Naphthol AS-E is a potent and cell-permeable inhibitor of KIX-KID interaction. Naphthol AS-E directly binds to the KIX domain of CBP (Kd:8.6 µM), blocks the interaction between the KIX domain and the KID domain of CREB with IC50 of 2.26 µM. Naphthol AS-E can be used for cancer research.

Product information

CAS Number: 92-78-4

Molecular Weight: 297.74

Formula: C17H12ClNO2

Chemical Name: N-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide

Smiles: OC1C=C2C=CC=CC2=CC=1C(=O)NC1C=CC(Cl)=CC=1

InChiKey: OHAXNCGNVGGWSO-UHFFFAOYSA-N

InChi: InChI=1S/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)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 41.67 mg/mL (139.95 mM; Need ultrasonic).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

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-E inhibits CREB-mediated gene transcription with an IC50 of 2.29 µM. In HEK293T-based complementation assay, Naphthol AS-E dose-dependently inhibited Renilla luciferase activity with an IC50 of 2.9 µM by directly binding to CBP's KIX domain (Kd ~8.6 µM using a recombinant KIX). Naphthol AS-E exhibits low µM activity in inhibiting the proliferation of all these cancer cells, which is consistent with its cellular CREB inhibition potency. The average GI50 values for A549, MCF-7, MDA-MB-231 and MDA-MB-468 are approximately 2.9µM, 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.

References:

1. Fuchun Xie, et al. Synthesis and Evaluation of an O-Aminated Naphthol AS-E as a Prodrug of CREB-mediated Gene Transcription Inhibition. Lett Org Chem. 2013 Jun;10(5):380-384.
2. Bingbing X Li, et al. Discovery of a small-molecule inhibitor of the KIX-KID interaction. Chembiochem. 2009 Nov 23;10(17):2721-4.

Products are for research use only. Not for human use.