An inhibitor of the protein-protein interaction between CREB and KIX domains
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Naphthol AS-E Phosphate

Item No. 33602

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(4-chlorophenyl)-3-(phosphonooxy)-2-naphthalenecarboxamide
CAS Number
18228-17-6
Synonyms
  • KG-501
Molecular Formula
C17H13ClNO5P
Formula Weight
377.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
232, 273 nm
SMILES
O=C(C1=CC2=C(C=C1OP(O)(O)=O)C=CC=C2)NC3=CC=C(C=C3)Cl
InChi Code
InChI=1S/C17H13ClNO5P/c18-13-5-7-14(8-6-13)19-17(20)15-9-11-3-1-2-4-12(11)10-16(15)24-25(21,22)23/h1-10H,(H,19,20)(H2,21,22,23)
InChi Key
RQAQWBFHPMSXKR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $69

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    10 mg

    $120

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    25 mg

    $263

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    Cayman Chemical
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    Product Description

    Naphthol AS-E phosphate is an inhibitor of the protein-protein interaction between CREB and the KIX domain of CREB-binding protein (CBP; Ki = 50 µM).1 It also inhibits the binding of the transcription factor Myb to the KIX domains of p300 and CBP (IC50s = 30 and 43 µM, respectively).2 Naphthol AS-E phosphate inhibits CREB-dependent transcription in HEK293T cells (Ki = 10 µM).1 It also decreases the expression of Myb target genes and induces differentiation in HL-60, U937, and NB4 myeloid leukemia cells when used at a concentration of 5 µM.2 Naphthol AS-E phosphate inhibits proliferation of NCI-H1734 lung adenocarcinoma cells (IC50 = 6.89 µM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Best, J., Amezcua, C.A., Mayr, B., et al. Identification of small-molecule antagonists that inhibit an activator: Coactivator interaction. Proc. Natl. Acad. Sci. USA 101(51), 17622-17627 (2004).

    2. Uttarkar, S., Dukare, S., Bopp, B., et al. Naphthol AS-E phosphate inhibits the activity of the transcription factor Myb by blocking the interaction with the KIX domain of the coactivator p300. Mol. Cancer Ther. 14(6), 1276-1285 (2015).

    3. Lee, J.W., Park, H.S., Park, S.-A., et al. A novel small-molecule inhibitor targeting CREB-CBP complex possesses anti-cancer effects along with cell cycle regulation, autophagy suppression and endoplasmic reticulum stress. PLoS One 10(4), e0122628 (2015).