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| Common Name | Naphthol AS-E | ||
|---|---|---|---|
| CAS Number | 92-78-4 | Molecular Weight | 297.73600 |
| Density | 1.399 g/cm3 | Boiling Point | 416.5ºC at 760 mmHg |
| Molecular Formula | C17H12ClNO2 | Melting Point | 255°C |
| MSDS | / | Flash Point | 205.7ºC |
| Name | N-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide |
|---|---|
| Synonym | More Synonyms |
| Description | 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. |
|---|---|
| Related Catalog | Research Areas >>CancerSignaling Pathways >>Epigenetics >>Histone AcetyltransferaseSignaling Pathways >>Epigenetics >>Epigenetic Reader Domain |
| Target | KIX-KID:2.26 μM (IC50) |
| 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. |
| Density | 1.399 g/cm3 |
|---|---|
| Boiling Point | 416.5ºC at 760 mmHg |
| Melting Point | 255°C |
| Molecular Formula | C17H12ClNO2 |
| Molecular Weight | 297.73600 |
| Flash Point | 205.7ºC |
| Exact Mass | 297.05600 |
| PSA | 49.33000 |
| LogP | 4.52410 |
| Index of Refraction | 1.735 |
| InChIKey | OHAXNCGNVGGWSO-UHFFFAOYSA-N |
| SMILES | O=C(Nc1ccc(Cl)cc1)c1cc2ccccc2cc1O |
| Hazard Codes | Xn |
|---|---|
| Risk Phrases | R42/43:May cause sensitization by inhalation and skin contact . |
| Safety Phrases | S7-S36-S24/25 |
| WGK Germany | 3 |
| RTECS | MR0176000 |
| HS Code | 29053980 |
| HS Code | 2924299090 |
|---|---|
| Summary | 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0% |
| MFCD00021639 |
| Amanil Naphthol AS-E |
| Cibanaphthol RC |
| 3-hydroxy-naphthalene-2-carboxylic acid 4-chloro-anilide |
| 3-Hydroxy-[2]naphthoesaeure-(4-chlor-anilid) |
| naphthol AS-E |
| EINECS 202-189-7 |
| Naphtoelan E |
| Naphtazol E |
| Naphtanilide E |
| 4'-Chloro-3-hydroxy-2-naphthanilide |
| Sanatol E |
| 3-hydroxy-[2]naphthoic acid-(4-chloro-anilide) |
| Daito Grounder E |
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