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Key Documents

70485

Sigma-Aldrich

Naphthol AS-E phosphate

suitable for histology

Synonym(s):

KG-501

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About This Item

Empirical Formula (Hill Notation):
C17H13ClNO5P
CAS Number:
Molecular Weight:
377.72
Beilstein:
6664478
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.83

Assay

≥80% (HPLC)

form

powder

application(s)

histology

storage temp.

2-8°C

SMILES string

OP(O)(=O)Oc1cc2ccccc2cc1C(=O)Nc3ccc(Cl)cc3

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

Application

Naphthol AS-E phosphate has been used as a cAMP-response element-binding protein (CREB) inhibitor to dissolve in dimethyl sulfoxide (DMSO) as a stock solution in the study to test the hypothesis that oncostatin M (OSM) may confer neuronal resistance against 3-nitropropionic acid (3-NP).

Biochem/physiol Actions

Naphthol AS-E phosphate/KG501, a small-molecule antagonist has the ability to prevent cAMP-response element-binding protein (CREB) pathway. It can also interfere with the interaction of Myb-KIX in vitro and block the actions of Myb in vivo.

Other Notes

Histochemical substrate for alkaline phosphatases,KG-501 blocks cAMP-induction of CREB (cAMP Response Element Binding Protein)-dependent target gene transcription (Ki 10 microM)) through interference in the binding between the KID domain of CREB and KIX domain of CBP (CREB Binding Protein), classic activator-coactivator interaction.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Naphthol AS-E phosphate inhibits the activity of the transcription factor Myb by blocking the interaction with the KIX domain of the coactivator p300
Uttarkar S, et al.
Molecular Cancer Therapeutics, molcanther-molcan0662 (2015)
Phosphates of the naphthol AS series in the quantitative determination of alkaline and acid phosphatase activities in situ studied in polyacrylamide membrane model systems and by cytospectrophotometry
Lojda, Z., et al.
Histochemistry and Cell Biology, 11, 13-32 (1967)
Hui-Chi Lai et al.
PloS one, 6(11), e28280-e28280 (2011-12-06)
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Proceedings of the National Academy of Sciences of the United States of America, 113(4), 1032-1037 (2016-01-13)
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