Name | Naphthol AS-E |
Synonyms | C.I. 37510 NAPTHOL AS-E NAPHTHOL AS-E Naphthol AS-E AcnaNaphtholPC DaitoGrounderE AZOIC COUPLING COMPONENT 10 C.I.Azoic Coupling Component 10 c.i. azoic coupling component 10 C.I. Azoic Coupling Component 10 4'-CHLORO-3-HYDROXY-2-NAPHTHANILIDE 2-Hydroxy-3-Naphthoyl-p-Chloraniline N-(4-CHLOROPHENYL)-3-HYDROXY-2-NAPHTHAMIDE N-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide 2-Naphthalenecarboxamide, N-(4-chlorophenyl)-3-hydroxy- |
CAS | 92-78-4 |
EINECS | 202-189-7 |
InChI | InChI=1/C17H12ClNO2/c18-13-5-7-14(8-6-13)19-17(21)15-9-11-3-1-2-4-12(11)10-16(15)20/h1-10,20H,(H,19,21) |
Molecular Formula | C17H12ClNO2 |
Molar Mass | 297.74 |
Density | 1.399±0.06 g/cm3(Predicted) |
Melting Point | 255°C |
Boling Point | 416.5±30.0 °C(Predicted) |
Flash Point | 205.7°C |
Solubility | soluble in Dimethylformamide |
Vapor Presure | 0Pa at 25℃ |
Appearance | Beige solid |
Color | White to Light yellow to Dark green |
pKa | 8.69±0.40(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
Refractive Index | 1.735 |
Physical and Chemical Properties | Properties light beige powder. melting point 258~259 ℃ solubility: soluble in O-dichlorobenzene. Dissolved in caustic soda solution was yellow. Insoluble in water and soda ash solution. |
Use | It is used as a priming agent for cotton fiber dyeing and printing, and can also be used as an intermediate for lake pigments |
In vitro study | CREB (cyclic AMP-response element-binding protein) is a downstream transcription factor of a multitude of signaling pathways emanating from receptor tyrosine kinases or G-protein coupled receptors.CREB can not be activated until it is phosphorylated at Ser133 and its subsequent binding to CREB-binding protein (CBP) through the kinase-inducible domain (KID) in CREB and KID-interacting (KIX) domain in CBP.In a cell-based CREB Renilla luciferase reporter assay, Naphthol AS-Einhibits CREB-mediated gene transcription with an IC 50 of 2.29 µM. In HEK293T-based complementation assay, Naphthol AS-Edose-dependently inhibited Renilla luciferase activity with an IC 50 of 2.9 µM by directly binding to CBP's KIX domain (K d ~8.6 µM using a recombinant KIX).Naphthol AS-Eexhibits low µM activity in inhibiting the proliferation of all these cancer cells, which is consistent with its cellular CREB inhibition potency. The average GI 50 values for A549, MCF-7, MDA-MB-231 and MDA-MB-468 are approximately2.9µM, 2.81µM, 2.35µM and 1.46µM, respectively.Naphthol AS-E (2.5 µM-10 µM; 48 hours) decreases the expression of anti-apoptotic protein Bcl-2. The expression of VEGF is also decreased. |