 4.2 µM using racemic mixture with 13% Z-isomer) and selectively disrupts β-catenin association with p300, but not CBP or LEF1/TCF4, exhibiting much reduced potency against KAT5, CBP, MYST4, MYST2 (IC₅₀ ≥38 µM) and little or no inhibitory efficacy toward GCN5 and PCAF HAT activity (IC₅₀ >100 µM). Shown to selectively prevents human & mouse β-catenin-, zebrafish β-catenin-1-, but not zebrafish β-catenin-2-, mediated transcription activity without affecting β-catenin activation or nuclear translocation. Induces apoptosis in Wnt signaling-dependent cancer cultures (IC₅₀ 15 to 22 µM; 72 h) in vitro without affecting the viability of Wnt-independent H460 (up to 200 µM & 72 h) and selectively abrogates Wnt signaling in ventral & lateral regions, but not within dorsal organizer, in 5.3 hpf epiboly stage zebrafish embryos in vivo. A great complement to the selective β-catenin-CBP interaction blocker ICG-001 (Cat. no. 504712). (E)-isomer is available separately (Cat. no. 509166) as negative control.

Azioni biochim/fisiol

Cell permeable: yes

Reversible: yes

Confezionamento

Packaged under inert gas

Attenzione

Toxicity: Standard Handling (A)

Ricostituzione

Use only fresh DMSO for reconstitution.

Note legali

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Informazioni sulla sicurezza

• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable